3 Ridiculous Interview Questions to Help Identify Top Sales Talent

Hiring top sales talent is tough — which is why, over time, most hiring managers develop their own system of interview techniques and questions to prosecute would-be sales reps.

 While I’ve shared some my favorite interview techniques in the past, when it comes to specific interview questions,  I’ve got collections of them sitting in an Evernote file that, much like a set of your aunt’s antique porcelain figurines, I’ve been carefully curating over time.

While many of these questions are what you might consider mainstream (e. g. “Tell me about a time when…..”, “How would you approach a situation where….”), I do like to mix it up with a few abstract ones that I seem to ask with a fair bit of consistency:

1. What’s your superpower?

I often see teams (especially sales teams) as a collection of superheroes, much like the Justice League or the X-Men. While each team member can be highly effective and impactful on their own, each of them tends to bring their own unique set of skills: things they’re simply better at that their peers. For example, some are killer negotiators, some are consummate solution or product experts, some pride themselves as being outstanding in the deal qualification process, some may be adept at quickly connecting with executive stakeholders, and others may simply excel at being what I call “the best friend.”

Regardless of what their superpower is, asking a candidate to describe it (or how their current manager would describe it) is a great technique for three reasons:

  • It helps you understand what strengths and diversity the person will add to your team
  • It highlights the candidate’s degree of self-awareness (i.e. of their own strengths)
  • It provides the opening for a related line of evidence-based questions (e.g. “Oh, so you’re awesome at connecting with executive stakeholders? Tell me about an especially challenging instance where you had to make such a connection.”).

Oh, and it tends to be a fun ice-breaker question that puts candidates at ease.

2. What’s your kryptonite?

It’s always interesting to ask a candidate about their superpowers and how they use them to win. It’s even more interesting to ask what they would do to win if they were selling against themselves! This technique works well after you’ve gotten them to describe their superpowers and a deal win they were especially proud of — for instance if I were your competitor on that deal, what would/should I have done to steal it from you?

This technique is great for three reasons:

  • It helps you understand the candidate’s degree of awareness of their weaknesses; either personal, professional, or organizational
  • It highlights how familiar the candidate is with the competitive landscape in their business or industry
  • It will help you identify potential areas for coaching and development.

3. If you were a plant, what care instructions would you come with?

I usually introduce this question with a build-up that goes something like this: suppose I were to call your current manager and ask them to describe you in the same way they’d describe a plant they wanted me to take care of while they went on vacation. You know like, “Oh, Steve likes to be watered three times a day, indirect sunlight in the morning, and he really perks up when you play Mozart!” Essentially, what would your current manager tell me to do, to help you perform at your best?

Do you crave autonomy? Do you need constant encouragement? Do you consistently need advice at certain stages of the sales cycle?

This technique is great for three reasons:

  • It provides specific insights into how you’ll need to manage this person for maximum effectiveness
  • It provides insights into the affinity the candidate has toward their current manager and why (also very helpful for you!)
  • As with the previous technique, it helps you identify initial areas of focus for coaching and mentoring.

Hiring top sales talent is never easy, but injecting a little fun and creativity into the interview process can not only help you secure ideal candidates but also help you get the most out of them once you do!

What are some of your fun and creative interview questions?

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