What’s the biggest mistake a leader can make that weakens their influence? When someone asks me that, I don’t have to think very long. It’s avoiding confrontation. It’s the leader who is unwilling to say the thing that needs to be said.
Most of us could name the conversation we’re putting off right now. Maybe it’s a team member whose deadlines keep slipping, or a strong performer who treats everyone else like they’re in the way. Difficult conversations at work don’t disappear when we ignore them. Let’s look at why leaders wait, what the waiting really costs, and how to have hard conversations sooner.
The Biggest Mistake a Leader Can Make
In the video I say there is nothing that will reduce your value in a leadership role faster than being unwilling to say what needs to be said. I mean that. You can be smart and well liked and still lose your team’s confidence if they watch you look the other way.
Influence grows when people believe you’ll act on what you see. I’ve written before about growing your personal influence as a leader, and this is the piece that rarely makes anyone’s list. It’s whether people can count on you to handle the hard things.
What Counts as a Difficult Conversation at Work?
A difficult conversation at work is any conversation where the stakes feel high, the other person may not like what you have to say, and you’d honestly rather skip it. For leaders, the most common ones look like this:
- Performance that dipped a while ago and hasn’t recovered
- Behavior that breaks a team norm, like showing up late, missing commitments, or being dismissive with colleagues
- A boundary someone keeps crossing
- Telling someone that a role, project, or promotion isn’t going to work out
- Disagreeing with a peer, or with your own boss, about a decision
Research from VitalSmarts, the company behind the book Crucial Conversations, found the same patterns. In a 2016 study of 1,025 people, 72 percent reported times when they or others failed to speak up effectively about a peer who wasn’t pulling their weight. Sixty eight percent reported a failure to address disrespect.
Why Leaders Avoid Hard Conversations
If you’ve been avoiding one, you’re in good company. A 2016 Interact survey conducted by Harris Poll, written up by Lou Solomon in Harvard Business Review, found that 69 percent of managers said they’re often uncomfortable communicating with employees. More than a third, 37 percent, said they’re uncomfortable giving direct feedback about performance if they think the employee might respond negatively.
The reasons leaders give for waiting are pretty human. “I don’t want to hurt their feelings.” “They’re going through a lot right now.” “What if it turns into a fight?” Each has some truth in it, and caring about how someone feels is one of your better qualities. The trouble is that every one of those reasons quietly assumes the issue will shrink with time. It almost never does.
Waiting It Out Never Works
We all do this. We walk around telling ourselves, “I’m going to wait it out. I’m going to see if it changes.” In the video I put it plainly: it never changes. It never gets better.
Here’s a test I’d offer you. You’ve never fired anybody and thought, “Wow, I didn’t wait long enough.” And you’ve never had a hard conversation with someone and walked away thinking, “I think I did that too soon.” We nearly always wait too long to have those conversations.
I made a similar point years ago in Great Leaders Don’t Fire Anyone. Very few people are let go too quickly, and most teams can name the person who should have heard the truth a long time ago.
Waiting also changes the conversation you eventually have. A problem raised in the first week is a small course correction. Raised six months later, it comes with a history, and the other person will reasonably ask, “Why didn’t you tell me sooner?”
The Collateral Damage on Your Team
Please don’t skip this part. When you avoid a hard conversation, the person you’re avoiding isn’t the only one affected. The collateral damage on the team is real, and you have to be really mindful of it.
Think about everyone else who is doing the right things. If you’re not willing to say what needs to be said, what are you telling the people who show up on time and do what they’re supposed to do? You’re telling them the standard is optional. You’re telling them the culture doesn’t matter. The very things that create safety and security on a team start to wear away, and they usually go quietly.
The VitalSmarts study put numbers to that cost. Half of the respondents said they had wasted seven days or more avoiding a crucial conversation, and they estimated the avoidance cost their organizations an average of $7,500 per conversation in lost time and resources. Instead of speaking up, people complained to others, did unnecessary work, and ruminated. They also described damage to morale, relationships, and the culture itself.
Boundaries Only Work When You Enforce Them
In the video I talk about creating boundaries and enforcing them. Most leaders are good at the first part. The second part is where things fall apart.
A boundary that’s never enforced is really just a suggestion. People learn the real rules of a team by watching what the leader does when someone crosses the line, not by reading what’s posted on the wall.
Clarity up front makes all of this easier. When expectations are specific, you’re simply talking about the gap between what was agreed and what happened. My post on holding people accountable without hovering over them walks through how to set that up, and so does an older piece on spotting where accountability leaks out of a team.
Ask What Your Silence Is Costing
One shift I find really useful comes from the VitalSmarts researchers. Most of us decide whether to speak up by weighing the risks of saying something. The people who are best at crucial conversations flip that around. They think first about the risks of not speaking up.
So before you talk yourself out of it one more time, ask:
- What happens to this person’s growth if no one tells them?
- What are the people doing it right learning from my silence?
- What will this cost us three months from now if nothing changes?
Answer those honestly and the conversation usually stops feeling optional.
How to Have Hard Conversations: Prepare First
Preparation doesn’t need to take an afternoon. Ten or fifteen focused minutes is usually enough. The Center for Creative Leadership’s five steps for tackling difficult conversations build on the book Difficult Conversations by Douglas Stone, Bruce Patton, and Sheila Heen, which says every difficult conversation is really three in one: what happened, how people feel, and what it means for each person’s identity. Here’s how I’d use that before you walk in:
- Get clear on what happened. Write down two or three specific examples. Specific beats general every time.
