What is your favorite sales interview question and the best answer you've heard?

One of our company’s core values is having the courage to be vulnerable. This behavior is key to being successful at Culture Amp and within a sales role. In order to better understand someone’s ability to lean into this value, I like to ask the question “What are you currently working on professionally or personally to develop yourself?” I also ask this question because the best talent never rest on their laurels. Top performers are always looking for ways to improve.

The most common answers I receive are around reading sales books or applying new sales tactics. The strongest answer that I ever received was someone who shared that they were working with a therapist and shared how their committed approach to mental health had made a positive impact on their life. It's an example of taking on hard things and not being afraid to show their genuine self.

I have 2 questions that I love to ask to guage self-awareness.

1. The first is simply - What is the 1 thing that you think you could really improve on or do better?

2. The second - Tell me about a time that you weren't successful and help me understand how it impacted your approach to your job.

These are the kinds of questions that I like to use to determine if the candidate is focused on self-improvement or, is an excuse maker. 

Why: In sales - having humility enough to qualify 'why' I lost that deal... and then being big enough to lean in and say, it was my fault. I should have put a plan together to get unstuck or get multi-threaded from the get go... etc. 

These are the reps that I know will work super freakin hard and I'll see marked improvement from over time. These are the kinds of reps who become future leaders.

On the otherhand, if I hear "yeah, they went with the competition because we didn't support feature x" I am likely going to be less interested with this candidate because they likely lack the sense of ownership that I require from my top performers. 

My favorite sales interview question is meant to figure out if a sales rep has really run complex deals regularly. 

• I ask them to name their top 3 large and complex deals they've closed. 
• Then I ask them to tell me in more detail about a large & complex deal which is not in the top 3 list they shared. 

Most sales reps would prepare for an intierview with details about their top 2-3 deals but if a sales rep has truly run multiple complex sales cycles, they should be able to answer this question quite comfortably and in equal detail. The depth of the answer is a good indicator of how well tenured this person is in running complex deals. 

Personally my favorite interview question, which I ask all of my hires from SDRs/BDRs to Sales Directors, is:

"Of everything in your life (professionally, personally, academically, athletically, artistically, etc.), what do you consider to be your greatest accomplishment?"

Of the hundreds of times I've asked this question, I've received so many incredible answers. Some people have talked about the accomplishments of building a family, qualifying for the Olympics, summiting mountains, changing careers, moving to entirely new countries and starting from scratch. All were great, and the reality is, there is no one "best answer".

To me the reason I love asking this question early in an interview process is, I get to:

• Quickly learn more intimate details about someone's life to begin to understand who they are as a person and discover what they value

• Listen attentively and observe how they tell a story they are passionate about, and

• Use that answer as a jumping off point to probe into other attitudinal & behavioral competencies

From that simple question, you can then take the conversation into so many follow on questions like:

• What were some of the biggest obstacles you needed to overcome to achieve that accomplishment? (which gets into the topics of resilience & adaptability)

• If you were to re-live that experience again, knowing what you know now, what would you change? (which addresses self-reflection and learning)

• Now that you've accomplished [insert accomplishment], what are you setting your sights on next? (which uncovers ambition & motivation)

I'm curious to hear from you...what do you consider to be your greatest accomplishment?

One of my favorite sales interview questions to ask is "Tell me about a time something did not go according to plan in your personal or professional life. What happened and what would you do differently, if anything?" This one's great because it helps the interviewer see if the interviewee is just as comfortable talking about their failures as they are about their successes. It allows the interviewer to see how the person handles setbacks, what they do when setbacks occur and what their overall ability to handle unexpected curveballs is like. The best answers are usually authentic, vulnerable and showcase a growth/abundant mindset. Abundant mindsets allow people to see setbacks as opportunities for further improvement rather than limitations. 

One of the key attributes I like to test for in interviews is the candidates self awareness and grit. My favorite question to ask here is "What is the most difficult feedback you've received professionally? How did it shape your career?" The quality of the answer demonstrates the candidates ability to internalize feedback and take action.

My favorite to ask always starts with, "Tell me a story about..."

The ending can be anything from professional to personal.

Tell me a story about your proudest customer win.

Tell me a story about a lost opportunity that you wished you won.

Tell me a story about the last vacation you went on.

Tell me a story about someone you stopped being friends with and why.

For me it's not the answer, it's how you give the answer. In sales you need to be quick on your toes and engaging. Storytelling is the key to all of it.

I love to ask a rep to walk me through a deal they closed.

Then I ask for a second deal.

Then I ask for a third. And I really spend time having a deep conversation on the third.

I'm a huge fan of behavioral interview questions (and most hiring analytics suggest they are the only types of interview questions that correlate at all to future job success, which is why you see them so often.)

But it also requires skill from the interviewer. The goal of the interviewer is not to sit back and listen to a rep deliver a perfect STAR format behavioral interviewing response, but to really spend time and curiosity learning about the sale.

So I might ask about the 3 deals, and on that third deal I want to really explore with questions like:
-How did you initially find the deal?

-What was your first conversation like?

-What problems were they experiencing in their business?

-Was there ever a time where things went sideways? What snags did you run into?

-How did you negotiate to close the deal?

And many more - the idea being if I can understand how they think and sell and what actually happened - I'll have a better handle on their skills as a salesperson.

For example, if we are talking through your deal, and I ask about closing, and your response is that you gave a super deep discount to get it across the line, I would suspect there might be a gap in getting to pain or opportunity in your qualification. So I'd want to further explore how you understand pain, build value, and present a point of view that solves for that business problem.