How to Hire a Team
Table of Contents
(What I learned hiring my first 10 people—and what I’d do again)
Hiring your first team changes everything.
It’s exciting.
It’s stressful.
And it’s where a lot of businesses quietly break—not because of bad ideas, but because of bad hiring decisions made too fast.
Your first 10 hires will shape:
- How work actually gets done
- How problems get solved
- How much of your time disappears
- And whether your business feels lighter or heavier as it grows
This is how I think about hiring now—after doing it wrong, fixing it, and building teams that actually work.
Step 1: Don’t Hire a Role—Hire for a Problem
Before you write a job description, answer this:
What problem am I trying to remove from my plate?
Not:
- “I need a marketer”
- “I need an assistant”
- “I need a designer”
But:
- What’s slowing the business down?
- What work keeps repeating?
- What tasks only exist because I’m still doing them?
If you can’t clearly define the problem, the hire will disappoint you—and you’ll blame the person instead of the clarity.
Step 2: Write a Job Description That Filters, Not Sells
Your job post isn’t marketing.
It’s a filter.
A good job description:
- Clearly states the outcomes, not just responsibilities
- Explains how success is measured
- Sets expectations honestly (pace, autonomy, feedback style)
- Includes one small instruction to test attention to detail
Example:
“Include the word ‘context’ in the first line of your application.”
This one line will save you hours.
If someone won’t read your job post, they won’t read your SOPs.
Step 3: Go Where the Right People Already Are
Don’t spray jobs everywhere.
Different roles live in different places:
- LinkedIn for operators and managers
- Niche boards for specialists
- Communities and referrals for high-trust hires
- Direct outreach for people already doing the work well
The best early hires often aren’t “actively looking.”
They’re quietly competent.
Step 4: Test for Judgment, Not Just Skill
Resumes lie politely.
Interviews reward confidence.
Work reveals truth.
Every early hire should have:
- A small, paid trial task
- A realistic scenario
- A chance to show how they think, not just what they know
You’re not testing perfection.
You’re testing:
- How they approach ambiguity
- How they ask questions
- How they respond to feedback
Skills can be taught.
Judgment is expensive to fix.
Step 5: Interview Like a Teammate, Not a Boss
Early interviews should feel like collaboration—not interrogation.
Questions I care about:
- “Tell me about a project that didn’t go well.”
- “How do you like to receive feedback?”
- “What do you need to do your best work?”
- “Where do people usually misunderstand you?”
I’m not hiring a résumé.
I’m hiring someone I’ll be solving problems with.
Step 6: Onboarding Is Where Most Teams Fail Quietly
Hiring doesn’t end with an offer letter.
Bad onboarding creates:
- Confusion
- Insecurity
- Micromanagement
- Missed expectations
Good onboarding does three things:
- Explains how work flows
- Clarifies what “good” looks like
- Makes it safe to ask questions early
Every new hire should know:
- What success looks like in 30, 60, 90 days
- Where information lives
- Who to go to when stuck
If onboarding feels chaotic, the business is chaotic.
Step 7: Use Systems to Reduce Friction (Not Control People)
Tools like Notion aren’t about control—they’re about clarity.
You want:
- One place for documentation
- One place to track work
- One place to onboard consistently
Systems exist to protect people’s time, not monitor them.
If your team needs you for everything, you don’t have a team—you have helpers.
Culture Isn’t Perks—It’s Behavior
Culture is what you tolerate.
Culture is how decisions get made.
Culture is what happens when no one’s watching.
Your first 10 hires will define this whether you like it or not.
Hire slowly.
Be clear.
Fix mistakes quickly.
Final Thought
Hiring your first team isn’t about scaling fast.
It’s about building something you can stand behind—and live with.
The right hires don’t just grow the business.
They give you room to think.
If you want real tools, real systems, and real breakdowns from businesses being built in public
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