top of page
  • Writer's pictureMike Hanna

7 Questions to Ask a Software Sales Candidate

In our post two weeks ago we discussed some of the questions a software sales candidate should ask an HR or hiring manager during the interview. Of course, it goes without saying that the recruiter or hiring manager conducting the interview will have some questions of their own they’ll need to ask the candidate. The question we’re asking is—will they ask the right questions? Here are 7 great ice-breakers that will do more than break the ice...they’ll help you see beyond the resume:

  • What have you accomplished in your career that gives you the most pride?

  • Why do you want to work here?

  • Tell me about the most difficult deal you ever closed.

  • What kinds of activities or causes are important to you outside of work?

  • Tell me about a deal that didn’t go as planned.

  • What’s motivating you to move out of your current role?

  • Do you have any questions for me?

When you’re interviewing a candidate for a software sales job, you only have a limited amount of time to get to know them in as much depth as possible, and gauge how they would fit into the company. Whatever you learn about them at the interview will be what you hold against all the other software sales professionals interviewing for this job, so you want your questions to really illuminate the potential of each and every interviewee.

What have you accomplished in your career that gives you the most pride?

Software sales is fairly competitive, with so many companies on the market and startups proliferating every year. A salesperson who takes pride in their work and cares about performance will do a better job of evangelizing your SaaS or tech product to the uninitiated. A candidate’s answer to this question will also give you a sense of what type of work they find fulfilling, and gauge whether or not that lines up with company goals and values.

Why do you want to work here?

This question is so basic and direct, it can throw an interviewee off—but by cutting right through their first line of defenses, you’ll see how well prepared they are for battle. Not that you’re actually going to fight, but you’ll see how prepared they are in terms of what they’ve learned about your company, the market, and the products you offer. A software sales candidate who cares will have invested time doing their research, so this question won’t actually throw them off. Keep in mind, however, that the blunt nature of this question may still throw them off guard temporarily...which, incidentally, is also a good chance to gauge how they might handle a setback in the sales process.

Tell me about the most difficult deal you ever closed.

Whether your software sales candidate is coming from an inside sales position or they were responsible for securing enterprise accounts in an entire region, overcoming objections and closing deals is a basic part of the sales process. Sales conversations big and small have their challenges, so learning about how a candidate dealt with them and achieved success will give you an insight into the process, and their strengths as a software sales professional. Moreover, it will help you know how invested they are in their own professional growth; a good salesperson learns from what works and what doesn’t, and is reflective of their process.

What kinds of activities or causes are important to you outside of work?

There’s nothing inappropriate about this question (unless you make it creepy). In fact, it’s probably the best way to gauge a candidate's personality. People showcase their best points on a resume, distilling their entire being to a one or two page document. Even in the interview, most candidates are putting on a show, even if it’s a genuine attempt to place their best talents in the spotlight. Asking a candidate about their interests, hobbies, and personal hopes will give you a glimpse of their authentic and natural self as they answer...which in turn will help you gauge their ability to interact and their emotional intelligence. And don’t write off the importance of what’s beyond the bullet points of their resume, because emotional intelligence is quickly becoming one of the most important professional skills in today’s working world. Moreover, more and more software companies are finding that a good work life balance is more conducive to better performance. This question will also give you a good sense of how an individual might fit into the team.

Tell me about a deal that didn’t go as planned—and what would you have done differently?

The flip side of success—for all those who can learn from failure. And a successful sales professional lives by the maxim: always be closing. More than just an adage in the context of a sales conversation, it’s an outlook about constantly improving their sales game through education and experience. Transparency is also crucial in organizations that want to build elite teams of successful sales professionals and develop a working process for closing the most deals. If a candidate can share with you about a deal that fell through, without getting flustered, it shows you that they’re coachable and accountable—a knockout one-two combo in developing sales talent. Sharing what they might have done differently also shows that they are willing to learn from the mistakes of the past as they move forward.

What’s motivating you to move out of your current role?

It’s unlikely that you’ll get the entire scoop on a software sales candidate, even if you could talk to their previous employer, the software sales headhunter they’re working with, and their grandmother. Each person will give you a different puzzle piece of what they know—and some HR managers will try to put as many pieces together as possible. But even though you won’t always be able to get the whole scoop, it doesn’t hurt to just ask directly. You have a good chance of finding out. Is it compensation? Company culture? Boredom? The desire to find more meaningful or challenging work? This is a great question for gauging how a candidate will fit in with the rest of the team, what qualities of the company or job role or candidate might cause problems, and how dedicated they are to sticking with a workplace if they feel it offers reasonable opportunities for professional growth.

Do you have any questions for me?

Sometimes letting a job candidate ask the questions is the most revealing part of the interview. At one extreme end of the enthusiasm spectrum, a candidate who doesn’t care where they land and is just looking to escape from their current prison probably won’t have very many well prepared and genuine questions for you. On the other hand, a candidate who is competitive and very seriously considering your company will have some great questions that really uncover what the role is all about and what kind of place your company is to work for. You’ll get insights into their thought process as well, which can help you gauge how strong they’ll be at approaching potential clients or customers. Do they do their research? Do they ask good questions to uncover more information? This will also be your chance to give them honest answers and filter out candidates who are really not a good fit—with a decent chance that they’ll make that assessment themselves.

A final word about questions for software sales candidates:

There are dozens of other questions you could ask, and many of them will relate to the specific software sales role your candidate is interviewing for, while others will just be generic questions that an HR manager at any type of company would ask. Asking the right questions is a bit of an art, but once you have it down, you’ll find that your power to gauge and assess candidates is exponentially increased—helping you see beyond their resume.

As a software sales recruiter with almost four decades of experience in the software industry, I can help you connect with qualified candidates for the software sales role you’re trying to fill. Connecting with some pre-vetted talent can certainly speed up the search and make the interviewing segment of the process a lot smoother. Send me an email at and let’s connect over what types of roles you’re looking to fill—or if you’re a job seeker looking for your next role in software sales, what type of company you aspire working for.

87 views0 comments


bottom of page