What If The Founder's Personality Is A Startup's Liability?

"What do we do if we suspect our own personalities might be a problem in our startup? How do we know if it's even something to dig into? And if we do find out we're the problem, what do we do about it?"

March 4th, 2020   |    By: Wil Schroter

During the early days of my first startup I stumbled upon a huge liability that was killing us quickly — me.

What's funny is no one else needed to have this discovery. The rest of the organization had figured out long ago that I was immature, combative, prone to anxious tirades, and generally a pain in the ass to work with.

And looking back, I'm probably being kind.

As a Founder (and CEO), every single one of those idiosyncrasies becomes amplified a hundred-fold because my liabilities to the organization become rooted in every decision we make, every interaction we have, and the entire morale of the company.

If we don't exercise some serious self realization — and do it quickly — we may be creating one of the biggest hurdles our organization has to overcome.

"How do I know if I'm the liability?"

That's the hard part.

As Founders, we're often the last to know because our worlds aren't entirely set up for total honesty. It requires some actual digging, which, to be fair, is a scary exploration. It helps to have a friend, mentor, co-worker, or spouse that we can trust enough to shoot us straight.

Finding an honest person is the easy part though. Asking the right questions is the hard part.

If we use polarizing queries like, "Do people think I'm a total jerk?" we're going to invite potentially kinder responses in fear of offending us. But something more aspirational like, "Where should I be spending time improving myself?" could really open up some helpful insights.

Trust me, when we are the liability as Founders, it doesn't take a ton of digging to get some honest responses. Not asking and digging is the real problem.

"What do I do if I'm the liability?"

Get in front of it.

Confront the people that we've offended or pushed away. In this day and age, fundamental honesty and contrition are a rare commodity. When I pulled people aside and started admitting, "Hey I didn't realize what a jerk I sounded like in that last meeting..." it blew people away.

The truth is, I didn't want to be a jerk, and I definitely didn't want to be a liability. The reality is we can't prevent ourselves from becoming our worst liability unless we take the time to assess ourselves fairly — and more importantly, do something about it.

In Case You Missed It

The Cost of Toxic Employees (podcast). We all know the value of having a star player on our team. But what about the opposite? Wil and Ryan discuss how to identify and handle toxic teammates before their impact spreads across the organization.

How Does a Founder Get Fired? Fired as the Founder — totally a dream, or a nightmare come true?

Fighting Cynicism In Company Culture. What are the root causes of cynicism? And how we keep it from contaminating our company?

About the Author

Wil Schroter

Wil Schroter is the Founder + CEO @ Startups.com, a startup platform that includes BizplanClarity, Fundable, Launchrock, and Zirtual. He started his first company at age 19 which grew to over $700 million in billings within 5 years (despite his involvement). After that he launched 8 more companies, the last 3 venture backed, to refine his learning of what not to do. He's a seasoned expert at starting companies and a total amateur at everything else.

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