Building Teams: How to Interview Senior Sales Executives (Recruiting “A-Level & World-Class” Sales Leaders)

How to Interview Senior Sales Executives

Every high-growth company needs to hire senior executives to own and run different business functions – whether you’re hiring a COO, a CRO, a VP of Sales or others, the advice below applies equally well to recruiting any of these roles.

The simplest advice I wanted to offer to CEOs and Boards is to interview senior executives at a level that matches the seniority level.  Asking perfunctory or “junior-level” questions when meeting senior executives is ineffective and, unfortunately, can come off making the interviewer look either unprepared or inexperienced.  For example, the following are examples of the types of questions that should be avoided: “describe yourself in one word”, “what is your favorite music group”, “who is your favorite superhero”, “if you were an animal, who would you be”, “what is your favorite color”, etc.  These are not good questions even for junior candidates, never mind for senior managers or corporate executives.  Additionally, truly experienced interviewers and effective C-Level executives who know how to hire well should not even ask such *lazy questions* such as “tell me about yourself” because you should already know the high-level overview because you should have looked at the resume – it takes 10 minutes to review the resume and prepare some questions and there is a very high ROI on doing that when it comes to building teams.

So when interviewing senior people, you want to get an understanding of how they would execute their role. For example, you would want to understand how they set strategy, what kinds of KPIs they measure, how they build teams, how they hire people and what they look for, how they lead and develop their people, how they manage the organizational culture, and also go deeper into what they do when employees don’t hit their sales quota or don’t perform well on the job, how they fire employees, etc.  Those are real, tangible and objective questions that will help you get important information about the executive’s professional experience and capability. Asking junior-level questions may make your company look less attractive to the executive.  Senior people want to be part of a serious operation and part of the decision of whether they like your company will be based on their “candidate experience” during the interview.

Additionally, if you ask subjective and ineffective junior-level questions then you will just get unhelpful subjective responses that won’t provide you with any meaningful data points to make an intelligent hiring decision.


Example List of “Executive-Level” Questions Relating to Sales Management Experience:

  • How do you describe your leadership style? Are you a good leader and why?
  • How do you define the primary responsibility of and discern between a sales leader vs. sales manager?
  • How did you achieve the sales results stated on your resume – walk me through and what you did? (this is the most specific/detail question)
  • Walk me through how you manage on a day to day basis and at a very tactical level?
  • How do you recruit and hire sales talent? What do you look for in sales people when you recruit for your team?
  • Have you made mistakes in hiring, what did you miss and how did you deal with that?
  • What has been a sales rep attrition average on your teams and why?
  • How do you coach and develop your sales teams – discuss the specific approach and examples?
  • How do you run your sales team meetings? What kind of meetings do you schedule for your teams and why?
  • Who from your team has gone on to become a senior manager or a sales executive and how did you help them get there?
  • Describe the time when you had to deal with unmotivated staff or morale issues? How did you boost morale?
  • How do you define culture and how do you develop an effective sales organization culture?
  • What was your total sales target and what did you hit last year?  How much did it grow from the prior year?
  • What kinds of sales KPIs and metrics do you measure and what is the process of measuring your team?
  • What metrics/KPIs do you have your sales team track themselves?
  • How to you get the team to execute?
  • How do you create accountability on the team?
  • How do you create alignment across different organizational business functions?
  • What approach do you use to evaluate employees’ job performance?
  • Tell me about how you do performance management on your sales team?
  • How do you deal with employees / sales reps who produce inadequate and sub-par results?
  • How have you done a PIP process and terminated reps, how do you handle it?  What’s the “most important” thing in this situation?
  • How do you deal with “aberrant geniuses” who are difficult or hurting morale (when others complain)?
  • What specifically makes you a good fit for this company?
  • How do you know if you have a good sales team?
    • this is a non-obvious question and the best Sales Leaders understand this insight
    • counter-intuitively, the answer is not “when the team always attains the results”
  • As a Head of Sales, how do you “make the number / hit the overall sales quota target”?
  • How to you “execute” – walk me though your “blueprint for effective sales execution“?
  • How do you scale from a level of $A to $B in revenue?
  • What is your playbook for growing sales given the size of our organization? (they have to be able to explain it as a process and share risk factors to avoid/mitigate)
  • If you are hired, what would be your priorities for the first first 100 days?


Examples of additional “Executive-Level” Questions That Offer More Objective Insights (pick those that matter for you):

  • What do you consider to be the primary job of a “manager”?
  • How do you make decisions, what are the decision-making models you use? (remember, you’re hiring executives to make decisions)
  • How do you make hard decisions when you don’t have enough information or are missing a lot of information?
  • How would you choose to compensate if you could pay less and save the company money?
  • How do you do your “one-on-one” meetings and what is your typical agenda for them?
  • Walk me through how to build trust with your direct reports and team members?
  • What are some examples of how you inspired more courage from your team members?
  • How do you successfully motivate your team and can you share specific examples?
  • When dealing with any type of problem then how do you begin the process of solving that problem?
  • As a manager, how do you solve communication issues between people on your team?
  • Describe a Business or Group Strategy you designed & walk me through how you do Strategic Planning?
  • What do you think we are doing well here? What would you change at our company based on what you know?
  • What do you think are the top 3 things required in this role?
  • There will be situational questions like Challenge, Insight and Scenario questions you may ask
    • What are some of the lowest points in your career? What did you do?  What would you do differently now?
    • What would direct reports say about you that is not on your resume?
    • When you are in a difficult and stressful situation, how do you make good decisions?
    • What are you the best at doing – what are a few on-the-job situational examples of these?
  • Also, some questions about your company and products – do they have insights and understanding
    • What will you improve about our company
    • What do you think will be our next big product or innovation
    • If you could change any of the products that your team would sell, what would it be

Needless to say, you just need to pick a couple that match your context and you won’t have the time to ask all of them.  Plus this is not a full list because there are dozens of other specific questions I’d add depending on which type of executive you’re hiring (sales, or marketing, or customer success, etc. – the specific questions will vary by role). Also notice that these are more specific and objectively posed questions – they are not subjective or broad and won’t just lead to  ambiguous answers that have manifold interpretations. These are also not junior-level questions like “where do you see yourself in 10 years” (something you’d only ask a recent grad and not someone seasoned, accomplished and senior – they are not exactly confused about their career path at the senior stage of their career).

In other words, it’s important to ask the right types of questions when recruiting a senior executive and both sides will get the best outcome in finding a more objective way to measure whether there is a right fit.

Finally, as you can see, the good news for every company is that it’s not that difficult to make some basic adjustments to align your questions and the interview process to the level of the candidate’s experience or seniority for which you’re recruiting them.

What else?  What are some other thoughts on recruiting senior executives effectively?