Tough Conversations Don’t Have to Be Tough

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Last week, Art Petty interviewed me as part of his First-Time Managers Academy. I took questions from the participants. One asked for advice about a tough conversation he needed to have with one of his team members.

I responded as I always do to those questions with some techniques that have worked for me and the people I’ve trained. One of the most powerful is simply not using adjectives when you describe behavior or performance.

Those are good techniques. And they help. But techniques are only the above-the-water part of the iceberg.

Tough Conversations Don’t Have to Be Tough

If you want to have fewer and less-scary tough conversations, go upstream and do the things that make it all easier. What’s most important is what you do in the days and weeks and months leading up to the conversation, not tips, tricks, or hacks. That starts with touching base and having conversations.

Touch Base and Have Conversations

We’ve all heard about seagull managers. They’re the ones who swoop in, make a lot of noise, dump on everybody, and swoop out. That’s exactly the kind of boss you don’t want to be.

When you touch base a lot, you become part of the normal landscape of work for the people on your team. Otherwise, they’ve learned from bosses past that, when the boss shows up, it’s probably not good.

How do you head this off? Besides showing up, you must have conversations. These are real, adult conversations where everybody talks, and everybody listens. You will have some conversations about work. But most of the conversations in the workplace are about other things. A little bit of work and a lot of a kid’s soccer game. A little bit of work and an upcoming family reunion. A little bit of work and a lot of life.

Those conversations build relationships and trust. Those relationships and trust take a lot of the scary and tough out of tough conversations.

Touching base a lot and having conversations establish the human bond between you and your team members. But your work in heading off tough conversations doesn’t stop there. You must do your jobs.

Help the Team and Team Member Succeed

If you’re a boss, you have two jobs. One is to accomplish the mission through the group. The other is to help individual team members succeed. You need to have regular conversations with them about their goals and their growth. This is the coaching part of your job, and it’s vital.

It’s also your job to create psychological safety on your team. People should be able to share ideas, suggestions, and gripes. They should be able to disagree with you and other team members without suffering bad consequences. You should treat everyone fairly and consistently.


Tough conversations don’t have to be tough.

Touch base a lot. Have conversations.

Help the team member succeed.

Create psychological safety all around.

Act fairly and consistently.

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