Here’s the thing nobody tells you when you become an engineering manager: your job isn’t just helping your team do great work. It’s making sure the right people know your team is doing great work.

Yeah, it feels gross. Self-promotion by proxy. Corporate theater. All the stuff you probably hated about management before you became one.

But here’s what you need to understand: visibility isn’t vanity. It’s currency. And if you’re not spending it strategically, you’re watching your engineers’ careers stagnate while less talented people with louder advocates get promoted ahead of them.

The Wake-Up Call

A manager I know recently tried to get one of his engineers promoted. This person had been at the company 6+ years, consistently delivered solid work, beloved by their immediate team. Easy promotion, right?

Wrong.

Senior leadership had a “bad taste in their mouth” about this engineer. Not because of anything recent, mostly due to projects that failed for reasons completely outside the engineer’s control. Victim of circumstance, not incompetence.

The manager’s frustration: “Everyone on our team loves them. Everyone who works closely with them doesn’t have bad things to say.”

Translation: Being good at your job isn’t enough. The right people need to see you being good at your job.

The Brutal Math of Promotions

Nobody tells you this when you become an engineering manager, but promotions aren’t primarily technical decisions. In all sizes of engineering organizations, they’re political ones.

Not “political” like backstabbing. Political like they require building consensus among stakeholders, managing perceptions, strategic narrative control, and spending social capital wisely.

Persuasion, influence, politics. All the things you probably never wanted to care about in a tech role.

You can have all the performance data in the world. Every metric trending right. But if one senior engineer with a “pretty big voice” in the organization thinks your person underperforms? You’ve got an uphill battle.

I’ve had senior leaders who just hated an engineer on my team. One or two weird interactions. Their mind was made up. “This engineer suuuuuuucks,” worst dev they’d ever seen.

The engineer in question? Actually, really good and ready for promotion to senior.

This is the world we’re operating in. Fair or not, perception shapes reality when it comes to career advancement.

Let’s Get Po-litical, -litical

The political nature of organizations is frustrating. It feels like a waste of time, and the effort spent trying to “Little Finger” your way to a resolution is better spent elsewhere. But it’s an unfortunate reality in many organizations.

So how do you advocate effectively without becoming insufferable? Here are the tactics that actually work:

Name-Drop in Context

The wrong way to advocate: “Jill is doing amazing work, we should promote her.” Weak, vague, non-helpful.

The right way: During a meeting with senior leadership, when discussing a technical challenge they mentioned last week, drop it naturally: “Yeah, you should see the impact Jill’s work is having right now. Not only did she solve [that complex problem you were worried about], she did it faster than we expected, leading to [X Outcome].”

The difference is context. You’re giving your boss the platform and connection to understand how everything ties together. Make it easy for them to digest.

Tactical Tip: Keep a running doc of your team’s wins with context about what leadership cares about. When the right conversation happens, you’re ready.

Expand the Circle of Awareness

If senior leadership has a negative perception of one of your engineers, you need to do the detective work. Figure out exactly who holds that perception, then create opportunities for new, positive interactions.

This might mean getting your engineer invited to cross-functional meetings, having them present technical work to broader audiences (this has worked really well for me), facilitating mentorship relationships with senior ICs, or creating documentation that showcases their expertise.

I mentioned this in a previous post, but pound that pavement. Figure out who you need to talk to for the next milestone.

Seeing Is Believing

When credibility is damaged, direct repair beats advocacy from a distance every time.

Here’s what this looks like: An engineer on one team gets negative feedback from a well-respected senior IC on another team. Rather than defending your teammate from afar or arguing about the feedback’s validity, create opportunities for new, positive interactions between the two.

Have them work together on onboarding, rewriting documentation, mentorship strategies, or greenfield POC. Check in with the senior IC regularly to see how things are progressing.

This works because it creates new positive interactions that override old negative ones. Fresh experiences carry more weight than stale impressions. It also gives the senior IC a stake in your teammate’s success—once someone is mentoring or collaborating closely with your team, they become invested in positive outcomes.

The key insight: you can’t argue someone out of a negative opinion (trust me, I’ve tried). But you can create enough new positive data points that the old opinion becomes outdated.

Control the Narrative Early

Don’t wait until promotion time to start building the case. The groundwork happens months before. Remember those big reveals at the end of Oceans 11, 12, and any of the other resuscitations they did of that series? It wasn’t a smash-and-grab; it was methodically planned.

During regular meetings with senior leadership, casually mention when your engineer is crushing assigned work, running with it beyond expectations. Plant those seeds. Build a pattern of positive associations. Don’t lie, don’t embellish—show the results. Keep them in the conversation, but not as the heaviest part of the discussion.

Think Inception. By the time the formal promotion discussion happens, you want senior leadership to respond with “Yeah, that makes sense” rather than surprise or skepticism.

Think of it like a squirrel gathering nuts for winter. Each small mention, each casual update accumulates. When promotion time comes, you’re collecting on investments you’ve been making for months.

Celebrate Strategically, Not Constantly

There’s a fine line between advocacy and becoming the manager who thinks everything their team does is world-changing.

Doing their job adequately is not the same as being promotion-ready. I’ve made this mistake, and I’ve watched new managers make it too.

Not every pull request merged deserves an announcement. Not every bug fix needs to be broadcast to senior leadership. That kind of noise actually hurts your credibility and makes people tune you out when you do have something important to share.

Instead, make noise when an engineer:

• Solves a problem that was already on leadership’s radar

• Unblocks another team in a meaningful way

• Ships something that moves a key metric the business cares about

• Demonstrates significant growth in a skill area they’ve been working on

Use emojis, pick a great GIF, celebrate the win publicly, but focus it on the outsized impact. Something like:

”Yoooooo, Angie just dropped one of the biggest cost-saving changes of the year. With just two lines of code changed, she’ll save us $800k through [insert relevant outcome here].”

Tactical Tip: Track what leadership actually cares about. If they’re not talking about it in all-hands or leadership meetings, they probably don’t care if your team fixed it.

The Moral Conundrum

All of this can feel like performance theater. Like you’re playing a game instead of letting good work speak for itself.

And you’re right. It is a bit of theater, ya gotta give ‘em the ol’ razzle dazzle. Think Silicon Valley meets The Prestige, but with less cloning and no Michael Caine.

Here’s the reframe that helps me: Your job as a manager isn’t to evaluate whether this system is fair. Your job is to help your people succeed within the system that exists.

You can work to change the system over the long term. Push for better promotion processes, more objective criteria, and reduced bias. But while you’re doing that, you still have engineers who deserve to advance their careers now.

A manager I know framed this candidly for their engineer, who was facing a difficult path to promotion. He committed to being an ally, to working hard on the promotion, to being in the engineer’s corner. He’d throw every pitch he could. But he was also clear that the engineer needed to swing at those pitches, build their own promotion packet, advocate for themselves, and maintain their own accomplishments list.

That’s the deal. You can’t guarantee outcomes, but you can guarantee effort and advocacy. You can guarantee support and clear expectations. Most importantly, explain the game that must be played, as gross as it seems.

When Visibility Work Backfires

Not all visibility is good visibility. Here are the failure modes:

Over-promoting weak work. If you’re constantly hyping mediocre contributions, you’ll damage your own credibility. Senior leaders will stop trusting your judgment. When you do highlight something, they’ll discount it.

Creating resentment among peers. If other EMs feel like you’re always grabbing credit or taking up too much airtime, they’ll be less likely to support your people when it matters. Promotion decisions often involve consensus among peer managers.

Neglecting the actual work. Visibility without substance is just noise. Make sure the work actually justifies the promotion you’re pushing for. No amount of strategic communication can paper over weak performance. This is the “outcomes over “They completed 80 points this sprint!” “Did the work have any impact?” “Uhhhhhhhh, no.” 😬

Ignoring your team’s preferences. Some engineers genuinely don’t want visibility. Some don’t even want to be promoted, and that’s okay. Your job is to advocate for their career goals, not impose your vision of success.

The Meta-Game

While you’re doing all this visibility work for your team, you’re also establishing your own reputation as a manager.

When you advocate effectively—thoughtful about timing, strategic about channels, accurate about capabilities—you build trust with senior leadership. You become known as someone who develops people effectively, has good judgment about talent, delivers results consistently, and can be trusted with bigger teams and harder problems.

This compounds over time. The better your reputation, the more weight your advocacy carries. The more weight your advocacy carries, the easier it becomes to get your people promoted. The more success you have getting people promoted, the stronger your reputation becomes.

Round and round we go.

Look, I get it. We all want to live in a world where great work speaks for itself. But that’s not how most organizations run.

Great engineering managers are great translators. You translate technical work into business impact. You translate individual contributions into team success. And you translate quiet excellence into visible career advancement.

Is it uncomfortable? Yes. Is it gross? Sometimes. Is it necessary? Absolutely.

Your engineers are counting on you to do the one thing they often can’t do effectively for themselves: make sure the right people see them winning.

What’s your approach to visibility work? Have you struggled with the balance between advocacy and authenticity? Drop it in the comments.

While it was not my team, I had to sit in on a few standups for a cross-functional project. I had a 1:1 with the manager shortly after and gave a few pointers on how they could be more effective and trim the timing in half. They looked at me as if I’d intentionally spilt beans on their best tuxedo, and they replied, “I know what I’m doing.”

They were angry, they shut down, and we ended the conversation.

I still think about that interaction a lot. I was attempting to be helpful, but I’d neglected a key factor.

As managers, we’ve been taught to give feedback. On performance, on decisions, on day-to-day team operations, for potential hires, all over the place. There are whole books dedicated to delivering feedback (Radical Candor being the book I recommend most). Delivering feedback well is vital to a manager’s survival.

How exactly to deliver feedback well is likely its own post, but an interesting starting point that’s rarely discussed is that not everyone wants your feedback.

Shocking, I know, but when people say “feedback is a gift,” we tend to forget that some people are bad gift-givers, but there are also bad gift-receivers. I find that when someone doesn’t receive feedback well, it’s an opportunity to learn on both sides, making it productive instead of leaving a sour taste in our mouths.

For me, it’s a chance to question how I delivered the feedback, what was and wasn’t heard, why it wasn’t well received, and whether I should leave it alone or revisit it with them later.

In the case above, I was overstepping the comfort zone for the other manager. They held their ceremonies near and dear to their heart, had always done it that way, and didn’t want to change. While I disagreed, I needed to back off. (I also wasn’t in a position to force them to do it a different way, regardless of how I felt).

