10 Questions to Ask When Hiring Sales Reps for Your Company

The interview questions you ask when hiring sales reps are not only the gateway to great conversation, they are the tools you will use to qualify (or disqualify) them based on their responses.

At IMPACT, regardless of the position we’re hiring for, there is a very purposeful approach to the types of questions we’ll ask during the interview process.

We focus on solving for the following three things:

1. Organizational or culture fit from a core values perspective (i.e. what they’re like to be around)
2. Soft skills related to the position (i.e. coachability, adaptability, etc.)
3. Hard skills related to the position (i.e. technical knowledge, ability to use the tools, etc.)

It should be noted that the order in which the above items were placed was not arbitrary. Should the applicant not align with the core values of our organization or they prove that they’re not all that pleasant to be around, it doesn’t make sense to spend additional time learning about their soft and hard skills.

As Gregory Lewis of LinkedIn reports, “65% of hiring managers in sales agree that a lack of soft skills among candidates limits their company’s productivity.” Therefore, it only makes sense that once it’s understood that the candidate is a good organizational fit, questioning around soft skills should immediately come into play.

Should a candidate exude the soft skills necessary to succeed as a sales rep, only then does it make sense to test for the specific, industry-related hard skills necessary to execute the job function.

Keep in mind that despite there being an order of operations in our approach to questioning, it doesn’t mean that some hard skill-based questions won’t be found on the initial application.

While there are hundreds of questions that could be asked during the interview process, we’re going to review what I believe are the 10 most telling sales rep interview questions (and responses) specific to uncovering organizational fit, soft skills, and hard skills.

QUESTION #1: ORGANIZATIONAL FIT
Why do you think [YOUR COMPANY NAME] is the right place for you?

Why is this question important?

This question reverses the standard interview question we’ve all heard before… “Why do you think you’re a good fit for this company / role?” By doing so, it allows the candidate to first align their understanding of your organization with their own values, beliefs, abilities, and goals. It forces the candidate to think more critically about your company (versus themselves) and why your company is or is not the right place for them.

What should you look for in the response?

Their response should demonstrate that they’ve completed more-than-cursory research on your company and have a “we before me” tonality. Look for responses that start with something like, “I see that your company has won X award and I’ve always envisioned myself working with an organization like yours that is constantly innovating.”

When should it be asked?

Early on in the process as a question on the written application or during the initial phone screen.

QUESTION #2: ORGANIZATIONAL FIT
If you were already financially secure and didn’t need to work, what would you spend your day doing?

Why is this question important?

There’s an unfair and untrue stereotype that exists which is that successful salespeople only care and are driven by money AND that the highest performers will tell you that money is their number one motivator. That may have been the case in the “used car salesman” days...

This question is designed to help uncover the candidate’s true passion and intrinsic motivation beyond dollars and cents. Should the candidate proceed in the hiring process, the answer to this question also becomes an anchor by which you can build a stronger relationship and better guide their career growth.

What should you look for in the response?

There isn’t really a right or wrong answer.

The most important thing is that they have an answer. An immediate, excited, and detailed response demonstrates passion for something beyond the day-to-day / paycheck. Responses will vary from traveling the world, to starting a non-profit to, to staying at home and raising the family.

Those that respond with something to the likes of, “Hmm… I’m not really sure...” is an indication that they may not possess the right levels of internal drive required to turn things up and fight through those aggressive sales months.

When should it be asked?

Early on in the process as a question on the written application or during the initial phone screen.

QUESTION #3: ORGANIZATIONAL FIT
What does a successful, next, career-move look like for you? Where do you want to be in 2 - 3 years?

Why is this question important?

This is a two-fold question.

First, this question helps you as a manager, to forecast how long you may be able to keep this new rep onboard. Are they just looking for their next gig or are they planting roots for a long-term stay. If you had seen on their application that they’ve changed jobs each year, this question can validate (or invalidate) those inputs.

