First Hire: Employee, Contractor, or Wait?

The first 10 questions

This is where the conversation starts. Each answer shapes what gets asked next.

1. 01What's driving the hiring urge — what work is piling up, what's getting dropped, and what would you hand off tomorrow if someone great appeared?
2. 02Where's the business — revenue, growth, runway — and what could you actually afford: a salary, a contractor budget, or neither without cutting something?
3. 03Have you hired or managed people before — employees, contractors, agencies? How did it actually go?
4. 04Is the pile-up a capacity problem or a focus problem — if you dropped your least valuable work entirely, would you still need the hire?
5. 05Is the work ongoing-and-core (an employee), a bounded project (a contractor), or automatable (a tool)? Be specific about which bucket each piece falls in.
6. 06What does an employee actually cost in your jurisdiction — salary, taxes, benefits, equipment, compliance — and how many months of runway does that subtract?
7. 07What does managing someone cost YOU — hiring time, onboarding, ongoing direction? Are you ready to spend a third of your week making someone else productive?
8. 08If the revenue that justifies this hire slipped six months, could you still carry them — or would you be doing a layoff of one?
9. 09What's the cheapest test — a trial project with a contractor, a part-time or fractional hire — that would tell you whether the full hire is right?
10. 10Whichever way you're leaning — what's the strongest argument for the other options, and can you honestly refute it?

+ 2 more questions across discovery, validation, and the creative brief — each one adapting to what you've already said.

Related business planning project types

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• Quit Your Job or Nights-and-Weekends?Decide whether to go all-in on your startup or build it nights-and-weekends — what the leap actually costs, what staying actually costs, and what would have to be true either way.
• Solo or Cofounder?Decide whether to build alone or bring on a cofounder — what you actually need, what half your company costs, and what the right plan looks like either way.