The easiest way to approach feedback in these cases is by asking questions. There was likely a reason this manager was running the standup the way they did. Don’t assume that they want the standup to be an hour; there may be more to it.

If you still feel like you’re not making any headway you can jump to one of my favorite questions by asking “are you open to some feedback about XYZ?”

This can help diffuse tension and gives the receiver a chance to opt out. If they don’t want the feedback, leave it alone.

Sure, feedback is a gift, but sometimes people throw your gifts directly in the trash.

Sometimes people just want to be mad about it, which is also totally fine. You are not in control of how someone responds to feedback, you are only in control of how you deliver that feedback. Approaching the individual on their level, and with empathy, will help the feedback land.

My commitment is to delivering clear feedback with support. I know it will not always be received well, but I would rather assume everyone wants to grow than never give direct feedback again.

If you’re looking for two reads in 2026 to help with delivering feedback well, I highly recommend:

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott

• Holding the Calm: The Secret to Resolving Conflict and Defusing Tension by Hesha Abrams

Some quicker reads, especially in the engineering world:

• Your Code Reviews are unknowingly silencing your Intern and Junior Engineers

• Constraints on giving feedback from Will Larson

Employee writes their performance review with AI.

Manager reviews the review with AI.

Manager responds with an AI review of the AI-reviewed, AI-written review.

Employee responds to the response about the review of the review...

Stop. Put down your AI and come out with your hands up.

Please, I beg of you, don’t perpetuate this loop. We already live in a world of performance review theater, where everyone’s pretending to care while secretly trying to survive Q4. And now? You’re adding an AI wrapper on top like a little parsley garnish of detachment. It doesn’t make it better. It makes it hollow.

There are two sacred spaces where I implore you to keep the robots out: 1:1s and reviews.

These moments are personal. Human. Messy. They are not meant to be automated. You are responsible for the person sitting across from you. You owe them your actual, unfiltered thoughts about how they’re doing, not a prompt-engineered paragraph about “growth opportunities.”

“But it’s too much text! How can I read it all?!”

Really? The employee spent time thinking, writing, and sweating over this document. If you want something shorter, say so. If you only care about bullets, ask for bullets. Don’t make them write a novel you’re just going to feed to ChatGPT so you can pretend you read it.

Set expectations. Make it humane. Let people spend their brain space on real reflection instead of trying to come up with another synonym for “above and beyond.”

The Tax Analogy (And Why Everyone Hates It)

In most companies, reviews feel like filing taxes:

• The employee fills out their best estimate of their worth.

• The manager (a.k.a. the IRS) already knows the answer.

• Then they tell you why your math is wrong, and you owe them another 10%.

We don’t need AI to solve this. We need honesty, clarity, and a shared understanding of what actually matters.

Make It Easy. Make It Human.

If you’re giving real, honest feedback in your 1:1s, the review should never be a surprise. It should feel like closing a book you’ve already read together. A few nods about the past. A bigger conversation about what’s next.

Here’s the simple 3-line template I swear by:

Reviews Made Simple For Employees

1. Write down three things you’re proud of from the past [X time period] and the impact they had. (celebrate these!)

2. Write down three areas you’d like to improve and why.

3. Write down three things your manager can do to support you in those areas.

Reviews Made Simple For Managers

1. Write down three things the employee did well in the past [X time period] and the impact they had. (celebrate these!)

2. Write down three areas you’d like to see them improve and what that looks like.

3. Work together to write down three goals the employee will aim for, and you will support. I tend to break this into one personal, one team, and one broader career goal. After all, we likely only have the employee for 1-3 years, so what can we do to prepare them for the future?

That’s it. Review? Done. Goals? Done. Support? Done.

No AI. No theater. Just two people having an honest conversation about work.

And if you’re not comfortable putting your review together? Reach out! I’d much rather we chat about how you can put together a great review experience than have you turn into one of those managers who fill their reviews with fluff.

Helpful Links

• “Is performance management over?” [Hebba Youssef]

• “Why the annual performance review is outdated” [Dominic Joyce]

• “Rethinking the Review: Why We Are Getting Performance Evaluations All Wrong” [Inc.com]

• “Workers Want Fair, Accurate Performance Reviews” [Business News Daily]

• “The fairness factor in performance management” [McKinsey & Company]

• “How Effective Feedback Fuels Performance” [Gallup]

• “Preventing Surprises in Employee Performance Reviews” [WorkStory]

• “The future of feedback: Motivating performance improvement” [PMC]

New format for links, are they more helpful?

Waffle House somehow managed to create a universal menu language from scratch, using only the items in their restaurants. They’re using the system to make sure everybody is on the same page, everybody understands the same system across all of their locations, and even in the chaos of a bustling restaurant, they can flawlessly keep orders coming out of the kitchen.

No tickets needed, no deciphering speedy scrawls, pure efficiency. Waffle House has hundreds of locations in the U.S., and every single one follows the same system.

I’ll give you the short version because again, even I don’t fully understand exactly what’s happening. The Magic Marker system at Waffle House is about teeing up an order by arranging items on a plate like some sort of Guy Fieri fryomancer.

You place items (like jelly packets) on the plate to then indicate “here is what I need you to cook and how”, all the way down to how eggs are prepared (scrambled, over easy, over hard, etc). The placement of an item on the plate dictates how those eggs or that item will be cooked. It’s pretty ingenious, and seems a little insane (as with most great ideas).

Here’s the training video for the system, and a quote pull to give you a sense of what we’re dealing with.

Cheese omelet or a mushroom omelet: these are marked using a horizontal jelly packet in the number four position and a piece of the corresponding ingredient. Here you can see a cheese omelet also the Fiesta omelet which is indicated by a horizontal jelly pack with a right side up salad dressing.

If that sounds like nonsense, you’re right, but that’s also because you haven’t been onboarded appropriately.

Unwritten Rules

There are a lot of unwritten rules and micro-habits in organizations. I’ve recently gotten to onboard a few engineers at Trellis, and it’s interesting to try to figure out what all of those unwritten rules are and if we’ve appropriately written them down, or codified them. How do we create our own Magic Marker system so that new folks can learn quickly and slot right in within the team?

Especially in startups, you grow your teams because you are feeling the strain of too many problems, not enough people. As soon as someone walks in the door, you want to hand them a problem to begin reducing risk. Waffle House reminds us that while you may want to get your new hire involved right away, you have to teach them the system first.

We have language, but I think the beauty of this system, and the beauty of some of these more bespoke rules, are that it surpasses that. It gives you a quick chance to review and visually understand what something means. Think of this as architecture diagrams, or Loom walkthroughs showing every step in the path of your system, connecting the concept, the visual element, the code itself, and the data.

Other things to note are the visual queues a new hire is likely to see. We use 👀 reactjis in Slack to show we’ve seen something. Some orgs it ends there, but we know we mean “I’ve seen it and am taking action.” If there is both a 👀 reactji and a ✅ reactji, it means I’ve seen this, and we’re good to go. Even then we’ll usually add some notes with proof of why we’re good to go.

Consider how you’re arranging the plates at work and be sure to jot down the system so others can easily review and adapt.

Regardless of how bizarre the system seems, you have to write it down and you have to be able to get that information out and understandable to other people that will join your organization. Instead of having different words for things, a symbol can sometimes be enough.

@hotsoupandcrackerReply to @yostmalone1 #wafflehouse #linecook #eggs #fyp #foryoupage #blowthisupforme #shortordercook #linecook #fypシ #cooking #tiktok #foodtok #pov

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System Flexibility

Similar to the systems and rules that we build for both organizations and in software, the system also has to be flexible in case something changes in the future.

Think about current state of Waffle House. I’m no Waffle House expert, but the menu probably hasn’t changed much across its existence. Once you have the menu, it’s pretty set. In a fairly unchanging system, the Magic Marker method works great. But what if Waffle House added 18 new menu items. Could the current system handle the items? What would break?

Thankfully for Waffle House, their system creators were savants and each item has multiple dimensions, with different meanings for upside down, rotated horizontally, vertically, or diagonally, and stacked on top of each other. The system is flexible

Reactjis give a similar flexibility, especially because you can add more to your Slack workspace without issue. As the system evolves, so to will the documents that highlight that evolution. Your system won’t be perfect on the first go, nor should it be. I follow the “aim small, miss small,” method of people systems which lets you reap rewards without major change management overhead.

Try something new out this week, look at your communication channels and see where items are dropping. Is there a visual signal you can add that helps your team know immediately what to do with that item? It might not be as efficient as upside down butter on a plate, but we all have to start somewhere.

I’ll leave you with one more, because I’m still amazed and horrified.

Butter next to a jelly packet = biscuit

Helpful Links

Engineering Leadership & Management

• Why Great Engineering Managers Shouldn’t Code
  You might think coding makes you a great manager, but think again. This article slices through the myth that hands-on programming is the key for leaders. Instead, discover how empowering your team and focusing on strategy can turbocharge results and drive success.

• Clarity
  Stop the chaos and create laser focus in your team. This article dives into how leaders can strip away confusion, foster clear communication, and energize decision-making. By mastering clarity, you turbocharge team productivity without the burnout.

• High-Performance Teams That Scale
  Unleash the power of high-performing teams. This book dives into strategies for creating clarity, minimizing decision chaos, and safeguarding focused work periods. You will discover actionable insights that elevate your team’s productivity and morale, helping you lead with purpose and impact.

• Small Teams, Big Results
  Small teams can pack a punch when managed right. This article reveals how to harness streamlined decision-making and unshakeable focus to maximize impact. You don’t need a big crew to drive innovation; you need the right mindset and tactics.

• What happens when we eliminate the Agile leader
  Ditching the Agile leader might sound radical, but it could be your secret sauce to unleash team potential. This article dives into how self-managing teams can drive productivity and creativity without traditional hierarchy. If you’re ready to shake things up, this is your roadmap to a leaner, more dynamic workflow.

Remote Work & Organizational Systems

• Remote Work Makes Employees Happier: 4-Year Study Confirms
  Put a smile on your face. This study reveals that remote work boosts employee happiness, and it’s not just a fling. Engagement rises and burnout dips when teams embrace flexibility. You won’t want to ignore this trend as you shape your organizational culture.

• Become an Octopus Organization
  Ready to transform your organization? This article dives into the dynamic structure of octopus organizations where flexibility and interconnectedness reign. You’ll learn how to build resilience and adaptability in your teams to thrive in complex environments.

