7 Software Sales Interview Questions

Building an effective software sales team is mission critical for growing organizations. Your sales team is your front lines: they are the ones advocating for your product or solution to the market, countering objections, and generating revenue. 

When interviewing sales candidates it's helpful to divide the conversation into two domains: the numbers/process and the narrative/behavioural.

The numbers are essential to establish success. Good sales people have no problem recalling the exact metrics they use in terms of quota, attainment, deal sizes etc. Digging into their experience will help you determine how well they will fit within your organization—if they have a track record of success in a similar sales cycle, with a comparable degree of complexity and support. 

The narrative domain is attempting to capture the story of the candidate in terms of who they are and how they operate. These types of questions will help you understand their personality, communication style, and sales philosophy. 

Balancing the numbers with the narrative will allow you to ensure that you’re hiring only the best, well-rounded candidates, who will succeed in your organization. 

What are the best questions to ask in a software sales interview? 

  1. Walk me through a deal at your current/most recent organization from first contact to close.
  2. How does data and technology support your success? What tools do you use, and how do they help you sell more effectively? 
  3. How would you approach ramping up, to be able to quickly execute your go-to-market strategy for your territory? What would you need from us to be successful?
  4. Walk me through the last 2-3 quarters. What percentage of quota did you achieve? What were your biggest successes and struggles?
  5. What does a day (or week) in your life look like? How do you start and how do you end?
  6. Describe a difficult conversation you’ve had to have with a client. 
  7. Thinking back on your career, who was the best manager that you’ve worked with? What did you appreciate most about them?

 

Sales Hiring Checklist

Software Sales Interview Questions About the Numbers and Process. 

1. Walk me through a deal at your current/most recent organization from first contact to close. 

This is a great introductory question—perfect for an initial phone screen or first interview. The answer will give you a great deal of information in a short period of time, both about the type of deals the candidate typically works on (which helps to determine if they are a fit for your position), and about the overall attitude and approach of the candidate. 

In addition to evaluating their communication style, a thorough answer to this question will give you an overview of their current sales process and cycle. Within their answer, you should be able to determine the following information: 

  • How are leads generated? Are they cold calling, picking up warm leads from marketing, mining their networks, etc.? What is the scope of their territory? 
  • What are the steps in their sales process? What tools do they leverage when communicating with prospects? 
  • Who are they selling to? Do they sell to a single stakeholder, or do they work through complex processes to sell into a whole organization? 
  • What resources do they have access to internally? Are they working with a robust pre-sales team, or are they flying solo? 
  • What is the average deal size? What’s the average length of the sales cycle? 

 

2. How does data and technology support your success? What tools do you use, and how do they help you sell more effectively? 

Getting salespeople to talk about how they use data can give you insight into what type of sales talent you are dealing with. Do they rely on a robust tech stack for insights? Or do they wing it with spreadsheets and notebooks? Compare their response to the complexity of your product and sales process. Does their technical aptitude and ability to analyze metrics align with your needs as an organization? 

This question is a great way to gauge the candidate’s relationship with technology, and to understand what kind of management challenges you may encounter if you bring them on. Do they view their CRM as an asset, or as just another task that takes them away from selling? Most sales organizations will have a number of tools they need to use to keep things running smoothly—expense reporting, pipeline updates, the CRM, demo software, lead scoring, etc. Will the candidate embrace these tools, or view them as a (necessary) annoyance?

Compare their attitude to your existing tech stack and culture around technology and you’ll learn a lot about the candidate’s sales process, technical aptitude, and cultural fit within your existing team. 

 

3. How would you approach ramping up to be able to quickly execute your go-to-market strategy for your territory? What would you need from us to be successful? 

This question gives the candidate the opportunity to describe their overall philosophy and approach when it comes to sales, and can give you some strong indicators about their potential fit within your culture. It’s a great question for a second or third interview—they should know enough about the organization and product or service to answer thoughtfully. 

