Step 10: Understand Employer Responsibilities


“Be your own boss.” It’s the mantra that got me started on the business ownership bug. Even when dealing with the boring parts of forming my company—filing paperwork, paying fees, registering for taxes—I was doing things at my own pace, on my own terms. No one was telling me what to do or when (or how), and that turned even the boring stuff into something I could be proud of.

Being my own boss has been the best thing about venturing out on my own. I dreamt of my company’s future, of growing my business, of expanding my reach, and of working hard to get to that point. Finally, the day came when it was time for me to hire my first employee, and to become the boss of someone else, I realized I was treading straight into unknown territory.

Fortunately, I had my business partners—all of us co-owners of our company—around me, so I wasn’t facing this unfamiliar terrain alone. I’m grateful for that, because we faced several big challenges right off the bat.

More Busywork

In order to remain competitive, my partners and I needed a new employee now. But it turned out that “now” wasn’t realistic, because we hadn’t planned for the extra string of paperwork, expenses, legal obligations, and liabilities that came along with readying our company to hire its first employee. There were new forms to file, new expenses to pay, new accounts to set up, and lots more to learn.

And as we got closer to understanding our responsibilities as employers, we realized that more people on the team meant more room for things to fall through the cracks. Our current record-keeping system wasn’t going to cut it, so we had to form a new system on the fly and get used to doing things all over again. It was as though everything we did at the start of our business needed a reboot.

New Expenses

My partners and I wanted to hire our first employee so that our business could continue to prosper. And while we eventually succeeded in that, we suffered through our share of sleepless nights in the interim when we learned how easy it is to overspend on the hiring process.

In our case, the costs of hiring an employee included obtaining workers’ compensation insurance, paying unemployment taxes, and consulting our accountant on best practices for setting up all our new tax payments. And of course, all of that was factored on top of actually paying our employee’s salary.

Extra Stress

In the early stages of running our business, my partners and I ran like a well-oiled machine (for the most part). Adding another person to into the mix meant throwing off the rhythm we’d created. It meant reassessing the way we worked, training our new employee on all our systems and processes, and figuring out where we needed to improve so that integrated future employees into our company would be seamless.

It was a learning process for all of us. Hiring our first employee meant an adjustment period that we had to navigate, all while trying to run our business just a smoothly and effectively as ever. It was not an easy combination, and it led to some strife between us co-owners. It was something we’d anticipated to an extent, but we found ourselves surprised at how much we had to fail before we were able to succeed.

Lost Time

All the extra steps to take, all the forms to fill out, all the tax laws to research—it all amounted to extra time we spent on making sure we were legally prepared to take on new employees. Any time spent on those tasks meant time away from all the other important aspects of running our business.

It was another challenge we’d underestimated. There were plenty of rough days when I’d blocked out a half hour to make a quick phone call and check up on an employment issue, only to spend the rest of the day sifting through records, scouring old contracts, tracking down info, and playing phone tag in order to sort something out. Only then was I able to start all the other work I’d planned to do that day. Sometimes it was difficult not to get discourage. Hiring an employee was supposed to make things easier, not harder.

A Change in Perspective

There was another outcome I didn’t expect when I hired my first employee. The moment our new hire arrived on the scene, that’s when it finally sunk in that I wasn’t just responsible for my own schedule, my own workload, and my own income. That is to say, I wasn’t just my own boss anymore. Now I was the boss of my company’s newest employee as well. And as it turns out, I had a lot to learn about what it meant to be “the boss.”

Part of what so attracted me to the idea of being my own boss was the knowledge that I could do things better. I could be a better boss than those I’d worked for in the past. We all have stories about bad bosses, lousy managers, and stubborn supervisors. But in running my business, I’ve come to realize that “bad” boss behaviors can stem from many things. I even emulated some of those bad behaviors when I became someone’s boss for the first time ever.

Becoming a Bad Boss

Sometimes being a bad boss comes from inexperience. I was guilty of this when my company hired its first employees and the chain of command put them directly under my supervision. Even though I’d observed my past managers, and reflected on what I thought worked well and what didn’t, it was an entirely new challenge when I was the person in charge. Working with new people always takes some getting used to, and learning how to manage others is an even tougher challenge. And it’s one I could have only gained from experience, and from making plenty of mistakes along the way.

Bad boss behavior also comes from being fearful. Sometimes I was so afraid of failure that I overcompensated by doing too much, by setting my expectations too high, by failing to communicate, by over-communicating, or by failing to delegate effectively. I never meant to do the wrong thing—to be the bad boss—but sometimes I was so afraid of doing the wrong thing that I went too far to the other extreme. And in doing so, I set myself (and my employees) up for the very failure I was trying so hard to outrun in the first place.

Related to fear is the issue of being too controlling. As a business owner who became my company’s Project Manager, it felt strange for me to give up some of my control to another employee. Even though we’d hired a new person for the specific purpose of taking some of the workload off my shoulders, I found that letting go was actually much more difficult than I’d anticipated. It would take some time before I learned to gracefully and graciously let go of the control I’d enjoyed prior to hiring an employee. Which is ironic, because, after all, being in control was one of the major reasons why I started my own company in the first place.

Learning to let go, and to put an important part of my business (and by extension my life) into the hands of a new employee—practically a stranger—was one of the most difficult challenges I faced as my business began to grow.

Becoming a Good Boss

Being my own boss is very different from being someone else’s boss. That was a harsh realization to face, and when I hired my first employee, I definitely spent some time as the accidental bad boss.

But I’ve learned that there’s an important difference between bad bosses who are just plain bad, and bad bosses who are still learning how to be great. Over time, I worked at overcoming my fears and insecurities as a manager, and learned how to embrace the role I needed to embody as I grew my business into something great. I learned what it means to be a good boss, and I learned how to forgive myself for falling into those bad boss behaviors.

And with my employees’ help, I strive to improve as a manager every single day. If we as business owners want to see our businesses grow and succeed, we’ll have to go through the same evolution as managers. That’s not always easy, but it’s the most important thing we can do for the health of our business, our partnerships, our employees, and ourselves.


About Author

Robin Karleskint

Robin Karleskint has worked at several new businesses, both as an owner and an employee. Currently she is a project manager at Cosmital Designs, a company she co-owns in Orlando, Florida.