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VP sales interview questions

Corporate and HR leaders know that getting their interview process right is important. But when it comes to hiring a VP of Sales, it makes all the difference to the future success of a company.

Certain interview questions bring hidden information to the surface. At Peak Sales, we’ve assessed and interviewed over 10,000 sales leaders for our clients over the last 13 years, and we’ve compiled an exhaustive list of interview questions that will help you select your next VP Sales.

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Interview Questions for a VP Sales

Key Responsibilities of a VP Sales

“The average tenure of a new sales leader is 19 months. No other member of the executive suite fails as often as the sales leader.”

Matt Sharrers and Greg Alexander

One of the critical mistakes companies make is building an interview process and questionnaire before fully understanding the responsibilities and functions of a sales leader. It’s is one of the reasons why the most common mis-hires in business is that of VP Sales.

This role directly influences a company’s revenue, market share, expansion potential, and culture, and the disparity in sales leaders’ performance is stark. There was a 51% gap in quota attainment between high-performing and low-performing sales leaders in a study of 400 VPs of Sales and managers: the high performers achieved 104% quota on average while the low performers reported 54%.

Your company’s revenue will end up on one side of this rift or the other because of who you hire, and hiring the right leader depends on your ability how the candidate influences people, business strategy, and customer relations to drive performance.  Let’s start with the foundation skill of a sales leader – being a people leader.

1. People Management

Preeminent sales leaders instinctively create an environment—and a culture—for success.

A VP of Sales must be a great coach. They achieve their success through the sales talent that they build, guide, and nurture. They develop individuals and help them to navigate the company when they need support and resources. Structured approach to holding people accountable.

For this reason, investing in a top sales leader is often more important than investing in a top sales rep. ZS Associates found that a team with an average manager but excellent salespeople performs well in the short term. But in the long run, excellent managers with average salespeople consistently outperform. Great managers elevate their whole team, while average managers bring excellent salespeople down to their level. And sixty-nine percent of salespeople who exceeded their annual quota rated their sales manager as being excellent or above average, according to a survey by USC’s Steve W. Martin.

Excellent sales leaders are self-disciplined and fixated on target revenue goals. They’re skilled at guarding their team from any distractions and negative attitudes that may detract from this priority focus. And they implement a strict sales process and hold their team accountable to it; according to Martin, 43% of high-performing sales managers use a closely monitored, strictly enforced, or automated sales process, compared to just 29% of underperforming sales managers. Underperforming sales leaders were more likely to have an informal sales process or none at all.

And, perhaps most importantly, sales leaders drive their hiring efforts. After all, “first class hires first class, but second class hires third class.” The future success of the sales organization rests on the VP Sales’ ability to implement systems that find, hire, and cultivate above-average talent.

2. Customer management

Industry leading VP of Sales drives financial results through their understanding of their customer segments and their ability to connect with them today and into the future. They know how nurture customer engagement by setting high-level strategy and driving their sales force to focus on the right activities and behaviors. They also represent the needs of the customer to the rest of the company, directly and indirectly.

When evaluating a VP of Sales for customer management abilities, look for their understanding of the market, the competition, and how they plan to maximize revenue by optimizing the sales process. Dig deep to understand their strategic philosophy to gain market share, segment the customer base, and influence contract size and length over time—as well as their approach to collaborating with marketing departments to achieve these goals.

3. Business management

The VP Sales steers the direction of the sales function, aligns resources, and improve key selling processes & channels.

They drive operational improvements through investments in technology infrastructure, improved data harvesting, and analysis with better data tools. They also optimize budget allocation, sales force compensation, and a whole range of team development programs. At a go-to-market level, their forward-thinking strategies can help the company increase market share and focus their efforts during expansion into new territories and markets.

_______

With such a wide range of responsibilities and influence associated with the position, hiring managers should thoroughly assess a candidate’s ability to deliver on these sub-responsibilities:

    • Recruiting a sales force
    • Designing compensation plans
    • Overseeing rep training and coaching
    • Developing a sales process and ensuring that it’s executed appropriately
    • Helping the sales force to make use of tools, customer data, and research
    • Managing metrics and setting goals
    • Managing rep performance and ensuring that it is aligned with company direction
    • Driving a culture of success
    • Setting high-level sales strategy to drive revenue

Hiring managers should also closely examine a candidate’s success with previous companies as a key indicator of future performance.

Candidate Evaluation

When developing an interview questionnaire, the first task is to create a set of mandatory hiring criteria: the qualities, attributes, abilities, and experience that a candidate must demonstrate in order to be considered for the position.

