How to be a product leader today

Esteban Contreras
All Things Startup
Published in
6 min readMar 6, 2018

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I’ve found that many conversations about “product” tend to focus on product management — the intersection of strategy, technology and UX. And that makes sense: Amazing software requires amazing product management.

But how can product leaders develop and inspire high-performing teams to solve important problems and make an impact on the business? How do we get closer to our customers in order to envision, co-create and prioritize the right experiences at the right time? And what’s the best way for us to approach each sprint, plan each next quarter and scale year to year?

While product management is primarily about shipping product, product leadership also involves developing your team and partnering with others.

For anyone in a product leadership role, these questions are top of mind. And they’re what I (along with product leaders from Octane AI, Clio and Hootsuite) will discuss on a panel at SXSW Interactive this weekend. The conversation will focus on leading B2B product teams, including real-world examples about challenges, tradeoffs and controversial decisions.

You can learn more about the panel here. Ahead of the event, however, I wanted to share a bit of my own philosophy around the topic. Below are a few principles that I believe modern B2B product leaders should embrace.

It’s all about people

As a product leader, your job is to take yourself out of the trees and see the forest: Where is your company’s unique value in this world? What’s the vision for the business? And how do you guide and grow a team to passionately pursue that vision — without always having the formal authority to do so?

One thing is for sure: You won’t be able to do it alone. The best product leaders know that they only succeed when the entire team succeeds. Set your ego aside. Your ideas (and solutions) may often have to be set aside, as well. While product management is primarily about shipping product, product leadership also involves developing your team and partnering with others.

Hire the right people with the right attitude, support them and then trust that they’ll be able to get stuff done.

True leaders do two things: they start with “why,” and put people first. That means painting a picture of the future, while seeing and inspiring the best in others. It means being a mission-driven enabler that spends time in the trenches — not an authoritarian in a high tower. And it means giving credit publicly, owning and apologizing for mistakes, and delivering radical candor when needed. Soft skills like empathy and being like a team player are critical. As my friend John Cutler says, “Would the team hire you if they controlled the budget?”

Be strategically focused

Being strategic means thinking big while being able to adapt. Rather than creating a plan and setting it in stone, modern product leaders maintain a clear vision of where they want the product to go, but remain flexible in how they will get there. They anticipate change, help establish frameworks, and facilitate autonomy in their teams — ensuring that decisions made today still matter a year later. Like a good chef, sports team captain, film director or army general, product leaders position their teams for action.

If everything is important, then nothing is.

It’s easy to get caught up in JIRA tickets, feature requests, meetings and executing, executing, executing all day long… but if you don’t know where those things fit into the overall strategy and roadmap, you’re constantly going to be prioritizing the wrong things. Give every issue its due attention, but don’t get caught up in distractions. If everything is important, then nothing is; strategy informs what to do next with limited information and resources and, ultimately, when to say no.

Make things happen

Leaders make things happen. They overcome problems. They see opportunity amid chaos and inspire others to do the same. They get quick wins. And most importantly, they don’t whine, roll their eyes or hide behind their computer screens. When you’re leading, you need to be incredibly self aware (especially about the things you’re not good at). Make sure you have a team that supplements what you lack. Hire the right people with the right attitude, support them and then trust that they’ll be able to get stuff done.

As a product leader, I need to make sure our team keeps getting better. Sometimes that means working with them to figure out what’s getting in the way. And other times, that means I’m the one who needs to get out of the way.

And this goes beyond the product itself. Product leadership not only includes setting the strategy, guiding the roadmap, and scaling the team, but also contributing to the go-to-market process (which takes immense collaboration with marketing, sales, success, support and anything that has to do with helping get the product out there). In the eyes of the people using your products, everything they experience related to your company is “the product.” Make sure you are supporting and partnering with those in customer-facing roles.

And when things don’t go as planned, remain cool. Grace under fire is a beautiful thing. Channel any pressure, stress or fear in productive ways. Difficult times will test and refine a team; see this as an opportunity to lead by example.

Perpetually optimizing

I’ve always liked the idea of Kaizen: change for the better. Product leadership means continuously optimizing; constantly getting better; never feeling like you’re done. And products are never done, so everything can always be improved — from how we do agile processes, how we run sprints, how we present, how we question our assumptions to how we think about customer pains and needs. As a product leader, I need to make sure our team keeps getting better. Sometimes that means working with them to figure out what’s getting in the way. And other times, that means I’m the one who needs to get out of the way.

Leadership isn’t a task; it’s a mindset. Anyone on the product team can embody this.

Speed is a popular (and controversial) topic in product management. Some people believe you shouldn’t focus on it. Others think your team should always be getting faster. Without a sense of urgency (and some paranoia of the Andy Grove variety), startups do not survive and big companies start to decline.

I think it’s a case-by-case basis; there are some things you have to let brew and make sure you get them right. But at the end of the day, if you’re getting better at something, you should be able to gain velocity. It’s like exercise — the more your teams collaborate and measure progress, the better and faster they’ll be able to move. However, I think trying to be fast for the sake of being fast means losing sight of the customer. You should optimize for customer outcomes, not just software outputs. Velocity without impact is meaningless.

Take care of the customer

We’re not just here to deliver a product, but to provide value to each and every user — giving them the context and actionability they need to get the job done. And that requires good design, taste, creativity, and empathy for the customer. And those aren’t just empty words. Everyone talks about “empathy”; it’s become a buzzword, but there is real meaning and substance behind it.

True product leaders care first and foremost about the customer; they’re responsible for the customer’s success as it relates to the product. As Steve Blank says, it’s essential to “get out of the building” and in front of customers. After all, a customer’s success is the heart of any business. That’s why we need to unlearn rigid mental models from enterprise software’s past and raise the bar to the level of B2C companies: eliminating crappy user experiences, sneaky pricing and mediocre customer life cycles.

Other teams will have their own issues, but if the product isn’t at its best, it affects everyone.

Leadership isn’t a task; it’s a mindset. Anyone on the product team can embody this: From developers to product managers to designers — it’s everyone’s responsibility to take care of the customer.

Other teams will have their own issues, but if the product isn’t at its best, it affects everyone. Great product leaders elevate the entire organization, while bad ones bring everybody else down with them. That’s why, every day, we ask ourselves: What problem are we solving? Who are we solving it for? How do we measure success? And what have we learned?

If you’re heading to SXSW, I’d love to see you at our Modern B2B Product Leadership panel. Otherwise, I’ll leave you with a mantra we use on our product team:

Not everything we ideate is going to be built; not everything we build will be shipped; not everything we ship will succeed. But we will learn, and we will value each lesson we learn as we go from zero to 1 to 100.

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Esteban Contreras
All Things Startup

VP of Product at Fleetio. Created and curate the Product State newsletter www.productstate.com