Do they approach sales with process and rigour, or are they more inclined to fly by the seat of their pants? Do they have a track record of ramping up quickly? Are they realistic about how much time it will take to learn the ins and outs of your product or service, or to get up to speed in a new vertical? 

Their response will also help you gauge their overall interest in the role. Are they imagining themselves in the position? Have they thought realistically about the transition? If they are able to give a thoughtful response to this question, then it likely follows that they are very interested in the role. On the other hand, if they seem surprised or dismiss the question, that’s a red flag and you’ll want to dig in further. 

 

4. Walk me through the last 2-3 quarters. What percentage of quota did you achieve? What were your biggest successes and struggles? 

With this question, you’re testing for personal pride—which is often a big success factor for sales professionals. They should know their numbers, and be able to provide context around them. Are they generally consistent in terms of attaining their targets? If they missed quota, are they forthcoming about why they feel they fell short? Do they play blame games and get defensive—citing unfair territory re-carves, lack of resources, bad leadership, etc.—or do they take ownership of their outcomes? 

You can also dig in to get a more complete sense of their compensation structure and earnings. Compensation packages for sales professionals—which often include base salaries, commissions that are calculated in a variety of complicated ways, equity and/or stock options, and a variety of other perks—are notoriously complex. If you want to generate a competitive offer for the sales candidate you’re going to hire, it’s helpful to understand the various elements that make up their compensation. 

Lastly, it’s smart to ask about unpaid commission: if the candidate were to resign today, how much money would they be leaving on the table? This helps you to understand their willingness to make a move, whether they’ve thought through the implications, and their overall level of interest in your opportunity. 

Sales Hiring Checklist


Behavioural and Narrative Questions for Software Sales Interviews

5. What does a day (or week) in your life look like? How do you start and how do you end? 

Habits are often important indicators of success. How does this candidate execute on their plans? Do they impose a lot of structure on themselves, or do they have a more free-wheeling approach to their work? How do they interact with team members and managers? How do they balance personal habits with professional ones? 

This is a great question for understanding how a candidate will fit within your team and culture, and for getting a handle on how they deal with working from home, being on the road, etc. 

It’s also a great narrative question—how well does the candidate paint a picture of a day or week in their life? What elements of their work do they find most exciting or boring? What do they prioritize? Are they honest with you about the realities of their daily lives, or do they tell you what they think you want to hear? (I.e. do they mention things like getting to the gym, picking up their kids, spending some time on social activities? Or do they tell you that they work from the moment they wake up to the moment they go to bed?). 

 

6. Describe a difficult conversation you’ve had to have with a client. 

With this question, you can continue to qualify how well the candidate communicates and tells a story (I know we’re hitting hard on that skill, but only because it’s essential for an effective sales professional). You can also learn a lot about the integrity of the candidate based on the story they choose to tell. 

Are they telling you a story about how they made a difficult choice because it was the right move for their client? Did they walk away from a deal because they knew it wouldn’t solve the client’s problems? Do they take ownership of mistakes? Or do they tend to throw colleagues or the competition under the bus? How do they manage relationships when things don’t quite go according to plan? In the response, you're looking for self-awareness and integrity. 

 

7. Thinking back on your career, who was the best manager that you’ve worked with? What did you appreciate most about them? 

One more time, you can confirm that your candidate is an effective storyteller who communicates well. This question also helps to qualify the amount of self-awareness they bring to their work. Are they humble enough to admit that they’ve received guidance and support in their career? Do they arrogantly believe that they’ve achieved all their success on their own? Truly effective sales professionals are always learning, and always looking for ways to improve. 

This question is also a great way to further qualify fit within your existing team. Do they appreciate the style of guidance and support that your managers provide? Are they coachable? Conversely, if you have a very hands-off management style, you may be looking for the candidate who is more of that lone wolf profile. 

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Building an effective sales team is mission critical for any software organization. Use these seven questions to ensure that you’re effectively qualifying your software sales candidates throughout the interview process. 

Are you getting ready to grow your sales team? We've created a free checklist to help you refine your requirements, plan the interview process, and get aligned on competitive compensation. 

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