10 Lessons I Learned Growing My Business to 100 Employees: Part 1

Less than one in a million companies make it to 100 employees. Even for hard-core gamblers, those are pretty stiff odds. You’re probably more likely to be born with a tail than to reach 100 employees in your company. Okay, the odds aren’t that bad, but it’s pretty rare.

You know how some pictures show a long, straight road that disappears into a beautiful sunset? Yeah, that’s not the road to 100 employees. The road to the century mark is more like a bumpy lane with huge potholes that runs alongside a cliff (with the occasional landslide).

No, it’s not easy to reach this milestone. As a matter of fact, it can be downright painful at times. Anyone who makes it to this point has probably “gone fetal” more than once (curled up on the floor, thumb firmly ensconced in the mouth). But, among all of the challenges involved, you can’t help but learn a few things along the way. As we all know, with adversity comes growth.

So, I’ve assembled a list of 10 lessons I’ve learned in scaling our business to 100 employees. My hope is that they make your journey to this important landmark is a little less precarious.



In order for a business to grow, it needs policies and procedures. If you have a lot of employees and no rules, you get chaos. But if you add too much structure, you lose nimbleness. Nimbleness— the ability to quickly react to changing market conditions— is what allows small companies to grow and compete against big ones. The large firms simply can’t make adjustments swiftly.

So, the key is to add just enough structure for where you are as a business, and no more.



As a company grows, it will naturally form functional silos — such as sales, marketing, support, finance, etc. These silos actually even exist for tiny companies, it’s just that the walls either don’t exist or are paper-thin. In other words, if the person handling finance is sitting next to the person overseeing sales, both know what the other is doing. The silo walls are practically non-existent.

Now, if you’re a one-person company and you notice that silos are forming, you might want go back to your prior job and beg for forgiveness. You can thank me later.

But as a company gets bigger, it’s normal for the walls between departments to thicken. And when this happens, communication doesn’t flow as easily. This occurs all the time in big companies. We’ve all experienced situations where one department has no idea what another department is doing. They’re not only not on the same page, they aren’t even reading the same book. The walls of their silos have become nearly impenetrable.

Silos are needed for operations to function properly as a business grows, but keeping the communication flowing among them is critical for success.


the road to 100 employees quote



Every new person you hire will bring a different set of work and life experiences into the company. Because they’ll also bring a different personality, each new employee slightly changes the dynamics of the company. It’s like every new addition to the team comes equipped with a chisel and starts immediately contributing to the magnificent statue you’re building. It’s a wonderful and fascinating part of how a business evolves.




Management books will tell you that you have to manage each person differently based on their personality type and motivations. While that may be true, what’s even more true is that even though we’re all different, there is a core set of needs that we all have. These include:

  • We like to have our thoughts and feeling acknowledged. We want to be heard.
  • We like to have some control over what we do. No one wants to be micromanaged.
  • We want to feel safe and secure in our jobs. No one wants to be constantly wondering if they are going to get fired. It’s stressful and counterproductive. 
  • We want to have the ability to do our best work. We want to have the tools and environment that allows us to produce great work.
  • We want to be compensated fairly for our work. We need money to function in our world.
  • We want to get feedback. If we have done a good job, we want to know that. If we could improve, we want to know that, too. 
  • We all want to be part of something special. We want to contribute to something important and meaningful. 
  • We want to be part of a team. We all have an innate need to be accepted by the tribe. And when we feel we are an important, contributing member of the group, it feels good.                                                                                                             


We all have similar basic needs. But isn’t it amazing how often we don’t get these basic needs met? If you’ve ever wondered what your job as a leader is, the list above is a pretty good place to start.



How many times do we need to remind ourselves to be happy in the moment? How many times do we have to tell ourselves to be grateful for the lives we have right now? How many times must we remind ourselves to stop worrying about the future and be present in the moment?

Well, if you’re like me, you have to do this a lot.

Talk to any person or team that has set a lofty goal. When they reach that goal, it feels great. Emotions are high. It’s a time to celebrate. But, it’s also a bit anticlimactic. What you realize soon after you reach the summit is that the fulfillment wasn’t in achieving the goal; it was in all the hard work you had to put in to get there. This includes how you had to work as a team to overcome challenges, the anticipation and excitement of the better future you were creating, and the relationships you built along the way.

We’re at our best when we’re working toward something important and meaningful. And when we get to do it as a team, it’s that much sweeter when the goal is achieved. You did it, together.


Those are just some of the lessons I learned on the road to 100 employees. Even if your goal isn’t to reach 100 team members, I hope these ideas give you insight into growing your business. I’ll be sharing some more in a post entitled 10 Lessons I Learned Growing My Business to 100 Employees – Part 2. Good luck!