31 Sales Interview Questions, and Knowing Which Ones to Ask

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We recommend using our complete guide. It gives you information on what to listen for in candidate responses.

There are a lot of variables when it comes to hiring great salespeople.

How do they connect with prospects? How much preparation do they do? What drives them when things aren’t going their way? How successfully will they operate in a specific sales process? 

You do your best to make good hiring decisions, but it seems like you always miss something. The reasons why people fail seem painfully obvious much later on. “Of course,” you think. “How did I not see that?”

And the problem is compounded when you have multiple people making hiring decisions throughout an organization.

Say you’ve been directed to start hiring curious people. How do you know you’re operating on the same definition of curiosity as everyone else? How much curiosity are you looking for? Too much, and prospects will feel interrogated. Too little and they won’t get the information they need to close a deal. Where’s the sweet spot?

But what if you were able to limit the effects of these pains? What if you could avoid those “oh crap” moments six months after hiring a rep, and help everyone else do the same?

Introducing Objectivity to the Sales Hiring Process is Transformational

Making the right hiring decisions across an organization is a matter of knowing what questions, what quality you are measuring, and how to score that quality objectively.  

This post is all about helping you do exactly that. By the end of reading this, you will be able to transform the way you hire salespeople. With the proper process, these questions will allow you to:

    • Improve your ability to identify sales talent
    • Rely less on a candidate’s experience, and more on their genuine ‘fit’ for your team
    • Understand a reps potential shortcomings before you hire
    • Implement a consistent hiring strategy across your organization
    • Use data to continuously improve your ability to predict success
    • Eliminate interview bias
    • Avoid ‘gut feel’ and make more objective hiring decisions

Great questions have been used by the most successful organizations to build world class sales teams. They help Google identify the untapped talent they need to fuel innovative products. They helped HubSpot grow from zero to one-hundred million. And now they can help you do the same.

These Interview Questions Evaluate More Than Just Sales Skills

We asked our customers to send us their best interview questions, and we distilled them down to the top thirty-one.

Most sales interview questions tease out additional information about a person’s sales experience:

What are three important qualifying questions you ask every prospect?

Tell me about a time you salvaged a deal. How did you save it?

When do you decide to stop pursuing a client?

But the questions we’ve listed are different. Instead of evaluating sales skills, which account for only 11% of the reasons why employees fail, each of the questions addresses an intrinsic quality that would otherwise be invisible in interviews.

Read the “How to use these questions” section below to figure out which qualities you should be assessing. For further background on how each quality directly affect sales, and what to listen for in responses, check out our complete guide.

