31 Sales Questions to Help You Hire a Salesperson for Your Team

by Briana Morgaine 10 Minutes
sales questions

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If you’ve determined that you’re ready to hire a sales team (or take on a single salesperson), you might be wondering what kind of sales questions you should go about asking them to figure out if they are a good fit for your business.

After all, you might not know very much about sales yourself—so how do you vet a salesperson and make sure you are choosing someone who will be a good match?

Here is a list of great sales questions that will help get to the heart of a salesperson’s style, personality, and experience, to help you decide if they’re a good addition to your team.

sales questions

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Client-related questions

The first series of questions will help you determine how the salesperson handles their client base and gives you an idea of what to expect from them in terms of client interaction and sales techniques.

Are they hands off, or do they prefer to foster a strong relationship with their clients? Do they have a light touch, or are they pushy? Or, do they lack tenacity, and tend to give up too easily? Their responses will help you answer these questions.

1. How do you keep up to date on your target market?

Even if the target market they served in previous positions is different than your current target market, it’s good to get a sense of how they maintain an understanding of the industry they work in, and the needs of their clients. Do they keep up to date by reading blogs, listening to podcasts, following certain influencers on Twitter? Find out.

2. How do you go about finding information out about potential clients before you approach them?

This question not only helps you determine how the salesperson goes about researching potential clients before beginning the sales process, but if they do any research, period. It’s important to hire a salesperson who is thorough enough in their process that they get to know their prospects beforehand, so if they don’t do any research, that is telling.

3. In your last role, how much of your time was spent cultivating relationships with existing clients, versus building relationships with new clients?

The “right” answer here depends a lot on your specific business; are you more interested in a salesperson who can continually make new connections, or are you looking for a salesperson who prefers to build a long relationship with clients? Make sure to have a clear understanding of what you are looking for first—once you understand what matters most to you, it will be easy to see if their answer aligns with your company goals.

4. How did you go about cultivating these relationships?

Does the salesperson prefer to meet in person as often as possible? Do they check up on the phone on a regular basis? What does it meat to them to cultivate a relationship with a client? Their response to this question gives you insight into how they go about maintaining relationships with their clients.

5. What kinds of questions do you ask your prospects?

The best salespeople spend more time listening than talking. Get a sense of what they ask prospects, and how they determine the best way to help solve their problems.

6. How do you like to handle clients who are unhappy?

Though you likely work hard to keep your clients happy, there are bound to be instances where a client is dissatisfied, and it may be up to your salesperson to fix it. Determine how they would go about rectifying a situation like this and keeping a valuable client.

7. How do you qualify leads? What types of questions do you ask to qualify your leads?

The types of questions asked will vary by industry, but you’ll be able to get a sense of their experience as a salesperson from the types of questions they know to ask to qualify potential leads.

8. When do you know that it’s time to stop pursuing a client?

Not every lead is going to turn into a client. You want a salesperson that can be both tenacious, but still knows when to throw in the towel (and not waste time on a dead end).

9. Describe the time you had to handle a client who was especially difficult.

Is the salesperson able to turn a bad situation around? Have they brought a client back who seemed unlikely to ever return? Did they go out of their way to solve a problem for a client so efficiently that they became an extremely loyal brand ambassador? Find out how they handle difficult situations with this question.

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Process-related questions

Make sure to ask a few sales questions related to how the salesperson you are interviewing is used to conducting day-to-day affairs. Since every business is different, you want to make sure your salesperson gels with the organizational structure and expectations of your business.

10. Do you have any experience integrating any platforms (social, CRM, etc.) into your selling process?

If you plan on using a CRM, or your salesperson will be expected to use social media to interact with (or find) prospects, make sure to gauge their comfort level here. What you expect them to be comfortable with, of course, will vary by industry, but at the very least they should demonstrate a willingness to learn new systems.

11. What role does interacting with other departments (marketing, for example) play in your sales process?

The scope of their role may be limited to that of the traditional account executive, or they might be involved in the creation of sales emails or customer service. Whatever role you are hiring for entails, it’s important to make sure that they have the skill set and experience (or again, willingness to learn) to succeed in the position.

12. If you could create your ideal sales position, what would your day look like?

Plain and simple—asking a prospective hire to articulate what parts of their work they most enjoy will highlight both what they love doing, and what they don’t enjoy. This allows you to determine whether or not the candidate fits your current needs.

For example, if they seem to prefer getting a list of clients, a position where they will be required to source leads themselves might not be a good fit. Similarly, if they like to spend a good chunk of the day making sure current clients are satisfied, but you plan to hire a customer service team to take care of that end, they might not enjoy working for your company.

sales questions

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Sales-style questions

What kind of salesperson are you looking for? Are you hoping for someone who can be comfortable with a bold, slightly aggressive approach—or would that send your target clients running for the hills?

13. Describe your sales process. What are your steps, from beginning to end?

Learn a little about how the salesperson initiates and closes a sale. What is their method? How long does it typically take them?

14. Which matters more to you—hitting your quota or making sure your clients are happy?

Depending on your business, there may be a right answer here. Do you want a salesperson that focuses more on client satisfaction, or who can bring in big numbers? Make sure that their answer matches what your goals are in terms of your sales team and business overall.

