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How Long Should You Wait Before Giving Difficult Feedback To Someone?
Not long at all.
To answer this question, it’s important to know that every situation is different. Every company is different. Every individual is different. What’s not different is how long you should wait to deliver feedback, especially if it’s critical and difficult.
Give the feedback as soon as you can.
Rip That Bandaid Off
Giving feedback is hard. Giving critical or constructive feedback is even harder, but don’t overthink it. Yes, it’s important to approach the feedback with empathy and think about how to say what you want to say, but don’t let it get in the way of delivering the feedback.
Put yourself in the other person’s shoes. If I was doing something incorrectly or poorly, but didn’t find out for a month, I would feel like an idiot! (That has actually happened to me). I was embarrassed that I’d been doing something wrong for so long and lost trust in my manager for not telling me sooner. We eventually patched things up, but it made me worry I was doing something poorly without knowing.
Don’t Have A Long Lead Up
New managers sometimes struggle with determining when to give someone feedback. See the header in the previous section.
Never tell someone you are about to give them bad news several days before you plan to give them the bad news. Imagine how this scenario might play out:
Manager: “Hey, block off Thursday afternoon, I’ve got some tough feedback to deliver.”
Direct Report: “Perfect, thanks boss, I’m definitely not going to dwell on this for the next three days wondering what you’re going to say.”
As a manager, you may think you are doing them a favor by giving them a heads up, but 9/10 employees will want to get the feedback at the same time they are learning you need to give them the feedback. The last 1/10 is reserved for folks who aren’t in the right headspace at the time.
There are a few management books that give the advice to ask, “Are you open to some feedback?” before giving the feedback itself. I suggest reserving that for new teams or new team members, with whom you may still be building trust. The goal is to get to a point where there is no preamble, no tip-toeing, just straight to the feedback.
Even if you are asking the individual if they are open to feedback, it should be in the moment, not several days ahead of time. You are hurting more than helping at that point.
In the tech industry, we live in a world of consistency. Sometimes it’s consistent chaos, but with Agile, Scrum, and every other SDLC framework for project management, we expect consistency.
Consistency in communication is another expectation, so when something seems off, we go on high alert. This is exacerbated by prevalent Imposter Syndrome and an industry with widespread layoffs. Any change in flow or schedule can trigger someone into negative fantasies.
I was added to a “Quick Update” meeting on Friday, welp, I’m getting fired.
My boss said “hey do you have a sec?” with no other context, GETTING FIRED!
Oh no, a weird off-schedule all hands, we’re all getting fired.
If you need to deliver off-schedule feedback, give the person some insight about the context. No more “have a quick sec” asks. Make them “Hey do you have a second to discuss something I noticed in that last meeting? I’d like to understand your thinking.”
Build Trust To Stop Worrying About The When
The strongest teams and the strongest manager-report relationships are those built on trust. High-trust teams can deliver tough feedback, in the moment, without worrying about how it will be taken. This is not carte blanche to be a total a-hole, but if you don’t feel you’re far enough in your relationship to give direct feedback, think about how you can quickly establish that trust.
Give small bits of feedback that are easily actionable and thank them for making a change
Help them understand you are there for support
Show that you’re not afraid to get your hands dirty; join the triage or on-call rotation and feel their pain with them
Poke at blockers and help them get unblocked
Remove small annoyances, especially those that have lingered for a long time (Ted Lasso Shower Pressure)
Make small course corrections and ask questions to understand why things are done a certain way
Try Some of These Intros To Feedback
For new problems
Your goal here is to understand what’s happening and why. It’s possible there’s a logical explanation why the individual is doing something you don’t think they should be doing. Reset expectations, and make small course corrections.
In the next 1:1 say, “Hey, I noticed this the other day and wanted to chat about it a bit more to make sure I’ve been clear in terms of my expectations.”
After a meeting, “Hey do you have a second to discuss something I noticed in that last meeting? I’d like to understand your thinking.”
For long-running problems
If you’ve documented these in the past, it’s much easier to talk through.
I continue to see you struggle with Y, is there something I can do to make that easier?
Do you have the right level of support at the moment?
Anything I or the team can do to assist?
If you’ve not broached this topic, approach it again trying to understand the situation.
This seems like something that’s been going on for a while, can you tell me more about how you see the situation?
My expectations for you and the team are X, what can we do to make that happen?
I need to see progress on Y over the next two weeks. I am dedicated to supporting you in improving, but need you to communicate when you are struggling.
Give feedback as close to in the moment as possible. When feedback is left unsaid, it tends to snowball, or becomes harder to bring up in the future. Rip the bandaid off, give the feedback with empathy, and try to understand where the other person is coming from.