I have spent more than 25 years training managers at companies like Pfizer, Deloitte and Amway, and if I had to name the one skill that separates managers who grow from managers who stall, it would be this: the willingness to have the conversation they are dreading.
Every manager has one. The team member who keeps missing deadlines. The high performer whose attitude is wearing everyone down. The person who talks over colleagues in every meeting. Managers know these conversations need to happen. Most of them just do not have them, or they wait so long that a small issue has grown into a serious one.
Here is what I have learned about why that happens, and what actually works.
The problem is not that managers lack the words. It is that they were never prepared for this part of the job. Most people get promoted into management because they were good at the work itself. They were strong engineers, strong salespeople, strong analysts. Then one day they are responsible for other people, and nobody teaches them how to tell a colleague, someone they may have worked beside for years, that something is not working.
So, they avoid it. And they tell themselves reasonable sounding stories while they do. “I will bring it up at the next review.” “Maybe it will resolve itself.” “I do not want to hurt the relationship.” I have heard every version of these in my workshops, and I have said a few of them myself earlier in my career.
The real cost of avoidance is not the issue itself. It is what the rest of the team learns while they watch. When a manager tolerates a problem for months, the team concludes that standards are negotiable and that the manager will not protect them from a difficult colleague. I have seen good people quit over exactly this, and in the exit interview it is never phrased as the real reason.
After years of coaching managers through these moments, here is what I tell them. None of this is complicated. It just requires doing it.
Have the conversation while it is still small. The best difficult conversation is a five-minute one, held early. When you address a missed deadline the first time it happens, the conversation is light. When you address it after the sixth time, you are no longer discussing a deadline. You are discussing a pattern, and the person will rightly ask why you said nothing for three months. Waiting does not make the conversation kinder. It makes it heavier.
Prepare one sentence, not a script. Managers often over-prepare. They rehearse a whole speech, and it falls apart the moment the other person responds. I coach people to prepare just the opening sentence, one that names the issue plainly. Something like: “I want to talk about the last two client reports, because both went out late and I need to understand what is happening.” That is it. Get the first sentence right and speak like a human being for the rest.
Describe what you observed, not who they are. There is a big difference between “You missed the last two deadlines” and “You are unreliable.” The first is a fact the person can respond to. The second is a verdict, and people defend themselves against verdicts. Every time a manager tells me a conversation blew up, we trace it back and almost always find a judgment where an observation should have been.
Ask a question, then actually stop talking. Somewhere in that conversation, ask what is getting in the way, and then be quiet. Silence feels uncomfortable, so managers rush to fill it, and they talk themselves right out of the point they came to make. Some of the most useful things I have ever learned about a performance problem came out after a silence I had to sit through. People need a moment before they tell you the truth.
End with one specific agreement. Not a vague commitment to do better, but one concrete step and a date to check in. “So, we agree the draft comes to me by Thursday, and we will talk again next Friday to see how it went.” Without that, the conversation evaporates by the next morning, and you will be having it again in a month.
One last thing, and I believe this is the part most organizations get wrong. Handling difficult conversations is a skill, and skills are built through practice, not through reading about them. Nobody becomes good at this by attending a lecture. In my experience, managers improve when they practice these conversations out loud, in a safe setting, and get honest feedback before the real moment arrives. The managers I have watched transform over the years were not the naturally confrontational ones. They were ordinary, conflict-averse people who practiced until the conversation stopped feeling like a threat.
The conversation you are avoiding is rarely as bad as the one playing in your head. In most cases, the other person already knows something is off, and they are waiting to see whether you will be honest with them. Being honest, early and with respect, is not the hard part of managing people. It is the job itself.
Shawn Snyder is the founder of Leadership Edge Live, a Phoenix-based leadership development firm. Over 25 years he has led leadership and change programs for organizations that include Pfizer, Deloitte, Amway and the U.S. Department of Defense. He is hosting LEAP 2026, a one-day leadership workshop in Phoenix on September 16, with 100% of program profits going to March of Dimes.
