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? 
  2. Soft Skills – are they adept in dealing with people and building relationships?
  3. Culture Fit – do they believe in what you’re trying to achieve and do their career goals match the direction of your company (affects retention)?


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). 


  • What is the most creative thing you’ve done that’s helped you close a deal? Very few enterprise deals look the same. So it’s important that each one is approached with a desire to find a unique solution! Look for evidence of how creative they can be and how they think with this question.


  • How do you prioritize time between accounts? Knowing which accounts are worth spending time on and which are not is a very crucial part of the process. A lot of time and energy can be wasted if this step is not taken seriously! Asking this question will reveal a lot about how they approach that selection process.


  • What do you do to stay on top of what’s happening in your market? Enterprise sales is a long game. And the best enterprise sellers are always up to date with trends in their markets and their customers’ markets as well. Make sure they’re doing this regularly and can speak to how they do it.


  • Walk me through your sales process from start to finish… how do you prospect, connect, manage the process, and close deals? How are you involved in each step? Simply put, a candidate must be able to articulate their sales process from end to end. It’s not enough to have the numbers – they should be able to show you they didn’t just get lucky and can repeat their success for you too. There answer to this question will also tell you a lot about whether or not they value the small wins.


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. 


  • How do you stand out from others on the team? Pure and simple, this is about watching them sell themselves. Make sure they can show you how they stand out by the way they tell you how they stand out.


  • Tell me about a time when you lost a deal. Growth and progression are one of the hallmarks of excellent sellers at any level (because we’re not going to win every deal). Ask them this question to see if 1) they learned and grew from their mistakes and 2) they’re resilient in the face of defeat 3) that they’re playing the long game and not burning bridges.


  • Why do your clients buy from you versus anyone else? Standing out in a sea of competitors to a buyer that gets approached all the time is not easy. And if they can’t adeptly articulate what it is that makes them the de facto choice, it’s not a good sign.


  • Give me an example of when you didn’t reach your goal… why? What did you learn from it and how have you applied that learning since? This question is all about looking for proof of resilience, grit, and the desire to grow and learn from mistakes.


  • What’s the hardest deal you ever closed? What made it so difficult and what did you do to see it through? You want to see what they’ve done to close a tough deal as well as see what kind of strategy and grit they have.


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.


  • Why is now the right time/why are you open to making a change? Understanding why someone wants to make a move to your company (or why they’re looking in the first place) will tell you a lot about fit. Make sure they’re choosing your company and team for the right reason.


  • What’s your favorite deal? Understanding which deal they enjoyed most will help you understand whether they’ll be a good fit for your organization, buyer, sales process, and more. It will also give you a good sense of how they work. 


  • In each role, tell me about the territory you were assigned. This will help you understand if they are a hunter, farmer, did they have to create something from scratch, what was already billing, did they rely on warm leads only, etc.


  • Think about a time when you’ve had a conflict with someone on your team… what would they say about you? Modern enterprise sales is most successful when it’s played as a team sport. Look for indications that they’re a team player with how they answer this question.


  • What would your clients say about you? Relationships matter in a big way in enterprise sales. So ask this question to look for evidence they think about this and know how to start and maintain them. Keep these things in mind as they give you their answer: 1) Do I like you/would you fit in well? 2) Can I put you in front of my customer?


  • Why are you in sales? What keeps you here? Understanding what motivates the person in front of you is crucial to ensure they are a good cultural fit for your business.


  • What do you know about us? Why are you interested in this role? Are they really serious about you and have they done their homework to know what they’re getting into? If they haven’t, it’s not a good sign.


  • What are you most proud of in your sales career? People work towards things they like. Their answer to this question will tell you a lot about the things they value most and are motivated by. It also tells you a lot about how well they would fit with your business for the same reason!


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…”
  2. “What made you decide to ____?”
  3. “Why?”
  4. “What would ____ look like to you?”
  5. “How did you do ____?”


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.