I recently realized that at over 300 employees, my team at Techstars is now the largest team I've ever led. It's exciting, for sure, though also daunting. I suspect that every founder of a growing company has known the occasional moment of terror at realizing just how many mortgages, car payments, kid's braces, and meals on the table are relying on the continued success of their business

Even more challenging, techniques that used to work well for me when I was managing a smaller team have recently been breaking down. Running a company that employs hundreds of people just isn't the same as managing a team of 50

It's no surprise that success breeds new challenges. If you're lucky enough to have a growing company, you're going to run into the problem of how to manage your team as it gets bigger and bigger. 

Here's what I'm doing to keep growing both my company and my own abilities. 

Learn from the people around you.

Surround yourself with people who have experience at different sized companies. You probably already have them, if your company employs a couple of hundred individuals. Who's had a great experience managing a team within a large business? Who's been miserable in a leadership role, and why? Who's lived the challenges of aligning their work with the mission of a major corporation?

Be deliberate about figuring out who has worked at companies of various sizes, and then make sure you talk with them regularly to understand their experiences elsewhere. Ask about the good and the bad. Where did they see breakdowns in communication? How did they set budgets, motivate teams, balance what's working now with trying new things? 

You can learn a great deal about both what to do and what not to do through regular conversations with a small group of thoughtful people. 

Hire a coach.

I believe in experts, and in taking expert opinions. To me, hiring an executive coach is exactly this: taking the advice of someone who is an expert in how to do the job of an executive at a large or growing company. I'm not an expert at this -- yet. I don't want to waste my time making terrible mistakes and learning from them. I want to skip as many mistakes as possible. 

It's the same principle as bringing together startup founders with mentors who are experts in an industry or a particular aspect of doing business. Need help with PR? Talk with a PR expert. Not sure how to grow your company from two to 12 employees? Talk to the people who've done it again and again. This is what we do for startups at Techstars -- connect them to the experts they need. This model works, and hiring an executive coach is part of this same model. 

Stay humble.

A common trap that executives fall into is hubris, the excessive self-assurance that comes from too much success. This leads to an unwillingness to ask for help when you need it. Fight this mindset. There will always be times when you need help, and at those times, finding help is a mark of strength, not weakness. 

Hiring a coach is one way to find help. Just as important is to be humble and open with your team. Do all 300+ of my employees have to know, in-depth, my struggles with leadership? No, but all of my team leaders do. They need to know so that they can help. 

If I hide behind hubris, if I try to only project an image of success at all times, I'll never learn. And I want to learn -- from my friends, my employees, my coach. 

This is why I believe I'll succeed at managing Techstars at 300 employees and many more: because I'll keep asking for support, learning new skills, and relying on my team to help me succeed. 

Published on: Jan 29, 2020
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