158. How to Respond to Difficult People at Work (Without Getting Emotional) with Dr. Kate Mason
Secrets of the Career Game
October 19, 2026
Being right at work doesn't mean you're winning the room. Here's how to build influence without damaging trust. You can have the strongest argument in the room and still walk away having damaged your professional relationships.
Speakers Kendall Berg, Kate Mason
Kendall Berg (0:00)
I got the feedback at one point that like, hey, you are always right, you're great at your job, nobody likes to work with you. I was so focused on being right, on winning the argument, that I wasn't focused on winning the room. And I love that re-positioning for your mind of like, this is actually very important as to be liked.
Kate Mason (0:21)
Oftentimes, you mistake winning the argument or being right with winning the room.
And actually, you always have to do both. You can't just win an argument or just be right. It's not enough, because you can be as right as you want, but you can be on an island in that executive room. Kendall, you're great, but people don't like working with you. It's not gonna be the thing that gets you promoted or takes you to that next level if you are not demonstrating an ability to collaborate effectively and to be someone that people want on their team.
Kendall Berg (0:54)
Corporate life is a game, but no one hands you the rulebook.
Here on Secrets of the Career Game, we break down the unspoken norms and behind the scenes dynamics shaping your career today. I'm Kendall Berg, that career coach, and I guide professionals to grow, advance, and leave with clarity.
Each week, we explore the tools, habits, and conversations that build confidence, presence, and long-term momentum. Welcome, welcome back. We have an amazing guest today. We have Dr. Kate Mason with us. She is an executive communications coach, a world champion debater, of which hopefully we get into many debates today, healthy, constructive ones, of course. And she works with leaders at companies like Google, Netflix, Uber, and Microsoft to help them navigate that kind of tricky art of communicating while being female at work, right? And navigating these upper levels of leadership. She is a veteran of high-stakes Silicon Valley roles, and she brings unique perspective to leadership in her book Powerfully Likable, which we're really excited to jump into today. It's been called a game changer by Publishers Weekly. So Kate, thank you so much for taking time out of your day to chat with us. We're so excited.
Kate Mason (2:06)
Oh, thanks so much for having me, Kendall. It's a pleasure to be here.
Kendall Berg (2:09)
So why don't you tell us a little bit about your professional journey, right? Because if we look from today, we're in this position to help coach and get leaders upskilling in some of the major corporations across the country and the world. But what was your career journey like that ultimately led to what you do now?
Kate Mason (2:27)
It's such a funny question because at the time, it always felt like I was just following the thing that I loved, and it actually has been the thing that has brought me today, which sounds so cliche, and I'm somewhat embarrassed by that, but it's a path of joy. As you said, I started doing a ton of debate and really for a long time thought I would be a lawyer.
And so I studied law and then I realized halfway through that this is actually not where my heart lies. And I decided, well, I would be a professor. So I did my PhD thinking I would be a teacher. And you can see sort of certain threads coming through here. And then from there, I actually went into communications in tech companies. So I went to work at Google and at startups in San Francisco running communications functions. And at the end of all of that, kind of pulled together all of those threads as like almost lawyer, almost professor, and almost communications person to run my own communications consultancy. So it's a funny breed of like, oh, all these things did come together. But I'm not sure I should have or could have charted that path at the very beginning.
Kendall Berg (3:32)
I think it's so interesting. I worked with an executive years ago. And I feel like you'll appreciate the sentiment. And she did a speaking engagement at the company I was at, and she said that her career was accidental. She just kept doing the next job that she was really good at. And that got her closer and closer to ultimately where she ended up. And part of me hates that idea of what you didn't think ahead.
You didn't plan. You didn't have a strategy. And then I look at my own career, and I'm like, nah, nobody could have guessed that. So there's this combination of learning yourself really well and how that determines your career versus career planning. So I'd love to hear quickly before we kind of jump into our planned conversation. For you, at the time we never see the common threads, right? We're just doing the next thing. But what was that moment where you looked back and you were like, ah, this was the plan, even though it wasn't the plan, it got me to the place where like all of this makes sense. What was that kind of moment for you?
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