Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik)

**Anneka Gupta** (0:00)
When people say, I want someone that's strategic, what they're really saying is, I want someone that can come up with and articulate a compelling and simple why behind the decisions and the direction of the company and product. So that's number one. And the second piece is, I want someone that's going to champion and be a change agent to do things that may be hard, but actually best for the long-term interest of the product or company. Even though those things are not going to be easy to execute on. And I think if you have one without the other, ultimately people are not going to see you as strategic.

**Lenny Rachitsky** (0:40)
Today my guest is Anneka Gupta. Anneka is Chief Product Officer at Rubrik, a lecturer on product management at Stanford University's Graduate School of Business, and on the board of Tinuiti. Previously, she was president, GM and head of product at LiveRamp, where she spent 11 years and joined as one of their earliest employees, a bunch of former guests recommended Anneka come on this podcast, and you will soon see why. In our conversation, Anneka shares a ton of powerful advice on navigating difficult personalities, giving and hearing hard feedback, bringing humor and gratitude to every situation, managing your energy versus managing your time, super tactical tips for how to become more strategic, and how to make better decisions, and also how to break into product management for people that are trying to become product managers. There's something in this episode for everyone, and I am excited for you to learn from Anneka. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Anneka Gupta.
Anneka, thank you so much for being here and welcome to the podcast.

**Anneka Gupta** (1:50)
Thanks for having me.

**Lenny Rachitsky** (1:52)
I want to start with a question that I've started to ask. Guests that come on the podcast that have had extraordinarily successful careers and also just consistently successful careers. Here's the question. What do you believe are one or two skills or mindsets or habits that you think most contributed to your success, that you think might be helpful for other people to learn and build to help them have more successful careers?

**Anneka Gupta** (2:18)
It's funny, before we kicked this off, you talked about the post-it that you have on your computer that says, have fun. And my one mindset that I really have leaned into after someone actually gave me advice on this is to figure out how to have fun in my job, even in the most difficult of times. And the reason why I say that is because when you're hit with really hard times, it's easy to operate from a mindset of scarcity and to look at everything as an unachievable hurdle to overcome.
And when I was able to switch my mindset and say, well, I'm actually going to figure out a way to have fun with this, it actually changed my entire approach for how to deal with super difficult situations. And this advice specifically came up to me when I had a scenario where I had to essentially change out all of my direct reports in very short order. And I figured that out. It was a super daunting situation. I didn't know how I was going to manage. And at first, I felt so scared by what was ahead of me and how much change I was going to have to go through in a very short period of time. But when I got this advice, I started to try to reframe my thinking. And it actually really made it so that I was able to get through that hard time and opened my mind up to so many more opportunities. So now I try to embody that in every situation that I come up, come across where I'm faced with something super, super challenging.

**Lenny Rachitsky** (3:45)
I love this advice. It's something that I've recently seen also in public speaking. If you can just reframe your thinking from, I'm scared of this to, this is going to be fun. I'm going to have so much fun doing this. It's going to be like this energy and anxiety and feeling is me feeling like it's going to be a lot of fun. So spending a little more time here, how do you actually do this? So in this case, you shared an example of you're basically have to fire a bunch of people, not something one can quickly think about how to have fun with that. How did you do this? Is it just in your mind? You're like, I'm going to have fun with this? Or is there something tactically people can do to make something fun?