Playbook · People
Should I hire my first employee, or a contractor?
For someone running a business alone who has more work than hours, and has to choose between a person on payroll and help by the job.
In short
A board of named AI experts — The Operator, The CFO and The Lawyer — takes your situation, asks three things first, and hands back a decision memo: employee or contractor, the role in one paragraph, the monthly cost, and the first month. You see one price before anything runs.
Before the board starts
What the board asks first.
What decides this: whether the work is steady, what you can afford every month, and how much of it you need to control.
Is the extra work steady, or does it come in waves?
What could you spend on help each month?
An employee costs more than the salary; a contractor costs more per hour.
In your own words.
Which tasks would you hand over first?
In your own words.
What you get back: A decision memo: employee or contractor, the role in one paragraph, the monthly cost, and the first month.
A real run
One person’s version,
and what the board said.
I am a freelance bookkeeper working alone with 22 small-business clients and I am turning new clients away. I could spend about $2,500 a month on help. The tasks I would hand over first are data entry, receipts and chasing missing documents, about 20 hours a week. I would like to keep the client calls myself.
An example person, written for this page. Everything below is what the board delivered, word for word.
Hire a part-time employee, not a contractor, while keeping client calls yourself. Cap the total employer cost at $2,500 per month for approximately 20 hours per week.
What would change it: Reverse the decision only if a jurisdiction-specific review confirms that a qualified contractor with multiple clients, independent methods and scheduling legally passes the applicable classification test and offers 20 hours weekly for no more than $2,500 per month.
The LawyerHire a part-time employee: California classification risk, client-data exposure, and control needs make contracting a poor tradeoff.
The CFOHire a part-time employee: it fits the budget, lowers compliance risk, and creates more dependable capacity than contracting.
The OperatorHire a part-time employee because steady, core 20-hour workloads demand control and continuity that a contractor cannot reliably provide.
Send a request for a compliant, capped part-time employee setup
Questions
Fair questions
about this playbook.
What does running this cost?
Reading this page is free. Running it is a board: on Free it seats 3 experts and its card shows up to 135 credits before anything runs. A board never bills above its card. Nothing is charged until you confirm.
Is the example real?
Yes. The board above ran on a SynthBoard test account with the situation shown. The call, where each expert stood, what would change it and the first step are what it delivered, in its own words. The situation was written as an example; it is not a real person.
What happens when I run it with my situation?
You answer the same three questions with your own facts, then your Chief of Staff shows the board — The Operator, The CFO and The Lawyer on Free, more seats on a paid plan — and its one price. The board researches, argues it out and hands back the piece, with the first step and what would change the call.
Can the experts be wrong?
Yes. They are AI and can be wrong. That is why every board seats someone whose job is to argue against the obvious answer, and why the piece says what would change the call.
Keep reading
Close to this call.
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For an owner with a real offer on the table who has to weigh money now against what the business could become.
The playbookSynthBoard (synthboard.ai) is one place for your business, your life, and every hard call. Your Chief of Staff keeps what you tell her on file, and 24 named experts on different AI models take the calls — one expert for a consult, a board with opposed seats for the hard ones — and hand back a memo with the call, the dissent and the first move. How it works.