The 4 trickiest kinds of feedback to give
- mayadolgin
- Mar 4
- 4 min read
(March 3, 2026 Newsletter)
When I hear from clients about the moments when they shy away most from giving feedback, the situations tend to fall into a few buckets.
Nonhierarchical feedback – peers, bosses, and partners
Personality-related feedback – “that’s just who they are”
Feedback to a close friend/colleague – I don’t want to upset them
Feedback to someone who’s sensitive – no thanks…
Why it matters
As a leader within your organization, you have the responsibility to find ways to achieve your goals, which includes removing roadblocks as often as possible.
If you’re withholding feedback, you are noticing roadblocks and leaving them in place with the hope that they will move themselves or someone else will do it.
Sometimes that’s a good bet – plenty of times letting it go is the best option, as things resolve themselves or don’t repeat or escalate.
Sometimes, though, your own discomfort saying what needs to be said is contributing to a worsening situation, and then speaking up is truly an opportunity to rise to the leadership challenge.
When it comes to tricky feedback, there are understandable assumptions I hear from clients and key reframes that can help summon the courage to give it anyway.
Nonhierarchical Feedback
Assumption: I don’t have enough authority to give a peer or my boss feedback.
Reframe: Great leadership isn’t about authority, it’s about credibility. If I’m noticing something that would help them doing their jobs better, I can position myself as a trusted partner by broaching an uncomfortable subject with respect and openness.
Personality-Related Feedback
Assumption: This just is who they are. Pointing it out won’t make any difference.
Reframe: When giving feedback, my job isn’t to change anyone, but to offer my observations and help them expand the possibilities they see before them. No one is perfect, including me, so approach with humility and curiosity.
Feedback to a close friend/colleague
Assumption: I might lose this friendship by giving them this feedback.
Reframe: It’s another opportunity to build trust with this person who matters to me. If this relationship is as strong or important as I think it is, it will withstand my sharing a sensitive observation with plenty of generosity of spirit.
Feedback to Someone Who’s Sensitive
Assumption: I’m just going to upset them, and they won’t hear anything I’m saying.
Reframe: The more people shy away from being honest with them, the worse it will get for them. I will not tiptoe around them and indulge the fear. Approach with steadiness and care.
In all of these cases, here are a few other important reframes:
Tread lightly and confidently. You can be assertive and caring at the same time.
Map it out. You can be deliberate with your word choice, with how you structure or frame what you’re saying, so it has the best shot of landing as you meant.
They might dismiss your feedback, but at least you tried. This can be true with “simpler” feedback too. We all have the right to decide what feedback to internalize.
As I’ve written about before, feedback is just information. If you approach any tricky feedback situation as an opportunity to share specific observations, as a chance for both sides of the conversation to learn something, and as a moment to build trust, you’re already in the right direction.
Final Thoughts: Each of these scenarios deserves their own newsletter, so let’s make the following deal, ok? I’ll publish my next four newsletters on these tricky feedback situations and you’ll forward this post around encouraging your friends and colleagues to sign up and get them into their inboxes directly.
And if you have additional examples of tricky feedback situations, send me a note and maybe I’ll keep the series going.
The Coaching Corner
Agenda setting best practices
Meetings are an expensive use of time, so it’s best to set agendas in advance so that there’s agreement on what to discuss and people can come prepared.
Who sets? Typically whoever calls the meeting is the default owner. That being said, they can assign agenda setting to someone else.
How far out? Depends how much thought people need to put in beforehand. A good rule of thumb is a day per person involved – 1:1s can be one day before, a team meeting with 5 people, then 5 days before.
If an agenda hasn’t been set and the meeting is starting (this happens with recurring 1:1s regularly), do NOT start the meeting until you’ve decided what will be discussed.
And my favorite tip: write agendas as questions, not statements. It forces you to separate updates (can be sent asynchronously) and discussion topics.
Recommendations
I recently did a deep dive on strategic thinking, planning, and problem solving and picked out these few resources as especially helpful for my thinking. Hope they are for you too.
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