Second, you’ll be able to see if this candidate has a focused career goal in mind. In the previous question, we began to hint at, “guiding career growth.” It’s a critical motivator of any job function, but especially for a sales position. You, as a manager, must gain a sense of where this candidate envisions themselves and how fast they’ve gotten there in order to set up the relationship between you, the rep and the company for long-term success.

What should you look for in the response?

Similar to the previous question, an immediate, excited and detailed response about the future state showcases that the candidate has established internal clarity on where they’d like to get to from a personal and professional perspective.

When should it be asked?

Early on in the process as a question on the written application or during the initial phone screen.

QUESTION #4: SOFT SKILLS, CULTURAL FIT
What do you believe are three characteristics of a high-performing, successful salesperson?

Why is this question important?

According to Mark Roberge, former CRO of HubSpot, the characteristics of successful salespeople will vary from organization to organization - “It depends on your value proposition and the type of sale (transactional vs. complex.).” The good news is that even before hiring your your first rep, you’ll be able to make an educated guess on what those characteristics are. This question hunts for the alignment between the candidate’s and your beliefs.

What should you look for in the response?

• A verbalization of the characteristics that resemble or compliment your beliefs. At IMPACT for example, we’ve seen that successful reps are first and foremost, continuous learners - about the art of selling, the industry, the buyers, etc.
• The candidate can clearly articulate three. Listen for candidates that try to list more than three with weak anecdotes attached. If they drone on and try to “sell” you those qualities, it’s an indication of how they’ll communicate to your prospects.

When should it be asked?

During the initial phone screen or 30-minute interview.

QUESTION #5: SOFT SKILLS, CULTURAL FIT
What would prospects say you’re like during the sales process?

Why is this question important?

In the previous question (#4), you learned about their beliefs behind the characteristics of a successful salesperson. Here, we’re testing to see if they’re actually embodying some of those characteristics.

Secondly, if the candidate is self-aware and emotionally intelligent, we have the opportunity to uncover some potential, self-admitted shortfalls or areas of improvement (this is a very positive thing by the way).

What should you look for in the response?

Look for alignment with their response to question #4. If being a great listener was a characteristic they described and that’s important to you, listen for things that embody or result from great listening skills like, “the prospect would say that I’m engaging and attentive, that I’m able to make the conversation about them versus us, and that my recap emails post-meeting are always on point, but a little long-winded.”

When should it be asked?

During the initial phone screen or 30-minute interview.

QUESTION #6: SOFT SKILLS, HARD SKILLS
How would you handle a prospect that is very difficult and clearly isn’t good fit for us to work with?

Why is this question important?

As important as it is for sales reps to generate new clients, it’s equally as important for them to represent your brand in the best light during times where a potential client must be turned away.

What should you look for in the response?

1. The conversation with the prospect doesn’t just end abruptly. Listen for how the candidate will provide additional resources or support as the prospect continues through the buying process, ultimately leaving a positive feeling regarding your brand, and perhaps generating a referral.
2. The conversation with the prospect doesn’t lead to a closed-won deal. This might sound counterintuitive, but selling bad-fit clients is a dangerous way to grow any business and the candidate must be able to articulate that if the fit isn’t there, it’s not in the best interest of the buyer (or your company) to proceed.

When should it be asked?

During the initial phone screen or 30-minute interview.

QUESTION #7: SOFT SKILLS, ORGANIZATIONAL FIT
Tell me about the most recent sales, marketing or business book you’ve read?

Why is this question important?

Stephen Covey describes this as Habit #7, “Sharpen the Saw.” Responses here reveal a candidate’s intrinsic motivation regarding self-improvement and continuous learning. Buyers today are more educated than ever, which means that reps must continue to self-educate, expanding their own knowledge in order to have valuable conversations with prospects.

What should you look for in the response?

There isn’t necessarily a right or wrong book to have read - it’s more about are they actually doing it and can they describe to you the general concepts and takeaways from each.

