Today's topic hits close to home for me. So, before we jump into the content, let me share a quick story to illustrate the importance of finding and hiring the right VP of Sales.

A couple of years back, the startup I was working for dedicated over a year to building an exceptional product and was ready to take it to market. Just before our Series-A round of funding, we brought in a new VP of Sales to "shake things up," focus the sales team and align our sales strategy with the marketplace. Within a few weeks, this person decided we needed to make immediate cuts to our sales cycle and pipeline, and decided upon a complete overhaul of our outreach strategy. While these changes seemed beneficial for our future growth, they immediately led to upheaval on the team and ultimately led to misalignment with our customer's needs and caused more harm than good. In a short time, pipeline coverage fell short of the next quarter's goals, team morale tanked, and two quarters later, more than half the sales team was laid off.

Hopefully, my experience underscores the gravity of hiring the right VP of Sales and the lasting impact this decision can have on a company.

Hiring a VP of Sales is pivotal to the growth of an organization but it can also be a "double-edged sword." The right VP of Sales candidate can trim the fat, focus the team, and fuel rapid growth, the wrong one can hurt morale, ruin the customer journey, and even destroy the customer's experience.

The reason for this is, that the head of sales is not just a "cog" in a wheel - they're essentially the architect of a company's sales structure and sales team culture. Balancing the needs of today with a vision of the future. As such, they must bring a deep understanding of the customer, an overall perspective of market dynamics, and the leadership skills necessary to inspire the team while driving the changes necessary to achieve rapid growth - and the best way to determine if a VP of Sales is right for the job is to ask the right questions. Without asking strategic questions in a sales interview, you may end up hiring someone who will do more harm than good. We'll include a few strategic questions to ask in a sales interview in this article, but you can also find more on our blog and in our interview intelligence library.

Asking great questions in an interview can give you insight into a candidate's critical thinking skills, approach to problem-solving, leadership style, and overall knowledge of the industry. Here are 10 great questions to ask a VP of Sales in an Interview on those topics:

1. Tell me about your customer journey in your last role. How did you approach outreach to prospects, build relationships with customers, and ensure your team hit sales targets?
2. How do you motivate and inspire your sales team to meet and exceed goals? What steps do you take when the team is struggling?
3. In a constantly evolving marketplace, how have you successfully adapted your sales strategies to stay ahead of the competition and align with shifting customer needs?
4. What are some key metrics that you believe every VP of Sales should track regularly? Can you give examples of how tracking these metrics has helped improve sales performance in a previous role?
5. As the head of sales, what is your approach to building and maintaining strong relationships with existing clients to promote future company products and initiatives? How do you ensure customer satisfaction, retention, and opportunities to upsell?
6. What is your experience with implementing new technology and tools into a sales process? How have these changes impacted the sales team's productivity, revenue goals, and overall success?
7. Can you share a time when you had to make tough decisions within your sales team? How did you handle the situation and what was the outcome?
8. As a leader, how do you prioritize tasks and delegate responsibilities among your team members to ensure efficient and effective use of resources?
9. Communication is key to any successful organization. How do you ensure clear and effective communication between the sales team, other departments, and upper management?
10. The role of a VP of Sales requires a balance of short-term results and long-term vision. How do you strike this balance to achieve sustainable growth for the company?

There are thousands of great questions to ask a VP of Sales to assess their fit for your team, vulture, and long-term goals. One of the best ways to prep for an interview is to have a document circulated to your entire team of interviewers with the "10 best questions to ask a VP of Sales" (or really any sales leader) - this can serve as the baseline to help you find a great fit.

Essential Questions For VP of Sales Interview

As we dive deeper into the essential questions for a VP of Sales interview, note that this section will include more of the core concepts and questions for your organization to build on. Adding your own twist will help you hone them for the particular qualities and skills that matter most to your company.

Questions to ask a VP of Sales, Interview Question Examples:

1. Sales and Growth Targets:

"Tell us about a time when you needed to hit goals you felt were unrealistic. How did you adjust your mindset and rally your team to achieve them?"

2. Customer Understanding:

"What steps do you take to truly understand the needs and pain points of our target customer? Can you give an example of how this has influenced your sales strategy in the past?"

3. Leadership Style:

"Describe a time when you had to make a difficult decision as a leader, knowing it would impact your team's morale. How did you handle it and what was the outcome?"

4. Adaptability:

"In a constantly evolving market, how have you successfully adapted your sales strategies to stay ahead of competitors and align with shifting customer needs?"

5. Metrics and Tracking:

"What are some key metrics that you believe every VP of Sales should track regularly? Can you give examples of how tracking these metrics has helped improve sales performance in a previous role?"

6. Team Collaboration:

"Communication and collaboration are essential for any successful organization. Can you share an experience where you had to work closely with another department or team to achieve a common goal?"

7. Technology Integration:

"Keeping up with technology advancements is crucial in the sales industry. How have you successfully implemented new tools and what was the result?"

To reiterate, your revenue will be dramatically affected by this person, so the questions you ask a VP of Sales during the interview need to reflect the skillset and experience necessary for success in this role. Ensure that they have the core competencies required to drive growth across all aspects of your team.

Strategic Questions To Ask A VP of Sales Interview

Now, let's shift our focus to strategic questions to ask a VP of Sales in an interview. As the academic and professor, Henry Mintzberg stated, "Strategy is not the consequence of planning, but the opposite: it's the starting point."

Have you ever heard of the 1-in-60 rule? Pilots are taught that for every 60 miles of flight 1 degree off course, they will miss their landing by 1 mile. The same is true of sales strategy. A team that's just a bit off-course could end up missing important targets and costing the company dearly- one more reason for asking strategic questions during a VP of Sales interview.

Questions to ask the VP of Sales in an Interview to Assess Their Strategic Thinking and Approach:

1. Understanding the Market:

"Can you walk us through your process for analyzing market trends, competitors, and customer buying behaviors? How do you use this information to develop a successful sales strategy?"

2. Forecasting and Pipeline Management:

"How do you approach forecasting and pipeline management to accurately predict future revenue growth? Can you give an example of when this method was successful?"

3. Sales Planning:

"How do you prioritize and plan sales initiatives to align with company goals and drive long-term success? Can you share an example of a strategic planning process you've implemented in the past?"

Once again, strategic questions for an in-depth understanding of the market, sales, customer insights, and pipeline don't have to be complex, but they need to tap into a candidate's ability to take insights built upon data, turn them into actionable plans, and execute them.

In conclusion, when interviewing a VP of Sales, it's critical to your organizational future that you ask the essential leadership, market, and strategic questions to assess their skills, experience, and fit for the role. While the question examples we've given in this article can serve as a starting point, it's important to tailor them to your specific company's needs and culture. With careful planning and a thoughtful approach, you can hire a great visionary and team player.

If you're struggling to find a great sales leader and would like to see how interview intelligence can help you make better hiring decisions, book your demo of Pillar today. We'd love to show you how the power of AI candidate analytics can transform your hiring process.