Business Management / Human Resources

9 of the Top Sales Interview Questions

Ellis Friedman

Updated: Jun 07, 2023 · 6 min read

Toolkit for download in this article

sales team working together to come up with interview questions

I have good news and bad news about hiring sales people. The good news is that the more sales people you hire, the less time, effort and energy you have to put into sales. Hooray! 

Bad news: you’re not done with sales. Because now you have to hire, train and manage your sales team. But hey, it’s progress, and if you never wanted to have to deal with sales in your life, well, you probably would have just become a blogger, right? 

But let’s go back to that part about hiring a sales person. Once you get them in the door for an interview, what should you actually ask them? The best sales interview questions seek to understand motivation and performance. I sat down with Kate McMillen, hiring partner for sales and partner development here at Keap, to find out what the top sales interview questions are, and what sort of answers to listen for.

1. What’s the most difficult feedback you’ve ever received, and what did you do with that feedback?

This question helps you see whether your sales candidate can communicate openly and realistically, as well as show a bit of vulnerability. But more importantly, it shows you how coachable and adaptable they are—are they stuck in their own methodology, or are they open to trying new things?

If a candidate says they “don’t know” about any difficult feedback they received, or says they’ve never received difficult feedback, that’s a concern; it means they might not be in tune with feedback or their manager, they’re not self-aware or they’re defensive and not willing to hear difficult feedback. You want to find a sales associate who can be really open and receptive to feedback.

2. What’s the legacy you’d be leaving behind at your current place?

This is a different way to ask “What would your teammates say about you?” You’re looking to find out what they’re known for, good and bad. It also provides the opportunity for you to probe deeper into their pace and how they work best.

3. What’s an example of something you did in the last 12 months that you would characterize as remarkable?

Asking what the sales candidate has achieved allows you insight into what they’re passionate about and who they are as an individual. You want to discover how they learn, grow and stretch themselves so you know how they strive and achieve. It also gives you a great gauge for what they consider remarkable.

4. What is your biggest are of opportunity for improvement as a sales professional? Tell me what you’re not good at?

Everyone has flaws, and that’s fine. But it should be a red flag if your sales candidate tells you they have trouble closing, or if they say they’re not good at prioritizing or time management. Sales is a fast-paced environment, and you need someone who can manage their time well and close the sale. It’s not an immediate deal breaker, but you’ll want to dive deeper into that to see what exactly they have trouble with.

But if your prospective sales associate says they have a harder time with prospecting or details or paperwork, that’s fairly common for salespeople and not as big a deal.  

5. What are three of the best qualifying questions that you ask a prospect in your current role?

When you ask this question, you’re not looking for a specific set of questions; you should listen to how consultative and open-ended their questions are. The questions they ask prospects shouldn’t be one-word answers or fact-based, they should be asking cause-effect questions in order to gain a deeper understanding of the prospect. 

For example, a great qualifying question would be “Tell me more about … “ Other great questions include “Tell me about what’s working for you” or “Walk me through your vision.” 

6. What is your current monthly quota? What’s your three-month average? What’s average for your team?

These questions are a goldmine of insight. The answers will indicate what your prospective sales associate’s current expectations are, how they’re measured and how they’re doing in comparison to their peers. Their answers will also show you how they do with volume, monthly recurring revenue and their understanding of the sales model. 

You’ll also learn what that person considers to be a lot, sales-wise, what price point they’re selling at, and what their sales cycle looks like. You’ll want to compare their price point and sales cycle to yours; they don’t necessarily have to be the same, but if you’re interviewing someone who sells big ticket items with a long sales cycle and your business sells smaller items on a shorter cycle, it could be a big switch for them, and you need to be prepared for that and determine whether they understand how they can work within your model.

7. Describe your daily routine in a fast-paced, constantly evolving sales organization?

Your adjectives may vary a bit, but you want to see how the candidate prioritizes their day and what they consider to be the most important elements of the sales cycle. Everyone has different answers of the “right way” to do things, but their answer will give you a sense of if they have a proven structure of how they manage pipeline flow.

You do want a candidate who will say that the first thing they do is scan for what’s happening with their hot leads and follow up with them immediately. It’s an especially good sign if you have a candidate who says they spend 30 minutes the previous day setting up things for the next day – it shows good time management, forethought and the desire to stay ahead.

8. How do you typically align your sales process to the customer’s buying process? Tell me your stages.

When you ask this question, you’re looking to see what sales methodology they’re coming in with. Some may name a specific methodology while others will take a more fluid approach, but this question is about seeing what training they’re coming in with and learning about their thought process and how they think about the customer journey.

9. Rank these things by what’s most important to you: personal development, career progression, financial gain, working for a core values culture-focused company, recognition for accomplishments.

Then have them talk you through the reasoning behind their answers. You’re not looking for one specific order, you’re looking for what this person’s motivators are and what they value. 

And at the end of the sales interview, don’t forget to count what your gut says—because while answers are important, what your gut says is important too. Their answers might be perfect, but if you’re not feeling it, don’t do it. You want to make sure you have someone who’s the overall right fit—that’s the best way to get them to elevate your company goals and move you forward.

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