Hire help when you can write the job on one page

Quick answer: Hire when you're turning work away or dropping balls with clients you already have, and when you can describe the task on a single page. If you can't write it down, you're not ready to hand it off.

Busy isn't a reason to hire. Every self-employed woman is busy. Busy at 9 p.m. with a sleeping house and a cold cup of tea tells you nothing except that you're tired.

Two signals that count

The first is a waitlist. Someone asks for your time and you say "not until next month." You've said it more than twice. That's revenue you're declining because there's one of you.

The second is a slipping standard. A client email sat for three days. An invoice went out two weeks late. A deliverable landed a day behind. Nobody complained yet, but you noticed, and the people you work for will eventually.

One of those without the other is a yellow light. Both together is a green one.

If neither is true, you may not need a contractor at all. You may need to cap your hours first and build the business to fit. Plenty of good small businesses stay a one-woman shop on purpose.

Hand off the task you can describe, not the one you hate

Most advice says to delegate what you dislike. That's half right. Dislike is how you find candidates. It isn't how you pick.

Pick the task with edges. Something that starts the same way, ends the same way, and has a clear "done." Scheduling. Invoicing and follow-up on late payments. Formatting and uploading. Packing and shipping orders. Basic bookkeeping entry. Inbox sorting.

Bad first handoffs are the tasks that live in your head. Pricing a custom job. Deciding which client to fire. Writing the thing only you can write. You haven't figured those out in a way anybody else could follow, and a contractor can't read your mind. She'll guess, and you'll fix it.

Here's the test. Do the task yourself three more times and write down every step as you go, including the annoying ones, like where the login lives and what you say when a client pays late. If it fits on one page, it's ready. If it takes five pages and still has "use your judgment" in it, keep it.

The math, with an example

This is an example, not a real client.

Say you run a small editing business. You bill $75 an hour when you're working on client projects. Each week you also spend about five hours on invoicing, scheduling and sorting your inbox. Nobody pays you for those hours.

A part-time virtual assistant at $30 an hour for those five hours costs $150 a week. If you turn three of the freed hours into client work, that's $225 of billable time. The other two hours go to your kids, your husband, or the dishes. You're ahead by $75 a week, and you got two hours back.

Now the catch. That only works if there's client work waiting to fill the hours. If your calendar is half empty, paying someone to do your admin just lowers your profit. It might still be worth it for your sanity, but call it what it is.

Not sure what your hour is worth? Start with why your rate isn't your old salary divided by forty hours. Then compare the cost of the help to your real rate, not the rate you wish you had.

Start with a test project, not a commitment

Don't hire "someone to help me." Hire someone to do one defined thing, for pay, with a deadline.

Make it small. Three to five hours. Something real, so she's touching actual work, but not so critical that a mistake costs you a client. Give her your one-page instructions and nothing else. Then watch three things:

• Did she ask good questions, or guess?
• Did she deliver when she said she would?
• When she hit a snag, did she tell you early or go quiet?

Quiet is the dangerous one. You can train skill. You can't train someone to speak up.

If the test goes well, give her a second, slightly bigger one. If it goes badly, you spent a morning and a small check. Pay her for it anyway, on time. Pay before she asks. That's how people learn you're worth working for, and it costs you very little.

Put it in writing

A friendly handshake feels warm until the first misunderstanding. A one-page agreement fixes that. Cover:

• What she's doing, specifically
• What you're paying and when
• Deadlines
• Who owns the finished work
• What stays confidential
• How either of you can end it, and with how much notice

You don't need a lawyer for a simple scope-of-work note, but ask one to look at it if the work touches your intellectual property or client data.

Two cautions. First, the line between a contractor and an employee isn't set by what you call her. The IRS looks at how much control you have over how the work gets done, how the money side works, and the nature of the relationship. If you're setting her hours, supplying her equipment and directing every step, that looks like an employee. Second, there's a dollar threshold at which you must file a 1099 form for a contractor. It changes, so ask your CPA what it is this year. And set aside what you owe in taxes before you spend your profit, as covered in the money in your business account isn't yours yet. None of this is tax advice. A CPA who works with small businesses can sort it out in one meeting.

Serve her well, and keep your backbone

A good contractor deserves clear instructions, fast answers and prompt payment. Give those. Don't make her chase you.

But hold the line. If she misses a deadline once, talk about it plainly. If it happens twice, end the arrangement kindly and move on. You're not being harsh. You're protecting the clients who trust you and the family time you hired help to protect.

Skip two other mistakes. Don't hire a close friend you couldn't let go. And don't give anyone access to every account on day one. Start with what the task needs and widen it as trust grows.

What the first hire is really for

It isn't to grow a company. It's to buy back the hours that cost you the most, whether that's your evenings, your Saturday, or the half hour when the kids come home and you're still answering email.

Write the one-page job. Hire the test project. If it works, you won't spend another weeknight reformatting spreadsheets.