Remember, you’ve asked to hear about the most recent book they’ve ready, so this is another opportunity to listen for the number of books they share. Are they just trying to list as many books as possible to try to “sell” you on what they’ve read? Again, equate the reply to how they may interact with a prospect that has asked for something specific.

Here are a few books I listen for, specifically:

• Sales
• The Challenger Sale
• The Sales Acceleration Formula
• To Sell is Human
• SPIN Selling
• SNAP Selling
• Marketing
• They Ask You Answer
• Content, Inc.
• Killing Marketing
• Agile Marketing
• General business
• The 7 Habits of Highly Effective People
• How to Win Friends & Influence People
• Multipliers
• Radical Candor
• Your Brain at Work

When should it be asked?

During the initial phone screen or 30-minute interview.

QUESTION #8: SOFT SKILLS, HARD SKILLS
Who would you consider your best sales mentor or coach and why?

Why is this question important?

The most successful people in sales (or any role for that matter) have or have had mentors and / or coaches that have guided their skill and career development.

This question also reveals information about how the candidate may prefer to be managed: Are they accepting to criticism? How frequent were the coaching sessions? Are they speaking positively or negatively about them?

What should you look for in the response?

• The key lessons learned. Of all the potentially criticizing, motivating, and hard conversations had with a coach or mentor, can they pinpoint and articulate two or three lessons that impacted their personal or professional growth as a sales rep?
• What the candidate did with those lessons. Listen for how these lessons were put into action and drove lasting change in how they operate. Can they describe the moment in time in which it “clicked” and how it affected a sales conversation?
• They’d like more mentoring / coaching. Listen for implications that they’d like to continue receiving mentoring / coaching from you or others on your team as an opportunity to continue growing.

When should it be asked?

During the initial phone screen or 30-minute interview.

QUESTION #9: HARD SKILLS
What are some of your favorite closing techniques or language and can you share an example of how you used it with a prospect?

Why is this question important?

IMPACT’s Sales Coach, Jack Carroll, has been coaching sales teams and individuals for 30+ years. According to Jack, of the sales professionals he’s worked with over the years (including myself), approximately 80% of them weren’t equipped with the necessary techniques or language to effectively “close the business.”

Finding a sales rep who is armed with the ability to leverage closing language during the sales process will drive exponentially faster and better results.

Keep in mind, closing techniques are not the “hard selling” you might think of from the movie Glenngary Glen Ross. You might remember the line, “ABC… ALWAYS. BE. CLOSING.” As Jack Carroll would put it, “It’s simply and naturally asking if they’ve seen enough value from us in order for them to move forward.”

What should you look for in the response?

Listen for their “go-to” technique - one that’s proven successful, time and time again. More important than HOW they use the technique, listen for WHEN and WHERE they used it. During the sales process, closing happens at every single step of the process, including things as simple as closing the second meeting from the first, or on the opposing end, gaining commitment from the prospect to sign the contract.

When should it be asked?

During the initial phone screen or 30-minute interview. Answers to this question will also be revealed during the Situation Activity.

QUESTION #10: HARD SKILLS, SOFT SKILLS
Can you describe an aggressive sales target you were tasked with hitting and what you did to hit it?

Why is this question important?

You need to know and be confident in the candidate’s ability that either under pressure or during times of rapid growth within an organization, they’re able (and willing) to perform at or above level in order to reach their and the organization’s goals.

What should you look for in the response?

Listen (or ask) for an explanation around why the target was considered aggressive and how that compared to a typical target.

This is also a very critical point to uncover excuses around or ownership of these targets. Are they making excuses around how it was too aggressive of a target in the first place, they didn’t have exactly what they needed to do it, and that’s the reason they were only able to get close to that target? Or are they taking ownership of the fact that they performed to the best of their ability to hit or miss it, and providing insights on what they could’ve done better to do so?

The candidates that demonstrate complete ownership of their targets will be your best performers.

When should it be asked?

During the initial phone screen or 30-minute interview.