3 Gotchas to Delivering Critical Feedback

Jack Dempsey
Hyper growth engineering management
4 min readDec 26, 2017

Giving critical feedback is one of the hardest parts of being a manager. I’ve found that there are three areas where managers get stuck:

  • Not knowing what to say
  • Not knowing how to say it
  • Not wanting to say it

What Do I Say?

If you don’t know what to say, you can’t give the feedback. Ask yourself: “Do I really not know what to say, or do I just not want to say it? Am I using the excuse of not knowing precisely how to deliver this feedback as a way out, or do I truly not know what I want to communicate?”

If you’re not sure what to say, take a step back. Something triggered the thought that you need to give some critical feedback.

What happened? What was the impact? What opportunities exist to improve?

If you’re still stuck, write down facts. Remove emotion, subjectivity, and just list things out:

  • The code was shipped at 1am.
  • This feature could have waited til business hours.
  • The CI process was skipped.
  • It blew up the site.

Maybe it’s your star coder. Perhaps they were showing a great sense of urgency in getting something out the door. Still, the facts show a number of issues.

(An aside: be careful here, as sometimes you only have some of the facts. Perhaps the deadline was moved and a 1am deploy was needed. Maybe CI was broken. In the fast moving pace of many startups, things change constantly, and asking and verifying is a much better idea than assuming.)

Once you know concretely what to say, the next issue you may face is how to give that feedback.

How Do I Say It?

Communication lives within context and you should always consider a few aspects: the individual, the feedback you’re giving, historical performance and what the current reality is trending towards.

Some people need incredibly direct, plain communication. Others will bristle at overly concise and constructively critical speech. While you should always tell the truth and be objective, remember that you’re dealing with humans. Everyone is a bit different and will experience your feedback through their own perspective.

The actual feedback will influence your approach as well. If you’re having a tough conversation about inappropriate work behavior vs praising the fixing of a challenging bug, your tone and approach will be different. You should always be professional (and this varies per the environment), but tailor your approach as needed. Unsurprisingly, positive feedback and encouragement is easier to deliver than negative, but don’t let that stop you from giving either.

Also, be careful to not assume. Some people are tougher than they seem and if you go TOO far in trying to finesse an approach, especially when you haven’t built up a significant understanding of the individual, you may do more harm than good. People will feel the hesitancy if you over analyze, wordsmith, and otherwise communicate that something isn’t completely out in the open.

Especially if you’re an emotional, extraverted and/or empathetic person, be careful to not overly show your own emotions.

For example, if you say “this project was late by about a week; I really need you to focus on getting things shipped on time”, that’s direct and without emotion. Most people can hear that, understand it, perhaps feel a bit bad, but they’ll get it and move on. Contrast that with “gosh…this project was late by almost a week! ugh…I know this is hard, but please, I really need you to try more, ok?? *deep breath and hold*” Yeah, no good.

You can make feedback feel more serious than you’re actually thinking, just by not checking your own emotions at the door. The same thing goes for praise. If you make someone feel like they saved the company from death by fixing a non-critical bug, you will do two things 1) lose trust and credibility as at least their subconscious will feel some cognitive dissonance and 2) where do you go from there? How do you help them realize that while that bug was nice, the catch of the error at midnight and subsequent fix was a different level of ownership and truly great work. If the former feels about as good as the latter, guess where you just set the bar for great work.

Once you’ve figured out what to say, and how to say it, you may face the hardest part of this process.

Not Wanting To Say It

If I could run a poll and get answers from managers, especially those early in their careers, I would make a big bet that most of the time, the issue is that they basically know what to say, generally how to say it, but are having a challenge in saying it.

ugh, this feels awkward!…Ooh, a new bug to fix. I’ll go deal with that instead.

Take a breath. Step back. If this feels hard, ask yourself some questions:

  • Do you want to manage people?
  • Do you want to do it well and help your people improve?
  • Have you come to your position on this issue through facts and objective analysis?
  • Do you want your team to succeed?
  • Do you want to succeed?

It is literally your job to give this feedback. It is your job to help your people improve. Your team’s success is your success, so you better get to it. As long as you arrived at your position via a fair, balanced, and objective analysis, then it’s up to you to convey this information.

Into Action

The next time you’re going through the process of putting together some feedback, observe your hiccups. See where you stutter, bail, slow down or speed up. Consider the distinctions and proper attribution to what specifically you’re feeling. Make the proper adjustments and share the feedback. The more you do this process, the easier it becomes, until it is second nature to observe a situation, analyze it, consider how to share the feedback, and deliver it.

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