Over decades in the sales industry, I’ve conducted countless interviews for Account Executives, Account Managers, Sales Development Reps and Client Success. I typically ask many of the same questions – ones I know will help me determine if a tech sales candidate is the right fit for the open roles. Here are the three questions I always ask (and chances are, you’ll be asked something similar):
1. Tell me about your greatest sales ‘win’ and your worst sales ‘loss’.
This is a multi-stage question, and I start with the ‘win’ first. The reason for this is because I want to understand the candidate’s sales process for winning the deal. Specifically, I want to know:
- What the candidate was selling;
- How the lead was cultivated;
- Whether there was competition for this lead;
- How quickly (or slowly) the lead became an opportunity;
- What obstacles the candidate encountered, and how they were resolved.
A candidate’s answer helps me understand if the individual I’m interviewing can adapt to and/or manage my sales process.
When I ask about someone’s worst sales ‘loss’, I want to understand, most importantly, what the candidate learned from that loss. I also want to know how they incorporated what they learned into their sales process after that point.
When answering this question, always be as specific as possible. This helps the interviewer understand if you have perseverance, if you can be coached, and if you can adapt.
2. Who was the best salesperson at your last company (or on your last sales team)?
After I get the name of the top rep, I ask what he/she was doing differently than the rep I’m interviewing. Why was this rep number one? I want to find out if the rep I’m interviewing is curious, inquisitive, can adapt and self-correct, and is driven. Specifically:
- Can the candidate identify what that rep was doing to be #1?
- Did the candidate ever seek advice from that rep?
- Did the candidate incorporate anything they learned from that rep in their own sales process? If so, give a specific example.
If you believe you were the best salesperson at your last company, then make sure to give specific evidence and numbers as to why that was the case.
3. Tell me about your first job.
When I ask this question, I want to know what a candidate’s very first job was – even if it was as long ago as delivering newspapers in middle school. It can be incredibly hard to identify reps who have drive – a key part of being successful in sales. Honestly, most candidates simply don’t have it. I believe drive is something that is ingrained into your personality very early in life, and often is instilled by family members, mentors, or a personal situation growing up.
Reps with high drive typically know and understand ‘work’. They’ve been doing it for a long time and are driven by something beyond what drives most of us. If a rep didn’t work in high school, or if their first job was an internship, then that’s a red flag for me. I’ve learned over the years that in many cases, people who are given opportunities, rather than earning them, fit into this category.
There are always exceptions to this, of course, but if a candidate started working at an early age, that gives them an advantage in my interview process. It has helped me identify extremely motivated reps who are willing to go above and beyond what an average rep is capable of.
Sales is a complex industry; experience can absolutely matter, but many qualities necessary for success can’t be learned: drive, curiosity, adaptability. Before your next sales interview, prepare answers for these three questions. This may be the difference between getting the job or not.
Want to see more interview tips for employers and questions to ask candidates? Check out Five Great Questions to Ask Sales Candidates in the Interview