These criteria should be codified in a candidate scorecard that each interviewer fills out after interviewing a candidate. In sales hiring, these formal scorecards, as well as rubrics and structured interview questionnaires, yield the best results. They also combat hiring biases.

Indeed, research has shown that unstructured interviews and hiring methods can actually harm selection to such an extent that companies would be better off were they to select candidates entirely at random. Conversely, companies that use structured hiring tools in the interviewing process have been shown to have a more effective sales force. Research by CSI Insights indicates that a greater percentage of such companies’ reps achieve quota, and have a greater confidence in their organization. Particularly noteworthy is that retention rates are also significantly improved.

Our scorecard worksheet and template is available for download here.

Interview Questions for a VP Sales: The Complete List

We’ve collated the interview questions that have yielded the best outcomes. The full list of questions are grouped into four “buckets” covering each of the key areas associated with the role: personal, people management, customer management, and business management.

We’ve also called out our 10 most popular questions that shine a light on the most important attributes of a VP Sales.

Shortlist: Our 10 Most Popular Interview Questions for a VP Sales

  1. Please discuss your quota performance over the last three years. What obstacles did you encounter, how did you overcome them, and what were the actual results?
  2. What attributes make a strong leader and strong coach? Discuss the attributes you possess, and share examples of how you’ve leveraged them to drive team performance.
  3. Discuss your sales management process. In particular, what parts of it are structured, rigorous, and focused on accountability, and what parts of it are unstructured? Please share examples of how your process has worked in a past role, and why it’s been successful.
  4. Please tell us about your experience in hiring and growing a sales team. What characteristics do you look for when hiring sales professionals? In a specific example, past or present, what was your recruiting approach?
  5. How do you create a winning environment? Please share examples of strategies you use to motivate your team.
  6. Talk to us about the way you approach designing and executing a sales strategy, providing examples of your most recent strategy and the impact it had on the company.
  7. Can you provide one or two recent examples of significant deals with existing key clients where you developed and executed a sales strategy to increase account revenue?
  8. Please discuss the selling tactics that were most successful in a past role. How did you develop them and implement them across the sales force? What were the results?
  9. Please describe a time when you needed to rapidly scale your sales force. How did you implement the change and what was the impact (e.g., on quota, new client acquisition, gross profit, etc.)?
  10. Please describe the best sales infrastructure you’ve put in place in your past roles. What tools, systems, and support did you use? How did you go about implementing this?

Personal attributes

These questions are designed to uncover a candidate’s values, behaviors, and character traits away from the office.

  1. Tell us about a couple of the best and worst decisions you’ve made in the past year with regard to your team or sales approach.
  2. What attributes do you possess that make you a strong leader and coach? Please share a past  example of how these have come into play in relationships with your team.
  3. Please tell us about what drives you to succeed in the sales context.
  4. Describe a situation in which you had to quickly learn about a new product, service, or technology to serve a new customer base. How did you go about learning, and how successful was the outcome?
  5. Please describe your decision-making approach when you’re faced with difficult situations. Are you decisive and quick, or are you more thorough? Are you intuitive or do you go purely on the facts? Do you involve many or few people in your decisions? Please share one or two examples of difficult decisions you’ve made, how you approached them, and what the results wore.
  6. What are the biggest risks you have taken in recent years when it comes to your sales organization or sales approach? Include those that have worked out well—and not so well.
  7. What are some of the biggest challenges you have ever faced and overcome in your career as a sales leader?
  8. When you’re not at work, what do you do to enjoy yourself?

People management

A VP of Sales is not just a strategist and client manager—they are a key player in a company’s recruitment, training, and development of salespeople. The following questions address these responsibilities.

