Hire when the tasks someone else could do are eating so many of your hours that you’re saying no to work only you can do. Track your time for two weeks. If the hand-off-able jobs add up to a steady 20 hours a month or more, you’re ready. Write down how you do those jobs before you hire, and start with a few small projects so neither of you drowns.
You know the moment. It’s 11 p.m. and the CEO of your company is reformatting an invoice template because the logo looked “a bit left.” The CEO is you. So is the bookkeeper, the social media manager and the person who orders printer ink.
Why it’s harder than it sounds
Most women who run businesses never cross this line. According to the SBA’s Office of Advocacy, women owned 12.7 million businesses with no employees and 1.3 million with paid staff in 2022. That’s fewer than one in ten with a payroll.
Some of that is choice, and solo is a perfectly good business. Some of it is fear, and fear has good arguments. Payroll is a promise you have to keep every single payday. An employee also comes with paperwork. The IRS is blunt that if you have employees, you generally must withhold income, Social Security and Medicare taxes from their wages and pay your own matching share plus unemployment tax.
Then there’s the trust problem. Your name is on the work. Handing it to someone else feels like lending your car to a teenager. Who has just passed their test. In the rain.
What actually works
Track your time before you trust your gut
Your gut says you need help “with everything.” That isn’t a job description. One founder who built a 14-person content agency did the dull thing first. She “started time tracking and realized that some of these things were taking me 20 hours a month or 25 hours a month.”
Then she asked the useful question: “imagine how much more I could do if I had that 20 to 25 hours back in my schedule.”
Do the same. Two weeks of honest tracking. Highlight everything someone else could do to your standard. Add it up.
Hire for the ceiling, not the panic
Her trigger wasn’t a bad week. It was a hard limit. “I could not do more work alone.” She wanted to take on more clients and physically couldn’t, and she was a full-time college student at the time. (Midterms and client deadlines. In the same week.)
If you’re at capacity and the demand is real, that’s the signal. If you’re just tired, take a long weekend first.
Start with the jobs you hate
She noticed “there was a lot of things that I was doing within my business that I genuinely didn’t enjoy doing.” That list is gold. The jobs you dread are usually the ones you do slowest and put off longest. Someone who likes them will do them better. Annoying, but true.
Write the manual before you hire
Before her first hire, she wrote down how she did every task for clients, in detail. Then she could hand it over and say: “here’s exactly how we do things around here.”
It feels like homework. It’s the difference between onboarding someone in a week and answering the same question 40 times.
Start small, then hand over more
Her rule for new people: “I typically start off by giving them like a few small projects here and there.” Then more. Her warning: “if you just immediately dump a bunch of stuff on a new team member, of course it’ll overwhelm them.”
The first person she hired? Still with her.
Hear it from someone who’s done it
Ashley Mason started her content marketing agency, Dash of Social, at 19 as a college sophomore, and ran it alone for about two years before hiring her first team member. Jump to 7:03 to hear how she knew it was time, or listen to the full episode.
FAQ
How do I know my business is big enough to hire employees?
When you have steady demand you can’t meet alone and enough reliable income to pay someone for months, not weeks. If the work is lumpy, start with a contractor or part-timer and see if the hours hold.
Should my first hire be an employee or a contractor?
It depends on how much control you need. The IRS looks at three areas: whether you control how the work is done, the financial side of the job, and the relationship between you. Get it wrong and the taxes get expensive, so check with an accountant before you decide.
What should my first hire do?
The tasks that eat the most hours and need the least of you. Usually admin, scheduling, fulfillment or the repeatable parts of client delivery. Keep the work only you can do, and the relationships that pay.
What do I need to set up before hiring?
The SBA’s checklist starts with getting an Employer Identification Number, deciding between a contractor and an employee, and collecting a W-4 from new staff. Do the paperwork before the first day, not during it.
Next step
If marketing is one of the jobs eating your hours, Captrr runs a podcast for experts on two hours a month of their time. Full disclosure: it’s Serena’s company.