• A One-Pager Is All You Need
  Cut the clutter and elevate your team’s focus with a killer one-pager. This article reveals how distilling your project goals into a single page can enhance clarity, streamline communication, and drive faster decision-making. You’ll supercharge your team’s effectiveness without the overwhelm.

• The Full Catalogue
  Get ready to feast on a banquet of insights that will nourish your leadership style. This post serves up a comprehensive list of resources that elevate your understanding of organizational dynamics. You’ll transform your team’s performance with actionable strategies that stick.

AI in Engineering Workflows

• Why AI Can’t Do Hiring
  Hiring with AI? Forget it. This article lays out the critical human elements AI just can’t grasp in the recruitment process. You need nuance, judgment, and gut feel to build a killer team that thrives.

• Not Artificial, Not Intelligent
  Are you tired of buzzwords? This book dives deep into the messy truth about AI, distinguishing hype from reality. It provides actionable insights on how to harness technology effectively without falling for empty promises. Get ready to sharpen your engineering strategies and boost productivity.

• What most companies overlook when determining AI readiness
  AI isn’t just a shiny new toy. You need to dig deep, assessing not just technology but culture, skills, and strategy. Get ready to transform your mindset or risk getting left behind in the data dust.

Prioritization, Strategy & Metrics

• Vibe Engineering
  In the fast-paced world of tech, vibe engineering is your secret sauce for building high-performance teams. This article dives into creating an environment where people thrive, making collaboration seamless and focused. You will learn how to harness positive energy to supercharge your team’s productivity.

• Context Switching: The Hidden Productivity Killer
  You think multitasking is the secret sauce to productivity? Think again. Context switching steals focus and zaps energy. Learn how to streamline your workflow and reclaim your time for deeper focus and better results.

• Leadership Unblocked: How to Harness Your Beliefs and Potential
  Are your beliefs blocking your team’s potential? This book dives deep into the psychology of leadership, equipping you with powerful strategies to overcome mental roadblocks and elevate your leadership game. Get ready to unleash your team’s true capabilities and foster an environment where innovation thrives.

Broader Industry & Thought Leadership

• Respect at Work Returns to Record Low
  Attention leaders: workplace respect is hitting rock bottom. This article reveals staggering declines in employee engagement and outlines actionable steps to regain trust and respect. Don’t just serve another bland dish of policies—bring the heat and authenticity back to your culture.

• RDEL 113: What Are the Seven Team Behaviors That Build Belonging?
  Get ready to revolutionize your team dynamics. This article dives into the seven essential behaviors that foster belonging and improve collaboration. Unlock the secret sauce to a thriving work culture and maximize your team’s potential.

• An engineer’s guide to cultivating belonging in tech
  Belonging is not just a buzzword, it’s the secret sauce for team success. This guide dishes out actionable insights on how you can foster an inclusive environment, driving productivity and creativity. If you want to build a team that thrives, you need to read this.

• I Tried to Quit My Job by Faking a Health Crisis
  If you’re feeling burnt out or stuck, this article dives into the wild world of work-life balance struggles. It’s an honest look at the extremes people will reach when their jobs turn toxic. Take a hard look at your own environment and consider what change is truly needed.

If that’s true, that also means we’re headed into an era where you can’t believe everything you see. I studied Broadcasting in undergrad and wrote for the school paper, and it was drilled into me that above all else, you should always verify sources and validate leads before publishing a story. If something sounds too good to be true, it probably is.

It’s easy to take a video for face value and immediately react. There’s a whole side of YouTube dedicated to people reacting to videos. As more AI-generated content is created and anything can be made a reality at the stroke of some keys, it’s going to be extremely easy to bend the truth. Even small things, like public figures having public freakouts, or your co-workers saying something outrageous, could be manufactured with a quick prompt. You are going to have to do the leg work to figure out if it’s reality or not. Snopes.com won’t be able to keep up (is Snopes still a thing?).

Same goes for management (and don’t get me started on B2B sales! /s). You will hear things about your team, their work, what’s happening when you’ve given them autonomy, and you have to determine which version of reality is accurate. Half of management is detective work, following leads, and determining the version of reality you and your team will follow. It’s the same thing for data too. One graph could mean any number of things, so use your critical thinking skills to determine why it’s right or wrong. It’s one of the reasons I love the 1993 classic “How to Lie With Statistics.”

This is also not intended to be doom-and-gloom, but more of a warning to think before you react. I made a mistake early in my career where I assumed I knew the full story, but definitely did not. Learn from my mistakes. And by all means, don’t let me rain on your AI-generated video parade.

Take a moment to gather the facts of the situation, validate the sources, determine the credibility of those sources, and make decisions from there. Redactions and apologies are tough to come back from, so spend a few extra thinking cycles on the believability of what you’ve seen and heard.

Anyway, here’s a video I prompted for Sora 2 of a totally real guy eating totally real onion ring glasses on a park bench. flavors-you-see.io coming soon.

🧭 Engineering Leadership & Management

• Nothing Prepares You for Your First Director Role [Honeycomb]
  Moving into a director role is like switching from sous chef to running the kitchen. This piece nails the messy reality of moving from tactical execution to political influence. Bookmark it for your next promotion talk.

• Leading with Emotional Intelligence in the Age of AI [CIO]
  As automation grows, EQ becomes the most scarce leadership resource. This article makes a solid case for empathy as a competitive edge, not a soft skill.

• Reverse Impostor Syndrome [Wes Kao Newsletter]
  Instead of feeling unqualified, high performers often underestimate how capable they actually are. A sharp mindset shift that helps leaders stop playing small.

• On Good Software Engineers [Can Dost Blog]
  A grounded reflection on what makes great engineers stand out. Hint: it’s not raw speed, it’s ownership, clarity, and generosity.

• Async Programming for Humans [Braintrust]
  Not a coding tutorial, a management philosophy. Async thinking is a survival tool for distributed teams. This piece breaks down how to adopt it without slowing collaboration.

🤖 AI in Engineering Workflows

• Is AI Good Enough to Lay Off Your Engineers [Section AI]
  The question everyone’s whispering. Section AI runs the math on where LLMs actually deliver ROI and where human judgment still dominates. The answer is more nuanced than the headlines.

• The AI Bubble Is About to Burst, But the Next Bubble Is Already Growing [Medium]
  A sharp take on how hype cycles move faster than innovation. The next gold rush might not be AI itself, but the tooling around it.

• AI Podcast Startup Plan Shows the Chaos in Audio Automation [Hollywood Reporter]
  A wild glimpse at AI-generated podcasting. Think cloned voices, messy IP, and an industry still figuring out what “authentic” even means.

• How to Think About AI Progress [Marginal Revolution]
  Tyler Cowen at his best. A clear, skeptical lens on what counts as genuine AI progress versus what’s just packaging.

📊 Prioritization, Strategy & Metrics

• The Wrong Way to Use DORA Metrics [The New Stack]
  DORA metrics aren’t magic. Used poorly, they become performance theater. This post explains how to make them actionable and culturally safe.

• The Purpose of Prototypes [SVPG]
  Marty Cagan reminds product teams that prototypes are for learning, not validation. A tight, essential read for anyone shipping too slowly.

• Determination [Paul Graham]
  Graham revisits grit. Success often depends less on brilliance and more on stubborn progress. An evergreen piece that feels even more relevant in the AI era.

🔮 Broader Industry & Thought Leadership

• The Era of the Business Idiot [Where’s Your Ed At]
  A spicy critique of leaders who confuse buzzwords for strategy. Equal parts rant and insight. You’ll nod, laugh, and maybe wince a little.

• Is Waymo Safe [The Atlantic]
  A balanced investigation into the safety record and perception of autonomous vehicles. The debate around “safe enough” is just beginning.

• How to Think About AI Progress (Archived Conversation with Yann LeCun) [Archive]
  A preserved deep-dive on the philosophical and technical sides of AI development. Less hype, more history.

• The Future of Agentic AI and Automation (Google Share Link)
  A peek behind closed doors at how large enterprises are experimenting with internal AI systems. A little vague, but telling.

GPT-4o had this… warmth. It was witty, creative, and surprisingly personal, like talking to someone who got you. It didn’t just spit out answers; it felt like it listened.

Now? Everything’s so… sterile. Formal. Like I’m interacting with a corporate manual instead of the quirky, imaginative AI I used to love. Stories used to flow with personality, advice felt thoughtful, and even casual chats had charm. Now it’s all polished, clipped, and weirdly impersonal, like every other AI out there.

Hmmm, like talking to PhD-level expert 🤔(no shade intended toward those with PhDs).

The varied responses shine light on what each group wants AI to be. Standard users want their AI assistant to be consistent and reliable with some warmth and personality (like H.E.R.). Tech-focused users want it to be smarter, faster, and more efficient (nearing HAL territory).

Wherever you sit on the line (maybe you don’t even use ChatGPT), it’s interesting to see how a tool so ingrained in the day-to-day can trigger these reactions.

We’re in an age where vibe-coded vaporware is going to get looks from top VCs because of the possibilities. All of the products on ProductHunt have some sort of AI capability. Companies are scrambling to stay relevant the only way they know how, jumping on the hype train and embedding AI into all of their products regardless of whether or not its a good idea.

Call me old-fashioned, but I don’t think I need an AI-powered refrigerator to tell me what’s inside my refrigerator. Instead, I’ll just…open…the door?

On the flip side, as the Head of Engineering for a Conversational AI team, I focus on improving operational efficiency and delivering more value to the company through AI use. It’s a fascinating world out there, one that’s rapidly evolving and it’s tough to know what tools and trends will have staying power.

My advice on how to proceed with the hype is to try it for yourself. Figure out what the repetitive tasks are that you wish you didn’t have to do anymore, and think of a way to offload to AI. What do you wish you could spend more time on? How might AI assist you in getting more time? You could even start with a basic prompt like:

You are an automation expert for casual users. I want to spend more time painting miniatures, but I have X, Y, and Z tasks that take up too much of my day. How can I automate these tasks without a budget? 

If you’re looking for some reading on AI and still forming your opinions on whether it’s good, bad, or both, I’ll aim to have an AI section in this newsletter every week, along with my standard management and engineering leadership links.

🧭 Engineering Leadership & Management

• How Netflix, Stripe, and GitLab Built High-Performing Engineering Teams [Substack]
  Three elite orgs. Three playbooks for building engineering excellence. Talent density, decision-making frameworks, and cultural clarity. Steal shamelessly.

