You Can't Manage What You Don't Mention: Why Leaders Must Have Difficult Conversations

Meta Description: Learn why avoiding difficult conversations undermines leadership effectiveness. Discover how regular coaching conversations prevent toxic culture and employee surprises.

Key Takeaway: Effective leadership requires consistent, direct feedback. When leaders avoid uncomfortable conversations to be "nice," they're not protecting employees—they're setting them up to fail. Small coaching moments prevent big cultural problems.

There's a quote often misattributed to Peter Drucker that you've probably heard a thousand times: "You can't manage what you can't measure." It shows up in boardrooms, on motivational posters, in LinkedIn posts with sunrises in the background. The only problem? According to the Drucker Institute, he never said it. And honestly, the sentiment is actually wrong anyway.

In fact, Drucker said something closer to the opposite. In The Effective Executive, he wrote: "Moreover, because knowledge work cannot be measured the way manual work can, one cannot tell a knowledge worker in a few simple words whether he is doing the right job and how well he is doing it." Which is a completely different vibe from the tidy maxim we love to repeat.

But here's the thing. There's a variation on that phrase that I think is absolutely true for those of us in leadership and HR: You can't manage what you don't mention.

And what I mean by that is this: if you're not willing to have awkward, uncomfortable, sometimes a little painful conversations with the people you lead, you're not actually managing them. You're hoping they'll figure it out on their own. You're crossing your fingers that the problem will resolve itself. You're being nice instead of being honest. And those two things are not the same.

Coaching Isn't Just for the Big Moments

Think about a basketball coach for a second. They're not just diagramming plays on a whiteboard or calling timeouts during the final two minutes of a close game. They're constantly adjusting. Shot mechanics, hip placement, foot positioning, where your eyes are on the court. They're watching for the small things that add up to being a phenomenal player. And they're saying something in the moment, not six months later during an annual review.

That's what real coaching looks like. It's not a once-a-year performance evaluation. It's a steady rhythm of small, specific, timely feedback. And when you make it a habit, it stops feeling awkward. It becomes normal. Expected. Even welcomed.

But when you avoid those small moments? When you let things slide because you don't want to rock the boat or because you're hoping the person will just "get it" eventually? You're not doing them a favor. You're setting them up to fail.

What Silence Actually Looks Like

I've seen this play out in so many ways. Sometimes it's obvious. Someone on the team has a communication style that grates on people. Maybe they use sarcasm like a weapon, not the clever, self-aware kind, but the kind that's really just meanness dressed up as a joke. And everyone knows it's a problem. You can feel it in the room. You hear about it in side conversations.

But no one says anything to the person. Because we don't want to hurt their feelings. Because we don't want to seem critical. Because maybe that's just "who they are."

Other times, the silence is more subtle, but just as damaging. I once worked with a guy who was seen as a leader on the team. In meetings, he'd lean back in his chair, throw his hands up like he was surrendering, and say things like, "Well, you guys know better than I do," or "You know, I don't have any formal training the way y'all do. I'm just a blue-collar guy who found his way into this job."

He was trying to be humble. Self-deprecating. Maybe even relatable.

But here's what actually happened: every time he did it, you could feel the energy deflate. People would glance at each other, then down at their notes. The silence that followed wasn't thoughtful. It was uncertain.

Because everybody in the group looked to him as a leader. And every time he undercut himself, he wasn't just undermining his own influence. He was throwing everyone else's judgment into question. If he didn't trust his own perspective, how could anyone else trust theirs? If the person we all look to for direction is saying he doesn't know what he's doing, maybe I'm wrong for thinking I know what I'm doing.

He didn't mean to do it. But he was eroding the team's confidence with every self-deprecating comment. And the culture suffered for it.

No one ever said anything to him. Not once.

In both cases, the issue isn't just what happened. It's what didn't happen. The conversation that never took place. The feedback that was never given. The moment of coaching that could have changed everything.

The Small Team Trap

If you're leading a smaller team, I know what you're thinking right now. Your team isn't as big as you wish it was. Everyone is stretched thin. And you think, "Maybe they're just having a bad day. Maybe things are going on at home. I don't want to make it worse."