- Name your own feelings. Frustrated? Nervous? Knowing ahead of time keeps those feelings from leaking out sideways. My post on keeping emotions from making your decisions goes deeper here.
- Notice what feels threatened. Maybe you see yourself as the leader who is always supportive, and this feels like it puts that at risk. It doesn’t. Telling someone the truth is supportive.
- Decide what you want. CCL suggests asking, “What do I hope to accomplish by having this conversation?” If the honest answer is to prove a point, rethink it. If it’s to help the person and protect the team, you’re ready.
Say the Hard Part Early
A common mistake is the long warm up. Ten minutes of small talk and compliments, the other person relaxes, and then the real message lands as a surprise. Or it never quite lands at all.
Get to the point within the first minute. Something like: “I want to talk about how our client deadlines have been going, because I’m concerned and I think we can fix it together.” That’s honest, it’s kind, and it tells the person what the conversation is about. Lou Solomon’s advice in that HBR piece fits here: be direct but kind, and check your motives first.
If emotions are already running hot, slow down before you start. I cover that situation in my guide to feedback in a heated moment.
Listen Before You Decide What Happens Next
You’ve said the hard part. Now stop talking. The CCL steps put real weight on exploring their story as well as yours. You may learn about a workload problem or a misunderstanding that changes the next step, even if it doesn’t change the standard.
The questions you ask matter here. “Why did you do that?” puts people on the defensive almost immediately. “What got in the way?” or “How do you see it?” opens the door instead. There’s more on that in my post about swapping why questions for better ones.
End With a Clear Agreement
A hard conversation that ends with “Okay, thanks for listening” usually has to happen again. Before you wrap up, make sure you can both answer three things:
- What exactly is changing?
- By when?
- When will we check in on it?
Put that check in on the calendar before you leave the room, and then actually show up for it. If things got better, tell them. Recognition after a hard conversation is what makes the next one easier. Following through on the conversations you said you’d have is also a big part of earning trust with the people you lead.
Difficult Conversations With Peers and Your Boss
Not every hard conversation flows down the org chart. Sometimes the person who needs to hear it is a colleague, or the person you report to. The same principles apply: be specific, lead with your intent, and listen. You’re just relying on influence rather than authority.
When I need to push back on an idea in a meeting, I use a simple three part structure I shared in my post on speaking up without a big title. It helps you name what you agree with, raise your concern, and suggest a next step without turning the moment into a standoff.
Make Hard Conversations Smaller by Having Them Sooner
The more often you have honest conversations, the less difficult each one becomes. CCL says it well: difficult conversations often have to happen because better conversations didn’t.
When feedback is regular, nothing has time to pile up. A quick “That’s not quite what I was looking for, and here’s why” on a Tuesday is so much easier than a formal sit down three months later. That’s one reason I tell leaders not to go easy on new people. In Don’t Be So Nice to New Hires, I explain why holding back early coaching hurts the very people you’re trying to protect.
Back in 2014 I wrote that leaders who avoid tough conversations rarely get the best out of their people. I still believe it, and you can read the rest of that list in four things every team needs from its leader. If you’re building a team that can handle real candor, my post on how the best teams talk when the pressure rises is a good next read.
Have the Conversation This Week
Hard conversations protect culture. Avoiding them slowly erodes it. If there’s one you’ve been putting off, you already know which one it is. Put it on the calendar this week. Prepare for fifteen minutes, say the hard part early, listen, and leave with an agreement you both understand.
For a fun take on telling the truth from a completely different stage, listen to my Shift Out Loud episode with comedian Suzanne Westenhoefer on all out truth telling. And if you’re wondering what it’s like to work with me on skills like this one, you can read what other leaders have said on my testimonials page.
Frequently Asked Questions
What are difficult conversations at work?
Difficult conversations at work are conversations where the stakes feel high, emotions may run strong, and the other person might not like what you have to say. Common examples include addressing poor performance, talking about behavior that breaks team norms, enforcing a boundary, delivering news about a role or promotion, and disagreeing with a peer or a boss.
How do you have a hard conversation with an employee?
Prepare by writing down specific examples and deciding what you want the conversation to accomplish. Get to the point within the first minute, describe the gap between what was expected and what happened, and then listen to their side. End with a clear agreement on what will change, by when, and when you will check in.
Why do leaders avoid difficult conversations?
Most leaders avoid them because they don’t want to hurt feelings, they worry about a negative reaction, or they hope the problem will fix itself. A 2016 Interact survey by Harris Poll found that 69 percent of managers are often uncomfortable communicating with employees. Waiting rarely helps, because the problem usually grows and the rest of the team notices.
How do you prepare for a difficult conversation at work?
Sort out what happened using specific examples, name your own feelings so they don’t take over, notice what feels threatening to you personally, and decide what you hope to accomplish. Ten or fifteen focused minutes is usually enough. Plan your opening sentence so the real message comes early instead of after a long warm up.
What should you avoid in a difficult conversation?
Avoid long warm ups that bury the message, labels about someone’s character, and why questions such as “Why did you do that?” that put people on the defensive. Also avoid vague endings like “let’s keep an eye on it.” Be specific about what needs to change and when you will follow up together.
