Hiring revenue leaders? Don't confuse familiarity with capability.

Corporate hiring has somehow arrived at this:

WE NEED SOMETHING COMPLETELY DIFFERENT. Please send us someone exactly like everyone we already know.

Then everyone acts surprised when the candidate pool looks exactly the same. Same companies. Same backgrounds. Same networks. Same playbooks. Same answers.

Familiarity is not capability

I'm not saying industry experience doesn't matter. Of course it does. I'm saying we've confused familiarity with capability.

If someone has repeatedly entered new markets, learned new buyers, mastered new products, built teams, solved problems and produced results, the fact that they haven't spent 15 years in your industry might tell you something useful. They know how to learn. They know how to adapt. They know how to operate without already knowing the answers.

And they haven't spent 15 years being taught which things are "just how this industry works."

Want incremental improvement? Hire someone who knows every rule. Want transformation? Interview a few people who don't know which rules they're supposed to be afraid of breaking.

Apply your job description to yourself

Some job descriptions read like five people added their fears to a document and marked every line "required." Twenty years of experience. This exact industry. This exact growth stage. No failed ventures. No "job hopping." Below-market pay because the equity might be worth something.

Fine. Apply that standard both ways.

• More than two jobs in ten years suggests a lack of commitment? Three revenue leaders in five years suggests a lack of leadership.
• Concerned that a candidate's startup failed? You missed plan, pivoted twice and laid off part of the team.
• Want a 90-day GTM plan before the final interview? Then share the last four quarters of attainment, churn and board forecasts, and let the candidate talk to the person who held the job before.
• Equity could be life-changing? Then share the cap table, dilution terms and runway.

The system is broken when candidates have to look flawless while companies call their own problems "opportunity." Better hiring starts with being candid on both sides about what's worked, what hasn't, and what you'd need to build together.

The best interview question for salespeople

When I hire reps, one of my favorite questions is: "Tell me about a deal you lost that you should have won."

The best reps answer immediately. They know exactly where they screwed it up. The average ones tell you about pricing, product gaps, procurement, timing, or the competitor who "basically gave it away."

I've always learned more about a salesperson from how they explain a loss than how they explain a win. Wins tell you what happened. Losses tell you how they think.

How to write a better job description for a sales leader

1. Start with the outcome, not the résumé. What has to be true in 12 months?
2. Separate must-haves from preferences. If everything is required, nothing is.
3. Hire for the behaviors your strategy needs, learned from your top performers, not for logos.
4. Test how candidates think. Ask about losses, pivots and what they'd do without the answer.
5. Share the real situation. The candidates worth hiring will want to see the numbers.