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

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

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

3. Trust is earned, not assumed.

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

5. Communicate more than feels natural.

6. What gets tracked gets done.

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

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

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.

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.

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.

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.

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.

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.

Don’t assume someone’s “on it.”

Give trial tasks. Create checklists. Track deliverables.

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

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.