The Conversation You're Avoiding Is Simpler Than You've Made It
I coach a CEO who has a hard conversation waiting for him. Someone on his team is struggling. He respects them and wants to help them grow. It’s time to give feedback, but he can’t start the conversation. He’s worried he’ll sound like the bad guy, they’ll shut down, and worst-case scenario, leave.
Giving feedback isn’t hard because of what you have to tell the person. If your head of finance has missed three deadlines in a row, he knows it too. It’s hard because of what you've decided it means about them.
For most of us, our worth is entangled in the company’s success. When we aren’t doing our best work, the setbacks feel personal and huge. There’s no way to contain that belief. If you think your work is a reflection of who you are, that’s how you’ll see other people’s work too.
When it's time to talk to your head of finance about those three missed deadlines, you're afraid he’ll take your feedback as a verdict on him because, frankly, for you it is.
I’m positive that you know that isn’t true. If I asked, you would tell me someone’s mistakes have no bearing on their value. But if you talk to yourself that way, the habit of mind is strong. Untangling that thinking takes dedicated work. It’s worth it, it will change the way you build and lead, but it won’t happen in a week.
In the meantime, you’re still going to have to have those hard conversations, and they don’t have to be impossible.
The CEO I mentioned earlier isn’t conflict avoidant. He can comfortably debate a design decision, a roadmap, a budget. He only struggles when the conversation moves from the work to the person. Because that’s when he moves from making observations to making judgments.
An observation is a fact: he missed three deadlines. The judgment is whatever story you build on top of those observations: he missed three deadlines becomes he's always missing deadlines. That turns into he's checked out, he’s bad at his job, or he’s not right for the role.
A judgment isn’t necessarily wrong. Say you hire a new salesperson, and in the first month, at least twice a week, she asks you something she could have easily looked up. That’s the observation. The judgment might be, this person can’t operate alone. That may very well be true. And you might not have the time to teach her, or maybe you just don’t want to, so you fire her.
Judgments prompt judgment calls. That’s part of the job. But if you’re giving feedback, it means you’re not at that point yet. As long as you’re trying to help someone succeed in their current role, the judgment won't serve you or them.
When you lead with “here’s what I believe about you,” you immediately put the other person on the defensive. Either they’ll push back on your belief or capitulate and promise to do better. But what’s actually going on and how it can be addressed, there’s no room for those questions in a judgment based conversation.
You can’t turn off your judgment, but you can walk it back.
Before the next time you give feedback, write down your judgment in its most dramatic form. Then walk it back. Ask what you actually saw that led you there. Keep going until you’re standing on the simplest facts. Then write down what you need to happen. What would it look like if this wasn’t a problem anymore? And what are your limitations in getting there?
When you have the conversation, ground it in those facts. It might sound like this: “I see how hard you’re trying, and I’m observing that the last three quarters got planned in a scramble. We need a planning rhythm the team can run without you personally holding it up. I’m wondering what I can do to help. My limitations are that my time has to stay on product this year.”
You can offer an idea or two as a starting point and ask them what ideas they have that you haven’t thought of.
Feedback doesn’t have to be more personal than a conversation about a budget decision: here’s what’s happening, here’s our goal, how do we get from here to there.
Of course, this doesn’t take the emotion out of it entirely, but it tempers it. If you go in with “here’s what I believe about you,” they have to defend. If you go in with “here’s what I’ve observed,” they may write their own story about what that means about them, but it’s not being fed by yours.
None of this means you’re softening the feedback, it’s quite the opposite. Leaders who can’t give honest feedback are usually those most attached to the idea that a work mistake is somehow personal. Grounding in observations is saying: I’m going to treat you like a whole human by not pretending you’re doing great, because pretending is insulting.
The most generous thing you can do for someone who works for you is to tell them what you observe, not what you believe about them. It’s also the most generous thing you can do for your business.
If your feedback comes out as a belief about how things already are, you'll never find out how they actually are. Your head of finance knows things about those missed deadlines that you don't. Maybe priorities changed and nobody told him. Maybe he's been covering for someone else. If you lead with observations, you get an honest look at your company.
You also set yourself up to create real solutions. Judgments are vague, which makes the problem itself amorphous and hard to solve. It’s much easier to solve “he missed three deadlines” than “he’s bad at his job.” The faster you solve the problem, the better for them, you, and the company.
Your discernment is one of your most valuable skills. It absolutely has a place. But useful feedback starts with what you saw, not what you concluded.
What feedback have you been hesitating to give? How does it feel to imagine delivering just the observations, without your interpretation?
-Christine
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