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Sales - 9 min READ

The 12 Sales Interview Questions Every Manager Should Ask

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Author photo: Brittany Perez

Brittany Perez

Manager, Account Management

At Copper, we’re all about building mutually beneficial customer relationships and connecting companies with our product. Of course, to do that, we need a team of champions working to ignite and nurture those relationships.

As Copper’s Regional Manager and now head of Account Management, my job is to build that team of champions—aka. our sales team.

Contrary to what a lot of people think, however, building a sales team takes a lot more than simply finding outgoing personalities and giving them a product to showcase.

When interviewing sales candidates, an aura of confidence and energetic responses can come across as super appealing—but it’s not what matters most. Asking the right sales interview questions and honing in on how these questions are answered (while looking out for red flags) is what will narrow down your candidate pool, floating the best sales reps to the top.

Here are 12 of my go-to interview questions that separate the absolute sales rockstars from just people who can do the job.

1. “How do you organize your day?”

Productivity and time management skills are both insanely important attributes every sales rep should have, so how an interviewee answers this question is always very telling for me.

I want to know that candidates are in it for not only the exciting parts, but the not-so-glamorous ones as well:

  • Do they plan out what they’re going to do in a day before they start it?
  • How far ahead do they plan?
  • How do they adjust their plans when circumstances change?
  • What are their daily targets in terms of contacts? (And how many of these contacts move on to the next stage of the pipeline or ultimately become customers?)

A successful sales rep is one with a plan.

2. “What do you know about the company?”

This is a super basic one but let me tell you… it’s incredible how many candidates have come into the office for a sales interview and not known what Copper or CRM is!

Usually, you won’t need to ask this question directly. If a candidate’s done their research, it’ll show in the way they answer the rest of your questions.

They’ll likely sprinkle in some facts about the organization or demonstrate that they have ideas that’ll enhance its current business model—which are always good signs.

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3. “How do you establish trust with a prospect or lead?”

Depending on your business, there could be a few right answers to this one. The key here to evaluate the candidate’s relationship-building skills.

For example, if they’re coming from an outside sales role and did the majority of their initial contacts face-to-face, what channels did they use to follow up afterward?

  • Do they grab a business card and send a cadence of emails?
  • Perhaps call later to follow up with the receptionist to try and book some time with the decision-maker?
  • Maybe follow up in-person again next week?

If they’ve got a good communication plan in place, what kind of content are they following up with? Are they sending cut-and-paste emails or personalizing them to each lead? The latter speaks more loudly to effective relationship-building.

Bonus: the answer to this question will also give you a good idea of how badly your candidate wants the business and what they’ll do to get it.

Learn more about hiring and training a sales team:

4. “Why are you looking to leave your job?”

The trick with this one is the candidate usually reveals just as much in how they answer as they do with what their answer is.

For example, subtle jabs at former bosses or just general blaming is a pretty good indicator that this candidate might have had some issues with conflict management in the past.

While a bad company culture fit is a legitimate reason to leave a role, it gets a bit fishy when it’s the same reason they left their last three jobs. In that case, the common denominator in these abandoned positions is the person sitting across from you at the interview table.

The trouble with hiring a candidate like this is that when the going gets tough—which in sales, is inevitable at times—they probably won’t stick around.

5. “Can you give an example of when it was necessary to admit to others that you made a mistake? How did you explain/handle it?”

As humans, we all make mistakes. I don’t expect the people I hire to be perfect robots who don’t, but I do expect them to know how to handle things when they do make mistakes.

It’s better to have a rep who makes 10 mistakes in a year but owns up to them and does everything in their power to make things right than a rep who makes only one but refuses to ‘fess up (or is even willing to throw others under the bus to cover it up).

6. “How do you educate yourself outside of work?”

I want to know that they’re taking the initiative to perfect their craft—whether it’s sales-related or a personal hobby or interest.

Taking steps to improve yourself and the desire to continually learn are great qualities in a sales candidate. It shows me that they’re growth-oriented, open-minded, and aware of the fact that there’s always room to better yourself.

7. “Walk me through a time when you had a measurable impact on a job or organization.”

I want to know that they have a desire to go beyond the basic requirements of their role and make a difference.

