Lessons I’ve Learned About Hiring (The Hard Way)

Hiring’s supposed to be about finding “the best person for the job.”

Except… that advice assumes you’re a CEO with layers of middle management, not a founder wearing 14 hats, one of them sideways.

Here’s what I’ve actually learned—after hiring brilliant people who didn’t work out, great people who did, and a few I wish I’d trusted my gut about earlier.

1. Don’t outsource the high-trust items—do them yourself.

If you’re paying good money for leads, don’t just check that someone called them. That’s not enough.

Ask:

• Did they follow the script?

• Did they actually connect, or leave it in the client’s court and call it “done”?

• Did they follow up more than once?

When money’s on the line, vague admin isn’t good enough. If it’s make-or-break, own it yourself.

2. Don’t hire for the role. Hire for the relationship.

People say “hire for strengths,” but I’ve found that if someone is strong where I’m weak…

they often don’t think like me.

Which sounds good in theory—until you realize you can’t delegate without friction.

Instead: hire people who click with your rhythm, but whose zone of genius is the task you’re delegating. That’s the sweet spot.

3. Trust is earned, not assumed.

You can respect someone from day one. You can hope they’re aligned.

But don’t hand over keys to the kingdom until they’ve shown they get your standards.

Start small. Observe how they actually handle responsibility, not how well they pitch themselves.

4. Treat your team with respect, even if you’re the one correcting.

Sometimes they’re not pushing back—they’re pointing out something you didn’t see.

And you want those kinds of people around.

Especially if they’re respectful and curious. You don’t need clones, but you do need thinkers.

5. Communicate more than feels natural.

Remote work means assumptions multiply.

Slack, Notion, or email doesn’t mean people know what you mean.

Spell it out. Check in often. Over-clarify when needed.

6. What gets tracked gets done.

Don’t assume someone’s “on it.”

Give trial tasks. Create checklists. Track deliverables.

Micromanagement isn’t the goal—but neither is magical thinking.

7. Don’t expect staff to care like you do.

Most won’t. That’s not an insult—it’s math. It’s your business, not theirs.

But if you can find someone who thinks like you do?

Keep them. Pay them well. Train around that mindset, not just skill.

8. Ignore the “hire the most talented person” advice.

It’s not just about skill—it’s about fit.

You want someone who:

• Brings their own strengths

• Thinks at a similar tempo

• Doesn’t need hand-holding—but wants your vision to work

That’s not “culture hire.” That’s founder-friction reduction.

9. Let AI in the room (you already are).

People get weird about AI in job applications. But let’s be real:

If the job requires AI tools, why would you test them in a vacuum?

I want people who use AI well—not people pretending they don’t touch it.

10. Trial tasks > interviews. Every time.

Who cares if they’re charismatic in an interview if the job is solo and remote?

Trial tasks show:

• Whether they read instructions properly

• How they respond if you delay your reply

• Whether they follow up, or drop the thread

• If they ask unnecessary questions you already answered in writing

Forget how they speak. Watch how they work.

11. Systemize early, and divide roles granularly.

It’s better to have 9 people each doing one thing than 2 people juggling everything.

That way if someone’s sick, others can cover.

Think: task redundancy > role heroics.

12. Your best feedback sometimes comes from your clients.

We’ve had incredible staff.

We’ve also had people who didn’t make it past trial—not because we didn’t like them, but because clients spotted issues early.

If your community trusts you, listen to them. They often catch red flags you can’t see from the backend.

Final Thought:

Hiring isn’t just about delegation. It’s about preserving your energy, protecting your standards, and growing your ecosystem in a way that still feels like you.

It’s not about being controlling.

It’s about building something worth controlling well.