Stop Telling, Stop Selling: Why I Changed How I Interview Salespeople

I’ve personally hired over 600 salespeople and interviewed thousands more across 28 years of leading sales teams. In my early years, I hired mostly “duds” and very few “studs.” It wasn’t intentional, but history kept repeating itself, and it bothered me enough that I finally had to ask: what am I doing wrong?

The Problem: I Was Selling, Not Interviewing

Anyone good at sales is retrospective. Looking in the rearview mirror, analyzing why a deal was lost, isn’t just a nice-to-have trait for a salesperson or sales manager. It’s critical. If you don’t look back and figure out what went wrong, history repeats itself.

The same turned out to be true for how I hired.

When I looked back at my own interviews, I realized I wasn’t really interviewing at all. As a salesperson myself, I was being too nice. I’d treat the candidate like a customer: some small talk, a relaxed tone, buddy-buddy energy. Then I’d launch into how great our company was, what we do, what makes us different, why it’s a great place to work, while the candidate sat there nodding along.

Next, I’d walk them through the job itself, describing it as if they already had it. More nodding. Maybe a few softball questions. By the time I actually got around to interviewing them, I’d already warmed things up so much that it felt rude to ask anything hard. We were basically friends at that point.

The result? I was hiring on gut feel: rewarding good talkers, good nodders, and good-looking resumes. More often than I’d like to admit, those hires failed. When they succeeded, it was luck.

The Fix: Become the Toughest Customer in the Room

Once I realized the problem, the fix was obvious in hindsight: selling and telling should be their job in the interview, not mine. So I flipped my approach: poker face and a bit of a jerk.

I modeled it after one of the toughest customers I’d ever sold to as a rep: a man who never smiled, complained constantly, and was confrontational enough that most salespeople in our industry called on him once or twice and never went back.

I didn’t give up on him. It took nearly two years to land my first order, but he became my biggest account and along the way, he became my go-to interview persona.

I started acting like that customer in every interview. It wasn’t natural, and it wasn’t easy. But my logic was simple: if a candidate was a genuinely good salesperson, they’d treat my resistance as a challenge and sell through it. The tradeoff was that I had to interview roughly three times as many candidates before making an offer.

The Interview That Changed Everything

I remember the first hire I made with this new approach. I scheduled the interview for a Saturday morning. He showed up five minutes late.

I opened hard: “I’m not impressed you’re late, I’m not even sure I want to continue this interview.” Drill-sergeant mode, more or less.

From there, I kept the pressure on with tough questions. To his credit, he held his ground, good answers, and he pushed back with questions of his own. It felt less like an interview and more like an arm-wrestling match. I gave him nothing: no sign I was impressed, no sign he was even in the running. I wanted to see what he’d do next.

Monday morning, a gift basket showed up at my office. It was from him with a note apologizing again for being late and hoping he’d still be considered.

That sealed it for me. He’d taken every punch I threw as my toughest-customer persona, then followed up. I hired him after one more interview, reasoning that if he could handle me at my worst, he could handle it in the field.

He became one of my top performers.

Years later, over beers at an airport gate, we finally talked about that first meeting. He told me the story from his side and said he still tells it today as a badge of honor. He also told me he’s never been late to a meeting since.

That’s the mark of a real salesperson.

FAQ: Interviewing Salespeople the Right Way