  1. Discuss how you’ve built a high-performance sales culture. What are the elements you focus on? What’s worked, what hasn’t?
  2. Discuss your sales management process. In particular, what parts of it are structured, rigorous, and focused on accountability, and what parts of it are unstructured? Please share examples of how your process has worked in a past role, and why it’s been successful.
  3. Tell us about sales teams that you have directly developed, managed and led. How did you go about building your team?
  4. What characteristics do you look for when you’re hiring sales professionals in our business?
  5. Thinking about your own extended network, who do you currently know that would be interested in joining you in our company’s sales department, right now? Why would they be a fit?
  6. How do you alter your management style when working with very seasoned sales team members, as compared to less experienced reps?
  7. Walk us through, in detail, the process you use for onboarding and training new sales reps. In terms of training specifically, when and how often does this occur on your team?
  8. Tell me about the most satisfying sale a previous team member made; what made it special for both you and your sales rep?
  9. Tell me about your relationship-building skills and style, in respect of the following:
    • Your sales team
    • Your external customers
    • Your internal customers (sales support, service, the warehouse team, senior management, etc.)
  10. What are your expectations of:
    • Your sales team
    • Your internal team
  11. How have you gone about establishing performance goals for your sales team?
  12. How do you communicate your expectations for managers and individual contributors? Discuss how your approach has changed over your career as a sales leader.  
  13. How have you gone about building a teamwork environment in the sales organization’s you’ve led?
  14. Discuss how you typically run your weekly sales meetings with managers and individual contributors? What makes for an effective one-on-one meeting?
  15. How much feedback do you like to get from people you report to? What form do you prefer—written or face-to-face?

Customer management

These questions test the candidate’s aptitude for sales strategy and leadership, as well as their focus on results.

  1. What is your sales team’s track record for acquiring and retaining clients? Please share examples of results from past teams.
  2. Talk to us about your sales management process? Provide a brief description and tell us why it works.
  3. Provide one or two recent examples of significant deals with existing key clients where you developed and executed a targeted account sales strategy to increase account revenue?
  4. Discuss how you’ve implemented new go-to-market strategies, adjusted existing strategies, or developed new sales processes to achieve substantial revenue growth. Please provide one or two specific recent examples where your efforts and innovations resulted in significant gains.
  5. In your previous roles, what sizes were some of the largest contracts you obtained on an annual volume basis? What was critical for you and your team to win those deals and how have those learnings changed your sales strategies or selling approaches?
  6. Tell us about a deal you lost to a competitor in a previous role and what happened.
  7. Please walk us through how you approach field engagement—making joint customer calls with reps and understanding customer demands and expectations in today’s marketplace.
  8. Describe how you would involve marketing with your team for lead generation, at our company’s current stage.

Business management

The best candidates are more than just sales experts. In addition to their expertise in sales compensation and improvements to sales force efficacy, they steer the business and have influence in technology, tools, and budget allocation. The following questions are designed to help identify those candidates with outstanding business acumen and management skills.

  1. Do you have experience managing a company’s revenue forecast? If so, can you please provide a specific example of your achievement in delivering on it?
  2. In the past year, what have you done specifically to remain knowledgeable about our industry’s competitive environment, market and trade dynamics, product/services and technology trends, innovations, and patterns of customer behavior?
  3. Which sales tools do you use, and why?
  4. If you joined our organization, what specific actions would you take in the first month?
  5. What will our sales revenues look like 120 days after we hire you?
  6. Explain your strategies or thought processes around how our company can win over competitors.
  7. What do you expect from sales support roles (engineers, operations managers, etc.) at this stage of the company, and at future, scaled stages?
  8. How many salespeople do you estimate our company needs, given our goals and current position?

Finally, a closing question can help draw out the candidate’s thoughts and provide insight into how they feel about the position and the company in general:

  1. Do you have any concerns at this stage of the interview process?
  2. Do you have any questions you would like to ask me?

This comprehensive set of questions will provide a framework for filtering your candidates, based on their skills, experience and personality. The next step is to formally evaluate them.

 

Post-interview reflection

Once the interview is over, fill out your scorecard and reflect on the following five questions:

  1. Can this candidate hit their targets quickly?
  2. Can I obtain verifiable proof to assure me that this candidate has delivered in the past?
  3. Is the amount of disruption this candidate will cause proportional to the amount of disruption the company can handle?
  4. How will the customers react to him or her?
  5. Is this candidate better than, equal to, or worse than the person in the same job at my top three competitors?

By taking these questions into account, along with the hiring criteria on a formal scorecard, hiring managers can significantly improve their chances of making the right hire. These carefully curated questions are specifically designed to do just that.

 


Your next VP of Sales is a crucial hire. They influence your people, your business strategy, and your customer relations, so it’s imperative to design interviews that weed out the bad candidates and deliver the one outstanding individual who is a perfect fit for your business.

Andrea Nellestyn

Candidate Marketing Specialist at Peak Sales Recruiting
Andrea spent her first few years at Peak as one of the firm's top headhunters before being selected to initiate and run the firm's candidate marketing division. A graduate of Carleton University, Andrea is a regular contributor to the Peak Sales blog.
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