Sales Interview Questions

  1. Adaptability: Tell me about a time when you had to adjust to a person’s working style in order to get something done.
  2. Altruism: Describe the last time you went out of your way to help someone. What was the situation? How did you know that they needed help?
  3. Brevity: What’s something you know a lot about? Explain it to me assuming I know absolutely nothing about it.
  4. Charisma: When was the last time you coached a team or led a group? How did you find yourself to be in that role? What was your approach?
  5. Coachability: Describe the last time you found a better way of doing something. How did you discover it?
  6. Confidence: Why are you the perfect person for this job?
  7. Conscientiousness: Tell me about a time when you had to deal with unrealistic expectations. How did you go about dealing with them?
  8. Competitiveness: When have you ever found yourself in a competitive situation at work? How did you handle it?
  9. Composure: Tell me about a time when you couldn’t get someone’s cooperation. How did you handle it?
  10. Creativity: Describe the last time you had to come up with your own approach to accomplishing a task. Why was a different approach needed?
  11. Curiosity: When was the last time you had to refrain from asking questions?
  12. Emotional Intelligence:Tell me about a time when a colleague made you angry at work. How did you handle it and what was the result?
  13. Extraversion: What do you do to decompress after a long day?
  14. Financial Interest: Describe the last few times you got a new job. What were the reasons you decided to change jobs?
  15. Goal Drive: What are your current goals and where are you in the process of achieving them?
  16. Grit: Tell me about a time you were able to maintain your motivation even with significant obstacles in your way. What would it have taken to stop you?
  17. Humility: Describe a time when it was necessary to admit to others that you made a mistake. How did you handle that?
  18. Individualism: Describe a time you had to bite your tongue when you did not agree with a course of action. Why did you decide not to speak up?
  19. Intelligence: What was the last situation where you had to solve a problem at work? Explain your approach, and anything you learned.
  20. Listening Skills: Tell me about a time when you strongly disagreed with what was being said. What did you do?
  21. Loyalty: What was your relationship like with you last boss? How did you guys get along?
  22. Meticulousness: Describe the last time you had to complete a project. What was your process, and how did you implement it?
  23. Openness: When was the last time you had to open up to someone at work? What was the situation and how did you make sure you didn’t come across as unprofessional?
  24. Optimism: Tell me about the worst situation you got into at your last job.
  25. Organization: Describe the last time you implemented something to help keep you stay organized. What was it and why was it necessary?
  26. Polish: Describe a time when it was really important for you to make a good impression. What did you do differently than normal? How did it turn out?
  27. Preparedness: Describe how we bring value to our customers. What else can you tell me about our company?
  28. Skepticism: When was the last time you felt like you stressed someone out by asking too many questions? What happened, and why did you have so many questions to ask?
  29. Synergy: Tell me about a time you worked (or played) as part of a team. What role did you play and how did you measure your success?
  30. Trustworthiness: Describe the last time you had to make a tough decision. How did you decide what to do?
  31. Urgency: Describe the last time you sprung into action before anyone else. What was the situation, and why were you so quick to respond?

How to Use These Questions

Each of the thirty-one questions measures a specific trait (or quality) that can indicate sales success. Because we don’t know which qualities lead to sales success at your company, the goal is not to ask all thirty-one questions.

Step 1: What Qualities Make a Salesperson Successful at Your Company?

The first step is to create a hypothesis about what you think it takes to be successful.

Read the list and familiarize yourself with what’s there.

Next, select a handful of questions you think are relevant to sales success in your environment. Ask yourself the following:

    • What qualities do my top performing salespeople have in common?
    • What would make a person successful working under our particular management?
    • How defined is our sales process, and how would it impact what it takes for a person to be successful?
    • Do we sell to early or late adopters? What qualities would help reps sell to our unique customers?
    • What factors might govern if a person is a flight risk? Are there qualities that make a person more likely to stick around?
    • What types of tasks do successful people tend to do more of? What traits would make a person seek out these types of tasks on their own?
    • Are there certain types of motivations that would make a person work harder and be more likely to succeed?

Step 2: How Will You Measure These Sales Qualities? And How Much of Each Sales Quality do You Need?

Once you’ve chosen what to measure, you need to figure out how to measure. For each quality, create an objective strategy for scoring candidates on a scale from 1-5. Consider the following example:

Quality: Adaptability
Question: Tell me about a time when you had to adjust to a colleague's working style in order to get something done.
Scoring:
1 - Doesn’t believe they need to adapt
2 - Understands they need to adapt, but...
3 - Adapts but...
4 - Adapts selectively….
5 - Extremely adaptable

For the qualities you choose to measure, more will not always better. Following the above example, people who are too adaptable may be too willing to stray from a sales process. In that case, you may want people who are adaptable, but not to an extreme – you may decide that you should look for people who are a “3” on your adaptability scale.

Look at the “advantages” and “downsides” section of each quality to help figure out how much of each quality you should be looking for.

Are some of the qualities you will be looking for more important than others? Perhaps “adaptability” is twice as important to you as “brevity.” Take note of how much you want to weight each quality.