• 20 Powerful Leadership Quotes That Will Transform Your Thinking [Medium]
  Not corporate fluff. These are quotes worth putting in board decks and taping to your fridge.

• The State of Engineering Leadership [Eng Leadership Newsletter]
  A high-level scan of today’s leadership climate. Retention, alignment, and where execs are quietly panicking.

• Top Performer Who Has Lost Faith in You [Reddit]
  When a high performer disengages, your leverage drops. Practical ways to rebuild trust without begging.

• When Team Structure Collides with Role Alignment [Medium]
  Organizational Jenga. Reporting lines and actual responsibilities out of sync. Fix it before velocity crumbles.

🌍 Remote Work & Organizational Systems

• Choosing Where to Spend My Team’s Effort [frederickvanbrabant.com]
  A clear framework for deciding what work truly deserves your team’s energy.

🤖 AI in Engineering Workflows

• Mastering AI at FAANG: A Roadmap from Junior to Senior Engineer [Medium]
  A career progression cheat sheet for AI-native engineers. Skills, tools, and mindset shifts that matter.

• AI Acceptance Rate Is an Easy Measure to Spot Misuse [LinkedIn]
  Laura Tacho introduces a KPI to catch AI misuse early. Keep code quality intact.

• Andrew Ng Calls Vibe Coding an Engineering Apocalypse [Perplexity]
  Ng warns that vague prompts plus AI lead to sloppy, hard-to-maintain code.

• Vibe Coding and the Coming Engineering Apocalypse [WIRED]
  Journalistic view of how AI-generated code could erode engineering discipline.

• Coding Agents Cross a Chasm [Singleton Blog]
  AI coding agents are entering production use. Progress is real but integration is messy.

• Seizing the Agentic AI Advantage [McKinsey]
  A structured guide to deploying AI agents as strategic assets.

📊 Prioritization, Strategy & Metrics

• 2025 Compensation Survey Report [SSUSA]
  Fresh salary benchmarks for engineering, product, and data roles.

• Default Alive or Default Dead [PaulGraham.com]
  The simplest way to measure startup survivability. Ignore it at your peril.

🔮 Broader Industry & Thought Leadership

• Disney and Universal Sue Midjourney Over Copyright Infringement [The Verge]
  A landmark IP case that will influence how generative AI trains on content.

• Can Your Brain Talk to Others While Asleep [Science Focus]
  Early experiments suggest dream-state communication might be possible.

• How to Avoid the Ethical Nightmares of Emerging Technology [HBR]
  A practical framework for responsible innovation.

• The Erosion of Quality in Large Language Models [ScienceDirect]
  Research shows LLM quality declines without human oversight.

I once had a non-technical leader ask me about someone hiding behind “perceived complexity” in a project we were working on. They worried that the project seemed to have stalled and we would miss a significant milestone, putting the broader project at risk. Their interpretation was that the engineers working on a primary workstream were dragging their feet, obfuscating to make it seem like they were working hard without hardly working.

The question inside the question was fair, “this feels behind, but I don’t know enough to help, what can we do?” The way it came out was much more pointed and less empathetic to all aspects of the milestone’s complexity. It was a core system that was being rewritten to facilitate a major migration, all while making sure the company didn’t accidentally stall out in the process.

I’m sure this is not a foreign question for engineering leaders. We’re dealing with stakeholders who don’t understand the underpinnings of the broader systems, and it’s hard to know how granular to explain. Here are a few things I’ve found helpful over the years (at least more helpful than asking them to write it themselves).

1. Show the work. Linear (my favorite ❤️) or Jira are two systems great at showing high-level data and breakdowns of work. I’ve written before about how velocity can be deceiving, so report out with a filtered view or an explanation of shifts. If nothing else, showing your work makes visible the chunks into which your team has broken the larger project. The benefit of charts is that you can see the ebb and flow of interruptive work (additions to scope) and the progression of work because of it.

   

2. Be objective about trade-offs. Something like, “I hear you saying that you are concerned about the completion of this piece of work, if we are able to drop X and Y, we can regain focus on Z.” Removing the emotion and focusing on what’s in the way of potentially completing Z can shift the focus of the stakeholder from defensive to advocate, bulldozing everything that is not Z out of your path.

3. Show diagrams. This is my go-to lately. Pointing at flow charts and architecture diagrams has been much easier than talking theory or writing out large documents. The diagram doesn’t even need to be high fidelity, it can be a generalization to get the point across. Having this tangible artifact can go a long way.

4. Build the trust bridge. The hope is that this is something you’ve worked up to already. In other experiences, I’ve had bosses ask “Hartley, should I be worried about this?” which led to solid, supportive conversation. From there, they trusted I would get the job done, as I had proven many times in the past. If you’re not at that point, have the hard conversation and find out how best to build trust for future situations.

Rarely do engineers drag their feet intentionally. Most are well-meaning and get enjoyment out of finishing complex projects. To assume they are hiding behind perceived complexity is to believe they do not desire to do well in their craft.

In moments of doubt, clarity is your best ally. The more we can demystify the work through visibility, honest trade-off conversations, and simple diagrams, the less room there is for misinterpretation. Stakeholders don’t need every technical detail, but they do need to feel confident that progress is real and purposeful. Our job isn’t just to lead the work, it’s to make it digestible. The hope being that, over time, we all need less TUMS.

Now, onto the links I found interesting this week.

🧭 Remote Work & Leadership That Scales

Remote Teams Need Systems, Not Surveillance
Micromanagement often shows up dressed as “visibility.” This piece argues that what remote teams really need is better systems, not tools that track every keystroke. Fits nicely into the above, no?

Remote Excellence Guide
More on trust! A structured, practical handbook for high-performing remote teams. It’s full of principles and templates you can actually use.

🏛️ Power, Privilege & the Toligarchs

Rise of the Toligarchs – Scott Galloway
The new power players aren’t politicians, they’re tech-native thought leaders. Prof G’s take on the rise of tol-igarchs is sharp, timely, and uncomfortable in all the right ways.

• Watch: The Rise of the Toligarchs
  The written piece is strong, but the video version is classic Galloway: data-backed, unfiltered, and genuinely insightful.

Bond Capital’s TAI Report
Mary Meeker’s latest breakdown on the state of AI, filled with data, perspective, and insight on what’s really next after the hype.

🛠 Engineering Culture & Career Moves

10 Years of Engineering Ladders – Camille Fournier
A decade later, Camille’s framework for IC and management growth still holds up—and this reflection shows why transparency and clarity matter more than ever.

The Engineering Manager Archetypes
Are you the Architect, the Catalyst, or the Fixer? This archetype model helps you better understand your strengths and where you might need backup.

⚙️ Quick Hits

Company Boards Pressuring CEOs to Replace IT with AI
The pressure is real, and boards are asking hard questions about AI-first orgs.

What Nobody Tells Devs About Docs – PostHog
A love letter to documentation that doesn’t suck. If your devs dread writing docs, start here.

100 AI POVs from Experts – Section AI
A goldmine of mini-perspectives from people shaping the future of AI.

9 of Anthropics best guides
All free in Anthropic Academy

Your Privacy Guide to AI Chatbots
Section AI offers practical advice to keep you and your team safe while using chatbots, from toggling off model training to being thoughtful about prompts.

Want more like this each week?
Hit subscribe or reply to let me know what themes you want more of: AI, leadership, systems thinking, team health, you name it.

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It might be a familiar situation or one you’re in right now. Senior leadership says you’re too slow. Engineers say they can’t go faster unless they spend time rewriting. Deadlines are made, band-aids are used, and the cycle continues.

Both groups have the same hopes and desires but end up talking past each other. There’s nothing inherently wrong with either side's position. Still, one group tends not to have enough involvement, depth, or understanding to figure out how to reach across the aisle and reach a common experience.

I saw a post earlier today that noted the “move fast, break things” motto had sunk their startup, with one engineer noting they were leaving because they were tired of “putting bandages on broken bones.”

What an image. We’re all hiking up the same trail with compound fractures, covered in Band-Aids that are doing their best to keep our bones in place.

So, how do you keep forging ahead? As an engineering leader, how do you explain a compound leg fracture to a group that might not understand what a leg should look like?

I’ve not found a fool-proof answer, but I’m going to find one…or fall off the mountain trying.

How have you solved this problem in the past?

Leave a comment

Been a bit, so the backlog of links is large and full of terrors:

📌 Strategy, Priorities, and the Big Picture

• How FAANG Really Prioritizes Work
  A teardown of how top tech companies prioritize without clinging to Agile dogma. If your roadmap feels more like a wish list, this one might recalibrate your approach.

• The Software Architecture Decision Canvas
  Architecture discussions dragging on for hours? Use this canvas to focus debate, clarify trade-offs, and stop decision fatigue before it starts.

• Illich’s Law: The Real Cost of “More”
  A reminder that more hours ≠ more output. Especially relevant if your team is sprinting but barely moving, Illich’s Law is also called “the Law of Diminishing Returns.” This law explains why, and how, to course-correct.

• The CTO’s Ouroboros
  A thoughtful piece on the cyclical nature of tech leadership, and how we often find ourselves solving the same problems with fancier tools (and higher stakes).

• The CTO’s Calculated Absence
  Yes, we’re linking this one again. Because stepping back strategically is still underrated—and this nails the why and how.

🔧 Tools, Techniques, and Ways to Build Smarter

• GreptimeDB and the Future of Observability
  A purpose-built, time-series database designed to meet modern observability needs. If you’ve ever cursed your logging setup, this one’s worth a peek.

• Properly Logging Tech Debt
  Tech debt isn’t just a nuisance, it’s a window into your culture. Documenting it well builds trust, shows accountability, and helps teams think long-term.

• Engineering Metrics That Drive Focus
  LeadDev’s metrics guide remains a banger, ideal for separating signal from noise when performance reviews and planning season hit at the same time.

• Jack Danger’s Pyramid Career Model
  Worth a revisit: grow outward before upward. Cross-disciplinary breadth builds the kind of depth that lasts longer than any title bump.

🤖 AI and the New Developer Toolkit

• Zero Human Code
  AI wrote the code, fixed the bugs, and stumbled all the way through. A brutally honest case study in just how far we are, and how close we’re getting (maybe).

• DX Guide to AI-Assisted Engineering
  A soup-to-nuts framework for embedding AI into your workflows; from planning to production. Less hype, more how.