But here's the thing: you can lead with that. You can say, "Hey, I know you might just be having a rough day, but I wanted to mention this." You can acknowledge the humanity of the moment and still coach through it.

This isn't about busting chops. This isn't about calling someone on the carpet or putting them on a performance improvement plan. This is about helping people grow. And if you're not willing to do that, you're not leading. You're managing by hope. Hope is not a strategy. Hope is what you do when you don't want to have the conversation. Hope is checking your email during a meeting because you're afraid of what you might see if you actually look someone in the eye.

You can't manage what you don't mention. And if you won't speak up when it matters, you're not protecting the person or the team. You're just postponing the reckoning.

The Wake-Up Call That Shouldn't Be a Surprise

William Vanderbloemen put it perfectly: "If firing an employee takes him or her by surprise, you have failed as a leader."

Read that again.

If someone is genuinely shocked when they're let go, it means you never gave them a fair shot. You never told them what was actually expected. You never pointed out where they were missing the mark. You let them believe everything was fine, right up until the moment you decided it wasn't.

Here's what's wild about that quote: it's not actually about protecting the employee. It's about protecting you. Because when you avoid those conversations, you're not just failing them. You're storing up your own guilt, resentment, and self-doubt. You're turning yourself into the kind of leader you never wanted to be.

And yes, firing someone is the extreme end of the spectrum. But this principle applies to everything that comes before that point, too. If your team culture is toxic, if people are constantly stepping on each other, if there's an undercurrent of resentment and frustration, it's not because you hired the wrong people. It's because you didn't coach the ones you have.

Small Conversations, Big Impact

Here's the good news: you don't have to blow up someone's world. You don't need a formal sit-down or a prepared script. Most of the time, it's the small, in-the-moment conversations that matter most. The ones that take thirty seconds. The ones that happen in the hallway.

"Hey, I noticed you cut Sarah off twice in that meeting. I don't think you meant to, but it came across as dismissive. Let's talk about how to make space for other voices."

"That joke you made earlier? It landed harder than you probably intended. Here's why."

"I know you're deferring to the group because you want to be collaborative, but the team needs you to lead. When you say 'you guys know better than I do,' it makes everyone second-guess themselves. You don't have to have all the answers, but you do have to step into the role."

These aren't performance improvement plans. They're not formal write-ups. They're just honest, direct, human feedback. And when you build a culture where these conversations happen regularly, they stop feeling like confrontations. They start feeling like what they actually are: coaching.

If you want to lead, you've got to coach. It's that simple.

This Applies Everywhere

The truth is, "you can't manage what you don't mention" isn't just a leadership principle. It's a life principle.

Think about your personal finances. If you and your spouse don't talk about money, you're not going to manage it well. It's always going to be a point of tension. If it's an off-limits topic or something you only discuss once a year (or once a month), you're setting yourself up for conflict. It needs to be an ongoing conversation.

Think about parenting. If you're trying to help your kids grow, but you don't address their behavior in the moment, how are they supposed to know what needs to change? You can't expect them to read your mind. You can't help them become who they were created to be if you won't talk to them about it.

Think about your health. If you don't have honest conversations with your doctor about what's going on with your body, you can't manage it well. You've got to be willing to speak up, even when it's uncomfortable.

The pattern is the same everywhere. Silence doesn't protect anyone. It just delays the conversation you're eventually going to have to have anyway. And by the time you finally get around to it, the damage is already done.

The Bottom Line

If you're avoiding difficult conversations because you want to be nice, you're confusing kindness with comfort. Real kindness is helping people grow. Real kindness is giving someone the information they need to succeed, even when it's uncomfortable to deliver.

You can't manage what you don't mention. And if you're not willing to lean into those awkward moments, you're not ready to lead.

So stop waiting. Stop hoping people will just figure it out. Stop letting "that's just who they are" be an excuse for behavior that's holding everyone back.

Say something. Coach in the moment. Be honest, be direct, and be human about it.

Because the alternative (silence, avoidance, and surprise) isn't kindness at all. It's just neglect in a nicer package.