Examples of Tough Conversations: Joe Rogan and Sheryl Sandberg

I’m always searching for examples of tough conversations. I recently came across examples from Joe Rogan and Sheryl Sandberg, which I’ve featured here.

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Difficult Conversation between Joe Rogan & Brendan Schaub

Joe Rogan critiques Brendan Schaub, a UFC fighter on his performance. It shows that one can be frank as long as the intent is good. Here’s the transcript:

ROGAN: A lot of things looked bad about the fight…. You looked very stiff. You didn’t look fluid…. You didn’t look like you were well prepared…. Your movement just didn’t look like an elite fighter’s movement.

I worry about your commitment to fighting, and I worry about where you stand.

SCHAUB: Really? I disagree.

ROGAN: The reality of your skillset, where you’re at now. I don’t see you beating the elite guys. If you had a wrestling match with Cain Velasquez, how well do you think you’d do? I think people would be surprised. I think you’d be surprised. I really do. I think he’d f—k you up…. There’s a bridge between you and the best guys in the world. And I don’t know if you can cross that bridge. That’s the reality of life.

I worry more about you than I do about them…. What I’m saying, I say with love. A hundred percent. I’m not saying this to hurt your feelings. That’s the last thing I want to do. If I didn’t love you, I wouldn’t be willing to do this. And I wouldn’t want to do this.

Difficult Conversation between Kim Scott & Sheryl Sandberg

Kim Scott made a big presentation to Google’s CEO. Afterward, her boss Sheryl Sandberg gave her some direct feedback.

While some hail Sandberg for having radical candor, most would say the phrase “makes you sound stupid” comes across as insulting, even though Scott did not take it negatively.

SANDBERG: But you said um a lot.

SCOTT: Oh, no big deal. I know, I do that. But who cared if I said um when I had the tiger by the tail?

SANDBERG: You know, Kim, I can tell I'm not really getting through to you. I'm going to have to be clearer here. When you say um every third word, it makes you sound stupid.

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