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When You Have the Right People, There Are No Rules for Structure

If you want to build extraordinary products, conventional wisdom must be challenged. The same goes for building extraordinary organizations, says entrepreneur Scott Belsky.

When You Have the Right People, There Are No Rules for Structure

By: Scott Belsky, from his book, THE MESSY MIDDLE: Finding your way through the hardest and most crucial part of any bold venture, published by Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House

Some of the most frequent questions I get from start-up founders and new managers in large companies are about how best to structure a team.

“Should I allow remote workers, or should I insist on the whole team working in the office?”

“Should marketing be a separate team or an extension of an existing team?”

“Can my co-founder and I both be CEO?”

“Should designers report to product managers or be the product managers?”

“Should we keep things non-hierarchical or start hiring and appointing managers?”

When structuring our teams, we tend to seek best practices and aspire to put our playbooks on par with those companies around us. We look for so-called rules, like every team should have a single leader, designers and engineers should be on different teams, and there should only be one CEO. 

While there is merit in each of these norms and I enjoy studying the structures of others, I have always found these questions difficult to answer without the context of the people and circumstances at play. 

Just as teams must challenge conventional wisdom to build extraordinary products, the same goes for building extraordinary organizations.

Breaking the Sole CEO Rule
The greatest teams I have worked with over the years were all structured with a few remarkable exceptions to the rules. During my years serving on the board of sweetgreen, a chain of locally sourced seasonal-food kitchens, I was struck by how well the company’s three co-founders, Jonathan, Nic, and Nate, functioned as tri-CEOs. 

When I first joined the board, many of my peers told me “Good luck—that is nuts!” But the three of them had transformed the traditional CEO role to uniquely serve the company. They divided and conquered most functions in the business but shared the same core values and intuitively knew which decisions could be made by any of them, only one of them, or required all of them. 

“I feel like we’re pretty lucky because we can share the responsibility of taking action. It’s not just one person’s job to figure something out. It’s not just one person that has all of the weight on their shoulders,” Jonathan told me when I asked him about the arrangement. 

Nic added, “We can have a CEO in three times the number of places and moments . . . we cover three times the surface area of a normal CEO.” For a period of time, this was an advantage.

There are many horror stories about co-heads of teams and companies, but there are also so many examples of such arrangements being a strength. Why should there be any rules either way?

Be Flexible with Leadership 
In the early years of Behance, we had five leaders of our engineering team rather than a single CTO managing them all. There was a comfortable tension I was optimizing for having a leadership team that had to work together to build out our various engineering functions, such as front-end development, back end, systems architecture, and mobile. 

The personalities of each leader, and their varied level of management experience, also factored into my approach to structuring the leadership team.

Another norm I broke was having our senior designers report directly to me. While designers don’t normally report to the CEO, I knew that our business was different. We were serving the design community and were very design driven as a company. Being close to designers helped me ensure that design was, in fact, at the heart of our priorities.

When I first joined Adobe after Behance’s acquisition, I continued to step out of bounds when it came to structuring the organization, which ultimately grew to almost five hundred employees. 

I had some designers report to me rather than work in the company’s central design unit, just as I did at Behance; I created very small teams to explore the largest strategy shifts first rather than include every stakeholder at the onset; and I developed a marketing role within some of the product teams to ensure the copy and campaigns were aligned with the product vision. 

Of course, breaking norms in big companies causes the occasional fire; I had to explain myself quite often. But I tried to mold structure to the kind of work we were doing rather than the other way around. 

Just as it is remarkably hard to innovate using the same code or materials as your competitors, it is hard to build something new within the confines of a structure built for the past, or later stage products.

When you have the right people, there are no rules for how the team must be structured. When your A players are playing their A game, you can be creative with how they work. In fact, you need to be. The extremely talented people you love and trust know how good they are, and they thrive working on their own terms. 

As the leader, you need to carefully balance the need for structure with the need to accommodate the autonomy and idiosyncrasies of your team. Optimizing how you work requires unconventional experimentation while letting go of norms.

Be Comfortable with Risk
As I think about the nature of the advice I give to start-ups and the number of times I defy my own advice, I am struck by how frequently rules should be broken. For example, while I feel strongly that you should never outsource your competitive advantage, sometimes the perfect designer—or other domain expert—insists on working on her own as a freelancer. Sometimes the circumstances necessitate defying your own beliefs. 

The willingness to break your own rules and keep structure permeable to circumstances is as important as the rules themselves. Exceptions shouldn’t happen too often, but when they do, they could be differentiating and critical to your success.

As long as you have the right people aligned around the right objectives, be flexible. If superstars insist on working remotely, let them. If two people with complementary skill sets make great candidates for the same leadership role, experiment with co-heads. Observe, learn, and then adjust. Despite all the conventional wisdom out there, you’re allowed to change the rules. 

These tweaks could help you or hurt you, but you’ve got to take some risk to achieve an irregular outcome. Embrace best practices until you need to change them. Then break them.

The Messy Middle by Scott Belsky


From THE MESSY MIDDLE  by Scott Belsky, published by Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2018 by Scott Belsky. 


Scott Belsky has spent more than a decade leading in the worlds of technology, design and start-ups. Now chief product officer of Adobe, he is the founder of Behance, the world’s leading creative network used by more than 12 million professionals. He serves as an adviser and early-stage investor in fast-growing companies such as Pinterest, Uber and Periscope.