Savage Mindset: Master The People Puzzle

Welcome to my newsletter. Each month, I share things that have recently inspired me. This March, I’m focusing on the importance of understanding and continuously getting to know your people in your efforts to scale your business.

Creative teams are the engines that drive business. Building teams of individuals can be tricky. It’s like putting together a human chemistry solution. Get it wrong, and the whole thing explodes. Get it right, and it mixes seamlessly.

Here are a few observations and ways my Co-founder Brendan Schwartz and I have navigated this complex task over the past almost 18 years at Wistia.

Individual Attitude Affects Everything

I get more convinced by the day 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.

People all have default mindsets, where they tend to fall when it comes to outlook. Do they take on the day with confidence? Do they have the general mentality everything will work out? How do they manage adversity? They can vacillate and shift perspective, but they tend to default to the same place repeatedly.

When the attitudes fit together, it’s an incredible feeling.

But they can also be fragile. If someone has a defeatist mindset, they will naturally start interjecting issues into existing systems. Over time you can lose trust. Think about your experience of building teams. If your team didn’t mesh, I guarantee that, with hindsight, you can trace it back to individual mindsets.

Great teams care; they push to be better. They aren’t afraid to speak the truth. They expect greatness. They need trust, and ultimately, they need camaraderie. Get the right people together, and things click. The vibe is right, and you can go much faster and have more fun than you ever thought possible.

Different People Are Built To Solve Different Problems

The attitude dynamic is just one piece of the people puzzle. Matching the right people with the right kind of challenge is one of the most important things you’ll do as an entrepreneur.

Not everyone wants to be in an early-stage startup. Not everyone wants to be in a late-stage scale-up. Figuring out where you are on your journey and what you need along the way can make or break you.

Brendan and I have a shorthand for categorizing these stages that takes inspiration from the different personalities that built the American West. We’ve found it helpful during our journey to understand what drives different types to better understand how they’ll fit into the business at different stages: 

+ Pioneers — Pioneers are risk-takers who are willing to work long and hard hours doing whatever it takes, for the rush of finding something of value. They’re willing to adventure into the unknown. This role is not for everyone, and most fail. These are the kind of people you often find at early-stage start-ups. Once they strike gold, a solid agricultural area, or an area they’ve been testing in the market that seems promising to scale, pioneers will quickly become dissatisfied.

+ Settlers — Settlers are different types of people. There's less risk in that they know there's gold, fertile land, and ideas to cultivate, a guaranteed upside. These people are energized by putting in the semblance of a structure. They know everybody. They communicate and connect the dots to build a community around the proven promise of the idea or opportunity the pioneers found. But, once the business gets bigger and turns into a city with systems and structures, settlers may feel less and less at home.

+ City-Builders — City-builders thrive when they're building more regimented roads, rules, and law enforcement. As your company grows, you need city builders to grow your infrastructure and stabilize your company for the long haul. If you think in terms of pioneers, settlers, and city-builders, you’ll be more equipped to identify people’s respective drives and determine if their values align with the challenge at hand. And, if you mismatch people, you could squander their talent for exploring the great unknown, unintentionally sabotage stability, or, they’ll move on.

There is one exception to these types: You will find people adaptable enough that they can work at any stage. Do whatever you can to keep those people happy and in your party.

How to Keep a Good Thing Going

Once you’ve built a team with a good thing going and the right people working on the right problems, you need to continuously foster synergy to keep momentum going.

Many entrepreneurs neglect this on their mission to scale.

Focusing on connection on an ongoing basis keeps tension at bay and makes it easier to resolve tension between people when it arises. Tension builds much easier when there is a lack of connection. If we care about someone, it's much easier to feel motivated to improve a relationship than when you don't. It's a simple idea but easy to forget.

The solve? Find easy ways to get to know each other. Don't force it or overcomplicate it.

Recognize that spending time together gives you the basis of trust, which makes it easier to give feedback, makes it easier to get better, and ultimately makes it easier to reduce tension when you want it gone.

Creating a connection-first environment, whether in person or virtually has been key to growth at Wistia over nearly two decades. It's hard work and takes continuous investment, but it turns out that if you are a human who genuinely cares about other humans in business, it can be a superpower.