Dear Crucial Skills,

How can I respond when staff bring me a “Crucial Conversation” that turns into unproductive venting about work issues—some of which are within my control, and others that are not? Is there a way to redirect those conversations so they’re more constructive?

Signed,
Dumped On

Dear Dumped On,

We call these drive-bys—those moments when people swing by a boss’s office or a teammate’s desk and vent their frustrations about someone else. Instead of talking to the person they have a concern with, they do these drive-by venting sessions.

Drive-bys can be incredibly damaging. They reinforce people’s negative stories. As they vent, they rehearse their frustrations, which makes them feel more justified and more locked into their point of view. And because they’ve “let off steam,” they often feel like they’ve done something productive. In reality, they’ve just complained to a third party. The real conversation never happens. The problem doesn’t get addressed. And over time, the complaint often becomes a self-fulfilling prophecy.

So the first idea is this: you want to discourage drive-bys. They rarely solve the problem, and they never involve the person who needs to be part of the conversation.

And the second idea is equally important: you want to encourage talk-throughs. When someone comes to you with a concern and starts venting, instead of shutting them down, redirect them.

Start by asking, “Have you had the conversation with ____?” If the answer is yes, get curious. “How did it go? What didn’t work? Why do you think it didn’t land well?” At that point, you can begin to help facilitate the next conversation.

Most of the time, the answer to “Have you talked about it” is going to be no. When that happens, simply ask, “What’s holding you back?” And I know this might sound a little cheesy or awkward, but it’s exactly what leaders should do in this moment. Say something like, “If you’re open to it, let’s role-play this for a few minutes. Tell me what you want to say, and I’ll pretend to be the other person.”

Then coach. Help your team member think through how to approach the conversation. You might point out what they’re doing well and where they can try something different. Most leaders don’t do this. Instead, they lecture—“You should say this, this, and this. Good luck.” Or they don’t provide aid—“If you haven’t had the conversation, go have it,”—and leave it at that.

It’s good to set that expectation, but if you don’t provide coaching or support it can be deflating rather than productive.

The next idea is about control. As you pointed out, some of the things people vent about are within your/their control, and some aren’t.

I’ve always loved what Stephen R. Covey said. “Proactive people […] work on the things they can do something about. The nature of their energy is positive, enlarging and magnifying […] Reactive people, on the other hand, focus on […] the weakness of other people, the problems in the environment, and circumstances over which they have no control. Their focus results in blaming and accusing attitudes, reactive language, and increased feelings of victimization.”

As a leader, it can be incredibly helpful to coach people through that distinction. Often, the only thing they truly control is their own response.

What we teach in Crucial Conversations is that our emotions are less about what other people are doing and more about the story we’re telling ourselves about what they’re doing. That story drives our emotion. So your job as the boss is to set the example. When things go wrong, don’t perpetuate negative stories. Help people consider a different story.

You might ask questions like:

• “If we assume this person is reasonable and rational, why might they be doing what they’re doing?”
• “What part of this situation do you actually have influence or control over?”
• “What could you do differently next time to improve the outcome?”

Ultimately, as a leader, it’s not if you’ll face these moments—it’s when. And when you do, you have to set clear expectations.

You can say, “I’m not going to play along with venting—not because I don’t care, but because it’s not actually helpful. Me joining in would do more harm than good.” Then redirect, reframe, and coach.

When you do this consistently, you’ll probably see fewer drive-bys—and more people coming back to you saying, “I actually had that conversation… and it went a lot better than I thought.”

Warmly,
Justin