Leader Spotlight: Energizing your leadership style, with Navya Rehani Gupta

Navya Rehani Gupta is Chief Product Officer at Peek, a SaaS company in the travel vertical with more than $1 billion in annual bookings and serving 10 million customers. She began her career as a PM for private wealth management (PWM) technology at Goldman Sachs, where she worked for five years before being promoted to Vice President. Navya then took a product lead role at Disney Interactive before transitioning to tech, where she held various product and leadership positions at Uber and StyleSeat. She has been at Peek for seven years and helped them earn the #1 spot in G2 for tour operator software.

In our conversation, Navya talks about her three main pointers for mastering the art of zooming in and zooming out: making room to zoom, having conversations about conversations, and knowing when and how to flex. She discusses the importance of making strategy fun, memorable, and unique to your culture and product to get people to rally behind it. Navya also shares her technique of holding her own personal retrospectives to uncover areas she may have overlooked.

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Learning to get out of the way

You've had a lot of experience with scaling product teams — in some cases by 4x. Scaling in periods of hypergrowth presents significant leadership challenges. Could you talk about the approaches that you employ to keep your team energized and motivated during those times?

I think about it in three ways: you have to focus on your product, on the processes, and on your people. On the product side, leaders have to learn to get out of the way. You have to trust that your team will make the right decisions. It's not your job to make decisions about the product, but it is your job to orient your team and verify their recommendations. When I was a junior product manager for many years, I was handed my roadmap by senior management, which helped me build my execution chops. But when I came to Peek and I was building my own process, it was important for me to build a product that was moving in the direction that was decided by an empowered team.

On the process side, be really obsessed with the impact and the outcomes that your team is making. The process can evolve over time. I always tell my team that we shouldn't be celebrating launches of features. We have a process where we set upfront a target goal that every product line and feature is looking to achieve. We do whatever it takes to get to that goal. Keep the process fluid but focus on the outcomes.

Thirdly, people always come first. In a remote environment, it is especially important to keep the team motivated. As a leader, always keep your door open so that people can reach out to you. They should feel confident and safe to give you feedback. Feedback is a gift, and if you embrace that, then you'll notice that the team is driving the best outcomes because they're empowered to make decisions and know their feedback will be heard and acted on. They’ll be focused on the impact that they're driving. They’ll know that it's okay to make mistakes and to be the person who says things aren't working.

Was learning to get out of the way a hard lesson for you? I imagine it would be difficult for many people who are used to being in the weeds and then take on a leadership role.

I would say I've seen a lot of people struggle with that. Personally, I didn't because I was very fortunate that I went through leadership and management classes at Goldman Sachs during the early stage of my career. They have a unique culture where they really invest in management training. I learned a lot of things the right way early on in my career, which I continue to carry with me.

How to effectively zoom in and zoom out

One of the strategies that you promote to help product managers become more effective is to strengthen their zoom-in and zoom-out muscles. Could you say a bit more about that and also provide a few examples of that technique and action?

The ability to zoom in and zoom out isn't called out as an important skill. But implicitly, we're telling product people, "You need to be strategic, but you also need to get your details and execution perfect. You should have every little detail figured out, but never lose attention to the big picture." We tell product leaders to empower their teams and let them make the decisions. But ultimately, the product leader is still the one who is accountable for the decisions. There are so many ways that we expect people to effectively manage perspective, but we don't tell them how.

I have three practical tips to master this art of zooming in and zooming out. The first is as a leader, we need to make room to zoom. Is your life running you or are you running your life? Your time isn't created equal. Every week, religiously, I categorize my time into four categories: planning, execution, thinking, and reflection. If you're making room to zoom by thinking about your time in these four categories, you can actually do something about it. Until you measure what you're doing, you're not able to improve it. You will be able to create greater room to zoom out if you see and adjust the time you’ve allocated for thinking and reflection.

Second, have conversations about conversations. It's very normal to go from one meeting to the next and be expected to switch context. You can set yourself up for success by having a conversation about what you're expected to come in with. That sort of thinking and preparation helps you come in with the right mindset.

Lastly, know when and how to flex. I'm a firm believer that bringing in ideas from analogous fields turns out to be a great source of radical innovation. When you see yourself deep in a problem, take a step back and say, "We can't be the only ones trying to solve this problem. What can I learn from others who've done this?" Seeing how other companies and other industries have solved a similar problem can be a great source of inspiration.

Making your strategy fun and memorable

I would think that carving out time for thinking will provide you with the space to come up with those ideas. What is your approach to ensuring your teams have bought into the product vision and are aligned on how to get there?

I would say there is no way out of not repeating yourself. The only way to do this is by constantly repeating your product vision and how you're going to get there. Don’t stop until you get sick of saying it and see that your team can repeat the vision and your strategy. Repetition is number one.

