There’s never a bad time for introspection.
When we track projects, we think about data:
How much work was completed?
At what speed?
More or less than last time?
Better or worse than last time?
Better, neutral, or worse outcomes? (I’d argue this is the most important)
But how often do we use the same lens more broadly with our teams, ourselves, and our organization as a whole?
As engineering managers and leaders, we should be in constant evaluation mode of:
Below I’ve outlined questions that I ask myself frequently as I go about my day-to-day or at the end of a week/project/quarter. Let me know which you find most useful!
1. Ourselves
As a leader, it’s not all about you, but in many cases, we are the root of our problems.
Am I showing up the right way for our teams?
Am I providing enough support?
Have I given enough clarity in the following four categories?
Am I giving the appropriate amount of autonomy to our teams?
Where am I struggling day-to-day?
Where am I falling short and how do I improve the areas where I’m failing?
What am I really bad at right now?
In what areas am I doing well?
Spend some time being introspective to determine if there are things that can be adjusted in your day-to-day management that are beneficial for all areas that follow.
Keep a journal if needed, but ask yourself the above questions at least once a month and be honest with your answers.
2. Our Processes
When implementing new processes or firming up elder processes, why are we doing so? To what end? What does it help? Asking some critical questions can assist with the evaluation process.
Who does this process benefit more (myself or my team)?
Are our processes an impediment to getting work done?
Could we adjust anything about the current processes?
What is the most frustrating piece of our process?
What is the most beneficial piece of our process?
A good place to start is writing down all ceremonies performed throughout a batch of work and then scoring each for the above questions. Once done, have teammates run through the same exercise to drive conversation and change.
3. Our teams
I love inspecting team dynamics. Project to project, focus on what can be improved upon with the following questions:
Who works well together and why?
What strengths or weaknesses stand out on this team?
Do we have the right levels of seniority?
What holes do we need to fill externally?
What training can we provide to sturdy the current team?
Is our team the right size for what we’re trying to accomplish?
Could we support a larger team?
Could we be effective with a smaller team?
What archetypes are on the team and are we leveraging them properly?
There are so many factors and variables when it comes to teams. If you’re not in constant evaluation mode it’s easy to let things slide and get out of control. Be your best accountabili-buddy and monitor changes or shifts.
4. Our work
In some organizations this will be the area you have the least amount of control over, especially depending on your role and level as a leader. When involved with work/project decisions evaluate the following:
Why are we doing this work?
Does this line up with our OKRs or goals for the year/quarter/month?
What work are we not doing because of this work?
If we had no deadlines and no limitations, what would we work on?
What outcomes are we trying to achieve?
How will we determine whether our work was successful?
Are we focused on micro-work instead of work that unblocks bigger chunks of work later on?
Are we only doing the work because it is in our area of expertise?
How will we grow with this work?
Poke at every piece of work and determine an evaluation strategy for yourself and your teams. Some sort of feasibility matrix or analysis can also be impactful in determining how a project fairs in terms of prioritization.
5. Our tools
I’m an engineering leader, so when I think about tools it’s specifically about technology. Build vs. Buy is a great example of evaluating technology. A while back a CTO told me that they only work on what makes them a differentiator, everything else can be bought, and that still sticks with me.
Is this the right tech stack?
What is the value proposition of changing what we currently use?
Are there new techniques we should be exploring?
Are there old pieces of tech we should deprecate/eliminate?
If we stay with our current tech, how does it help or hurt in one year/five years?
Are there small optimizations we can make?
Do we have enough expertise across our entire stack?
Are there areas we care less/more about?
None of these have wrong answers. As each question is asked, I tend to find myself feeling more strongly about certain things and questioning my stance on others.
Final Thoughts
Each of the above should be inspected daily, weekly, and monthly to see trends emerge. Are we hitting the mark? Where could we be better? Where are we exceeding expectations?
Find a baseline first, then keep tracking to see how things evolve over time. Watch how the evolution goes as new changes are implemented. Did things get better? Worse? By having a baseline and constantly evaluating tweaks can be made to get things back on course or lean further into the changes that are beneficial.
Ask yourself some of the questions above and post your thoughts in the comments!