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To build a strong sales organisation, it’s imperative to find people who can hit target, handle rejection, and be persistent without turning aggressive. Sales isn’t an easy job to hire for, and the wrong person can keep your company from meeting important business goals and cost you a great deal of time and money in recruiter fees.

Here’s a selection of questions I’ve used over the years to gain insights into candidates skills, attitudes and motivations.

Technical Sales Interview Questions

1. How do you keep up to date with what’s happening in your target market?

Even if the target market of their last job is totally different from the one they’re interviewing for, this will show their ability to find and keep up with relevant trade publications and blogs. Dig deeper and ask for a recent piece of information they’ve learned from one of the publications.

2. What are your favourite questions to ask prospects?

Good salespeople spend more time asking questions than pitching. Look out for open-ended questions that will help a rep thoroughly understand a prospect’s needs.

3. What’s your approach to handling customer objections?

Preparing to deal with objections, rather than simply winging it is critical. Listen for evidence of a process.

4. What role does social media play in your selling process?

Social selling is becoming more important in all industries. If the candidate has not used social channels to research prospects or look for leads in the past, make sure they have a willingness to learn.

5. How do you research prospects before a call or meeting? What information do you look for?

Neglecting to use LinkedIn to research clients is not a viable option in today’s sales environment. Ensure that candidates are searching for personal commonalities in addition to professional information so they can tailor communication as much as possible. Looking into company trigger events would be the cherry on top.

6. What do you think our company/sales organisation could do better?

This sales interview question serves two purposes: It shows how much research the candidate did before meeting with you, and it demonstrates their creative thinking and entrepreneurial capabilities.

7. How does [your company name] bring value to the customer?

This is another question that shows how much research your candidate has done on the company. If they can’t even slightly articulate the benefits of your product/service, it might mean you need to move on.

8. What are three important qualifying questions you ask every prospect?

This answer will be different for every candidate based on what they’re selling and whom they’re selling to. But their answer will allow you to gauge how they qualify prospects. It also gives you a further sense of their sales training and instincts. Their questions should be focused and get to the root of whether a prospect is a good fit or not.

Situational Sales Interview Questions

9. When do you stop pursuing a client?

The right answer here will depend on your company’s process, but in general, the more tenacious and persistent a rep is willing to be, the better. I usually recommend six to eight attempts before using my “last attempt email”.

10. How do you keep a smile on your face during a hard day?

Appraise the person’s attitude towards rejection. Do they need time to shake off an unpleasant conversation? Or do they bounce back immediately? See which strategies they use to recover and move on.

11. Have you ever turned a prospect away? If so, why?

Selling to everyone and anyone — even if a salesperson knows it’s not in the prospect’s best interest — is a recipe for disaster. Make sure your candidate is comfortable with turning business away if the potential customer isn’t a good fit.

12. Have you ever had a losing streak? How did you turn it around?

Everyone has bad spells, so beware of someone who claims they’ve never experienced a downturn. Nothing’s wrong with a temporary slump as long as the candidate learned from it.

13. If you started a company tomorrow, what would it be?

Many salespeople get into the profession because they’re aspiring entrepreneurs. By asking candidates about a fictional company, you’ll learn more about their future goals and motivators. You’ll also get a taste of how they pitch business ideas.

Inside Sales Interview Questions

14. What’s the best way to establish a relationship with a prospect?

Get insight into how they approach and maintain prospect relationships. If their answer is that they mainly communicate over email or via the occasional voicemail, that might be a red flag. If they tell you they collect lead intelligence and build strong rapport over the phone, that’s a good sign.

15. Explain the steps you take, from the beginning of the sales process to the end.

This shows how well your candidate understands and considers the sales process. It also illustrates how they organize their thoughts and communicate complicated concepts.

Do they explain their process clearly? And do they cover the main steps: prospect, connect, research/evaluate, present, and close? These are two things you should look for in their answer.

16. Walk me through the steps you took to land your most successful sale.

This question aims to better understand the candidate’s thought process as they approach a sale. Additionally, it is a good way to showcase their strengths using a real-life example.

17. Tell me about a time you didn’t close a deal. What did you learn from that experience?

Everyone loses deals, and it’s ok to talk about it. This question aims to dive into the lessons the candidate has learned, and how they have improved their sales techniques from less-than-stellar deals.

18. It’s halfway through the month, and you’re below where you need to be to make target. What course of action do you take during the second half of the month to ensure you reach your targets?

By asking this question, you’re positioning them to showcase their problem-solving skills.

Fit and Motivation Sales Interview Questions

19. What’s worse: Not making target every single month or not having happy customers?

Depending on your company’s goals, either answer could be the right one. But beware of reps who will prioritise target achievement over truly giving customers what they need — or withholding what they don’t.

20. What’s your least favourite part of the sales process?

If their least favourite part is the most important part at your company, that’s probably a red flag. Ask them what they do to simplify their least favourite part of the process or make it more enjoyable. This question can also alert you to weak areas.

21. What motivates you?

Money, achievement, helping customers, being number1 — there are a lot of potential answers to this question. What makes a good answer versus a bad one will depend on your company culture. For instance, if teamwork is an important aspect of your sales team, a candidate who is driven by internal competition might not be a great fit.

22. What is your ultimate career aspiration?

Lack of growth opportunities is often a reason given for sales people to look for a new job. If the candidate expresses a desire to pursue a career move your company can’t provide, you might be interviewing again sooner than you’d like.

23. What made you want to get into sales?

Commission, while perhaps part of the motivation, is not a great response to this question. A good answer will include a personal story or real-life example that illustrates the reasons why the candidate chose sales as a career path.

24. What’s your view on collaboration within a sales team?

Collaboration might be less important at some organisations than others, but candidates who aren’t willing to collaborate at all likely won’t make pleasant coworkers. Their uncooperative attitude will also block knowledge sharing.

25. Who are you most comfortable selling to and why?

Listen for whether they answer with a description of an ideal buyer, or a demographic with no tie-in to the buying process. Depending on your product or service, the second type of response might pose a problem.

26. What’s your opinion of the role of learning in sales?

If the candidate is thrown by this question. It may be a sign that your candidate isn’t a life-long learner — an increasingly important trait in salespeople. An ideal candidate should communicate they’re willing to learn and grow in their role.

27. How would you describe the culture at your last company?

This tells you a lot about what the candidate values, how they worked with others, and what kind of leadership they thrive under. If they complain about long hours or rigid goals and your company thrives off the energy created by late nights and challenging numbers, it’s probably not the right fit.

28. Describe your ideal sales manager.

Asking a candidate to describe their ideal manager shows you how autonomous they are, how they approach working relationships, and how they overcome challenges. Look for a candidate who’s able to work independently and is comfortable taking direction from their boss.

29. What core values should every salesperson possess?

To learn where their moral compass lies, look for answers like “Putting the needs of the prospect first,” “patience,” and “humility.” You want candidate values to align with company values to ensure a good fit.

30. What accomplishments in your life are the most important to you?

This might seem like a huge ask, but the answer illustrates your candidate’s values and motivations. If the candidate tells a story of overcoming great odds to achieve a specific goal, that signals a driven and highly motivated person. If a candidate’s most valuable accomplishment is finishing all seven seasons of The West Wing, you should probably move on.

Use these questions to gain more insight into what skills, capabilities and attributes each candidate has, but if you need help we’re always happy to talk

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