Today’s modern reps move to new companies and roles every few years (or less). With this ever-shrinking sales talent lifecycle, enablement feels increased pressure to maximize productivity. That means finding better ways to focus and deliver readiness efforts (like training or coaching) when, where and how the sales force works.
Achieving success in sales – or any other field – goes beyond just one factor. You need leadership with a vision, a product that addresses essential needs, and a dynamite strategy for bringing it to market for starters. But in order to make any of those things a reality, you also need talent.
These days, sales talent is especially hard to find. A historically tight labor market has taken leverage away from employers, and in most cases, proven sales reps are either happy in their current roles or expensive to hire away. According to SiriusDecisions, just 3% of high-performing sales reps are actively in the job market.
That’s why identifying talent has become crucial for B2B sales organizations. Finding the people who best fit your sales job openings – whether it’s an external hire or an internal promotion – depends partly on your ideal candidate profile, as well as the soft skills and competencies it should include. But having an effective sales interview process is just as important, if not more so.
By asking the right sales interview questions, you can uncover more information about candidates’ skills, personality and track record, better project how they’ll perform in the role, and avoid costly hiring mistakes. The following 30 sales interview questions (suggested by sales and sales enablement experts) will help you do just that, whether you’re hiring for reps, managers or sales leadership.
Sales Interview Questions to Ask Reps
1. Tell me about a time in your sales career where you needed to start a territory from scratch. What did you do the first 30 days? What would you have done differently?
“I’m a firm believer in asking behavioral questions versus ‘what would you do?’ type of questions,” says Brainshark’s Chief Readiness Officer, Jim Ninivaggi. “I think asking ‘what would you do in your first 30 days?’ is a nonsense question. Ask ‘What did you do in your first 30 days at your current organization?’”
2. Give me an example of a time where you had to choose between what was morally right and the easy way out. What did you decide?
Research shows that buyers already have a hard time trusting salespeople. Candidates need to demonstrate their ability to make an ethical choice – even (and especially) when it’s difficult.
3. How would you engage me with your current company’s offering?
You want an excellent sense of a candidate’s selling skills and approach when they’re at full productivity. This question gives you a glimpse into reps’ sales readiness and how they think on their feet.
4. Why did you choose to work in sales over another customer-facing role? (Or, why are you interested in a sales position?)
The best salespeople might enjoy problem-solving, the relative independence, or the competitive aspect of producing results. But some candidates might be more interested in the earning potential of the role, or – when it comes to less experienced candidates – they may not really know what they want! This question helps determine whether someone is in it for the right reasons.
5. Describe a time where you received difficult feedback. How did you change as a result?
Nobody knows everything, and everyone has weaknesses. Because there’s so much value in effectively coaching sales reps, you should determine whether a sales candidate is “coachable,” and that he or she has shown willingness to accept feedback and use it to improve.
6. What can you tell me about our company?
“I'm not expecting them to give me a perfect answer — I'm just looking to see what kind of homework they did to prepare for the interview,” according to Ninivaggi. “If it's clear they have not done any prep, the interview is over. A rep who does not do their homework for an interview is probably not going to prepare for sales calls either.”
7. If I was a buyer, what would your cold outreach look like?
This is not so much a question as it is (potentially) a short assignment. For sales reps – especially candidates for a sales development position – you want to test for good communication skills and see how they perform in the moment. This can be as simple as giving interviewees 15 minutes to write a cold outreach email based on a hypothetical product. Matt Heinz of Heinz Marketing advocates for a similar strategy with inside sales reps; he asks candidates to pitch his company on its own product using the information found on its web site.
Here at Brainshark, we use our own video coaching tool to have interview candidates record a sample sales pitch for hiring managers to evaluate. (Our sales hires will also continue using Brainshark throughout their time with the company).
8. When a customer was upset with you in the past, how did you handle it?
According to Collen Francis of Engage Selling: “Sellers must take full ownership of the conversion process from prospect to client. If they start to blame shipping, accounting, a team member, or their manager for any failed sale or disgruntled customer, it’s an immediate red flag.” It also gives the candidate a chance to describe how they handled adversity.
9. Tell me about an opportunity you lost. Why did you lose it?
Similarly, Francis says : “If they blame others for the loss, they do not get the job. I know that sales people who can't take responsibility are never going to be in the top 10%.” In addition, you can gauge whether the sales rep in question is willing to speak frankly about setbacks, instead of sugar-coating the truth.
10. Can you walk me through each step of your sales process?
“No matter your culture or approach, being organized both overall and ‘in the moment’ is a common differentiator that often separates the mediocre from great inside sales reps,” Heinz writes. Candidates that can go into great detail have a strong understanding of their sales process, of course, but they’re also more likely to bring the same commitment to whatever strategy your sales organization employs.
“When you interview, ask questions about and seek examples of how candidates keep themselves organized and focused. Get a handful of scenarios related to sales process, email management, etc.”
11. How do you avoid “just checking in” syndrome?
Suggested by David Priemer, founder of Cerebral Selling, this question prompts sales candidates to provide examples of how they add value to their interactions with buyers, instead of simply pestering them with repetitive check-in emails. “Nothing is more irritating than a sales rep who calls back week after week to ‘check in’ to see if they’re ready to move forward,” Priemer writes.
12. How do you establish trust? Which tactics have worked for you, and which ones don’t?
Sixty percent of B2B buyers distrust salespeople, according to a 2018 study by ValueSelling Associates. That means reps who have the emotional intelligence needed to establish meaningful relationships with buyers have a huge competitive advantage!
Primer writes: “We often train sales reps to probe for intimate details about a customer’s business and related challenges without considering why the customer would open up to us in the first place. The key: trust.”
