3 Things That Happen When Your Company Reaches 100 Employees

Casual discussion between coworkers

By Jessica Stillman

Here's the funny thing about starting a business -- many people do it to escape the sluggishness and inefficiencies of big organizations. But at the same time, if you're successful with your start-up, soon enough you may find yourself at the helm of... a pretty big organization.

This transition from steering a small team to managing a proper company with dozens of employees can be challenging for many entrepreneurs. Christine Tsai, a founding partner of 500 Startups, feels your pain. The accelerator now has a headcount of 100, she reported recently on Medium, and it's been a roller coaster getting there.

"You make mistake after mistake after mistake. You suffer from a severe case of imposter syndrome. You constantly wonder WTF you're doing," she writes. So how can you minimize the inevitable bumps in the road as you follow in Tsai's footsteps to become a boss to 100? On Medium, she offers a half dozen lessons learned. Here are the basics of three to get you started.

1. Rituals become indispensable.

You probably got into entrepreneurship because you hated bureaucracy. That's sensible, but don't let your hatred of systems and processes go too far. You'll never need pointless paperwork, but when you reach 100 employees you definitely will need rituals, counsels Tsai.

"Rituals are absolutely necessary to keeping a company nimble and setting your team up for success. Moreover, they will help you actually practice your values day-to-day and make them more tangible," she writes. "Rituals are applicable to anything and everything, be it team communication, meetings, quarterly OKRs, sales, customer engagement, data, team bonding events, etc."

Tsai goes on to offer a few examples of 500 Startups rituals including weekly one-on-ones and using employee engagement software before concluding, "professional athletes don't play it by ear when it comes to practice and conditioning. They have insanely disciplined regimens and rituals which enable them to perform when it counts. The same applies to companies."

2. You'll need to let stuff go.

A lot of stuff, according to Tsai. At least if you want to empower and motivate your team.

"This may mean removing yourself entirely from discussions or even offering your two cents unless explicitly asked. Become ruthless about delegating and trusting your team to make smart decisions. In fact, do it at the expense of your own recognition. This is often one of the toughest things for founders to do. After all, it's much more fun to build product than to review your 2016 budget forecast, right?" she writes.

3. High school will come back to haunt you.

The more people there are in a company, the more scope there is for cliques to form, Tsai warns. That means you're going to have to deal with their rivalries and disagreement -- just like in 9th grade. Even if that's really not what originally got you interested in management.

"You may be accustomed to fixing bugs in code. Now your time may be spent fixing 'bugs' within your team. Your role becomes a lot more about people--hiring, firing, and firing them UP and setting them up for success. But rather than perceiving this as a hassle, take it seriously," urges Tsai.

She also offers this pro tip for those hoping to keep the high school drama out of their companies as much as possible: "Preventative medicine is more effective than reactive medicine. If you've waited until something manifests into a real problem to address it, you waited too long. Invest heavily in solutions (rituals!) that will prevent problems before they happen. It will make your life easier, and your team will be happier as a result."