• Prompt Engineering Whitepaper (Kaggle)
  A surprisingly deep dive from Kaggle on what makes prompts actually work, whether you're coding with GPT-4 or running research-grade inference.

• OpenAI Prompting Guide
  If you’re still guessing at prompts, stop. This guide gives structure to the madness and is an essential read for anyone building with LLMs.

• OpenAI Academy
  Self-serve, well-structured, and designed for builders who want to get good, fast. Still one of the best places to start your AI journey.

• Netflix’s Foundation Models for Recs
  How Netflix is using massive foundation models to supercharge personalization. It’s enterprise-grade, high-stakes LLM work, and it’s live.

• The End of Programming as We Know It
  O’Reilly lays out the future: less “write code,” more “design intent.” The skill shift is coming, time to start practicing. Tim O’Reilly then recently wrote this “AI First Puts Humans First” piece. Interesting combo of articles.

🧠 People, Motivation, and Team Dynamics

• How to Motivate Your Team
  Skip the fluffy platitudes. This is a refreshing, real guide to figuring out what your team actually needs to stay engaged.

• Async Communication for Leadership
  Async isn’t just for ICs. If you want deeper, more focused collaboration, especially with other leads, this is the case for slowing down to go fast.

• Lenny + Cutler on Team Rituals
  Bookmark this one. From calendar audits to reflection prompts, these are the high-signal habits that separate chaotic teams from consistent ones.

• Learning is a Learned Skill
  Still one of the best pieces on intentional growth. Especially useful if you're onboarding a team, coaching a direct, or just hitting a wall.

• The Productivity Phantom
  You feel productive, but are you moving the needle? This piece calls out the illusion, and offers strategies for measuring what really matters.

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It goes beyond the ineffective meetings, though. There’s something about how we show up in meetings that makes me want to throw hands.

I’m reminded of a story in an HBR case study about an army rowing team with strong rowers but no team cohesion. The team leader, having tried all sorts of team-building activities, finally let the team fight it out, literally. The team fought, and once they’d traded blows, they were stronger and more cohesive, and the snippiness immediately left. They then went on to win several crew trophies, and the rest is history.

In most cases, we can’t fight each other with our fists and get the physical energy out, (though this would make for an interesting case study in organizational hierarchies), but we can spar with our words. Some organizations have code words, like “Level 10,” to help break the ice of saying something that might sound mean or offputting but is intended to challenge directly.

Whatever your method, you must figure out how to get past the hesitation of being nice in order to beat up the ideas being presented. Remember, it’s not you against the individual, it’s all of you against the ideas. After all, you’re hoping to come out with the best path forward.

Kim Scott has a whole section in Radical Candor about “ruinous empathy,” a phrase that I think of regularly, in which, “you care personally about someone, but don’t challenge them.” This is where we get to, in most cases, at work. We build relationships, and we generally get along with our co-workers, but we don’t challenge them directly, especially in meetings. We let ideas drift out with no response, and we don’t punch at them until we’ve got the best version of that idea.

Which fights are you having this week? Are you trading blows or hanging out outside of the ring?

Let me know in the comments below!

🌟 Leadership, Strategy & Decision-Making

Using the Balanced Scorecard as a Strategic Management System
A timeless framework for aligning business strategy with execution. This is a must-read if you’re struggling with prioritization or measuring success.

Dear CTO, It’s Not 2015 Anymore
The role of the CTO has changed dramatically. This article is a wake-up call for leaders who still operate under outdated tech leadership models.

Overwhelmed at Work?
Leadership burnout is real and this article offers practical strategies to manage workload, set boundaries, and focus on high-impact work.

🔐 Security, AI & Innovation

Red Teams: Breaking Things to Build Resilience
A great introduction to red teams and how they can improve security, engineering, and organizational resilience. Every leader should consider this approach.

Securing Generative AI on AWS
As AI adoption grows, so do security risks. AWS’s new course provides a solid foundation for securing AI models in enterprise environments.

The Carbon Footprint of AI Tools
AI isn't just expensive in computing, it’s costly for the planet. A thought-provoking look at sustainability and the environmental impact of AI tools.

Devin, the AI Assistant Revolutionizing CX
AI assistants are reshaping customer experience, this deep dive on Devin explores how AI-driven automation is becoming more sophisticated.

🛠️ Engineering & Organizational Excellence

What Every Non-Technical Manager Needs to Know About Engineering Managers
Engineering leadership can feel like a mystery to non-technical leaders. This article provides a solid foundation for understanding what makes engineering teams tick.

The Deadline Doom Loop
How do you escape the cycle of unrealistic deadlines and constant firefighting? This piece unpacks how leaders can shift from reactive to sustainable planning.

Estimating Complexity
Why are some projects so hard to estimate? A great read on the nature of complexity and how leaders can set better expectations.

Building Barrels, Not Bottlenecks
Scaling isn’t just about hiring—it’s about structuring teams effectively. These four tips will help you avoid growth pitfalls.

The Big Tech Layoffs Playbook
A deep dive into how major tech companies approach layoffs—what’s driving them, and what leaders can learn from the patterns.

Now, nearly 15 years later, finding a job as a Junior Engineer is even more difficult. I have friends who have gone through developer bootcamps, only to find that there isn’t a job on the other side. Even worse, you have companies like Meta saying they will replace mid-level (and I assume junior-level) engineers with AI.

“No take, only throw” is a solid meme that really encapsulates how companies are missing out on the opportunity of junior engineers. We want better talent! But, we don’t want to foster it by hiring juniors.

Meta is doubling down on that statement by reducing its 7k workforce by 5% this year. Companies looking for lower-cost options are aiming toward Latin America, Europe, and Canada. How can newly minted software engineers compete?

We need a mindset shift as an industry. After all, junior engineers become mid-levels, seniors, and so on. Two companies I admired for how they approached creating their own talent were CoverMyMeds and Branch here in Columbus. Both created their own bootcamps where, as a junior engineer, you would come in and learn how to write software at that company. They were willing to take the initial hit of coaching and mentoring junior engineers to drive the results they needed.

The benefit? Engineers that are more loyal, more engaged, and better prepared for the sort of work your company produces. Not to mention, mid-levels need reps at mentoring as well. You need the full engineering spectrum to get the most out of your engineers, and I fear we’re veering far away from that world.

It’s sad that we’ve gotten away from this as a broader industry, and it makes it a bleak world for new engineers to enter. There’s a lot that needs to change across tech for this landscape to improve, but I was thinking about the advice I would give myself 15 years ago in this environment.

Some thoughts…

First, prepare to underbid yourself. Companies are looking at cheaper options like AI or offshore solutions. When I started, I applied for around 40 positions and was repeatedly told that I was too junior. The only offer I got was $20/hr for 10 hours a week. It was not ideal, but it got my foot in the door. You can always renegotiate your contract after you’ve consistently delivered solid work.

Expect challenges and be ready to learn on the job. One of my first projects was a WordPress site that crashed multiple times. Because I was learning on the go, the hours billed were less than the hours worked. Underbidding yourself might not feel great or pay well initially, but it's about building your resume and moving beyond junior status.

Consider platforms like Fiverr or Upwork where you can gain experience, even if it means working for $1 an hour initially. Exposure and experience are invaluable. Are you underselling? Absolutely. Is it sustainable? No. The biggest complaint I heard when I was a junior was that I was too junior. Getting some projects under your belt will help build out your resume and prove you have what it takes to see a project through.

Contribute to open-source projects. These projects often have issues you can tackle, helping you understand workflows and processes while pushing your boundaries. If you’re not sure where to start, “Good First Issues” can point you at projects with low-hanging fruit to get you started.

Personal projects matter too. They show how you think and solve problems. Don't just fork repos; build something from scratch, even if it's simple or niche like a D&D AI agent for random encounters. Personal projects help you break down work into chunks and execute them—skills that are increasingly important as engineers take on more product management roles. More thoughts here: What I Love About the Engineering Graveyard (and Why You Should Mention It When Interviewing)

Lastly, get involved in your local dev community through Slack channels, Discord, startup weekends, or GiveBackHack events. Networking is crucial—find mentors locally or globally who can share their experiences and guidance.

Pound the pavement, talk to folks, and keep pushing forward. Hopefully, this advice will help you navigate these challenging times as a new engineer. In the meantime, if you’re a junior engineer struggling to find a role, feel free to reach out! No, I’m not selling a service, I truly want to do what I can to help folks break into the tech industry.

In my future roles, I will aim to carry this forward, insisting on leaving space in the budget to ensure we have an active junior pipeline. This pipeline is critical to our industry, and it’s our responsibility to keep the next generation engaged.

You can also ask questions at askhartley.com

Now, on with some links I found interesting from this last week (including Episode 4 of Ask Hartley Anything):

🌟 Leadership & Team Dynamics

How Leaders Can Instill Hope in Their Teams
An inspiring guide on how leaders can foster hope during challenging times, building resilience and motivation across their teams.

Finding Joy as a Manager, Even on Bad Days
Practical advice for rediscovering joy in leadership, even when the going gets tough. A great reminder to focus on purpose and small wins.

The Complicated Role of Hope in the Workplace
Research on how hope impacts workplace dynamics—offering valuable insights for leaders looking to balance optimism with realism.

🛠️ Culture & Decision-Making

A Values Engine to Transform Culture
A compelling framework for driving cultural change through clearly articulated and lived values. Essential reading for leaders shaping organizational identity.

How to Make Effective Decisions by Comparing Alternatives
A simple yet powerful method for decision-making that helps avoid analysis paralysis and leads to better outcomes for your teams.

The Case for the Ambidextrous CIO
Why today’s leaders need to balance operational excellence with strategic innovation—and how to do both without dropping the ball.

🤖 Innovation & Hiring Trends

Building Tiny Viral Apps
I love this take on forgetting about the long-term and building silly little apps to learn something. It’s a great look at how simple, focused apps can go viral—and what leaders can learn about product design from their success.

Why No One Wants to Hire Junior Engineers
A candid discussion on the challenges of hiring and mentoring junior engineers, with takeaways for improving hiring processes.

Most Engineering Hiring Processes Are Broken
This piece explores how hiring practices fall short and offers actionable steps to create more inclusive, effective pipelines.

🗞️ Trending Topics

Meta Targets Lowest-Performing Employees in Latest Layoffs
A sobering look at how performance reviews are being weaponized during layoffs. Leaders should reflect on how performance metrics impact morale and trust.

