Over the years, my teams and I have interviewed thousands of tech sales candidates. It’s very important for the collective hiring team to be consistent in their interview methodology. Everyone involved in the interview process should be trained on key questions to ask, interview format, and the process for reporting on the information obtained during the interview. However, great interviewers won’t always stick to a script and will follow the train of the conversation to also come up with relevant questions in the moment.
One of my favorite questions is:
Tell me about a time when you lost a deal.
Every rep loses deals (many lose more often than they will admit); so if a candidate says he or she has never lost a deal or a sale, it’s a red flag. But I’m really asking this question because I want to know if the rep is (1) coachable (2) introspective and (3) can adapt and improve.
I’m looking for details. I want to know specifics about the opportunity – how it originated; if the candidate was the primary sales contact; the size and type of the opportunity; who the competition was; how long the sales process was; and why the sale was lost. A great sales rep will remember these details when reflecting on a lost opportunity.
Follow-up Question A: What did you learn from that experience?
After I get the information on the deal, I ask the candidate what they learned from the experience. Every lost deal comes with a lesson. Was it due to a process breakdown, financial difference, or product loss? A good rep will be introspective and honest, not defensive or evasive.
What could the rep, if anything, have done differently? This provides insight into whether the rep has the ability to think critically and insightfully, which will drive opportunities to improve – a key trait in a coachable rep.
Follow-up Question B: Tell me about a successful sale where you incorporated what you learned from that lost sale.
This is where ‘the rubber meets the road’. Has the sales rep learned from their experiences and improved? The sign of a great sales rep isn’t just one who identifies mistakes or lost opportunities, but who applies these lessons on future deals.
Great sales reps are agile. They are constantly evolving. Reps should be able to identify and admit to things they could have done better; think introspectively about opportunities (successful and not); and incorporate what they have learned into future deals.
For more interview questions and content, check out Five Great Questions to Ask Sales Candidates in the Interview
