9 Questions You Should Ask in the Sales Job Interview

Typically when getting ready for a sales job interview, there are a few things that you do to prepare. You do your research on the company and people you’re meeting with. You also prepare answers to questions you anticipate being asked around your job search, experience, knowledge on the company, and interest in the role.

However, most candidates fail to prepare a list of questions to ask the hiring manager.

Asking thoughtful questions is important. It helps you to decipher whether or not the company and job is a fit for you. It also shows the hiring team that you’ve done your homework and are interested in the role.

It’s important to note that thoughtful questions should not have to do with how much money you will make or how many days you have off. Dig a little deeper.

So what are some thoughtful questions that resonate with hiring managers?

We asked top sales leaders to share some of their favorite job interview questions they’ve been asked by candidates and why they are important.


Tim Wackel
President at The Wackel Group

“Tell me: what are some of the things that have helped you get to where you are today?”

I liked this question for three reasons:

  1. It was flattering. It made me “feel” like I was successful and this candidate was acknowledging that.
  2. It allowed me to express my ideas about the “secret” to success in the firm.
  3. It gave the candidate an inside peak into my values (is the secret hard work, or relationships or technical skills, or etc?)

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Donald Kelly
President at The Sales Evangelist

“What would success look like for someone in my role? And how would I achieve it?”

I liked this question because it asked about what it takes to go above and beyond the call of the typical responsibilities.

Anyone can do the basic requirements to get by. An extraordinary seller “acts” rather than waiting to be “acted upon.” They live the “why not me” principle which is not expecting someone else to get the job done for you. They say “why not me,” take responsibility, and act. Successful individuals in this role will seek to identify challenges that are hindering them/their company from accomplishing their/our goals (increasing sales), and offering solutions/ideas to fixing them. Again, they act, rather waiting to be acted upon.

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Deb Calvert
President at People First Productivity Solutions

“I’m intrigued by the company’s mission, vision and values. How do these translate to the work this team does and how people in my role advance the team towards this vision?”

When interviewing, it’s important to show two things: that you are interesting and that you are interested. Far too many candidates focus exclusively on being interesting and fail to demonstrate their interest in the job, company, and people.

This interview question masterfully conveyed the candidate’s genuine interest and gave her an edge when we made our final selection. Her question let us know that she’d combed the website, visualized working with us, and wanted to make a meaningful contribution.

As the conversation continued, her enthusiasm for these specific values was apparent. The “fit” was clear and we never would have known it as clearly as we did if she hadn’t asked this question.

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Jason Maxwell
President at MassPay

“Why would I want to work for you?”

It is important for leaders to reflect on how impactful we are on the careers of those that invest themselves in our company. We can have all these great perks and benefits for our employees, yet it’s their direct manager that will impact their experience with MassPay the most. We need our leadership here to drive a higher level of purpose in the work of our team.

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Stephanie Jean-Baptiste
Team Lead at Treeline, Inc.

“Before Treeline, you didn’t have recruiting experience, but I see you have a degree in Philosophy. How do you feel that has played into your success?”

I liked this question because it showed me that the candidate did their research, and took the time to look at my LinkedIn profile. They also used it to parallel where they were coming from. This candidate did not have sales experience, but was looking for their first sales job.

This question also showed me that they know how to think critically (like a Philosophy major) and understand how subtleties translate into success. You don’t always have the exact experience or requirements that a job description calls for, but you may have the soft and transferable skills that will make you an asset to the company you are interviewing with.

Connect with Stephanie on LinkedIn


Mike Kunkle
VP, Sales Tranformation Services at Digital Transformation, Inc., a division of Fast Lane

“How does [your company] address sales reps who are habitual low performers?”

This question came about during the ensuing discussion that this candidate was a top-producer for another company in the past, whose managers lacked the will or desire to address, and if needed, manage out poor performers who dragged down the team (and in this case, also affected team performance bonuses). Top producers became resentful and gradually began exiting the company.

I liked this question because it showed this candidate, who was a proven top-producer (and became one with us), was concerned about the type of sales culture we had cultivated. He looked for companies that trained, coached, and supported reps and treated all with respect, but that didn’t tolerate ongoing poor performance without action.

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Emmanuelle Skala
VP of Customer Successs at Toast

“Your strategy has been to do online sales only, yet you are now hiring for sales reps so what’s changed? Why? Is the company all aligned on this new strategy?”

I liked this question because it was a bit controversial, but it was also clear that this candidate did their due diligence on the company and our strategy.

Other questions that are indicative of great due diligence are “what’s your close rate? What’s the most common loss reason? Breakdown your pipeline by lead source. Are you happy with this breakdown? Why or why not?

Hiring is a two-way street. Your questions should be indicative of that.

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James McIlroy
Director, Sales Center at the University of New Hampshire

“Who in the organization is typically your buyer and why do they most often decide to buy from you?”

This question showed that the candidate not only understoood sales, but where the value comes from. They were interested in where the company’s current success comes from and how they will be best able to replicate that when establishing new clients.

It also showed their genuine interest in what makes us different from our competitors.

Connect with James on LinkedIn


how much do vp of sales make, sales job adsMichael Stone
Senior Executive Sales Recruiter at Treeline, Inc.

“What are some of the challenges you see me facing in this role? What will the first 30/60/90 days look like?”

Candidates always ask about the fun parts of the job. They never ask about the bad days. Hiring managers have an opening and they need to fill it. They are going to focus on selling their company and opportunity to you. It is the candidate’s responsibility to ask about challenges. By asking, you may find you are up for the task, or maybe it’s something you want to avoid altogether. Gain a deeper understanding of the pros and cons before taking a role.

Connect with Michael on LinkedIn

So the next time you go in for an interview and the hiring manager asks “What questions do you have for me?” do NOT be that candidate who says “None that I can think of.”

Ask well-thought out questions that are important for you to learn more about the company and the sales role and show the hiring manager that you’re interested.

Sales Jobs -Treeline Inc- Sales Recruiters

Published On: January 23rd, 2018Categories: Blog News, Job Search and Career

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