Interviewing a Candidate about Past Sales Performance

Written by
Lucas Price
August 9, 2023
5 min

Context is everything. As a sales leader, you know setting up the context of how your solution meets their pain points will be critical in leading to a buying decision. The same is true when interviewing a sales candidate. Getting context on their past performance is important to understanding if you’re making the right hire.

Sales matter, and in a slowing economy, getting the right sales hires in place is more critical than ever. With a 13% drop in overall quota attainment for account executives in the past year, your company can’t afford to waste time on the wrong person for the job.

The problem is often at the beginning of the hiring process. Most interviews don’t go deep enough, instead focusing on asking generic questions about the resume. This gives a chance for the candidate to frame their answers in a way that’s most favorable to themselves and doesn’t give the interviewer a good idea of how a candidate may actually fit into the role.

So change it up. Get the tools and questions you need to ensure you have all the context you need about a candidate’s past performance.


Getting to the Heart of a Candidate’s Past Performance

A failed sales hire costs as much as 70% of their annual quota, with far-reaching effects across your pipeline, team, and forecasts. Sales hires fail for a number of reasons, but often it’s just that they’re not a great fit for the role.

With the right interview questions, you can eliminate many candidates that won’t be a great fit. You’ll be able to get clear answers on their background and dig deep into getting answers that will allow you to evaluate their fit for the role, not just how they frame their performance.

We spent hundreds of hours researching the top interview questions for sales candidates. Here are 17 well-researched questions you can use to ensure you get the heart of what drives the candidate, how they’ve performed in the past, and get an idea of how they’ll perform in your role.

  1. Tell me about this job. What was the reason you took this job?
  2. Tell me the basics of this role.
  3. Who was your customer?
  4. How did the sales process work?
  5. What was the product, and how was it priced?
  6. What was your quota, and how was it structured?
  7. What was your performance relative to quota? (make sure you understand the performance for each period, year or quarter that the candidate was at the job)
  8. How many people were on your team?
  9. Where did your performance rank on the team for each period?
  10. What are your biggest accomplishments how did you achieve them in this role?
  11. What mistakes did you make?
  12. Who was your boss in this role?
  13. What would your boss say about your strengths in the role?
  14. What about your weaknesses?
  15. How would your boss rate your performance overall?
  16. What did you like and not like about working for your boss?
  17. Who internally at this job was most important to your success?

How should you use these questions?

There typically isn’t enough time in an interview to ask all these questions about every prior job. If they only have one prior sales role, ask them all. Otherwise, ask only the first one or two questions about the oldest and least relevant jobs. Ask the first four questions for prior roles that seem relevant to the current role you’re interviewing for. Then, use the remaining questions to dig into their most relevant role and most recent experience.

How do these questions help?

Imagine you’re interviewing a candidate who said they led their sales team in quota attainment in their past role. While this sounds great in an interview, and some interviewers may end there, asking additional questions can help build out the context around that.

If you’re interviewing for a sales position at a startup, no matter how much the candidate led sales in their last role, they won’t be a good fit if they were selling in a well-established market, as a leader, and with a battle-tested playbook.

It can also help you determine whether the candidate led quota attainment consistently. Perhaps they only achieved quota for the one month prior to interviewing for this position. Or they could have succeeded for the first time during a pandemic-led sales boom and have been unable to replicate any kind of success in a more challenging sales environment.

While the majority of candidates are not trying to lie about their past experience and are simply working to present their best performance in interviews, these questions will also weed out anyone who is grossly exaggerating or misrepresenting their experience. The details you are going to get on their past performance will ensure you get a clear picture of how they can perform.

Helpful tip: Write down the names of the people mentioned as people you may want to ask the candidate later to set up reference calls with.

More questions for success

Separate from the questions that are asked about every relevant job on a resume, these standalone questions are also valuable.

  • Tell me about the job you’ve had that was your favorite. (Start with this question.)
  • Tell me about the job you’ve had that reminds you the most of this job. (End with this question and see if it matches the answer from the favorite job question.)
  • Tell me about the most complex buying organization you’ve ever sold into. How did you navigate dealing with multiple buyers and influencers?  (Leave lots of time to ask follow-up questions to see if they really know how to navigate a complex sale.)
  • Tell me about a time you built an account plan to map out the details of an important prospect. How did you prepare and structure it?
  • Tell me about the most complex negotiation you faced.

The Framework For Success

These questions will make your team very good at interviewing candidates about their work history. But by themselves, they won’t change your success rate on sales hires or help you find the best candidates. They need to be part of a solid hiring process. This is one that will reduce any bias that may unintentionally creep in, allowing you to analyze candidates consistently across the same criteria. These tools include:

With this framework around these questions, you can use them to ensure you’re getting the most out of a chronological interview with the candidate. This interview focuses on their experience and how it will translate into your current opening and should be one of the four interviews you use in your hiring process.

Find these questions useful? Get more helpful resources on how to build a hiring process that will allow you to source, interview, and hire the most successful sales reps for your organization.

Spot A-players early by building a systematic interview process today.

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