May 26, 2026 · 8 min · 6 segments
Most managers think difficult feedback conversations are hard because they don’t know what to say. But often the real problem is that the conversation they’re preparing for is the wrong one. In this…
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You're sitting in your car in the parking garage, and you've not turned the key yet.
You're rehearsing the conversation that you're going to have with, let's call him Jordan.
Jordan is on your team, and he's been there for, I don't know, maybe eight months, and there's this thing he does, or maybe it's this thing he doesn't do, and it's been bothering you for a while now.
This is the week I'm gonna talk to him." And every Friday, you tell yourself, "You know what? Next week is better.
Next week I'll have that conversation." So here you are, Tuesday, eight forty-seven AM, hand on the gearshift, garage lights flickering, mouth dry, running through the opening line for what is honestly probably the fortieth time.
"Hey Jordan, do you have a minute? I wanna talk about, um, something I've been noticing." No, that is terrible.
And you sit there, and you don't turn the key off, and eventually you just get out of the car and tell yourself, "I'll do it next week." I've been there.
I've sat in that car, or in my case, the subway train, and I've come to understand after sitting in a lot of metaphorical cars that the reason this conversation is so hard isn't the reason you think.
It's something else entirely, and until you see what it actually is, you're going to keep sitting in that car.
Today, we're talking about the feedback conversation nobody wants to have, and what you actually have to do when it's your turn to have it.
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You're sitting in your car in the parking garage, and you've not turned the key yet.
You're rehearsing the conversation that you're going to have with, let's call him Jordan.
Jordan is on your team, and he's been there for, I don't know, maybe eight months, and there's this thing he does, or maybe it's this thing he doesn't do, and it's been bothering you for a while now.
This is the week I'm gonna talk to him." And every Friday, you tell yourself, "You know what? Next week is better.
Next week I'll have that conversation." So here you are, Tuesday, eight forty-seven AM, hand on the gearshift, garage lights flickering, mouth dry, running through the opening line for what is honestly probably the fortieth time.
"Hey Jordan, do you have a minute? I wanna talk about, um, something I've been noticing." No, that is terrible.
And you sit there, and you don't turn the key off, and eventually you just get out of the car and tell yourself, "I'll do it next week." I've been there.
I've sat in that car, or in my case, the subway train, and I've come to understand after sitting in a lot of metaphorical cars that the reason this conversation is so hard isn't the reason you think.
It's something else entirely, and until you see what it actually is, you're going to keep sitting in that car.
Today, we're talking about the feedback conversation nobody wants to have, and what you actually have to do when it's your turn to have it.