156. Why Your Boss Gives You More Work—but Not a Promotion with Maya Grossman

Maya Grossman (0:00)

I have always been the kind of person who goes all in and works really hard to prove themselves, but at some point, I got stuck. I was doing all the right things, I was executing, I was hands down the hardest worker, and yet other people were getting promoted, and it drove me crazy. People think they get promoted based on their past. No, you get promoted on what you can do in the future. So that's the story you need to sell. It's not about doing more work, it's about showing the right signals, because until you convince yourself, especially us high achievers who take so much pride in doing more, it's actually going to be hard to let go. So I think that's the first step. But then you need to understand, what does executive material actually mean? What does it look like?

Kendall Berg (0:42)

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 lead with clarity.

Each week, we explore the tools, habits, and conversations that build confidence, presence, and long-term momentum. Guys, buckle up for an exciting episode today. It has been a long time coming, and we have Maya Grossman on the podcast. So Maya has been an executive herself. She's a two-time VP of marketing. She grew up in companies like Microsoft and Google, and now she is an executive coach who you guys will appreciate. We think very similarly about a lot of things. We're going to have a wonderful chat about how to get promoted without burning out and what that upward trajectory really looks like. But Maya, thank you so much for coming on the show.

Maya Grossman (1:39)

Thank you so much for having me. We were just kidding before we started recording that we are so aligned, and we're such big fans of each other's work. So I'm excited for today. We are going to show people what it really takes.

Kendall Berg (1:53)

Yeah, I love this.

The name of the pod is the Secrets of the Career Game, and the Career Game does exist. Otherwise, you guys wouldn't be listening to my show if you didn't agree. So Maya, why don't you tell people a little bit about your backstory? Because you had an interesting career journey yourself that ultimately culminated in the coaching that you do now. So I'd love to get listeners up to speed.

Maya Grossman (2:13)

If you look at the highlight reel, you can see that I was a VP for two different companies. One of them was worth half a billion dollars. So yay, amazing, that's the dream. But what most people don't really see is how we got there. And the 17, yes 17, I counted them, rejections that I had to go through on the way to getting there. Because like a lot of the people listening, I consider myself a high achiever. I have always been the kind of person who goes all in and works really hard to prove themselves. But at some point, I got stuck. I was doing all the right things. I was executing. I was hands down the hardest worker. And yet, other people were getting promoted. And it drove me crazy.

And I had to figure out what I was doing wrong. And for me, it took a long time, a lot of pain, right? Seeing other people get promoted ahead of me. But then I asked myself the right questions. And I actually ended up doing something I wish I did 10 years sooner. So anyone who's listening, if you're even close to being stuck, do this now.

I went ahead and I interviewed other executives. Not just people at my company. I literally reached out on LinkedIn to complete strangers, especially VPs, because I wanted to know what they had that I didn't. And through that experiment, I actually realized, hey, this is what it actually takes to become an executive. It's not the more hours you thought it was. I completely flipped the script. I changed what I was focusing on. And within just a couple of months, got the director promotion I really wanted. And a few years later, the first VB role. But that time, I didn't have to go through 17 rejections. I literally had two offers after a couple of interviews.

And that's what I do today. I teach people how to make this shift so that they can actually keep growing their careers.

Kendall Berg (4:00)

I love it. Maya and I lived the same life in a different font.