For example, maybe they went above and beyond to create their own pipeline of leads in addition to what the Marketing team was bringing in, or initiated a referral program with existing customers. Maybe they mentored a colleague into bettering their sales skills as well.

This answer shows me whether a candidate is concerned with helping the company as a whole succeed, not only themselves.

8. “Tell me about a time that you had to re-explain something to a prospect in a different way. What did you do to modify your approach?”

At Copper, we get all types of prospects: those that haven’t used a CRM before, those that are on their fifth CRM, and so on. The approach that our sales reps take to explain the product to each of these prospects is going to be different.

I want to know that the candidate I’m interviewing understands that.

If the candidate doesn’t have a whole lot of sales experience yet, I’ll modify this question to: “Explain a process to me.”

Any process at all! Having a candidate describe to you how something is done, whether it's in the professional realm or not, is an excellent way of demonstrating whether or not they can get across important information in as little time possible.

When they’re explaining the process, do they stumble, use jargon, or ramble on about seemingly irrelevant things? Or do they keep it on track and to-the-point? Most importantly: do you get it?

When a sales rep has less than a minute in front of a busy decision-maker, any hesitation or deviation from the point can make a prospect lose interest and break the deal. Being able to keep the message short, sweet, and easy-to-understand means they can keep the conversation on track and drive the deal home.

9. “Tell me about your proudest professional accomplishment.”

I’m always curious about this! What makes them proud?

Just as a professional athlete would know the exact parameters of the world record they set, a prepared sales candidate will have their most outstanding metrics memorized and in their mental back pocket (if not already presented on paper with lead conversion rates, exceeded quotas, and earned revenues).

What I look for here are specifics in the interviewee's response. If you're getting generic terms such as “a bunch of cold calls,” “a few accounts,” or “some high-dollar deals,” it's likely the candidate is blowing smoke and might attempt to exaggerate numbers as a way to make themselves look good. Don’t fall for fluff.

10. “What is a criticism you received and how did you handle it?”

The point of this question is to shed light on a candidate’s character, and find out if they have an essential attribute that can't be taught: humility.

This is a clever way of asking, "Can you admit your own faults?" and “Are you coachable?”

Any denial or arrogance in their answer won’t do them any favors here. This is also a question that people tend to answer insincerely.

For example, they might try the old disguise-a-strength-as-a-weakness trick. “I’m a perfectionist,” or “I’m a workaholic,” are two statements that don’t tell me that you know how to handle criticism—they tell me you either think you’re perfect, or know that you aren’t but are scared to let other people know that. Either way, this is how you flop this interview question.

On the other hand, if the candidate shows that they genuinely understand their shortcomings—and that they can respond well to coaching and put in effort to overcome these weaknesses—then you’ve got a keeper.

11. “What are your hobbies outside of work? What do you like to do in your free time?”

I want to know who a candidate is besides a salesperson.

  • How do they spend their time outside of work?
  • What are their interests?
  • What are they passionate about?

This is mainly for interest purposes and to help me see their human side versus just their technical strengths. I want to know that this person has some sort of personality outside of work.

Although… when a candidate says they play sports, that’s always something noteworthy to me. It shows they have experience being a team player, likely have a competitive nature, and know how to have fun—all great transferable skills to a sales role.

12. “What are the qualities you value in a manager?”

It’s interesting to flip the table and hear what a candidate is looking for in a manager.

Not a lot of salespeople expect this question, so the answers you get are usually raw and genuine.

If they don’t have an answer, I think it benefits them to take on the perspective that their employer needs to be just as much a fit for them as they are for the employer. This is, after all, an environment to which they’ll be dedicating 40 hours a week.

It also gives me a chance to reflect on what I have to offer my team.

Finding a candidate who’s the right fit for the company—including your management style and sales team dynamic—will be the difference between a long-term employee and someone who's here today and gone tomorrow.

How a candidate answers your sales interview questions is their first sales pitch at your company. Can they close the deal?

Sales candidates often have answers to run-of-the-mill interview questions ready to roll. It’s the more complex questions that’ll really show you if they’ve got what it takes to take your sales team to the next level.

Being able to think fast, answer questions effectively, and overcome objections are all key traits in sales, after all.

Interview prep isn’t just for the candidate. As the hiring manager, be ready to ask the right questions, and know what to look for in an answer to pick out the winning candidates.

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