The questions you ask tell you so much, make them count!

20 Enterprise Sales Interview Questions To Hire Right

One of the things I hear most often on sales calls and kick-offs with startups who want to hire enterprise salespeople is:

“We didn’t get our last enterprise hire(s) quite right and it hurt. It’s mission-critical for us this time around.”

I wanted to know why this was so common for so many we engage with. So I dug deeper into each of their stories to learn more.

And I found this is most often because startups (self-admittedly) were looking for the wrong things in a strong hire.

I also found that the businesses we worked with who had made great hires in the past were all asking similar interview questions that looked for similar things.

Namely, in 3 specific areas:

  1. Sales Skills — do they have the enterprise sales mindset and process in addition to a proven track record to repeat their previous successes with you?

And since another question we often get from startups is “How do we do the interview process better?”, I thought it would be best to address these concerns by sharing the 20 questions most frequently used by those who were doing this well.

20 enterprise sales interview questions.

I’ve split these questions into each of the 3 different categories above. But keep in mind that some of the best indicators of soft skills, for instance, may come from asking a question on sales skills or culture fit.

Sales Skills Interview Questions

Ask these questions to learn more about their skills, process, and track record. And most of all, that they could repeat it if they joined your team.

  • How do you earn the trust of your prospects and establish credibility? The old adage “people buy from those they know and trust” is still as true as it has ever been — even more so in enterprise sales. Ask this to make sure they value relationships and aren’t transactional. If they can’t answer this question it means they either don’t care about this (major red flag) or they don’t really know how they do it (meaning their success could be inconsistent).

Soft Skills Interview Questions

Since enterprise sales is all about relationships, soft skills are exceptionally important. Ask these questions to understand how their soft skills stack up.

  • What’s the biggest challenge you’ve had to overcome? How did you handle it? Enterprise sales is hard and you need to know they won’t give up when the going gets tough. So ask this question to learn more about 1) how much they’ve been tested and 2) how resilient they were in the face of it.

Culture Fit Interview Questions

Culture is one of the biggest reasons we see salespeople itching to make a move from one company to the next. To make sure the people you hire are going to stick around, ask these questions to assess how well they’ll fit with your team and customers.

  • What’s important to you? If what’s important to them aligns with your mission and they care deeply about what you need and why, you’ve just reduced your margin for error.

How to avoid “false positives.”

It’s really easy to get answers to these questions that sound good, but don’t really tell you what you need to know to make the right hire.

So it’s important to dig deeper.

For example, let’s say you asked question #12 above — “Why are you open to making a change?”

And let’s say (for example) they answered something like “I’m looking for a place where I can continue to grow in my career.”

That sounds legit. But it actually doesn’t tell you what you need to know.

Do they feel like they don’t have room to grow where they are now? Why? What would having a place they can grow actually look like to them?

It’s critical to get specific. Otherwise, there’s too great a chance that each other’s expectations will be mismatched (leading to turnover).

5 follow-up questions to dig deeper.

Although the best way to ask a great follow-up question is going to depend on their first answer, here are 4 that work in most situations:

  1. “Tell me more about that…”

Use these (and other questions like them) to dig into the details together and make sure you’re both truly on the same page!

How do you know if they’re “the one”?

Unfortunately, there isn’t a formula for this. What works for one business won’t necessarily work for the next.

However, there are some qualities a good enterprise sales hire should have if you want to ensure they’ll be successful when they join your team.

Think of these as foundational traits.

While it’s nice to have things like industry experience, big logos, etc., anyone you hire who doesn’t exemplify these qualities will struggle in any industry you put them in.

Your enterprise sales interview checklist.

In addition to the qualities above, there are some things you should be able to say about an enterprise salesperson worth hiring for your business after you interview them.

Use this list as a quick gut check:

Final thoughts.

Keep in mind that hiring is a two-way street. The goal here is the same as it is in your sales process — a mutually beneficial partnership. So ask these questions to understand whether the people you’re interviewing meet your needs… and that you also meet theirs.

Think of this as embarking on the discovery process together!

If you have questions about your enterprise sales interview process and need to talk shop, our hotline is always on.

Originally published at

I help startups hire sales leaders without the cringe • Founder/CEO • 2X Entrepreneur • Personally closed $100MM+ in revenue (and counting) • LinkedIn Top Sales

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