15. What is your least favorite part about being a salesperson?

If, for example, you prioritize creating a long-term, engaged relationship with clients, and the salesperson in question lists something such as “following up with current clients” as their least favorite part of selling, they might be a bad match. So too would a salesperson who hates cold calling, if your outreach strategy relies heavily on cold calls.

16. Who are you most comfortable selling to?

Listen to who they are describing. Are they your target client or customer base? If not, how far off are they from the audience the salesperson, if hired, would be selling to? It’s not necessarily a deal breaker if the salesperson in question isn’t already comfortable with selling to your exact target client base, but it certainly helps.

17. How do you think former clients would describe you?

Think of how you’d like your sales team to be known. Would you hope they’re helpful, charismatic, warm, or maybe bold? Look for answers that match the sales culture you hope to build within your company.

sales questions

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Questions about your company

18. From your stance as someone outside our company, what could we be doing better?

This question demonstrates that the salesperson has an understanding of your business, as well as the niche you serve. The former shows they’ve done their research, and the latter shows that they have an understanding of your industry—two very important components of a good hire.

19. How does [your product or service] bring value to [clients/customers]?

If they cannot clearly articulate the value you bring, they may have trouble doing so with clients, too. A salesperson who can sell you on your own product or service, however, is worth investing more time into.

sales questions

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Self-improvement and personality-related sales questions

20. What is something you have taught yourself how to do recently?

If a person can teach themselves how to do something, chances are they have a strong sense of self-motivation. This is a good quality in a salesperson, who need to be motivated when pursuing clients and working hard to close sales.

21. How do you handle a disappointing day at work?

Not every day is going to work out in your salesperson’s favor. There will be dead leads, deals that seemed like a sure thing but that suddenly went south, and so on. This can get the best of plenty a good salesperson, but what matters is how they handle it. Do they get especially down on themselves? Do they need plenty of time to regroup? Can they jump right back in? Find out how they handle the bad, as well as the good.

22. Have you ever turned away a prospect?

Your product or service likely isn’t a fit for everyone, and it’s important to take on a salesperson that knows when to say no. If they cannot think of an instance when this has happened, consider asking them to come up with an example of when they might not wish to pursue a potential client any further.

23. Have you ever had periods where you felt like you couldn’t make any sales? How did you turn that around?

Again, this helps you determine their attitude toward periods of failure. Do they bounce back easily, or do they tend to get stuck in a bad mood?

24. What have you learned from deals you’ve lost?

There is usually a lesson in every bad experience, and the key is to find a salesperson that is perceptive enough to pick up on it. What lessons have they learned from sales experiences that didn’t go the way they had planned?

sales questions

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Goal-related questions

Does the salesperson you are interviewing have lofty goals? What do they hope to aspire toward in the near future? More importantly (for both of you!) do their goals align with where your business is going?

25. If you were hired, what would be your goals that you’d like to accomplish in the first month? What about first three months?

This question will help you understand what short-term success looks like to your prospective hire. What would they consider a successful start to their career with your company? Is it about building relationships with clients, getting the lay of the land in your industry, meeting a certain quota? What motivates them and how do they measure success?

26. What are your career goals?

Where do they hope to take their career? This can tell you a lot about whether or not they will be a good fit with your business.

If, for example, they hope to become a sales manager in the next three years, and you are not planning on expanding your team to include a sales manager within that timeframe, you may want to consider going in a different direction. However, if you’d love an experienced salesperson who can move up in the ranks as your business grows, this might be the perfect candidate for you. As with so many things, it will depend on where your business is going, and your plans for growth.

27. What made you want to go into sales?

What motivates this particular salesperson? If the answer is simply “commission,” you might want to consider looking elsewhere. While it’s not always realistic to expect hires to have a deep passion for every aspect of their job, it is important to find a salesperson who enjoys being in sales for reasons beyond a paycheck.

28. What do you consider your greatest accomplishment?

Is the salesperson you are interviewing interested in pursuing self-improvement both inside and out of the office? What motivates them overall, and what makes them feel accomplished? This is also a great question to get a sense of if they will mesh with your company culture, too.

sales questions

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“Show and tell” questions

29. Sell me [something].

While “sell me this pen” is a common example, ask your prospective salesperson to sell you anything—what they had for dinner last night, their favorite brand of t-shirt, the last movie they saw, and so on. Can they sell it to you effectively, in a style that seems fitting with your business and the product or service they would be selling while working for you?

30. Explain something to me.

On a similar note, can they convey information in a way that feels clear, and appropriate to your desired voice and tone? Are they good at breaking down something complex for those that might not be familiar with the concept? And, can they do it on the spot? All these qualities indicate that they are likely to be an adept salesperson.

31. What is your ideal sales environment?

Can you provide the type of setting to help this salesperson thrive, or do the two of you have poorly matched work styles? Do they prefer a close working relationship with a sales manager, or would they rather have more independence and autonomy within the company? Make sure their expectations and preferred environment mesh with the environment in which they’ll be working—or you may find yourself hiring a new salesperson sooner than you’d anticipated.

Have you hired a sales team? Which sales questions helped you best determine if a candidate was a good fit? Let me know in the comments!

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by Briana Morgaine
Briana is a copy writer, copy editor, and freelance writer, covering the various facets of the small business and entrepreneurship space. She can be found writing for Bplans, and also on Twitter.