With Me, Not For Me: Hire People Better Than You

I'll start with my weakness, because the whole framework is built around it. I see the good in people and I trust too fast. In life, that's a strength. At the hiring gate, it's a liability.

Every bad hire I've made traces to one of two causes: I liked them too much, or I was in too much of a hurry. Both are bias. So the discipline I teach is how to decide around your own bias, on the way in and on the way out.

Why do smart operators make bad hires?

Because the hiring process usually tests the wrong thing. An interview tests how well someone interviews. A dinner tests how well they do dinner. Neither tells you what the person does on a Tuesday afternoon when nobody has told them what to do next.

The failure signature I've learned to watch for most often shows up in a sales hire. He sells you. He says everything right, passes the interviews, hits the goals on paper, and then doesn't do. He waits to be told and waits for structure. In a company where everyone carries their own bag, that's fatal.

I hired a man like that in 2025. I did almost everything right: about three months of recruiting, many interviews across different settings, my business partner interviewed him several times, a personality assessment, reference calls. By week twelve there was not one new lead in the CRM. He had passed every gate and still sold me. The cost was about four months of salary, plus the wind it took out of a team that had invested in him.

How do you hire someone you can trust?

Slow, and never alone.

Slow to hire is old advice and it's still dead accurate. Take a long time to make the offer, and make sure both sides are fully sold on the fit.

Take yourself out of the solo seat on purpose. The CEO's job is to recruit, hold the vision, and keep a bench, with other people in the room when the call gets made. I want at least three interviews, other people interviewing too, and a personality expert assessing the candidate against the seat: the role, the team, the people they'll touch. Even if I like someone, the assessment can veto them. It reads what drives a person and what they truly want long-term, because anyone can tell you what you want to hear.

Read them across environments, over time. The hires I nailed were people I'd watched for a long time with customers, vendors, and teams. The answer to hiring a stranger is to refuse to. Turn them into someone you've watched. The best hire I ever made took the better part of a year, and I'll tell that story here.

Hire people better than you. Fill your gaps. Don't be the smartest person in the room. You're still the CEO driving the strategy, but you bring in people who know more and who like the work you don't. That's the heart of the name: you want people working with you, which is a different thing from people working for you.

Then onboard them hard. My best hires get the most onboarding. I hand them a role, a vision, and guardrails, and let them fill in everything between. Full decision authority under my Five Questions gets earned during onboarding: about a month if they're solid, up to three if they're slower. That structure doubles as the test. A carry-your-own-bag hire thrives on it. A wait-to-be-told hire exposes himself fast.

When is it time to let someone go?

Quick to fire is something I earned over the last decade. The egregious cases are easy. The hard one is the quiet "they're just not working."

Read the external signal. Usually the peers know first. And if you know it, they know it. Most exits I've had end with "it's about time" or "thank you, it wasn't a fit." The call is already mutual; you just name it.

When it's unclear, I use a real 3-6-12 month improvement plan. It's a genuine chance, and it's also a diagnostic: half the time the person says they don't want to do it, which surfaces the decision for both of you.

Be humane on the way out. Turning someone over isn't a verdict that they're a bad person. It's the wrong seat. Help them agree, and help them find a better spot. I do better when I take my emotion out of it.

Which of your two biases shows up more at the hiring gate: liking them too much, or being in a hurry?

~b