From “me” to “we” – surviving my first hire

Lindsi Gish is owner of gish&co, a small strategic communications and digital marketing firm in Minneapolis. She will be presenting “Hiring employee #1 (gulp!)” as part of the “Getting Serious” series for solopreneurs, on Tuesday, Dec. 11 at Fueled Collective Uptown.


I was fortunate to start my business in the company of a few key contacts who’d been at it for several years – contacts, and eventually friends, who helped answer questions like:

“Wait, so how do I run payroll?”

“Should I do my own bookkeeping?”

“How do you get your own health insurance?”

“How do I even pay taxes? What is the difference between personal and business taxes?”

“How do you track time? What software do you use?”

So when I found myself at capacity just a year and a half into launching gish&co., these same folks also helped me answer a multitude of questions about what adding an additional team member might mean for my business, my workload, and my life.

Here are a few of questions I asked, and what I’ve learned since. (Join us for Getting Serious to hear more!)

Should I hire an employee or a contractor?
There are pros and cons to both options. For me, hiring a part time contractor was a way to dip my toe into the hiring waters, without feeling like I was making a commitment I was uncertain I’d be able to sustain long into the future. I wound up settling on a 20 hour/week contract role, and was fortunate to work with someone who appreciated a bit of financial stability in her own life, but who didn’t need a sense of permanence to feel committed and secure.

After several months, though – I realized it wasn’t the right answer for the long term. I was half committing to someone, and they were half committing to me, naturally. But I found that I needed more, and my clients needed more. I needed another person to be part of the team, who’d invest energy and time into the business as their primary professional endeavor. And my clients – especially for those whose accounts this person was going to be managing—needed to know their person wasn’t going anywhere, and truly cared about the success of their business.

But how will I know if I’m ready to commit to a full time, permanent employee?
We often attach the word “permanent” to FTE positions, not considering that Minnesota is an employment “at will” state. But permanent. It still just sounds so scary! How do I even know if the business itself is permanent? What if I’m not sure I want to do this type of work permanently?

The reality is, nothing is certain. But I remembered enough from middle school science class to have a hypothesis:

Hiring an employee will help me fulfill current contracts, accept new ones, and will give my clients and me more peace of mind.

To test that hypothesis:

Hiring a part time contractor will help me discover how workflow and operations would be affected by making a longer-term commitment.

And to conclude:

Assuming I can make payroll, this is the smartest move.

I also quickly realized that I wasn’t hiring a robot who would read the word “permanent” and think, “Well, I guess I’m working at this teeny young company for the rest of my life!” In truth, the median employee tenure ranges from 4-5 years, depending on certain qualifiers. I was going to hire a human, and we were going to have human conversations about the reality of this business, and it was going to be critical for that person to know exactly what she or he was getting into.  

How will I know when I’m ready?
I’m about as security-minded as solopreneurs get, as evidenced by my business structure (i.e., ongoing contracts for a set fee for a statement of work—vs. project-based work that tends to show up in revenue peaks and valleys). So with every significant business decision, I do my best to find (or create) as much certainty as possible before moving forward.

But here’s the truth: There is no such thing as security or certainty in this business. The best piece of advice I got was this: If you’ve consistently been securing work, you’re making more money than you need, you are fairly certain you could take on more opportunities if you had more help, and you have the legal/accounting/payroll/etc. services in place to support you in making it happen – you’re probably ready.

Sara will hit the three-year mark with gish&co. in March. Having a co-conspirator, supporter, handler-of-all-the-things, and friend by my side has been one of the most rewarding experiences of my professional life.

I look forward to sharing more about the journey with you at Fueled Collective on December 11!