Why Leaders Put Off Tough Conversations

Addressing challenging employee feedback with clarity and empathy.

The Chartered Management Institute found that 57 percent of people would do almost anything to avoid a difficult conversation. Not some people. Not just new managers. Most of us.

We usually explain that away by saying the conversation is hard on the person hearing it. And it is. Nobody enjoys being told they are falling short. But that is not why we put these conversations off for weeks. We delay them because they are hard to deliver. Most of us do not like conflict, and almost nobody wants to be the person who says that someone is not doing well. The difficulty is not only in the message. It is hard on everyone, and we tend to avoid feeling or causing any level of pain.

So we find reasons to wait. The person is nice. They usually do good work. We are worried they will quit. It was just one mistake. Each of those feels reasonable in the moment, and each one makes the conversation harder the longer it sits.

When the person is nice and usually does good work

This is the version leaders tend to put off the longest. The behavior is real, but the person is pleasant, generally solid, and someone you like working with. Spending goodwill on a seemingly small issue feels like it could damage the relationship, so you wait for a better moment. The better moment rarely comes.

Two things usually bring the issue back to the forefront. The first is seeing someone else react. You catch a wince, a head shake, or somebody going quiet. That tells you the behavior is not only bothering you. It also tells you that the people affected by it may be noticing it, but not reporting it. They are protecting the person for the same reason you are, or they just don't want to be seen as someone who "tells on peers." Either way, the problem is growing where you cannot see it.

The second is less comfortable to admit. Sometimes a leader finally moves because the issue is about to escalate past them. You know something that was said is going to come up somewhere else, and you realize there is a big difference between telling your boss that you saw a problem and are addressing it, and having your boss or HR ask why it has been going on for months.

If that is where you are, you are already late. Have the conversation with the individual, then go to your boss or HR yourself. Be honest about the situation: an issue came up, it went on longer than it should have, you are addressing it, you have documented it, and you wanted them to be aware. That is ownership and leadership, even if it isn't fun. Tough conversations do not get easier on any side of the equation when you wait.

If you are afraid they will quit

This fear is real, but it is usually misplaced. Good people do not generally quit because they received honest feedback about a problem they already suspected was there. They quit because of how they were treated. If you are respectful, specific, and clear about why the issue matters, the odds of losing someone over one conversation are low.

It helps to separate the person from the behavior. You should not tell someone they are doing great work while coaching them on the same work, because they will not believe you and you will muddy the message. You can tell them that you think they are capable, that you are confident they can handle this, and that the behavior needs to change. That is different from making the conversation a verdict on who they are.

You can also be direct about consequences while showing genuine concern. For example, "I know this was a one-time thing, and I don't expect it to happen again. But I need you to understand that there are consequences if it does, and I'm telling you that because I don't want anything bad to happen to you."

If you have a respectful, honest conversation and the person quits over it, that tells you something about the situation. It will not feel good, and replacing them will not be easy, but you still had the conversation you needed to have. You will usually get a sense of what comes next during the conversation itself. If they fight the facts, dispute everything, or become upset rather than curious, they may not quit that day, but you should start thinking about what you will do if the behavior does not change.

There is one more question worth asking yourself: "Am I avoiding this conversation because I do not have a plan for replacing this person?" If the answer is yes, you have a succession planning gap, and it needs attention whether this conversation happens or not. Nobody wants to lose good people, but you cannot lead from that fear.

The cost of looking the other way

When someone makes a real mistake, they usually know it. They are expecting to hear from you. When you say nothing, they notice that too. You lose some credibility, they lose a little trust in you, and you quietly begin to show where your line actually is (or isn't). Someone else watching may decide it is worth testing for themselves, and one overlooked mistake becomes the new floor for everyone else.

The conversations about a clear, one-time mistake the person already knows about are often among the easier ones. Half the work is done because they know what happened. It still requires a conversation. A quick, direct conversation is usually more respectful than leaving someone to guess whether you saw it, whether it matters, or whether the standard applies to them.

How to start when you have already waited

If you have already let something sit, you do not have to pretend otherwise. Dan Rockwell at Leadership Freak has written about opening sentences for tough conversations. He offers several, including, "I need to discuss something difficult because our relationship matters to me." The one I like most is simpler: "There's something important I've been avoiding."

I like that opening because it closes the time gap before the other person has to point it out. Think about how these conversations usually start. You walk in and say you noticed something, but the something happened three weeks ago. The person across the desk immediately starts wondering why you waited, whether this has been simmering for a while, and what else you have not said. You have handed them a way to avoid the issue before you have even made your point. Admitting the delay takes that off the table. It might sound like this:

"We need to have a conversation. Something has been on my mind for a while, and I should have brought it up sooner. I didn't, and that's on me. But it matters enough that we'll discuss it today."

Then keep going. Name what you saw and when it happened. Explain how it affected you, someone else, or the business. Be clear about what needs to change and what cannot happen again.

That opening does not make the message soft. You still have to say that the behavior was not acceptable and that it could become serious. Even with a good opening line, you are still having the difficult conversation, so do not treat the opening as a way around that part. Brené Brown says it well: "Clear is kind. Unclear is unkind."

What makes these conversations tough

Tough conversations are tough because someone has to choose to have them, and that someone is usually you. Nobody is going to assign the conversation at exactly the right moment. The behavior will not announce that it is time. There is no version where the timing feels perfect.

That doesn't mean the conversation has to be terrible. You can be clear about expectations and consequences without damaging the relationship. In many cases, being straight with someone about something they already half-know is the most respectful option you have. And as much as I have always hated these discussions, more often than not they turned out to be far easier than I expected. The waiting was usually the worst part.

Next week, I'll cover what happens once you are in the room: why the same feedback can be heard two very different ways, and how to make sure the person hears what you actually mean.

What conversation have you been putting off, and what is really keeping you from having it?

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