I would also say to make your strategy fun, memorable, and unique to your culture and your product. Focus on the storytelling around it. At Peek, our roadmap planning process is called a product avocado process. We talk about avocados and making guacamole together. My strategy docs have things like houses and pillars in them, and I have another version of the strategy that takes the various flywheels and creates a solar system. My point is that you have to have to make it so that people look forward to talking about the strategy. It should be something that speaks to people.

How do you promote a culture of innovation within your teams?

Our company went remote during the pandemic and embraced that. In many cases, building a culture of innovation remotely is actually quite hard. I mentioned that you have to get out of the way and empower people to innovate with psychological safety. From a product perspective, how you build that culture requires intention. When we went remote, we talked every single week about how things were going. We looked for ways to replicate the awesome culture that we have and adapt it for remote work. We started bringing the voice of the customer to our entire team, not just product managers.

Engineers get to see how our customers are using the product and hear feedback firsthand. Many times when we were doing that, engineers said, "I have an idea about how to fix something." They get excited about that. In the product design process, virtual whiteboards weren't working for us so we started sessions called creative combustions. The idea is to identify a difficult problem and push the team to come up with blue-sky ideas. The person who leads the creative combustion will clearly outline the problem, and then all ideas are welcome. As you welcome people to brainstorm, they collectively come up with the best solutions that wouldn't happen if you were constrained to a structure.

The final thing I would say is from the beginning at Peek, we've always had a culture of being not competitively focused, but competitively aware. Every quarter, we have a goal to say, “We have a list of things we need to do that our customers need. But what can we do that nobody else is doing?” That has really pushed the team to develop a passion for new ideas. Some of the best innovations have come from that. It motivates people to continue thinking outside the box or even as if there’s no box.

‘Don’t sympathize, empathize’

Stakeholder management certainly is a very critical component of the product function and it can be challenging. Could you talk a bit about your approach to managing that?

I did an MBA in strategy, and I would say the negotiation skills class was probably my favorite because we learned that to be able to get buy-in, you have to truly understand the incentive. Don’t sympathize, empathize. Understand what's driving their interest to be able to actually collaborate with them. When I'm at an executive table with stakeholders, it’s less about what the product is doing and more about actively listening to what each person is saying. I come into those conversations asking how I can help. Being proactive about how you can help people and make others successful is the biggest factor in effectively managing stakeholders.

How do you leverage your personal impact retrospectives to communicate the value that you're bringing to your role?

I'm a product person, so I have my own personal roadmap with things that I want to work on. And yes, I do my own retrospectives. The questions that I typically ask myself is, “How can I further maximize my impact? What are the root causes of recent lowlights?” I’m not thinking about what went wrong, but taking a step back and thinking about what actually caused this issue that's impacting me and my team. What are some of the activities that I'm doing on autopilot that I need to take a step back from and may need to adjust?

Answering these questions helps me prioritize areas of the business that may be overlooked. It leads me to create new side projects where I get to zoom into details and drive greater impact as an individual. More tactically, this retrospective helps me create new rituals for myself on how to zoom in and zoom out.

Giving props and celebrating failures

Celebrations are one way to help drive team energy and cohesion. Do you have any examples of how you've celebrated successes and milestones for your team or even failures, for that matter?

Whatever rituals or tactics you come up with have to align with your culture and team. We're fortunate to have a very collaborative and customer-centric culture. In our Slack props channel, people openly give props to others who went out of their way to make an impact. Every week, in our team meeting, we have an agenda where we bring the product engineering team together. There's a section there called shout-outs where we encourage people to go off mute and give shout-outs to the team members who have gone out of their way to accomplish something.

In terms of failures, in my last job, we had a feature that didn't go well and we had to completely rewrite it. We actually held a funeral for the feature. Everybody came. It was morbid, but it really gelled. We had a cake and our CEO gave a speech about all the things the feature did and how we were going to miss it. We also had two siloed features that weren't talking to each other, so after we integrated them, we held a wedding. With celebrations for successes or failures, making it fun is so important.

Lastly, what advice do you have for product folks who are currently in an IC role and are looking to move into leadership?

There are a lot of product people who struggle with letting go. If you catch yourself saying, "It's actually faster to just do it myself," or if you catch yourself driving the decisions on what the team is building, that's problematic. That holds people back. It's important to start small and identify the right things. You can delegate and set up the person you're working with for success so that they don't make the mistakes that you've learned the hard way. Trust them, but also verify.

I would say this is easier said than done. But be disciplined about doing a retrospective and saying, "Am I just doing all the work myself? Am I catching myself not investing in the person who could take this off me?" That is really important. The last thing I would say is there's a book called High Output Management that I always recommend to people moving into leadership. It’s by far one of the best management books out there.