Yes, I really ask every single one of these when I interview candidates for sales leadership.
Last week I posted some thoughts about what a new sales leader should focus on in their first 90 days. Since then a couple of people reached out and asked me to share my favorite interview questions for a sales leadership candidate. So, here goes. I made 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. It’s worth 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.
The 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?
- Whar 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?
- What is your preferred tech stack?
- Probe for their level of familiarity and proficiency in the tech stack. Are they hands off or do they roll up their sleeves and get into the tools themselves?
- In your opinion does outbound work?
- How would you approach building an outbound program from the ground up?
- What is a sales playbook in your own definition? Do you use one? How do you leverage it? How important is it?
- How do you organize your department (what does your ideal org chart look like)?
- How do you structure your pipeline review meetings? How often do you conduct them?
- Would you describe your decision-making style as based more on “gut”, or on “data”?
- Describe in detail what a typical day is like for a sales leader?
- What is it like for your reps to interact with you?
- Are you formal or informal? Meeting-driven or open door? Hands off or hands on?
- What is your typical team and individual meeting cadence?
- In your view, what is the difference between leading, managing, coaching and mentoring?
- What are the fundamental metrics for any SaaS business?
- Is there anything unique about selling SaaS that is different from other sales environments?
- Describe your hiring process.
- Describe your general approach for managing your A+ players
- Describe how you manage an A player who is hard to work with/bad culture fit/not a team player?
- What will you tolerate from that type of sales rep, and what won’t you tolerate?
- How do you coach/manage reps who are underperforming?
- How do you know when you need to let a rep go? What process do you follow once you have made that decision?
- Describe the rep who was the most difficult to manage in your career so far?
- Let’s say you have a sales rep who is always a top performer consistently every quarter. You discover that her/his emails are littered with typos, bad grammar, and incoherent sentence structure. What do you do?
- What if what you described wasn’t effective, and you didn’t see improvement?
- Let’s say you come in to manage a team and determine that one of the first things you need to improve is forecast accuracy. How do you go about that? What if it doesn’t work? Forecasts continue to be inaccurate after several months—the team is professional and engaged, but non-compliant with your process, they don’t update their deals, they don’t accurately follow the sales process, etc. What do you do?
- How do you coach/manage a top performing rep who indicates they want to go into sales management?
- How do you manage conflict between peers?
- Have you ever had a situation where you had a conflict with a peer? What happened? How did you handle it? What was the outcome?
- What OTE are you looking for? What mix of base and variable?
Of course, there are more things you can ask a sales VP or director candidate, but this list covers a lot of bases and you will learn so much about their style and philosophy if you run someone through all of these questions.
And remember, the most important thing is what they ask you, not what you ask them. Really.