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Sales Interview Insights: Top Questions to Ask the Hiring Manager

Ryan Walsh, CEO and Founder
Ryan Walsh, CEO and FounderMar 01, 2024

When preparing for a sales interview, it’s important to remember that the interview is a two-way conversation. The hiring manager is interviewing you as a sales professional, of course, but you’re also interviewing the sales organization. 

After being questioned, probed, grilled for several hours, the hiring manager will often say the classic line: “OK, we have a few minutes left in the interview, do you have any questions for us?” When you’re offered your few minutes, most salespeople will usually just check their notes for the standard list of generic questions, hoping not to annoy the interviewer with any tough ones.

This trend of candidates only being afforded a few rushed minutes at the end of a job interview to ask the hiring manager or HR representative questions seems to be worsening, and hiring managers interviewing account executive and sales development roles are some of the worst offenders.

That’s not a lot of time to ensure that you are also making the best decision for you personally and professionally, so you need to make sure you’re ready with some questions that will allow you to get right to the heart of your decision process. 

Below, we’ve collected thoughtful questions that demonstrate your interest in the company and your understanding of the sales role — and questions that drive real conversation related to whether you think you can succeed in that sales organization.

Picking the right org to sell for is one of the most critical decisions and in many cases it will be the single biggest factor that will influence your success. So ask the right questions, and choose wisely!

Ask about Performance Expectations

Probably the most important aspect of a sales role is hitting targets and quotas. It’s important to ask the hiring manager about the specific targets and quotas you will be expected to meet, as well as how they are determined. This will help you understand the level of performance required for the role and whether it’s a good fit for you.

Start with a couple of basics:

Those questions are table-stakes. Where you’ll really learn about the company is with these follow-ups:

  • I’m joining a division that has X reps — how many of them hit their number last quarter?
  • Has the team gotten bigger or smaller in the past year?
  • How many reps have been let go from this team in the past year?  
  • How many have left on their own?
  • Can you share with me the compensation plan template for this year?
  • Can you share with me the compensation plan template for last year? Were there any changes?

Ask about the Sales Cycle

Understanding the sales cycle is crucial for a salesperson as it helps them identify where a prospect is in the buying process and how to move them towards a sale.

During the interview, you can ask questions to gain a better understanding of the sales cycle for the company. 

To really get to the heart of the matter, I’d recommend adding these questions:

  • What is the average percentage of pipeline generated by marketing vs. SDRs vs. AEs for this role?
  • What are the top three reasons you’ve lost deals over the past couple quarters?

Be sure to look for specificity here for all of these. Generalized, non-specific answers or responses that don’t answer the question at all are definite red flags.

Ask about Growth Opportunities

It’s important to ask questions about growth opportunities to show that you’re interested in advancing your career within the company — and to determine if the company will support your personal goals. 

You can ask questions like:

  • What is the typical career path for someone in this role?
  • How have other people in this role advanced in the company?
  • Are there opportunities for advancement within the sales department or other departments?

Another important aspect of growth opportunities is professional development. You can ask questions like:

  • What kind of training programs does the company offer?
  • Are there opportunities for continuing education or professional certifications?
  • How does the company support employees in developing new skills?

Asking these questions can help you understand the company’s commitment to professional development and your potential for growth within the company.

Overall, asking questions about growth opportunities during a sales interview can demonstrate your interest in a long-term career with the company and help you understand your potential for career advancement.

Ask about Sales Methodologies and Segments

One important aspect of a company’s sales strategy is their sales methodology. Understanding the sales methodology used by the company can help you understand how the company approaches sales and how you can fit into their sales process.

For example, you can ask “What sales methodology does the company use?” or “How does the company approach sales?”

Or try one of my favorites: “How would you describe your ICP (ideal customer profile)?” 

A question like this will get a deeper answer than just saying a known methodology like MEDDIC or Challenger Sales. Their answer will give you an idea of who they target prospects are and why. From there, you can decide whether that suits the type of customer you prefer selling to.

Ask about the Company Culture

Company culture is a critical factor. But it can be exceedingly difficult to get a read on a company culture by asking direct questions about it. Questions like “How would you describe the company culture?” and “What are your core values?” will often elicit platitudes that may not be very helpful. 

In many cases you’ll learn more about the company culture by how your interviewer answers the other questions you’ve asked than by asking them to describe the culture directly. What they do matters more than what they say.

But there is one question that I really like that can give you a glimpse into the true culture of the company:

  • If I asked the last three reps who left voluntarily about the org, what would they say?

There are a lot of reasons salespeople leave an org — good and bad — and this question can help you determine if you would be a good fit for the company and if the company would be a good fit for you.

Look for Transparency in All Their Answers

These questions are designed not only to extract some very critical information about the organization that you can use in your decision process, but also to allow you a very good sense of whether the organization is transparent. 

If the company isn’t willing to share or disclose deep information so you can make the right decision, it’s probably not a sales organization you’ll want to be part of. And chances are, if you look up the company’s RepVue score, other sellers will say the same.

That’s a lot to ask in “a few minutes left”

These are questions that you want to ask primarily of the direct hiring manager — who should be the person who you’ll be directly working for if you get the job. 

If you’ve only been given the last 5 minutes to answer questions, that’s a potential red flag right there. In that case, here’s an approach that you could take:

“I have several questions actually and I’d like to make sure we’re not too rushed. Do you have another 15 minutes or do you have a hard stop?”  

If they don’t have time to talk now, see if you can schedule a phone call later that day or the next day.

If the interviewer is a good sales leader who is taking the process seriously, not only will they want to make sure that they have time to thoroughly answer your questions, but they’ll appreciate you asking them. (That is, if they think you’re potentially a good fit for the role.) No matter what response you get to this line of conversation, it will be very valuable in helping you to make the right decision.

Good luck out there!

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