20: Hiring#

Hire the Willing, Not Just the Skilled#

Skills can be learned. Drive can’t be installed. When you sit across from a candidate, pay less attention to what they’ve done and more to why they want to do it again. A person with moderate ability and fierce willingness will outgrow a polished expert who showed up because the salary was right. Willingness means they’ll stay late not because you asked, but because the problem hooked them. It means they’ll teach themselves what they don’t know. It means when things get hard—and they always do—they’ll lean in instead of leaning out. You can’t train hunger. You can only spot it.

The Best Teams Are Built on Difference#

It’s natural to hire people who remind you of yourself. They think the way you think, laugh at what you laugh at, see problems through the same lens. Feels comfortable. It’s also a trap. Homogeneous teams are efficient at running familiar plays and terrible at navigating new territory. What you need is friction—not the destructive kind, but the generative kind that comes from different backgrounds, different thinking styles, different blind spots covering for each other. A team of complementary strengths is messy in meetings and magnificent in results. Comfort isn’t the goal. Capability is.

Ask Why They Want It, Not What They’ve Done#

Résumés are rearview mirrors. They tell you where someone’s been, not where they’re headed. The most revealing question in any interview is some version of “Why this? Why now? Why here?” Listen for specificity. Listen for energy. The candidate who gives a generic answer about growth opportunities is reciting. The one whose eyes shift when they describe the problem they want to tackle is showing you something no credential can match. Past performance matters, but it’s a trailing indicator. Intention is a leading one. Spend eighty percent of your interview time on the future and twenty on the past.

Don’t Clone Yourself When Building a Team#

There’s a quiet narcissism in hiring: we drift toward people who validate our own approach. But a team of five yous would have the same strengths repeated five times and the same weaknesses repeated five times. What you need is someone strong where you’re weak, cautious where you’re reckless, detail-focused where you’re big-picture. The discomfort of working with someone who challenges your assumptions is the price of a team that can handle complexity. Pay it gladly. Your mirror isn’t your ally in team design—your opposite is.

Willingness Cannot Be Taught#

You can teach spreadsheets. You can teach presentation skills. You can teach someone to write a decent email or run a meeting with an agenda. What you can’t teach is the fire that makes a person care about getting it right. That fire is either there or it isn’t, and no amount of onboarding, mentoring, or performance reviews will light it from the outside. This is why willingness has to be your first filter, not your last. Everything else is buildable. The foundation isn’t. When you trade drive for experience, you’re swapping something irreplaceable for something learnable. That trade never pays off.

Try Trusting Potential Over Proof#

Think about the person with no track record in your industry but who radiates curiosity and adaptability. The one who’s failed before but can articulate exactly what they took away from it. The candidate who asks sharper questions than they give answers. These are signals of potential, and potential is the most underpriced currency in hiring. Proof is safe. Proof is defensible. But proof only tells you someone can replay the past. Potential tells you someone can build the future. Next time you’re torn between the safe hire and the bold one, ask yourself which you’d bet on over five years, not five months.