Why Difficult Conversations Get Harder the Longer Managers Wait

"I've never done this before"

Often I'm brought into an organization to help leaders have a difficult conversation. It is eye opening when a CEO sits down across from you and says, "I've never done this before."

That sentence explains a lot. Most leaders and managers are expected to hold hard conversations without ever having been shown how, and without much practice at the smaller versions that come first. So the first time many of them do it, the stakes are already high.

A cultural fit conversation, worked step by step

My first big task in one of my roles was to coach a manager through a difficult conversation. The person "wasn't the right cultural fit," which, as we all know, is very hard to make objective.

So I sat down with the SVP and we worked through the steps together: documentation, separating emotion from fact, and mapping out the conversation that ultimately needed to happen. Then I made her wait, until she could make an objective determination about the person's capability and capacity to be successful in the organization.

Sometimes you don't have that luxury. We were pretty clear on our rule of "no assholes," but that didn't mean we skipped the process. A clear rule about behavior still needs the same documentation and the same honest look at what was actually observed.

Why managers wait

Most managers do have the difficult conversation eventually. They have it after the situation has become a problem, after the team has noticed, and after the founder has started to wonder whether it will sort itself out. By then the conversation carries more weight than it needed to.

The usual explanation for the delay is that managers avoid conflict. Some do, but in the situations I get pulled into, the cause is more often simpler. Feedback was never part of the team's regular routine. When it only comes up at appraisals, probation reviews, or after something has gone wrong, everyone treats it as an event. People get nervous before an event, and that includes the manager.

So the manager puts it off. Over time the conversation picks up a lot of ceremony. It needs documentation, a private room, and a good moment, and nobody decided that on purpose. Waiting makes it heavier, and what would have taken a few minutes early on becomes a difficult conversation later.

Short, specific, timely conversations

The conversations I help managers prepare for are usually the big ones, with a lot of emotion and a lot at stake. Often the conversation that would have helped was a much smaller one, months earlier, when the issue was still a pattern someone had noticed on a Tuesday morning.

What I encourage is a habit of short conversations. Tell the person what you noticed this week and what you'd like to see instead. It takes a couple of minutes and doesn't need an agenda or anyone from HR in the room.

Small conversations held regularly are the skill I would build first, because they mean far fewer difficult ones later.

What to try

A few steps help a manager start earlier:

1. Say what you noticed this week, while it is still small, and say what you would like to see instead.
2. Keep it to a couple of minutes, and keep it separate from reviews and formal check-ins.
3. When a larger conversation is needed, do the preparation: write down what you observed, separate observation from opinion, and map out what you want to say before you say it.
4. If you are coaching a manager through one, ask them to show you the facts they have before they decide.

If your managers only raise performance issues once they are unavoidable, it is worth asking whether anyone has ever shown them that earlier is easier. Who on your team could use that example from you this week?