I’m often asked to participate in interviews when companies are hiring new sales leadership, and people are surprised by the depth of questions I ask. I thought it could be helpful to capture them here. I also created an interview question bank with notes about what kinds of responses to look for.

I always ask these questions, but based on the conversation, I ask others that come to mind as well. And yes, I really do ask every single one of these questions! Hiring a sales leader is a big deal no matter what stage your company is in. It’s worth investing the time to get it right. I will ask all of these questions over a series of interviews, and I’ve been known to ask some of them repeatedly until I get a sufficiently detailed response.

Below is a summary of the interview questions, but I really encourage you to hop over to the actual spreadsheet, where I include notes about what to look for in candidate responses.

50 Sales VP or Director interview questions

• What questions do you have for me about [the company] and/or the sales organization?
• What makes a great sales leader?
• Your first 30/60/90 days. What do you focus on? What do you accomplish?
  • Probe for detail.
• What kind of sales leader are you? How would you describe your leadership style?
• How would you describe the ideal sales culture? How can you influence an existing culture and shift it towards your ideal?
• Largest team/smallest team built or managed?
  • Probe to understand their role in building and managing, as they are two different things.
• How do you approach territory creation? What do you consider? What do you need to know before you can design territory?
• Describe your general approach to setting quotas.
  • What about in cases where there is little to go on? Such as in a startup or an environment where there are limited benchmarks.
• Describe how you determine OTE for your team. What factors do you take into consideration?
• In your opinion, should sales or customer success own expansion? Why or why not?
  • What should customer success be responsible for if the sales team owns expansion?
• Should sales or customer success own renewals? Why or why not?
• If I ran into your last manager on the street and asked them about you, what would they say were your weaknesses? Strengths?
• Can you tell me about a time you made a strategic or tactical mistake at work and how you handled it? What was the outcome? In hindsight, what would you have done differently?
• What are you most proud of professionally?
• What sales metrics do you look at daily? Weekly? Monthly?
• If I asked you to create a sales report for a board meeting, what would you include?