The Manager’s Dilemma: How to Have Tough Conversations

by | Nov 3, 2020

Darcy Luoma is one of America’s most highly credentialed coaches. She’s worked in 48 industries, with more than 500 organizations, and has impacted tens of thousands of leaders and employees.

In a recent coaching session, my client Bob described a frustrating issue with one of his direct reports Eddie (both names changed to preserve confidentiality). When Eddie receives feedback or people disagree with him, he gets defensive. He stops listening to what’s being said and starts to explain why he did what he did.

Recently, Eddie’s defensive behavior reached an unacceptable level. He was defending his work to a customer—instead of listening to their feedback. Eddie’s other team members were able to clean up the mess, but word still got back to Bob that the customer wasn’t happy.

Bob knew he needed to talk to Eddie about his defensiveness—yet again. While Eddie does good work, Bob realized this pattern of behavior consistently gets in the way of doing his best work.

Bob’s dilemma: How do I have a conversation about his defensive behaviorwithout him getting defensive? 

The Frustration of Talking in Circles

How often do you spend time figuring out how to have a tough conversation? Maybe you’ve had the same conversation multiple times before and nothing’s changed. Or maybe you’re anticipating how the conversation will go, and it just doesn’t seem worth it. 

In Bob’s case, he was trying to figure out how to talk to Eddie about being defensive—without him getting defensive. But this is just one example. In recent weeks, I’ve had other clients trying to figure out:

  • How to create more engaged employees—with those who don’t want to be engaged.
  • How to reduce the number of political arguments—without getting into a political argument.
  • How to address when they shut down in certain conversations—without them shutting down.

Do you notice a pattern here? What could you add to the list? 

If you spend more time thinking about how to have conversations than actually having them, don’t worry. You’re not alone. If you’re going in circles—and you find yourself trying to figure out the right thing to say—it’s time for a new strategy. 

Talking About How You’re Talking

The next time you’re preparing for a tough conversation, look at the bigger picture. Consider instead talking about the pattern you’re noticing. This shifts the focus to naming the underlying issue, so you can have better conversations in the future.

In Bob’s case, he let go of trying to find the exact right thing to say that wouldn’t make Eddie defensive. Instead, he decided to ask Eddie how he likes to receive feedback. 

What Bob heard? Eddie doesn’t like being surprised. He’d rather have time to reflect and prepare a thoughtful response. When he gets feedback he needs to immediately respond to, he feels flustered and gets defensive. Eddie brought up the customer meeting on his own, saying he felt blindsided and embarrassed.

Everything was not resolved in that one conversation, however Bob was relieved to have something meaningful to work with now, instead of just talking in circles.

One-minute Workout

Over the next few weeks we’ll explore how you can have the courage, compassion, and curiosity to have conversations like Bob had with Eddie. In the meantime, try this one-minute Thoughtfully Fit workout.

PAUSE: When you notice you’re working hard to figure out the right thing to say, Pause. Stop the circling!

THINK: Instead of fretting about what you should say, ask yourself: What’s the larger issue here? What could I get curious about? How can I have a conversation about the pattern I’m noticing?

ACT: Commit to have a conversation about the larger issue.

Choosing to have a thoughtful conversation takes courage in the short term, but provides huge value in the long term.

And there’s good news! Just like with daily sit-ups, the more you do it the easier it gets.

P.S.– Not sure where to start? Take a look at for more information or to sign-up for our free November masterclass: A Thoughtfully Fit Communication Masterclass for Team Leaders.

Recommendation– I’ve had many friends recommend Untamed​ by Glennon Doyle​. So when I was in Barnes and Noble last week​ doing research for my book​, I​ ​picked​ it up. I expected to be disappointed—as I usually am when something comes highly recommended. I wasn’t. As a matter of fact, I spent the whole weekend reading it. It touched me deeply​,​ and I’m still trying to figure out what it is stirring in me. Stay tuned as it unfolds. There is certainly more clarity and magic on the other side. But also some heart wrenching self-reflection.

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