Mammoth Rebirth: Closer in 2025
While not directly related to engineering leadership, the woolly mammoth's return is a testament to bold innovation. It reminds us to dream big and embrace the unknown. It also could mark a weird time in science where we adjust ecosystems by re-introducing extinct animals only to see them go extinct again. Dystopia much?

Have questions? Let me know in the comments!

I’ve been thinking a lot about the concept of "ghost engineers" lately—those engineering ICs who seem busy but contribute little meaningful work. It’s a fascinating and (mostly) frustrating idea, and I think we’re missing the bigger picture, primarily because engineering output (as flawed as the measure is) is easier to track than elsewhere in the engineering hierarchy.

What about "phantom managers"? These are leaders who look incredibly busy, run countless meetings, and send endless Slack messages but don’t actually drive impact. Unlike ghost engineers, phantom managers can disrupt an entire team’s output by wasting time and energy.

I’ve caught myself slipping into this trap before—weeks where I feel busy but know I didn’t really move the needle. It’s a humbling realization, and it’s forced me to reflect deeply on how I spend my time and what outcomes I’m driving. But how many leaders are doing this kind of self-assessment?

As we approach a new year, maybe it’s time to focus less on engineering metrics and more on evaluating management effectiveness. Are your managers empowering their teams, or are they just creating noise? Are they creating environments where their teams can thrive, or are they stifling innovation and ownership? Are you yourself preventing managers from achieving those outcomes?

Before pointing fingers at "ghost engineers," let’s hold a mirror up to our leadership practices. Are we modeling what effective management looks like, or are we just as guilty of hiding behind busyness?

Anyway, on with the helpful links! As always, if you have questions about engineering leadership or your engineering journey in general, ask me here or at askhartley.com. Next episode will be out on New Year’s Day, but you can check out the latest below:

🤖 AI, Decision-Making & Future Trends

The Future of AI
MIT’s comprehensive exploration of AI's societal impacts is essential for leaders considering how AI will shape their teams and strategies in the coming years.

The AI Trap
Mike Fisher warns of common pitfalls in AI adoption, urging leaders to focus on meaningful value rather than chasing trends. A must-read for balancing innovation with practicality.

🛠️ Developer Experience & Team Dynamics

Measuring Developer Experience Benchmarks
Will Larson shares a framework for evaluating and improving developer experience with real-world benchmarks. Perfect for leaders looking to drive incremental, data-backed improvements.

Communication Structures in a Growing Organization
Jessica Kerr dives into how communication evolves as teams scale, offering actionable insights to prevent silos and foster collaboration in growing organizations.

🌟 Leadership & Decision-Making

Tenets for Faster Decision-Making
A concise guide to making decisions more efficiently without sacrificing quality. Use these principles to speed up execution while maintaining alignment.

Read the Room
Rich Mironov reflects on the importance of emotional intelligence in leadership, especially when navigating high-stakes conversations and organizational shifts.

🔮 Emerging Tech & Long-Term Impact

2024 in Review
A thoughtful retrospective on 2024’s most impactful trends in tech and leadership, with lessons you can apply to prepare for 2025.

Deloitte’s Tech Trends 2024
Stay ahead of the curve with Deloitte’s take on emerging technologies, from generative AI to sustainable innovation strategies.

📚 Big Ideas in Software Engineering

Rewilding Software Engineering
A fascinating perspective on breaking free from rigid processes and rediscovering creativity in software engineering. Great for sparking innovation in your teams.

The Psychology of Remote Work
A research-backed exploration of how remote work impacts team dynamics and individual productivity. Essential for leaders managing distributed teams.

Scaling Excellence
This video offers practical advice on scaling teams and organizations without compromising culture. A great watch for leaders at any stage of growth.

I hope your holidays are restful and enjoyable. Here’s to an excellent 2025.

👉 Have a favorite resource or question? Reply below share your thoughts and insights.

Best part, you can participate! It’s an advice podcast for engineers of all experience levels, tech leaders, and anyone navigating the tech-adjacent world and if you’ve got a question, just submit it here. Or comment at the bottom of this newsletter. New episodes released every Wednesday.

Enough plugs, one thought for the week. It’s December 16, which means we’ve reasonably got ~10 business days left in 2024. Use this time to work on your prioritization skills, leveraging the Eisenhower Matrix to determine what truly needs to wrap up before 2025.

⏱️ Workplace Efficiency & Leadership

Dropbox’s Secret for Saving Time in Meetings
This simple trick from Dropbox has the potential to save your team hours in wasted meeting time. At the end of the day it’s all about leaner collaboration. Dropbox did it before the recent waves, and it proved extremely helpful.

Bosses Say They Want the Truth—Do They Mean It?
Building trust starts with modeling vulnerability and accepting uncomfortable truths. This article challenges leaders to evaluate their openness to honest feedback.

💼 Remote Work & Team Dynamics

Remote Workers and Organizations Drifting Apart
Gallup's research reveals the challenges of keeping remote teams connected. Offers actionable insights to foster engagement and alignment in distributed workplaces.

“Lazy Girl Jobs” Are Just Healthy Jobs
I love this callout, especially as a millennial who had burnout issues in the past. This trend emphasizes the growing demand for balanced, sustainable roles. Leaders should reassess whether they’re fostering environments that encourage meaningful work without burnout.

🛡️ Security Insights

Why Security Still Has a Password Problem
Despite advances in authentication, passwords remain a weak link. Learn how to reduce vulnerabilities and improve your organization’s security posture.

Cross-IDP Impersonation: A New Security Risk
This deep dive into cross-IDP impersonation exposes vulnerabilities in identity providers that could compromise your security strategy. Essential for leaders overseeing authentication systems or IAM policies.

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💡 Strategy & Perspective

The Ultimate Guide to Willingness to Pay
An excellent primer for product leaders on pricing strategy. Engineering leaders can use this to align product development with business goals.

What Are You Getting Paid In?
Aviv Ben-Yosef’s take on non-monetary compensation is a great reminder to evaluate your team’s intrinsic and extrinsic motivators. While almost no one will say no to cash, it’s not always the main motivator.

🛠️ Engineering Culture & Productivity

The Death of the Stubborn Developer
A compelling look at how modern tools and collaborative practices are reshaping the stubborn, isolated developer archetype. A must-read for leaders navigating cultural change in their teams.

Measuring Developer Productivity with the DX Core 4
This research highlights the DX Core 4 framework to measure developer experience and productivity effectively. Use this to align engineering metrics with business outcomes. Always interested in what Laura Tacho and the folks at DX are doing!

How to Ruin an Engineering Organization
A spicy title, but also a brutally honest guide to what not to do when leading an engineering team. Keep this checklist of anti-patterns handy as move your org forward.

👉 Have a favorite resource or question? Reply to this email to share your thoughts and insights.

Featured image: “Winter” Joseph Rubens Powell (artist) British, active 1835/1871

I ignore it for a few weeks (like when I released 4 podcast episodes) but it comes back louder and I shut down.

The shoulder gremlin has always been there. High school, college, when I owned my own hot sauce company, and especially now, writing about real-world experiences in my career field. But it feels different here and I don’t know why.

• Professionalism? I’ve written about management through the lens of Ted Lasso and Training Day, so probably not.

• Not wanting to be told I’m wrong? That’s rarely been a problem in the past. I expect to be wrong 1/5 times.

• The grossness of being an “influencer”? I was a Columbus micro-celebrity for writing a popular Friday “Spiciest Dish in Columbus” series for two years.

• Having someone dismiss my experiences as invalid because my resume doesn’t have a FAANG company on there? How important is that though? I don’t know I’d ever attempt to work in those companies.

• Trying to do too much and getting overwhelmed? Honestly, this might be the closest to an answer.

Whatever the reason, I’ve let it get to me. The last post I wrote was two months ago, “Navigating that Failing Startup Feeling” and I had many of you reach out and say how helpful it was. The shoulder gremlin gets to me, but I’m going to see if I can get rid of it for a while (or at least mute it).

Chatting with a co-worker this week we both realized we were going through the same thing. We both were feeling self-imposed pressure to make something helpful, though none of you are forcing us to.

Why am I telling you this? Well, partially to let you know you’re not alone in feeling like your content or contributions aren’t worthy of people seeing it. It’s also to call myself out for being a wuss and worrying too much about what no one has said.

I mean…I’ve even had folks tell me my eyes are too far apart in YouTube comments for the latest project I’m working on with a friend in the Dungeons & Dragons space and it rolls right off. I don’t know why this feels more high-pressure, but I’m going to stop worrying about it. This blurb is part excuse, part processing, part outward therapy, part promise to silence the gremlin moving forward.

Permission to fail/miss, granted. How have you overcome the shoulder gremlin? Interested to know any other tips and tricks folks find helpful.

Helpful Links From This Week

• Decoding New Engineering Team Members

• Behind the scenes of LinkedIn's developer productivity metrics [Podcast]

• No Risk It, No Biscuit

• The Skills and Traits of Elite CTOs

• Why Your Best Managers Quit

• The “Niche” Canvas and Product Market Fit

• How to be a better software engineering leader (top-down or center-out?)

• Blameless culture should be a standard in the engineering industry

• Use Engineering Strategy to Reduce Friction and Improve Developer Experience [Will Larson Presentation]

• What causes new engineers to “sink or swim”?

I’ll cap it there for now, but let me know what other weekly features would be helpful for you. Always looking to make improvements and want this to be as valuable as possible.

Thanks for reading!

A bit of a rant incoming, so if you’d prefer some links, head to the bottom! This is going to sound weird, but writing things on the Internet is a bit of a bummer. Especially if it’s not super motivational. LinkedIn and social media in general so often show off the successes of others, and rarely highlight failures. I’m sure you’ve seen it (or felt it as well).

This week, I came across this post on LinkedIn that said:

“Leaders don’t see failure, they see unfinished success.”

I began to worry about the leaders just starting out in their careers and how they might read such a slogan. And, excuse my bluntness, but…barf. Failure is not a bad thing! It’s not a dirty word. Failure, especially fast failure, is one of the greatest things we can achieve in business. We tried something, we tested it, and it didn’t work. Great! What did we learn as a result? How do we apply those learnings in the future?

