Your First Hire: What to Sort Out Before They Start

The short version

• Your prices have to cover a second person before you hire one.
• Write the job down before you hire for it, or you will hire a version of yourself.
• Employee or contractor is a legal classification, not a preference.
• Decide what they can see in your systems before day one.

The first hire is where most service businesses either become a company or get much harder to run. The owner goes from doing all the work to doing all the work plus managing, which for a while feels like a step backward.

The way through it is preparation. These are the things that have to exist before someone new shows up.

Check that your prices support a second person

A second person adds wages, taxes, insurance, equipment, possibly a vehicle, and time you spend supervising instead of producing. If your current prices barely cover you, they will not cover two of you.

Run the numbers before you post the job. If the math does not work at current prices, raise prices first. Hiring into thin margins is how owners end up working more hours for less money.

Write down the job before you hire for it

Owners hire vaguely, describing someone who can help out. Then they are disappointed when the person does not do the work the way they would.

Write the actual tasks, the standard each one has to meet, and what a good week looks like. That document is your hiring filter, your training plan and your first performance conversation, and writing it takes an hour.

• The specific tasks, in the order of a normal day
• What finished looks like for each one
• What they decide and what they escalate
• What you expect in customer facing moments

Classification is not a preference

Employee or independent contractor is determined by the nature of the working relationship, and the tests vary by state and at the federal level. Control over how the work is done, who supplies tools, and whether the person serves other clients all matter.

Getting this wrong is expensive and the liability lands on you, not on the worker. Ask an accountant or an employment professional about your specific arrangement before the first day, not after an audit.

Sort insurance and licensing before day one

Workers compensation requirements, general liability coverage that contemplates employees, and any licensing that has to name the person doing the work. These have to be in place before anyone touches a customer's property.

This is also a call to your insurer, not a search result. Tell them what you are doing and let them tell you what changes.

Decide what they can see

A field employee needs today's jobs, the addresses, the scope, and a way to reach you. They usually do not need your margins, your full customer list, your pricing logic or your financials.

Set those boundaries on day one rather than after something walks out the door. It is a normal, unremarkable part of setting someone up, and it is very awkward to retrofit later.

Before the first day

| Item | Why it comes first | | --- | --- | | Pricing checked against a second wage | Prevents hiring into a loss | | Written job description | Gives you something to hire and train against | | Classification confirmed | The liability is yours, not theirs | | Insurance updated | Coverage must exist before the first job | | System access scoped | Much easier to set than to take away | | First week planned | Training that is not improvised |

Do this before your next job

Do the preparation before you post the job, not after.

1. Run your current prices against a second wage plus taxes, insurance and equipment.
2. Write the tasks, the standard for each, and what the person decides versus escalates.
3. Confirm employee or contractor classification with a professional for your specific arrangement.
4. Call your insurer and tell them you are adding a person, then update coverage.
5. Decide what they can see in your systems and set it up before day one.

Common questions

Should my first hire be a helper or another qualified tradesperson?

It depends on what is limiting you. If you are the bottleneck on skilled work, a helper frees your hours cheaply. If demand exceeds what one skilled person can serve, you need another.

How do I train someone without losing a week of production?

Ride along for the first jobs and accept that the week is not fully productive. Trying to skip it costs more in rework and customer trust.

What if the first hire does not work out?

It happens often. A written job description makes the conversation clearer and faster, because you are comparing performance to something specific.

When is the right time to hire?

When you are consistently turning away profitable work or working hours you cannot sustain, and your prices cover the second person.

Keep reading

• How to Schedule a Full Day of Jobs
• How to Price a Service Job Without Guessing
• Invoicerus for landscapers
• Invoicerus for handyman businesses

Try it on your next job

Open the job price calculator and run one real job through it. No account, no card, nothing to install. If it saves you time, the free invoice generator is the next one to try.

Invoicerus does the same work on autopilot once your services and prices are set up. Start free and bring one week of jobs with you.