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How surfing helped a new CEO ride the crazy waves of 2020

This top Contentful executive took over just before the pandemic hit and turned to lessons he learned navigating the ocean swells to keep from wiping out.

How surfing helped a new CEO ride the crazy waves of 2020
[Photo: Jeremy Bishop/Unsplash]
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I was lucky. Very often when an outsider gets “the phone call” to take on the CEO role of a company, it isn’t because things are going well.

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But when I was asked to join Contentful as CEO in 2019, all signs were positive. The market potential was enormous and our cofounder and first CEO, Sascha Konietzke, was ready to move the business from the startup phase to the scale-up phase. Sascha transitioned to Chief Strategy Officer and did an incredible job ensuring a smooth transition.  None of us could have predicted the year ahead.  

While in many ways we’re ending 2020 as planned, with strong growth and revenue, this certainly wasn’t the path we thought the year would take. We made business plans before any of us had ever heard the word “COVID,” so adaptation became the essential ingredient in our business plan. 

What helped me most in cultivating an attitude that could navigate so much uncertainty? The ocean is a powerful teacher. Lessons I first learned as a kid surfing with my dad in California resurfaced again and again in 2020. 

The mega-trends matter

Surfers are constantly watching the weather in search of far-off storms that might kick up a new swell. The right swell, the beach facing the right direction, and the right contour of the ocean floor combine to produce a great wave. If there is no storm, or if you are in the wrong spot on that day, you can paddle around all you want—but you aren’t going to get a good wave. Additionally, on a really great wave, even those of us who are just OK can have an epic ride.

This applies in the business context as well. We might borrow from something Warren Buffet has said on multiple occasions: “Given the choice between a great market and an OK management team or a great management team and an OK market, I would pick the first.” 

As executives, we are looking for those great conditions and the great waves on any given day. We try to position the company to capture those great waves—mega-trends. These are the conditions that make for a great ride—the shift from traditional retail to e-commerce for Amazon, the birth of the PC for Microsoft, and the rise of digital advertising for Google are just a few. 

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The mega-trend for us is the digital-first era. The evolving preferences of consumers, particularly with mobile devices, and the new demands for the digital experiences that brands create mean that companies need a next generation playbook and technology platform in order to be successful. Those who aren’t making this shift have been in the headlines each week as we see venerable brands disappear. This digital-first mega-trend is the swell we are chasing and the conditions of this market will determine the magnitude of our success. Luckily, our founders, Sascha and Paolo, found a great beach when they started the company. Now our job is to ride it to the best of our ability. 

Question for us as leaders: What is our mega-trend or swell? Are the waves picking up or dying off?

Choose your waves carefully

When I was first learning to surf, I would paddle around eagerly trying to pick up any wave that came along. As I improved, I learned to spot the better waves and focus on them. If you listen to interviews with competitive surfers, when they talk about the best competitive surfer of all time, Kelly Slater, they frequently talk about wave selection. He just seems to know which ones are going to be great. As leaders, one of the hard things about picking opportunities is that we have to be willing to let some good ones pass in order to get the great one. We also have to let go of the noise that comes with critics, inside and outside of the company, who will be quick to point out some of the things the company isn’t doing—the waves we didn’t take. This year, I have learned that “should” is a very dangerous word and that I need to be wary of it at every turn. The critics are frequently sitting on the beach watching, not out in the surf making the hard choices. 

Question for us as leaders: Are we clear about the “must do” priorities and how we are dampening the noise that comes from the critics on the beach? 

Never surf alone when the stakes are high  

I learned very early on that when the waves are big or you are in a new spot, you don’t go out alone.  The same is true in business.  Creating something valuable and durable takes time and the shared dedication of a broad set of people. When I took the role, Sascha and I talked about “starting with the place.” The first project we worked on together was the clarification and reaffirmation of the company’s core values to ensure we could attract and engage the right people for our adventure. We leaned on the existing expressions of them and some work the team had done at an all company offsite. We updated the values document, circulated them for feedback and refinement, and then made them the centerpiece of our awards at the company, as well as our interview process. The intent was to be clear about who we are, and to reward that as well as seek out people who are naturally aligned with the way we choose to work together. In the midst of COVID, we switched from a culture that was very face-to-face to one that is now almost exclusively virtual and distributed. Having explicit, strongly shared values has proven to be critical. The clarity that came with the reaffirmation of our values has enabled us to continue to evolve and grow without losing the core elements that led people to join the company. During times of great change, without a conscious effort like this, you risk splintered efforts and teams moving in different directions.

Question for us as leaders: Is our culture clear and explicit? Do we look to core values in both who we hire and the behaviors that we celebrate? Will those core values enable us to attract the people with whom we can navigate the challenges that crop up?

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The best athletes (and leaders) make time for recovery 

I often hear that these leadership jobs are a marathon, not a sprint. This year has reminded me that we need an even longer view than that—we need to focus on performing season after season. Laird Hamilton is one of the big wave pioneers of our time and led the stand up paddling trend. When we look at his impact on water sports, it is measured in years or decades, not weeks or a season. In business, the scoreboard isn’t just the annual financial performance or market capitalization (in fact those are lagging indicators) but the culture we build, the next generation of leaders we train, and the companies we help as they have their own positive impact on the world. These things take a long time. Laird has been generous with his perspectives on what it takes to lead, invent, and perform over time. Paradoxically, one of the things he focuses on most keenly is recovery. If the challenge before us has a long timeline, then self-care and recovery are at the center of leading through it. In my first year in this role, I started using a fitness tracker that helps me to journal and measure sleep, heart rate variability, and other stress indicators. The leaders who have come before us have taught us that if we don’t take care of ourselves, we cannot serve our teams or our mission. Personally, I find that incredibly hard to balance on a daily basis but its importance cannot be overstated. 

Question for us as leaders: Are we carving out time to recover, recharge, and get ready for the next challenge? Are we able to quiet our inner voice telling us to just keep grinding it out, when we really need to recover so we can be our full self rather than a burnt out shell? 

Don’t be frightened by choppy seas

The toll of the pandemic would have been hard to imagine a year ago. We can’t decide what the storms of life will kick up. However, we can decide the waves we will pick, the place we create, and how we will lead through the conditions that appear. For us at Contentful, the mega-trend of the digital-first era and the changes that have been accelerated during this crisis have meant an even bigger wave. Your challenges will have a different face, but all that’s left to do is ride your wave well.


Steve Sloan is the CEO of Contentful, bringing a background in high-growth SaaS companies, leading product, marketing, and engineering. He was most recently Twilio SendGrid’s Chief Product and Marketing Officer and previously led global product and engineering at Marketo. He also held leadership roles at Amazon and Microsoft.