Behind the Roadmap with Productboard’s Stephen Walker

Editor’s note: This post is part of a brand new video series to understand what goes on behind the roadmap – it’s an inside look at the life of product managers. Watch the full first video with Productboard’s own Sophie Lalonde here, find the second with Hope Gurion here, and keep an eye out for upcoming installments!

The road to product management as a career isn’t always a straightforward one, and that’s why we’re taking you Behind the Roadmap for a deeper look at the life of product managers and product leaders.

We dive into their journeys into product management, their biggest challenges, greatest strengths, and so much more. It’s one part lifestyle, two parts nerding out on product.

Meet Stephen Walker

Senior Product Director at Productboard’s Prague office, Stephen discusses empowering his team as a product leader, the way he thinks about product strategy and OKRs, and how product leaders can unite their teams around shared objectives (plus he shows off his polka dot socks).

“My favorite part about the job is helping the team succeed. When you’re an IC or a maker, your day to day is about shipping the product. But when you’re a leader, it’s about shipping the team, which means you’re hiring and developing the talent that is responsible for building the product.”

 

 

 

Thinking about product strategy as a product leader

Having views at different time scales really helps with prioritization, Stephen says.

“Setting product strategy is incredibly complicated, but how we do it here at Productboard is we look at multiple year horizons as well as the current year and the next six months. And having this six month view, the one year view – and let’s say the three year view – helps us really break down what’s the most important work that needs to get done to help us execute against our strategy.”

As for putting that strategy into place, Productboard has a number of artifacts and rituals in place, including an annual product strategy document shared across the entire team and that’s reflected back in company and product team OKRs. Everything is also reflected on quarterly to make sure it’s on track.

What product teams get wrong about OKRs

There is a lot that can go wrong with OKRs, but something very specific stands out to Stephen.

“The number one thing is that the company or the teams just aren’t ready for a goal setting culture. What do I mean by this? It means that the best companies, they could use any framework to set their goals, doesn’t matter if it’s OKRs or something else. And so if a company wants to succeed with OKRs, they should really be reflective on what it means to set goals and achieve goals.”

These will also differ depending on the size of the company.

How product teams differ at large corporations vs. scrappy startups

Obviously there’s a lot that’s different in the day-to-day operations of a small, scrappy startup vs. a large, established corporation. Stephen has worked at both in his career and knows the ups and downs of both environments well.

“There’s two things that are really different. One is the amount of ambiguity and the second is the amount of process. So in a large corporation, you’re going to have a lot of stability in terms of the process and the focus of your team, where in a small startup, you’re going to have a lot of ambiguity in what needs to be done and how to do it. And so you have to choose which environment you want to spend learning and really developing your career.”

Some thrive in the ambiguity that comes along with a smaller team and company and some really prize the stability of a large corporation — and of course there are a lot of companies at sizes in-between. Any aspiring product manager should consider what’s most appealing to them while recognizing that can change over the course of a career. (More on this at the end.)

How to build clarity around product vision and strategy

A big part of the product leadership role is building clarity around product vision and strategy. Yet in a recent survey, Productboard found a big discrepancy between how much clarity product leaders have versus the individual contributors (ICs) that report to them. (Want to weigh on on the current state of product excellence? Take our 2022 Product Excellence Survey!) How can product leaders avoid this? Communication.

“I think the number one thing is the amount of time that leaders spend really over communicating the message. It’s really easy for ICs to be busy in their day to day work and to maybe not catch some of the details that maybe are only shared once or twice a year. So I really think about in terms of vision and strategy, this is a recurring message that has to happen several times a quarter in my opinion, and possibly not just in group settings, but also face to face.”

To be truly successful and stay top-of-mind, product vision and strategy have to be treated like an internal marketing campaign; share it across available channels (in meetings, on Slack, at events, in the company Wiki) and share it often.

Final thoughts

What’s Stephen’s advice for those previously mentioned aspiring product managers?

“I think the first thing that a product manager who wants to become a product leader should think about is that it’s an entirely different role. What made you successful in your current role will not necessarily make you successful in your next role. And if you just want to climb the ladder, well, maybe you’re better off climbing the wall.”

Thanks for coming with us Behind the Roadmap!

The conversation continues in the rest of the series, so keep an eye on our social feeds or right here on the blog for the next installment. And if you haven’t yet, check out the video here.