Step 3: Seek Input and Get Buy-In From Your Team

Now that you have a formal hypothesis, get input from the rest of your team. Do they agree with the questions you have chosen? Can they think of other things you might want to look for? It’s possible you may have thought of something that isn’t on the list. In that case, do some research and develop a measuring strategy.

Doing this has the added benefit of getting them bought in to the process. Get them to take partial ownership of what you’re doing, and they will do everything in their power to see that it’s successful. 

Step 4: Start Scoring Sales Candidates

Once you have agreed on a strategy, it’s time to implement. To assess a candidate for fit, subtract the value of every answer scored from your target score. Take the absolute value of each score and multiply them by the values you have chosen for weighting. Finally, add up the total. Candidates with the lowest aggregate scores will be the best fit for your organization.

If possible, you will want to have more than one interviewer score each candidate. This will help control for extraneous variables like bias.

Side note: You don’t always have to hire the person with the greatest aggregate score. Sometimes you’ll have a hunch about a person you cannot ignore. That’s okay. The point is that you’re collecting data.

Step 5: Validate Your Sales Scoring Methods

The scoring and aggregating is helpful, but how do you know if what you’re measuring is actually predicting success? What if some traits are better at predicting than others? What if some are actually hurting you?

This is where it gets interesting. Once you have enough data, you will be able to run an analysis. For every person hired, see if you can correlate how they were scored on each question to how they ended up performing on the job.

HubSpot Used This Method to Debunk Sales Stereotypes

Conducting this analysis will yield results akin to the following. These are the actual results from HubSpot’s analysis of their own hiring data:

As you can see, the results can be surprising. In the case of HubSpot, assessing candidates for traditional sales skills like “needs evaluation,” and “closing ability” actually hurt their ability to identify good salespeople.

While most of what they measured was helpful, some of the qualities were more predictive than others. Preparation, for example, was twice as predictive as brevity. With this information, they were able to weight the important qualities more heavily, throw away non-predictive factors, and replace them with all new hypotheses. All this helped them to improve their hiring quality over time.

Key Takeaway: Not All Salespeople Are the Same

This method of structured interviewing works because it throws away the idea that all salespeople are the same.

It would be great to give you a list of interview questions that works every time, but sadly it doesn’t work that way. Through analyzing the psychological profiles of close to 100,000 salespeople around the world, we’ve found that stereotypes about salespeople aren’t always true.

For example, extroverts aren’t always the best salespeople. For some businesses, hiring extroverts is actually detrimental to success. They’re much better off hiring introverted people who have a natural sense to sit back, listen, and choose words sparingly.

Likewise, not all salespeople are motivated exclusively by money. At some companies, the most successful salespeople have a deep and genuine drive to help customers solve their most pressing problems. Money isn’t what gets them out of bed in the morning, it’s the desire to help people.

The Ultimate Sales Hiring Strategy is Right Under Your Nose

We’ve found that you don’t need to look further than the business to develop a predictive sales hiring strategy.

Startups need salespeople who evangelize products to early adopters. Enterprise reps need the patience to stay motivated during longer sales cycles. Companies who sell engineering products need salespeople with a neurotic obsession to learn all the details.

And these general patterns only begin to scratch the surface. Once you start thinking about all the variables involved – industry, sales process, management style, company culture, etc. – you begin to realize that every company’s needs are unique as a fingerprint.

So, what’s the point?

Don't Leave Your Success as an Interviewer Up To Chance

While using these questions properly requires a bit of overhead to get started, it’s the only way to do it right. Unless you want to sit back and hope you’ll become a better interviewer over time, this is how you can proactively take power into your own hands.

Building a great sales team doesn’t mean going out and hiring as many ‘generic’ salespeople as possible. It means hiring people who are likely to be successful at selling your products to your customers in your environment.

This is how you engineer your own sales hiring formula.

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Chris Hill

Chris Hill

Chris stands on street corners educating people about the new world of data-driven hiring. If lost, please return to Hire Smarter.
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