Why the Best Entrepreneurs Succeed by Matching Talent to Roles


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We often underestimate the importance of building world-class teams in our efforts to scale. You can’t hire a world-class team. There are no hacks or shortcuts — you need to build them. But effectively building those teams is easier said than done.

Teams are a puzzle of different personalities and strengths that you need to piece together to succeed. When you get it right, your wins will compound, your company will grow, and your culture will thrive.

Getting it right involves assessing and understanding individuals’ attitudes, mindsets and personalities to match people to the problem at hand properly.

Related: 3 Big Ways to Make Your Business Last Forever

Gathering personality information

I am becoming more convinced that A) it’s harder to change people’s attitudes, and B) attitudes matter so much when we consider what it takes to create great teams.

My co-founder and I have put together some really great teams, but we have also missed the mark by not aligning peoples’ personalities/attitudes and skills with the right tasks. Having the right people in the right seats has catapulted us through every product launch, company growth phase and market change. As your business scales, it’s especially important to understand your people.

This information-gathering process should start during the hiring phase. Ask open-ended questions about a prospect’s career. Are they generally optimistic? Do they take on tasks with confidence? What excites them? How do they manage adversity? You’ll quickly discover that not everyone wants to be at an early-stage startup or even a late-stage scale-up.

Administering personality tests — although a less personal method — can also be helpful for quick results.

Once hired, encourage managers and other organizational leaders to take the time to really get to know their employees. Scheduling regular check-ins or even quick outings outside of work (who doesn’t love a mid-afternoon coffee run?) are great ways to build these connections. Take note of what situations employees thrive in, but equally important, what they shy away from and any other personality drivers.

This information is a great starting point for matching employees with the right tasks at your company. But at my company, Wistia, we found we needed a more formal framework to arm our leadership team, which led us to the American West.

Related: Why Being People-First Can Help You Succeed When Expanding

Pioneers vs. settlers vs. city-builders

Not literally, but we did take inspiration from the American West — yes, think Oregon Trail — to create a system to help categorize different personality types with business phases. This resulted in pioneers, settlers and city-builders. Each has its own unique role to play and value to add to a growing business.

  • Pioneers are risk-takers willing to venture into the unknown. They will do whatever it takes to find something of value, and because of this, they often thrive at early-stage startups.
  • Settlers are more risk-averse. They are driven by implementing some initial structure and building a community around a guaranteed opportunity or idea discovered by a pioneer. But they feel less at home once the business grows and the “town” turns into a big “city” with more complex systems.
  • City-builders shine when tasked with constructing more laws, rules and roads as your company grows. They can help build and expand the infrastructure that will scale with your company in the long term.

And every once in a while, you’ll find someone versatile enough to succeed at any stage. Hang on to them as long as you can.

Every company will have its pioneers, settlers and city-builders. Regardless of the theme, the concepts remain the same. This system helps us better match employees to the right role for their personality at whatever company stage we’re in. This helps teams, and ultimately our business, thrive.

Even after almost two decades of trying to unlock the people puzzle, we’re still learning something new every day. But it’s undisputable that when you get the right people together working on the right problems at the right time, everything clicks. With great teams, you can move much faster and smarter as a business.

Entrepreneurs who quickly identify people’s working styles have the best shot at getting the right people in the right seats to scale. This does not happen overnight. It takes investment from leadership to get to know their people and put the right frameworks in place. But if you are lucky enough to piece together a team with a good thing going, don’t let that go. After all, a business is only as strong as its team.

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