Why “Sell Me This Pen” is the Best Way to Find the Best Sales People

The best question to ask a candidate during an interview for a sales position isn’t a question at all. It’s a request.

Hand your sales candidate a pen and ask them to, “Sell me this pen”.

Honestly, if I could only ask candidates one thing, it would be this. I don’t really need to know anything else because this one request will show me their sales style and skill level.

I know some of you are probably rolling your eyes at this. The question was made famous in the Wolf of Wallstreet, but it was been a legendary sales interview question long before that. It’s probably the most cliche sales interview question there is.

It’s such a cliche, in fact, that it’s embarrassing to ask. I always cringe a little inside when I do it, ready for someone to say, “Really? This again? Give me a break”.

But no one ever does, and most candidates have actually never heard the question and don’t know of its cult status among sales management.

It’s the most effective sales interview question

The pen question is remarkably good at demonstrating a candidate’s sales skill. It has stood the test of time for a reason. When you ask a candidate to sell you the pen you will genuinely get to see their sales style. It will show you:

• How they think on their feet. Even if a candidate has rehearsed their response to this request, every conversation is unique. They don’t know how you will respond and behave as the ‘buyer’. How they navigate the conversation will give you an idea of how they will interact with your real buyers.
• Their sales style. Are they candid? Direct? Overbearing? Robotic? Funny? There isn’t a right style, but there is the right style for your company. When you ask them to sell you the pen, you will get an immediate sense if their sales style is a good fit for your team and your customers.
• Their skill. This is what matters the most, right? Does the candidate launch right into a pitch about why you should buy the pen? That’s an immediate (and I do mean immediate) fail. Do they ask questions to understand your needs and goals first? That’s starting off on the right foot. Do they then use what they learn through those questions to specifically entice you into a buy-able moment? BINGO!
• Their coachability. When a less experienced candidate tanks their answer (which is to be expected), I usually give them some on-the-spot coaching and see how they adapt their response given a second chance. This shows their conversational agility and their coachability. I don’t expect a less experienced candidate to be as seasoned as someone with more experience, but I do need to know that I will be able to coach them up quickly.

How a sales candidate handles the “sell me this pen” request is so telling about a candidate, it shocks me that more sales leaders don’t use it and that more sales candidates don’t know how to nail it. In fact, with a cursory review of a bunch of articles on the pen question, only this one really articulated why the question is so good and how a sales candidate should answer it.

As much as I love this question, I went through a period when I stopped asking it because so few people responded correctly that it was depressing. And that’s perhaps the only reason not to ask it during an interview. This question will absolutely weed out sales candidates far faster than you are comfortable with. Despite how expected, and trite, “Sell me this pen” is,  it’s remarkably good at showing someone’s true sales ability.

I’ve been in interviews with sales reps where they spoke at length about their approach to sales conversations, how they run a discovery call, how they focus on needs before ever pitching (all the right answers) and then turn around in that very same interview and start pitching me the pen. There is a difference between knowing the right things to say to get the job, and actually knowing how to do the job.

I love to ask sales candidates to “sell me this pen” during the first interview. I will know what level of experience, skill and style I am dealing with far better than I would if I drilled through a bunch of standard interview questions. As sales leaders, we need to consider increasing our situational questions like this one during interviews to help find the best candidates and avoid the wrong hires.

By the way, if you are a sales candidate and want to be prepared to nail this in your next interview, here’s a good place to start.  But I would much rather you take some inspiration from Zig Ziglar selling an ashtray to Johnny Carson. That’s some superhuman skill right there.

Podcast: Embed

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