The Founder Against the World (And His Team)

“I hold things back from him because I’m afraid of what he’s going to say.” -Team Member

At first, it felt magical. Each new team member had never been a part of something so real, where so much was actually happening. “We get shit done here,” the founder would say. “Hell yeah!” the team responded.

It was thrilling and terrifying; so much potential and so much responsibility.

Then, a few months in, that thrilling feeling began to feel like a drowning one. Overwhelmed with work, people struggled to know what to prioritize. Then, a months-long project got scrapped. All that work wasted. Sure, the company is growing, but every new customer brings a totally new set of tasks. They are re-inventing the wheel every time.

And the founder is getting increasingly frustrated. What’s the problem? He asks. Why can’t you make this happen? He starts to think maybe he’s picked the wrong people.

The team starts asking the founder for more direction and clarity. Who is our customer? Where are we headed? What’s our biggest priority?

But when they meet with him to voice their concerns, it’s like they’re caught in a reality distortion field. You get into the room with him and suddenly everything he says just makes sense, all the issues you walked into the room with don’t matter anymore. He’s right — we just have to do more. That’s the problem. Then, you walk out and realize not a single thing has changed.

So, the team does what the founder asks, they figure it out. They do whatever it takes to fix whatever is on fire. The problem is, now communication has almost completely broken down between the “management” (even if it’s just a management of one) and the front-line. You can see it physically: a wall separating he and them, an empty desk that was once filled with a founder who’s never in the office anymore. Where is he? He’s out frantically pitching a vision that’s nothing like the actual work that the team is getting done.

“He’s just not a good manager,” they say.

“They don’t know to take initiative,” he says.

“He refuses to close any doors,” they say.

“They don’t want to take responsibility,” he says.

Who’s really at fault here? Is this a failure to get things done or a failure to define the goal posts? Maybe there’s something else going on entirely…

So, how does it end?

Have you been here? What happened? You’re an advisor to the team. You’ve been watching this for months. Write an impassioned email to the founder telling him your story and what you think he should do next.

Want to join the conversation? Comment or click here to send us your response. We’ll gather your responses and share them next week.

Clues for finding a way out…


About the Founder Chronicles

This is the first episode of The Founder Chronicles, a choose-your-own-adventure journey into the chaos and triumph of starting something.

We release stories (“episodes”) of a team facing a challenge or puzzle. The episodes are purposely left unfinished; readers have the chance to share their stories to help us finish them. Each episode will have a list of tools or resources that might give clues for a way out. We bring together your responses to co-create a “way out” of the puzzle and send it out the following week.

Click here to get the next episode.

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