Interview Questions to Ask a Sales Leader

Matt Lopez
January 31, 2024

Landing an exceptional sales leader can take a business to new heights. But finding that ideal candidate starts with asking the right questions during the interview process. Sales leaders shoulder immense responsibility - building high-performing teams, executing growth strategies, and driving critical business metrics. The interview serves as a vital window into identifying leaders up for the challenge.

Crafting the optimal set of questions allows you to dig deep and reveal how candidates think, strategize, motivate, and execute. The goal is to surface red flags early while uncovering standout qualities you want in a sales leader. With the right insights in hand, you can zero in on hiring the best fit for the role and your organization.

So what questions should you ask potential sales leaders during interviews? Here are some of the most effective options to reveal who has what it takes to excel.

Evaluating Experience and Track Record

Past performance offers one of the strongest predictors of future success. Diving into a candidate's experience and achievements paints a useful picture of how they might fare in your sales leader role.

Consider questions like:

  • Walk me through your career progression and major accomplishments as a sales leader so far. What results are you most proud of driving?
  • What experience do you have coaching and developing sales teams? Can you give examples of helping improve rep performance?
  • Tell me about a time you led a successful sales turnaround. What were the biggest changes you implemented?
  • How have you built and developed a sales team from the ground up? What challenges did you face in the process?
  • What experience do you have creating and executing strategic sales plans? How did your strategies translate into business growth?
  • Give me examples of how you identified needs and opportunities in previous positions. How did you capitalize on them?

Gauging Leadership Style and People Skills

Sales leaders live and die by the strength of their teams. Evaluating a candidate's leadership style and people skills is crucial.

Ask questions such as:

  • How would you describe your management style when it comes to sales teams?
  • What approaches do you find most effective for motivating and inspiring sales reps? Can you share examples?
  • How do you go about building trust and relationships with sales reps?
  • Tell me about your mentoring and coaching style. What tactics have worked well for you in developing sales talent?
  • What do you see as key qualities of an empowering sales leader? Which of these come most naturally to you - and which do you need to work on?
  • Describe a time you had to address conflict or performance issues with a sales rep. How did you approach it and what was the result?
  • What do you think the sales leader's role should be in maintaining company culture on their team?

Assessing Problem-Solving and Analytical Abilities

Top sales leaders have the problem-solving skills to overcome obstacles and analyze data to drive continuous improvement.

Asking tactical questions gives insight into these capabilities:

  • Tell me about a time when your sales team wasn't achieving goals. What were the main causes and how did you tackle them?
  • Describe a situation where your initial sales strategies weren't working. How did you change course?
  • How do you use data and metrics to identify opportunities for improving sales workflows and processes?
  • What sales tools and systems are you familiar with? How have you used them to increase sales productivity?
  • Give me an example of when you had to quickly adapt your sales plans to changing market conditions. What was your decision process?
  • How have you leveraged technology and automation to improve sales operations in past roles?

Determining Alignment with Company Values and Priorities

A sales leader needs to exemplify your company values and champion strategic priorities.

Explore culture fit and alignment with questions like:

  • What appealed to you most about the sales leader opportunity here based on our company culture and mission?
  • Why are you interested in leading sales teams specifically in our industry?
  • How would you look to create alignment between sales initiatives and wider company goals in this position?
  • What techniques and frameworks would you leverage to keep sales priorities focused on core company values?
  • How have you gone about building a sales culture that reflects company values in previous roles?
  • What challenges do you anticipate in upholding our desired culture and ethics standards on the sales team?

Assessing Knowledge and Passion for the Product

Passion for the product comes through loud and clear when a candidate deeply understands what you offer and how it solves customer needs.

Ask:

  • What excites you most about our products/services? Why?
  • What do you see as the biggest competitive advantages of what we offer versus alternatives?
  • What interests you about our target customer base and markets? How could you help us better serve them?
  • What steps would you take early on to immerse yourself in knowledge about our product/services if hired?
  • How can our current products/services improve based on emerging market and customer needs?
  • Where do you see growth opportunities for new products or expanded offerings we could provide?

Gauging Long-Term Vision and Leadership Potential

Hiring a sales leader is an investment in the future. Be sure to explore the candidate's long-term vision for success:

  • Where do you see your sales career in 5 years? How would this position help you work toward your goals?
  • How have you developed the skills throughout your career to be an effective sales leader? How do you aim to continue growing?
  • What are 1-2 areas of sales leadership you feel less confident in? How could you improve them in this role?
  • How would you evaluate your first 90 days as a sales leader here if we were having a performance review? What goals would you set for the 12-month mark?
  • If we were having this discussion a year from now, what would you hope to have accomplished as our sales leader?
  • What legacy would you want to leave behind from a culture and leadership perspective if you eventually left our company?

Evaluating Critical Thinking

Asking candidates to analyze hypothetical scenarios tests critical thinking relevant to sales leadership:

  • If you came into this role and found low sales rep morale, what would be your approach to improve it?
  • How would you go about creating a culture of continuous development and coaching on the sales team?
  • If given 20% more sales budget next quarter, where would you invest it and why?
  • If we asked you to build sales training programs from scratch, what subjects would you cover and what formats would you use?
  • If you observed inconsistencies in our sales processes between teams, how would you address it?
  • Imagine you took over our team of ten sales reps. How would you assess their strengths and development opportunities?

The interview questions for a sales leader should always align back to the core competencies needed to excel in your organization. And it often helps to get input from other sales leaders at your company on the types of questions they find most insightful.

With data-driven hiring processes, you can feel confident in your ability to hire sales leaders who will propel your business growth to new levels. Approach the interview as an invaluable chance to gain insight into how a candidate thinks, strategizes, motivates and executes based on their past experiences and leadership style.

Asking the right questions will help ensure you find and hire leaders with the mix of sales acumen, people skills, culture fit and vision to maximize success.