I’d be willing to wager that if you put two individuals or companies side by side and one of them only had wins while the other was split 50/50 between wins and losses, the 50/50 folks would end up better off in the long run. We’ve created a social landscape where bragging about wins is lauded and praised, ending in a swirl of toxic positivity. There’s a great article on this phenomenon “How the Toxic Positivity of LinkedIn Serves the Status Quo.”

I’m tired of slogans and mottos that read this way. “Take that hill!” or “If you believe you can achieve!” Look, sometimes you get kicked in the face. That’s okay! Some of the best lessons I’ve learned were from losses. As humans, our brains have a habit of hiding the wins and making the losses a glaring reminder of where we weren’t good enough. So why not lean into it?

Astro Teller has a great Ted Talk on “The unexpected benefit of celebrating failure,” and it’s a great 15 minutes. It’s not about not failing. It’s about “shifting your perspective.” Going from “I failed” to “I learned so much from that failure,” and building upon it.

Look at SpaceX. Regardless of your feelings on Elon Musk, SpaceX is amazing. The Falcon 9 rocket that would land and touch down on a floating dock to preserve its parts exploded, failed, and failed many more times before it landed successfully.

It’s less about believing you can, and more about doing something without being scared of failure.

Getting off my soap box, I want to add my favorite quote on this subject and it comes from the best movie in the Indiana Jones series (Last Crusade of course). Young Indy has gone on an insane chase to righteously bring an artifact to his father, only to have the cops show up and make him hand over the cross of Coronado. The main guy who’s been chasing him leaves him with the parting words, “You lost today kid…but that doesn’t mean you have to like it.”

That doesn’t mean you have to like it.

I love that part. Sit with your failures. See how you feel about it. Figure out how to take that feeling and do better next time.

As you’re finishing up your week, give yourself permission to fail. You don’t need to be perfect, and you don’t always need to win. Do your best, learn from your failures, and be better because of it.

Links I Found Helpful

• How to empower your team through autonomy, mastery and purpose

• 20 traits of highly effective project managers

• Are Remote Workers and Their Organizations Drifting Apart?

• Developing high performers

• How Candid Can You Really Be With Your Boss?

How else can I be helpful this week? Let me know in the comments below!

New from Hartley’s Handbook:

• Episode 2 of my new podcast, this episode focuses on prioritization

• My latest 9 books that are helpful for Engineering Managers

I sometimes worry that I’m not taking enough risks as a leader, which is very different than when I was an engineer. Early on I would take risks by looking for untread ground that had the potential to make things X times faster if it worked, but always knew I could fall back on the old ways if it failed.

I encouraged my teams to do the same. “Know the length of your runway,” is something I still say. The intent is not to scare people out of a decision, but to help them understand when to let it go. This was especially true when working at a digital agency.

Example: We have 6 weeks to get this done (the runway), spend the first two on this multiplier tool, but we pull the ripcord at 2 weeks. Essentially at that two week mark, we’ll make a decision of whether or not to pursue the higher risk, higher reward option, or revert to what we know will work.

This example has played out several times in my career and it is successful about 50% of the time. The 50% of the time where it doesn’t work out, the risk was still a net positive from a learning perspective and helped with future projects.

As managers and leaders, we have to give space for experimentation and risk. Ask your teams this next week if they think they have the ability to do so.

Links I Found Helpful This Week:

• Where Will AI Have the Biggest Impact? Healthcare.

• Manage your priorities and energy

• Build a Thing to build The Thing

• Uber Generated a Profit For The First Time In Its History

• Compensation for Startups: Implementing and “Defending” Your Compensation System

• Meeting = Greeting + Reading + Leading

• Workdays now end 37 minutes earlier than one year ago

What I’m Watching: Moneyball

I’ve watched this movie close to ten times and I’m still impressed by it. The performances, story, Brad Pitt eating endless calories on-screen, all great. One thing I keep keying in on is how Billy Beane handles a massive pivot of the organization. He understands the constraints (dollars), and understands that they have to completely change how they think about getting players. This comes to a head when Beane’s Head Scout confronts him about what he and “Google boy” are doing.

Just because it hasn’t been done that way in the past, doesn’t mean it can’t work. Not every business can be run like teams following the Moneyball handbook (nor should they), but you can think differently.

• How have people been doing things in the past and what if we chose to do something different?

• Whether forced into it or of your own volition, what if you took that step into something completely opposite of how everyone else thinks?

• Where might it get you?

• What might it change?

Love this movie.

A Quick Poll if you don’t mind:

Thanks again for subscribing and have a great week! As always, feel free to comment down below or reach out on LinkedIn if I can be helpful in any way.

In his book “Leadership Strategy and Tactics,” Jocko Willink talks about needing to step back from a situation to properly assess and determine the best course of action. That initial step back is hard. Even if things aren’t on fire, the day-to-day tasks can drain you to the point where you can’t see past the end of your nose (or gun in Willink’s case). Stepping back is tough, but the further you progress as a leader or manager, the more important being able to step back becomes.

How do you get into that headspace?

I know for me I have to set a timer, put headphones on, crank some instrumental music (heavy metal, dubstep, or chiptunes generally), and push all notifications to the side. Even then the ability to step back comes in waves. I can usually push for 20-30 minutes to get the bulk of my ideas onto a page, but then need to let it sit and come back later to dissect further.

Our second-half roadmap breaks down into a few key categories:

1. Broader business enablement

2. Localized optimization within our internal customer bases

3. Big, bulky initiatives that are too blurry to define other than the problem we’d love to solve

Starting broad, I had to look across the organization to understand where we are aiming and what our broad goals are, along with the business context and the microenvironment of what other teams are attempting to accomplish.

It’s easy to be selfish and say, “well, our team has x, y, z things we want to do, so we’re not worried about what other teams are up to,” but that’s a quick way to make your team irrelevant. Looking across the org requires a step back and requires communication with functions you may not normally talk to. Working with customers (easy when they’re internal) helps paint the picture of what each function cares about and gives you a lot of avenues to investigate. The investigation then refines the categories even further, helping you break them down into smaller chunks.

Those smaller chunks tend to become the projects that you and (hopefully) your Product Managers get to chase down. From there it’s either a prioritization exercise, dependency tree, or confidence exercise about how you order the projects for the remainder of the year.

Ultimately by taking a step back, reviewing the total landscape of your organization, and making some blurry decisions, you can more easily move forward. You can’t predict the future, but that doesn’t mean you shouldn’t try. Take your best stab at what the future holds and examine, measure, and course correct along the way.

What scares you about roadmapping or planning for the future? Let me know below!

Helpful Links

• Google to crack down on office attendance, asks remote workers to reconsider

• Appfire CFO touts ‘people-first’ approach to profitability

• Rekindling US productivity for a new era

• When AI Overrules the Nurses Caring for You

• My Super Simple 1:1 Template

• Why Leading a Remote Team Requires Radical Candor

• Scaling as a Manager

What I’m Re-Watching: Fullmetal Alchemist: Brotherhood

Not everyone enjoys anime and I get that, but FMA Brotherhood is probably one of the best out there. With the right mix of humor, seriousness, fighting, and science, I’ve probably watched this series four times.

Something that stuck out to me this time around is Mustang Unit, the team hand-selected by Colonel Roy Mustang. Each has a unique set of specific abilities, each complimenting the other and forming an unrivaled squad. This is peak team building, so if you’re ever wondering how to add to your team or build a team from scratch, Mustang Unit is a great model to follow.

As an engineer moving into management, I was initially a player/coach, but had to shift my mentality from doing the big, heavy lifts, to teaching others how to complete those while sitting further back and tackling smaller items. Not exactly I would have done them myself, but to the extent of completing the goal as I would expect it to be completed.

As an engineering manager, I wasn’t in control of the code at all, so I had to teach the code skills and thoughts processes that I’d learned in my time with my hands on the keyboard. Teaching how to debug, how to think about architecture, how to think about building the minimum viable product, and how to meet the customer’s needs helped the team hit the expectations that were set at a broader level.

As a manager of managers, my head is further in the clouds. I’ll still spend time at the tactical level, but it is way more hands-off. I work with my managers and leads on what I expect from them and their teams. It’s not about creating a carbon copy of yourself but teaching the foundations that are important to you as a manager and leader and holding your folks to those standards.

Ron Swanson once said “Give a man a fish and feed him for a day. Don't teach a man to fish…and feed yourself. He's a grown man. And fishing's not that hard.” It’s hard to argue with that from a fishing perspective, but in engineering, there is much more ambiguity and uncertainty. By teaching more, you do less often. Avoid the trap of teaching someone to be like you and instead, teach and coach them to be what fits into your expectations and goals as a group. Teach and coach them on how to become what they want to be. Find opportunities that match up with skillset and desires and go from there.

If you absolutely can’t fathom being hands-off, think through what taking a vacation looks like. What are the areas you’re concerned would fall apart? What are areas where you wouldn’t be able to understand when you got back? Set up structures that support your individuals and support your team’s broader goals.

Teach them how to see things like you see them, but don’t teach them to be exactly like you. By teaching more and doing less, you give yourself the ability to expand your reach and thinking about the future instead of granularly looking at the present.

Agree? Disagree? Let me know below!

Helpful Links

• Ethan Mollick on Noise Effects On Cognition

• When Blind Hiring Advances DEI — and When It Doesn’t

• The Slow Decline of Highly Motivated Developers

• Self-healing code is the future of software development

• The evolution of React APIs and code reuse

• How large DOM sizes affect interactivity, and what you can do about it

• Workplace well-being: U.S. Surgeon General lays out some guidelines

What I’m Watching: I Think You Should Leave

Season Three of the comedy sketch series is out and I’ve definitely watched it a few times already. It’s not for everyone, but humor-wise it’s right in my Q-zone (watch the show, you’ll understand).

All three seasons are streaming on Netflix. Definitely curious what percentage of folks reading this will find it enjoyable.

What’s on your mind this week? Let me know below or reach out on LinkedIn!

I love asking my teams and direct reports for feedback. In many cases, I’ll end our one-on-ones with, “any feedback for me?” or “anything I could be doing to better support you?” When the answer too consistently is “nah, all good,” I’ll sometimes assign homework of bringing at least one piece of feedback for our next conversation.

Hearing that things are going well is good, but I believe as managers and leaders there is always more we can be doing to help our teams grow.

The further I’ve advanced in leadership roles, the more complex and difficult the feedback and challenges become. Where earlier in my career requests were more tactical around projects and day-to-day assistance, questions and requests now are around vision, meaning, and what we’re doing for the next three years.

