10 Lessons I Learned Growing My Business to 100 Employees: Part 2

In the first article of my two-part post, I shared some of the things I learned along the way to reaching 100 employees at AppointmentPlus. It’s been an incredible journey in overcoming one challenge after another. Without a doubt, the combination of problem-solving experiences and the passage of time has taught me some valuable business — and life — lessons.

So, without further ado, here is Part 2 of the “10 Lessons I Learned In Growing My Business to 100 Employees.”



When I meet people and they say, “Congratulations on your success!” I say, “Well, thank you very much.” But inside I’m saying, “You have no idea what our company has gone through to get to this point.”

There is no direct line to success; its path looks more like that of a roller coaster. Sometimes you’re up, sometimes you’re down. Sometimes, you’re upside down and the change is falling out of your pockets. Sometimes you’re going fast, sometimes you’re going slow. Sometimes it feels exhilarating. Sometimes you feel a little sick.

And even when you do reach “success,” all you have to do is stop and listen closely. Do you know what you’ll hear? Click, click, click, click. The roller coaster is ready to start all over again.



Just like the roller coaster to success goes up and down, so does the energy level in a company. It’s very important that you pay close attention to this. It’s almost as if the organization is a single person with feelings. Sometimes they’re happy and they feel good. Other times, they may feel anxious, worried or just plain blah (yes, that word is actually in the dictionary. Look it up.).

As a business leader, your job is to adjust your actions to how the company is feeling.

If things are going well and morale is high, feed the energy. Be the emcee of the company. Add more pep to your communications. Talk a lot about all the great things happening in the organization. Have a little more fun than you normally would. Allow people to relish the positivity.

Because it won’t last forever.

When morale inevitably starts to dip, be sure to react appropriately. Don’t force the fun. Periods of lower energy are okay. Keep the communication positive and supportive, but pull back a bit on the level of energy in your words. Maybe even use this time to be a little more serious.

This is also a time to make sure your team knows they are appreciated. Do something nice for them or just let them know you value them. It matters.

Before you know it, morale will pick back up again.


Bob pull quote #2.png



Just as it’s often necessary to remind ourselves to “be in the moment,” we also continually need to nudge ourselves about  the value of focus. We are drawn to shiny objects like insects to a light. We can’t help ourselves. There’s always some new idea, a can’t-live-without feature, or some strategic shift that we think is the Holy Grail for propelling the company forward. As painful as it is to admit this, it rarely works out that way.

When we shift around priorities too much, it causes confusion and reduces productivity. Everyone understands that some modifying of priorities or strategy is normal and necessary. But, too much is frustrating.

This negative feeling about shifting priorities and ideas only intensifies when you grow as a business. And the way it manifests itself should keep anyone who leads people up at night. Annoyance with too many changes causes people to check out. They stop caring, thinking that if they just wait another week, things will change again. Thus, there’s no reason to spend any mental energy on buying into the shiny “object du jour.”

But when a company stays focused on a clear strategy with only minor occasional adjustments, magic happens. Morale increases, teamwork improves, communication flows more smoothly, and employees are engaged.

It’s difficult to stay focused. But for those who can pull it off, bountiful rewards await.





There’s a phenomenon that happens to most every business. In the early days of a company, the excitement level is high. Leadership can clearly envision an amazing future for the business. The world is their oyster.

They may or may not raise some money, but friends, family and others are all pulling for this little engine that could. Good news seems to be coming out of the company at a rapid rate. A new client just came on board. A company goal has just been achieved. A new team member is already making a contribution. The company is crushing it!

And this positive and promising news goes on for a while. Everything is falling into place. Everyone is super busy, but that’s okay. Business is good!

Then something happens.

A competitor starts to gain traction. A key employee leaves the company. A critical feature is delayed six months. Revenue growth starts to flatten a bit. The easy laughter among the team isn’t so easy anymore. That clear future starts to look a little blurry.

Welcome to the slog.

This is a period when the leaders of a business realize that world domination is not going to happen any time soon. It’s when the realities of operating a business set in. The honeymoon is over, and now it’s time to truly focus on building a long-term business. Yes, you heard me: long-term (Ugh!).

The decision to commit to the long, slow process of building a company is a tough one. It requires that things change. It may even require that some people are removed or replaced. It’s a painful period, but a necessary one in the development of an organization.

Some companies never make it through the slog. The thought of years of mundane work is too much to bear. They pivot, they go for broke, or they just throw in the towel.

But what they don’t realize is that this period is normal. In fact, it’s not only normal; it’s necessary. This is the point when a business grows up. If a company makes it through this trying time, they generally achieve some measure of success and become a healthy, more resilient organization.

The ones who fall prey to the slog fade off into oblivion.

Embrace the slog.



It never ceases to amaze me how people rise to the occasion. Whether it’s in taking on a project, getting a chance to supervise a team, or giving a presentation, they always seem to step up and deliver.

Whether they face challenges with some trepidation or with a can-do attitude, people inherently like to test themselves. They want to be pushed a little. It may be uncomfortable for them, but they generally end up feeling pretty good about themselves in the end.

It’s okay to nudge people outside of their comfort zone every now and then. It gets the blood moving and keeps the mind sharp. It also allows them to grow.

So, give employees a shot at that new role or in leading that project. You might be pleasantly surprised at the result.


I hope these lessons were helpful. The experiences you have on your own journey will no doubt be different, but they’ll be just as meaningful. Even if your company never reaches the 100-employee mark, the point is to continue learning along the way. Remember, it’s not about reaching that milestone; it’s about the blood, sweat, and tears it took to get there.