Your BFF Is a Giraffe: 4 Interview Questions That Help You Hire Sales Reps with Drive

Over the past decade I've interviewed hundreds of salespeople for my clients. Not the early screening calls. The late-stage, go or no-go interviews, where someone's about to get an offer or a polite "we went another direction."

After 30 years of selling and a whole lot of reps, you start to spot two types fast. The pretender tells you what you want to hear. The producer tells you the truth, chip on the shoulder and all.

But nothing in hiring is 100%. People still slip through, and some great people just aren't the right fit for your culture.

If you read my post on how to hire high-performing salespeople you know I'm a big fan of "Tell me about a time when..." interview questions that pull real stories out of candidates instead of the rehearsed answer.

Still, plenty of candidates sound like Tom Brady after a win. Polished. Gracious. Zero authentic information.

That's because "Tell me about a time when" shows you what a candidate did. I wanted a way to see what they do.

Then I heard J.B. Kellogg speak at Builders & Believers in Denver.

J.B. is the co-founder and co-CEO of Madwire, a company he helped grow to more than 500 employees. When Madwire was scaling like crazy, he had to hire a lot of people, fast, with a lot of other things on his plate.

So he boiled his interviews down to four questions in about 15 minutes. They take the interview somewhere unexpected, where candidates stop giving lip service and reveal themselves. J.B. will tell you it isn't perfect, but he got the hire right way more often than not.

Here's why it works. Salespeople are experts at knowing exactly what to say in an interview. But you can't rehearse a question about a giraffe.

Here are his four questions, and what they reveal:

1. "Tell me about your best job and your worst job. And why."

It's an easy opener, and a stealth one. It's a "tell me about a time when" question in disguise, so you get real stories instead of rehearsed answers.

Listen closely. Within a couple of minutes you'll hear their optimism, one of the three parts of drive from my first post. You'll also hear whether they're running toward something or away from something.

The worst job story is the real prize. Do they own their part of the mess, or is it everybody else's fault? That's accountability and authenticity in one answer.

And the whole time, ask yourself the big hiring question: would I personally buy from this person?

2. "Sell me on [your company]."

Swap in your own company name. This isn't a trick question, it's a preparation test.

The best salespeople always do their homework, on the company and on the person across the table, because that's how they build rapport. Nobody made them do it. Did they do it anyway? That's need for achievement, another key piece of drive.

Did they dive deep and bring energy? Or is this a phoned-in answer from someone who needs a job? And any job will do.

You'll know in about 60 seconds.

3. "Your best friend is a giraffe. He did something wrong and you need to hide him from the authorities. How do you do it?"

Yes, really.

There's no right answer, and that's the point. J.B. wanted someone with a sense of humor who's willing to play along. Drain the swimming pool and hide him in there? Put a lampshade on his head? Perfect.

You're watching how fast they shift gears, how creative they get and whether they're a good sport. That's improvisation, and every great salesperson needs it when the meeting goes sideways. We teach reps to think of their feet and improvise at Pitch Lab. J.B. figured out how to test for it.

And here's my favorite part. Nobody has a perfect giraffe answer. It's my line from the first post in action: a great interview is about connection, not perfection.

4. "Compete with me on something."

J.B. looks the candidate in the eye and says, pick something you're great at and I'll compete with you. Anything. You can even go home and grab it if it's a guitar or a football.*

Then, whatever they choose, he tries to psych them out. "Are you sure? I'm amazing at that. I think you picked the wrong thing."

That's the moment. You're not watching who wins. You're watching their eyes for determination and how steady they stay when someone pushes back. That's competitiveness, the third key piece of drive. It's also where you find the chip on their shoulder.

And if you've ever sold anything, you know a prospect pushes back exactly like this when you hit the investment slide.

(Yes, all four work over Zoom. Maybe skip the one-on-one basketball challenge though.)

Four questions, 15 minutes, same ones every time. That's a repeatable process, which is step 7 from my first post. Pair it with more than one interviewer so no single opinion makes the call.

Be More Like J.B.

Don't copy his questions word for word. Use J.B. as inspiration and get creative. Design a few questions that make candidates stop performing and start being themselves, so you can see their drive and what's really motivating them.

Here's mine. I open every late-stage interview with the same question: Forget reality. If you could do anything in the world for a living and get paid as much as you wanted, what would you really be doing?

My favorite answers? A race car driver, an astronaut, a travel blogger. (If you’re wondering, mine personally is a park ranger at a nature preserve in the Florida Everglades. Watching gators from my golf cart.)

I'm not listening for the job. I'm listening for how honest they'll be with me. If the answer is "I'd be in sales," that's a yellow flag. Nothing against sales, I've built my whole career on it. But nobody's actual dream job is in corporate America, and a safe answer usually means a guarded candidate. I can't get to know a guarded candidate.

The goal isn't a perfect interview. It's a real one.. And I'd love to hear your giraffe answer.

Want your sales managers to hire high performing salespeople with more certainty?

Pitch Lab's sales manager training teaches managers how to spot drive, screen resumes and catch red flags before an offer goes out.

*A quick note from Pitch Lab HR: ask every candidate for the role the same questions, score the answers against criteria tied to job duties, and keep any pushback friendly. Choose mental or skill-based competitions over physical ones, and check with your own HR or legal counsel before rolling any of this out. These are creative ideas to get your hiring managers to improve interview effectiveness. This article should not be considered an HR-approved playbook.