09/09/2026
You Can't Coach Someone Into Wanting It
Most business owners hire leaders the way they hire staff. Same process, higher salary, bigger expectations. Then they wonder why it doesn't work.
Here's what I've learned across the Army, the Police, and twenty years working with owners: the leadership hire is the one you cannot afford to get wrong. A bad staff hire costs you money. A bad leadership hire costs you your team.
Hire for judgement, not experience.
Experience tells you what someone has done.
Judgement tells you what they'll do when things go sideways — when a key client walks, when the numbers don't stack up, when two of your best people are at each other's throats.
Ask candidates about a decision they got wrong. If they can't name one, they're either not honest or not experienced enough to have been properly tested.
Watch how they talk about their last team.
The person who describes their previous staff as the problem will describe yours the same way in eighteen months. Real leaders take responsibility for outcomes they didn't fully control. That's the whole job.
Test composure, not charisma.
Charisma interviews well.
Composure performs.
Put a genuine problem in front of them — an actual one from your business — and watch how they think.
Do they slow down and ask better questions, or do they rush to sound decisive? The first one is a leader.
The second one is a performer.
Be honest about what you're handing over.
If your business runs on your constant presence, you're not hiring a leader — you're hiring someone to be you, which nobody can do.
Get the systems clear first. Define what decisions are theirs.
A good leader in a structureless business will leave within a year, and it won't be their fault.
The right leadership hire buys you back your time, your headspace, and your ability to work on the business instead of inside it.
Get it wrong and you'll pay for it twice — once in wages, and again in the people who leave because of them.