13. Can you show me how you prepared for this interview?
David Brock of Partners in Excellence suggests asking this question to see how candidates research and plan ahead of a sales call. And meeting with a potential employer, he argues, essentially is a sales call – where the “solution” is the rep being interviewed. This question will give you insight into how they prepare, and how serious they are about the job.
14. Can you give me a detailed breakdown of your numbers?
Past performance is not always indicative of future success, but it at least shows that a candidate can be productive. Beyond asking how they hit their quota, ask the sales reps how many calls, emails, and closed deals they needed to succeed in their current role? Which tactics were most successful for them, and why?
15. Tell me how you’ve incorporated storytelling into your sales process.
Brainshark’s Director of Sales Enablement, Jenn Haskell, says the ability to tell an authentic story will help differentiate sales reps and demonstrate that they understand how “like” clients have solved similar challenges with your solution. Can your candidate tell stories that are credible and compelling?
Sales Interview Questions to Ask Managers
16. Give me an example of when you needed to provide difficult, but honest, feedback to a friend or colleague?
Inevitably, your sales managers will need to have hard discussions with team members, many of whom they may genuinely like as people. Do they have the fortitude to say what is difficult, and can they do so in a way that is both clear and fair?
17. Describe how you handled a sales rep that was failing to meet quota. What steps did you take, and what was the result?
While the previous question deals more with their abilities to provide feedback, this one asks for concrete details around how a manager has handled underperformance. Did your candidate identify the underlying issue and take clear action to resolve it?
18. Share a time when a rep came to you with a sales challenge or problem. How did you manage it? What did the conversation look like?
Coaching is one of the most important skills of a sales manager. One common problem, however, is that many managers aren’t equipped to coach effectively. This question gives the interviewer greater insight not only into a candidate’s problem-solving skills, but also their ability to coach and mentor reps.
19. Why don’t you want to make more money as an individual contributor?
This question, suggested by Heinz, is good for gauging a potential sales manager’s confidence in their abilities to motivate reps and deliver results. When the entire sales team is performing at a high level, “the best sales managers know they can make far more money as a manager in these conditions,” he writes. However, you also want to know that a manager in it for reasons other than money; candidates should express passion for coaching and developing their reps.
20. How will you earn the respect of your team?
Sales reps can have strong opinions, especially when it comes to handling their daily responsibilities. HubSpot recommends this question to uncover how, exactly, candidates plan to win their teams over – whether that’s through hard work (“leading by example), acting as a helpful resource, or being more of a hands-off leader. The answer will also give you a better sense of their leadership style.
Sales Interview Questions to Ask Executives
21. Tell me about your first year at your current organization. What were your three top priorities and how did you execute them?
You want evidence that your potential sales leader can set the right priorities, hit the ground running and enact change quickly.
22. Share a time you needed to deliver bad news to your board. How did you do it? How was it received?
Disappointing quarters do happen, whether due to competitiveness in the market, changes within the company or simply poor sales execution. It’s critical to understand how your sales leader would handle any setbacks, and what sort of language he or she might use to address them. Word choice carries a lot of weight at the executive level.
23. How long are you willing to fail at this job before you succeed?
This is a difficult question that forces the candidate to think on the spot. Beyond determining how they would communicate setback with the board, this question will give you a glimpse of how they actually plan to handle or address failure (or at least the prospect of failure).
24. What books are you reading, and what are they about?
Acquiring new knowledge and skills is a key trait of any effective leader. As talent acquisition firm Y Scouts puts it, “Every candidate should have at least one immediate answer to this question. If not, be afraid.” If the candidate is reading a book about management tactics, you can also get better sense of what matters to him or her as a leader.
25. If I were to ask a bunch of people who know you, ‘give me three adjectives that best describe you,’ what would I hear?
A favorite of IBM’s SVP and CMO, Michelle Peluso, this question proposes a scenario involving family, casual acquaintances and even ‘the person who can’t stand you the most,’ giving the interviewer a sense of the candidate’s self-perception – and self-awareness. “It’s a tough question, and nobody wants to answer it, really,” Peluso says. “But I do want to know, ‘What is top of mind for you?’”
Sales Interview Questions to Ask Enablement Leaders
26. What is your interpretation of sales enablement?
“Sales enablement” can mean different things to different companies. For some, it simply means providing reps with the right content at the right time or aligning sales with product marketing. However you choose to staff the position, it’s important that your new sales enablement manager aligns with how the organization views enablement.
27. What would you need from the team you’re joining to be successful in this role?
Your candidate’s answer to this question will indicate whether they will be a good cultural fit for your organization. For example, if you need them to get into the weeds to figure out a project, make sure that willingness and lack of ego is demonstrated in their response.
28. What would X look like if you created it from scratch?
For example, ask them to design an onboarding program or facilitate a training session for senior leaders. Then, when they come in for their interview, have them present sales readiness exercises that go along with their plan. Look for answers that indicate they’ve executed successful projects before.
29. We’re experiencing X problem at our organization. How would you fix it?
Ideal candidates should be able to sift through your company’s data and identify which factors are affecting a decrease in rep win rates, for example. Effective sales enablement leaders will take a comprehensive look at all the data available before prescribing a solution. Ineffective leaders might say something like “well, we just need more leads in the funnel!” before taking a deeper look at the sales process.
30. Tell me about your first year at your current organization. What were your three top priorities and how did you execute on them?
Asking “what would you do in your first 30 days at our organization?” is a fairly common question, but it deals in the hypothetical. During the hiring process, it’s more important to determine what the candidate did do with their current opportunity, how they made it happen and what level of success they achieved.
What does a great sales enablement leader look like? Download our Special Report on where great sales enablement leaders come from.