These new questions scare me but are also one of the most fun parts of my job. What could things look like in two years? What will we have accomplished? How will our vision or mission evolve? What do we need to do now to get there?

One of the engineers on my team this week challenged me on why we’re doing what we’re doing. They asked how we connected to the bigger picture and how we could tell we were contributing to the overarching company goals. While I thought I’d been pretty good about explaining it previously, I found I was too myopic. I was too focused on the immediate connection and impact and less so on the broader company vision.

Accepting the challenge, I’ve spent a good amount of time this week thinking further about how we fit in as a team with internal stakeholders. It would have been easy to dismiss the feedback and point to a slide deck that we’ve already reviewed several times, but the hard parts are what make the job fun.

Feedback can be difficult to hear, especially when it is new and/or unfiltered, but when we view it as a challenge instead of a jab, we unlock new avenues we haven’t previously considered.

Tactical advice: In your next one-on-one, sincerely ask “any feedback for me?” or “anything I could be doing to better support you?” From there, think about what it would take to action the feedback at a small scale and at a larger scale where the root cause is solved forever.

Interesting Links This Week:

• DevEx: What Actually Drives Productivity

• How to be a -10x Engineer

• The Return to the Office Has Stalled

• Americans Have Never Been So Unwilling to Relocate for a New Job

• 14 essential book recommendations by and for IT leaders

• Beyond robots: AI automation in manufacturing is about visibility and flexibility

• Amazon Overhauls Deliver Network to Dispatch Packages Faster, More Cheaply

What I’m Listening To: The Infinite Game by Simon Sinek

The engineer in the anecdote above recommended The Infinite Game to me and I’ve really been enjoying listening to it as I go about my morning tasks. Sinek takes readers through finite and infinite mindsets, framing each with examples from Apple (infinite mindset) and Microsoft (finite mindset) and their releases of the Zune, iPod, and iPhone.

This is a tough book, not because the content is dense, but because (just as above) it is challenging me to think more broadly. Not just about work and the business as a whole, but even me personally.

An example is I swore I’d move off of Medium to Substack because it would give me a better way to monetize my content. That was a very finite mindset. Recently I realized I don’t care about that aspect and am more interested in putting my knowledge out there on all the platforms. I want to be a resource for other leaders that are growing and looking for tactical advice on management. Even if only one nugget resonates and helps, that’s enough for me.

I’m only about halfway through the book, but it’s been solid so far. Simon Sinek doesn’t tend to miss, and The Infinite Game is further evidence.

What’s on your mind this week? Let me know below or reach out on LinkedIn!

Spoiler alert and cop-out answer, it depends.

The answer is different per person, per situation, and per company. Some examples of what I mean.

• For documentation, 40% is good enough to get it in someone’s hands for review/early feedback

• For change management, 80% is good enough because you can’t predict everything

• For reading books, 10% may be good enough, depending on the outcome you are aiming to achieve

• For releasing feature sets, 50% may be good enough as long as it allows you to test or experiment with a small blast radius

There are certain scenarios where only 100% is good enough, like building and maintaining elevators, but in tech and in business, an acceptable version is likely less than 100%.

As an IC, my sense of good enough was: does the thing work as intended without bugs, and look the way it was designed (for the most part)? By staying mindful of when something was good enough, I learned how to push projects through on tight deadlines. I also learned that maintaining such projects can be brutal. Work to identify best practices with your teams and determine the line of “good enough” in your work.

In my mind, “good enough” is important to keep in mind, because most businesses can’t run on perfection. Startups that aim, aim, aim, aim, aim, then fire are usually too late on the uptake and someone else has jumped ahead of them. Think in simple terms. How do I get this out of my head and into someone else’s hands quickly, with the lowest risk? Knowing what you’re worried about and why will help you increase the speed.

Thinking about risk can be paralyzing, but the more comfortable you get, the faster you can go. I work on this weekly by writing down the risks I know I’m taking and the risks I’m worried about taking. By putting it on paper, it becomes more real, but when it’s real it means it can be solved. Don’t stew for too long with something in your head alone. Tell your dog, tell a piece of paper, tell anything or anyone to get it out in the open. Once you understand the risk, you can make a better assessment of what "good enough” looks like.

In what categories do you aim for perfection? In what categories do you spend less time worrying about perfection? Let me know in the comments below!

What Made Me Think This Week:

• Workers Now Spend Two Full Days a Week on Email and in Meetings - WSJ

• Real-Time Shipping Visibility, Thanks to Predictive Analytics - Multichannel Merchant

• Top 6 roadblocks derailing data-driven projects - CIO

• 9 upskilling tips that pay dividends - CIO

• Want to Raise Money from VCs? De-risk Things - SaaStr

• On hiring, rehiring, and one question to answer them all - Jason Fried

• Executive Coaching Can Be Your Secret Weapon - Sean Byrnes

• Why Few Organizations Adopt Systems Thinking - Russel Ackoff

• I'm an entrepreneur who lost myself to mental burnout until 3 simple habits helped me recover - Insider

Extra Nugget

I was sent this article earlier this week: Use this 2-word phrase when your boss asks you to do more work than you have time to do, according to a therapist. The thought behind it is nice and gives individuals a better way to say “no,” but there are times where the answer should be “no.” Saying “no” is painful. I did it this past week and was in my head the whole time afterward, but it got others to think more critically with me about why the request could or couldn’t be done, and to what degree.

Brandon Smith, the therapist interviewed for the article notes, “You always want to treat a boss like the number one client or customer,” but I disagree. If your boss doesn’t have a good sense of what’s already on your plate, then one of you is not getting the right information out in the open. A boss should be a partner, and while you want to do good work for your boss, it shouldn’t come at the cost of saying “yes” to everything. Same conclusion, different approach.

If you find yourself saying “yes” too often with your boss, broach that conversation. Don’t jump directly to “yes, and…” as it won’t get to the root of the problem.

What I’m Reading: Build: An Unorthodox Guide to Making Things Worth Making

Tony Fadell led the teams that created the iPod, iPhone and Nest Learning Thermostat and learned enough in 30+ years in Silicon Valley about leadership, design, startups, Apple, Google, decision-making, mentorship, devastating failure and unbelievable success to fill an encyclopedia.

This is another reference book for the engineering leadership shelf. Fadell’s candor and overall tenor are the right mix of amusing, direct, and insightful for anyone to learn something new. A quote from today I found helpful, especially for younger leaders:

Thinking about a world where everyone else is growing into the tasks that make up your day-to-day is scary, but it’s critical for moving up. How this book wasn’t on my radar last year is beyond me, but I am glad I found it.

As always, let me know below if you have any thoughts, questions, or comments!

Many have thought about it, many have come up with certain strategies to combat the dreaded M-word, but few have figured out how to completely squash them.

I’m putting the finishing touches on my live webinar for O’Reilly titled “Protecting Your Schedule,” on 5/5 (and later in the year), and am still scratching my head to determine if there’s a “one size fits all” approach to combatting meeting overload. Especially in a remote environment, how do we give focus time while also ensuring folks have the resources and conversations available to succeed?

Shopify led the charge earlier this year, killing off “every recurring meeting with three or more people,” but from a Hacker News thread, this wasn’t the first time they’ve done so. If I’m reading that correctly, Shopify previously killed these sorts of meetings, but like a zombie from the grave, the meetings came back to life.

The numbers are impressive. 322,000 hours of meetings they were able to scrap with the initiative, but if there’s no additional training, culture shift, or overall change in attitude toward meetings, was it worth it in the first place?

Harvard Business Review walked through “The Psychology Behind Meeting Overload,” in 2021. It walks through many of the reasons companies or individuals get into this rut. Their point around “pluralistic ignorance” was new to me, but something I’d felt previously. HBR defines it:

Agenda Theater

The authors, Ashley Whillans, Dave Feldman, and Damian Wisniewski, have more notes on HBR about meetings. Each one is increasingly fascinating and gives me something new to think about. Here’s a new term to know from the same authors, “agenda theater.”

agenda theater: They sink time and effort into agendas that create the appearance of effective meetings, without actually improving how meetings are run.

I cringed when I read this and had to review my best practices. Reading further, they outlined 5 key factors to think through to avoid agenda theater:

1. Start with the why

2. Move on to the what

3. Think about the who

4. Don’t overdo the how

5. Be careful with the when

Agendas help, but as with all things, tying yourself strongly to them does not a good meeting make.

Startups to the rescue?

Startups like Ro.am cite stats about shorter meetings through their software (8-minute and 30-second average meeting time). The fact that Clickup has a post on 25 meeting management tools (twenty-five!) further highlights that companies are trying to solve this problem. The list of SaaS is growing, but will we ever fully solve the root cause for all of this?

Meetings aren’t all doom and gloom, after all sometimes that’s where the best memories for folks are created, but we need to become more critical and defensive with our calendars. We need to attack the problem together.

How do you approach your week and your schedule? Are you in control? Or do you wait for someone else to fill it up?

A few other questions I’ll be asking in my webinar (yes, a meeting about meetings):

• What meeting this week can you say no to?

• What meeting can you delegate to someone else?

• What meeting can you delete and no one would miss?

• When was the last time you talked about your company’s meeting culture?

• If you could only pick three meetings to attend this week, which would they be and why?

• What is your goal for the meeting?

• Looking back a week from now, will you be happy you spent time on that meeting?

Let me know below what you’re doing to protect your schedule this year.

What I Found Helpful This Week:

• How to Use Engineering Metrics

• The Age of the Crisis of Work - Harper’s Magazine

• The State of Organizations 2023: Ten shifts transforming organizations - McKinsey

• Engineering Culture, Trust, and Accountability - Emily Dresner

• What 99% of Founders Get Wrong With Their Forecasts - Pete Sena

• The Psychology Behind Meeting Overload - HBR

• How skill-based talent management boosts productivity and fairness in the workplace - World Economic Forum

• Gartner Identifies the Top Cybersecurity Trends for 2023

• Inside Etsy’s Multi-Year DevEx Initiative - Abi Noda

What I’m Reading: The Hike - Drew Magary

A foul-mouthed crab, seeds that turn into iron towers, and a business trip gone wrong, I have no idea what awaits me at the end of this book. I found it when looking for humorous books in the fantasy genre, and Drew Magary continued coming up on lists. Halfway through it’s hard to know whether to recommend it, but we shall see where The Hike ends up.

As always, let me know below if you have any thoughts, questions, or comments!