On Building the Perfect Uncomfortable Team, Dirty Hands, and Math

L: What makes the team at Gravitate work so well?

Don Elliott, Gravitate Owner: We make them uncomfortable. Seriously. We’re not talking micromanagement, we’re talking virtually the opposite. Instead of explicit, prescriptive directions— “do x, do y,”—we give our teams an uncomfortable amount of freedom. This challenges them just enough, and people rise to the occasion. They discover they are capable of more than they imagined. It makes people believe in themselves.

When I first bought the company, I tasked the new leadership team to audit all of our products and offerings. Instead of saying “here’s exactly what to do and how to do it,” I had each team audit their own department. I wanted to give them the ability to share their opinion and perspective, from a natural and organic source. This approach was fairly new, and it pushed them just outside their comfort zone. Some would have preferred if I’d given them a checklist of what to look at, but that was exactly what I didn’t want to do.

I said come back to me with ideas, problems, and potential solutions. I told them if you feel uncomfortable, it’s by design. I want you to not worry about messing it up; because you cannot fail. We’d have check-in meetings where they’d ask questions, looking for my input, asking “Is this the right direction?” and my answer was usually “How does it feel to you? If this was your company, is this what you would do?”

But let me be clear. This philosophy can easily become an excuse for the president to not work hard! I didn’t hang them out to dry. I’d give them advice and direction, pointing out areas they could go deeper in, but only if they asked for it. I wanted them to fuel it, and be invested in the work they were doing.

L: What do you mean by “invested”?

Don: A huge part of what makes a company successful is having employees who feel genuine ownership over what they do. That’s easy to say, but as the owner/president, you must back that up with action. A lot of places claim to give “ownership,” but in reality it’s just a target on the backs of their employees, a way for leaders to say “You’re responsible if this goes up in smoke, I don’t want to deal with it.”

That kind of “ownership” can be toxic, and it breeds fear. That’s the opposite of what a leader should want. Leaders need to make their people a little uncomfortable, but also provide the support and coaching and guidance they need.  And then get out of their way! That’s how you get true investment from your team, and when I talk about an “invested employee”, that’s what I mean: someone we are supporting, who cares about their work; not someone we are prepared to throw under a bus when things get hard. Any failures that happen aren’t just theirs, they are mine too. We fail together.

But again, you cannot fail, because you will always learn, and so long as you act on your lessons, failure is a fallacy.

L: What do you mean by that, that their failures are yours too?

Don: I like the analogy of a coach for this. A coach doesn’t tell the team: “I did everything right, but you guys lost us the game.” That’s not only untrue, it’s a denial of responsibility. We win or lose together, in sport and in business, when a leader acts like they’re separate from the failures, the losses, especially if they start to blame others, everybody else on staff sees it and starts getting scared of messing up, so they don’t take risks. Fear is the mind killer. You need to be a team. And you’ve got to trust your people: you hired them after all.  Don’t create fear around failure; your failure is mine and a chance to learn together. Failure is data collection; it means we know more now.

L: Let’s go back to the idea of making a team uncomfortable. Does that mean you let them sink or swim all on their own?

Don: Definitely not. Your job as a leader is to make the employee uncomfortable, but knowing how to make them uncomfortable in the right amount is the key. A manager needs to be willing to get dirty and get into the work when an employee needs it. Acting as an assistant, a helper.

When I’ve challenged someone and they’re running into a snag, it’s lowering their confidence, getting into their head, disrupting their work and their team—that’s when I pop in and help them understand ‘this one thing’. I shore up their confidence and strength again. Knowing when to jump in for specific problems and issues is key. It shows the employee that you do care, that you’re paying attention. They see your dirty hands, and your trust, and they know that you’re on the same team, win or lose. But you can’t do the work for them. I learned that from my mom!

L: Your mom taught you how to manage a business?

Don: She taught me to teach. My mom is a retired math teacher, and she was fantastic. She was so good, she eventually broke her teaching down to where she lectures only 10-15 minutes, and this is at any grade level of math. And that’s it! Yet her kids win competitions and are known for kicking ass.

She would arrange the students in pods of four. She’d then teach a concept and the pods would have to do it. If people had questions, she would go over and then never answer their question. Instead she’d say: have you asked anyone else at your table? If everyone is struggling, she would drill down and get them to solve the issue themselves, leading them where the answer is, but not giving it to them. She’d wait to help too, getting there at just the right moment to help kids stay motivated. She kept that balance between challenge and support perfectly.

L: So what ended up happening after you first bought Gravitate, and gave your people “uncomfortable freedom”?

Don: I got the info I needed from the audit, but the bigger success was how the leaders stepped up. Most were initially scared about the freedom, and lack of detailed instructions. I kept them encouraged and supported them, and now we have a team who doesn’t suffer from fear of failure; they want to dive into initiatives even more, and they know they’re going to have support when they need it. It was a complete win.

When you’re too strict with a team, the bonds they form are much weaker than if you make them uncomfortable and make them solve a common issue together. Working together against uncertainty unites us. A  good manager is able to form a strong team by guiding them through their uncomfortability together. They have to solve problems together, that turns into habit, and then they become an unstoppable team.

L: What’s the one bit of advice you hope someone reading this takes away? If they learn nothing else, what’s the: TL;DR?

Don: Building a team that can propel your company forward requires a coach who knows the balance between unstructured autonomy and genuine, hands-on support. If you prescribe solutions, your team will be reactionary. If you describe goals and allow the person to find their way, free of the fear of failure, then your team will be proactive, loyal doers.