No one wants to upset people they like
- mayadolgin
- 4 days ago
- 4 min read
(March 31, Newsletter)

In the last few weeks we’ve discussed tricky types of feedback, like feedback to peers or your own boss and personality-related feedback.
Another common scenario I hear from clients is how hard it can feel to give feedback to someone with whom you have a close relationship at work, either because you’re good friends outside of work or work closely together.
Why it matters
It’s a wonderful thing to be close with people at work. It’s a special thing to develop close friendships, share life occasions, find people with whom you see the world eye to eye.
And of course, there’s a downside. Not wanting to upset the person can cloud professional judgment.
Not wanting to be forthcoming with them about disagreements or missteps once might not be a big deal, but if you find yourself holding back over and over, the organization in your care can begin drifting from its goals – which will eventually impact the close relationship.
Feedback to a friend
The main reason it’s hard to give feedback to a friend is that you know too much about each other. It can be hard to evaluate their work product simply based on what happens in the context of work, since you likely have significant context about life outside of work.
I’m not a fan of the advice to therefore avoid having close friends at work. We can train employees to be skillful communicators and even leverage the friendship to be direct with each other, instead of shying away from meaningful friendships out of fear that it will cloud people’s judgment.
Feedback to a close colleague
The challenge with giving feedback to a close colleague is different.
Instead, the hesitation is grounded in generally being very closely aligned and experiencing a big difference in opinion or a divergence of responsibilities. You might not have ever needed to call the person out for bad behavior or otherwise be unaccustomed to highlighting differences.
Leveraging the Big Reframe
In both instances, the big unlock is the same: high trust relationships aren’t necessarily low conflict. Instead, high trust relationships are skilled in handling conflict (I’m paraphrasing from one of my favorite podcast episodes).
So what does it look like to leverage the personal closeness to speak candidly?
Tap into your bank of goodwill: Start by assuming generosity of spirit and asking the other person to do the same. It’s obvious you care about the person, their wellbeing, their success; and addressing said gap is an expression of this care and not the other way around. I wouldn’t even assume that addressing the gap would cause a “trust withdrawal” necessarily; there is a good chance that giving whatever feedback you have to share would add more to the “trust bank.”
Wear your work hat: Don’t ignore a personal lens on the situation. Instead, acknowledge that you have two hats and indicate that you’re prioritizing the work needs at the moment. If relevant, acknowledge that having this conversation could negatively impact your personal relationship – and while that’s not what you’d hope for, it’s a risk worth taking in the moment to address this work topic.
Be direct and specific: When sharing your observations, don’t be vague or water down what you really mean to say. They deserve better from you. Position it as a sign of immense respect that you’re holding up as accurate a mirror as possible.
Make it a conversation: We don’t lecture those we care about (or at least not when we’re at our best). After sharing your observations, turn it to them with questions like: “What does this look like from your perspective?” “What’s really going on for you here?” “What do you really want out of X situation?”
Final thought: As is the case with all other feedback situations, we have to respect that the person has the right to take or leave what they want. We all know what it feels like to want to hold onto more control with people we care about, especially if you think someone is handling a situation inappropriately or ineffectively. Say your peace and let them be.
The Coaching Corner
Help them simplify complexity
Members of your team might come to you with dilemmas, frustrations, or stress that manifest as jumbled thoughts. If you sense that they’re all over the place or can’t articulate the real challenge they’re facing, try the following:
“Can I feed it back to you in a sentence?”
“I’m hearing a bunch of things; let’s separate them out.”
“It sounds to me like X is the core. Did I get that right?”
Either you got it and they’ll be relieved, or you’ve given them a moment to hear a version back and they can regroup and try again.
Recommendations
I love this short video from a recent basketball game of a coach giving tough love and it having an immediate, positive impact on the player. My brother Yoni sent it to me with the text “Great coaching moment, newsletter material?” and he was 100% right.
“How to build a superteam that keeps getting better” – this article has a few great charts. Just this morning I showed them to a client and we talked about what “Gives feedback that motivates improvement” and “Delivers feedback without sounding critical” really mean. Excellent fodder for you and your teams to discuss.
“How leaders create a high agency culture” – for all my clients who feel powerless in a system beyond your control, this one’s for you.
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