Selling Power Blog

News & Insights for B2B Sales Leaders

March 28, 2022

How to Interview a Sales Leader

By Nigel Green, Sales Team Architect and Author, Revenue Harvest
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Most sales leaders were comfortable in the years before COVID – and they could ignore strategic planning, expenses, and talent management and still look successful. But the pandemic exposed weaknesses in the sales leader talent market. While their experience may have looked good on paper, how much of their success should be credited to favorable market conditions rather than their unique talents?

The world is different now – not only with markets but with the sales staff’s work/life expectations. If you’re looking for a sales leader, you need to dig deeper in interviews to make sure they are skilled at strategic planning, have a high financial IQ, and are dangerously good at talent management. According to Gartner 70% of sales leaders express low confidence in their ability to translate strategy into action.

In this blog I’ll explore each competence, then offer some questions to ask candidates during interviews.

Planning Is Key to Sales Survival

I coach a lot of executive sales leaders. When I ask them to review their strategic plan – something that not only details revenue per month, but assigns the revenue to sales reps, products, and even customers – many of them say they don’t have one “in the true sense.”

Planning ensures the current sales strategy aligns with future business goals; anticipates the loss of key strategic accounts; and identifies potential offering pivots that can create competitive advantages.

When times are good, performance pressure subsides – letting sales leaders gloat at the scoreboard. As the job gets easier, planning gets neglected. Strategic sales plans consider everything – even the likelihood of misfortune during the selling year.

If It Doesn’t Make Dollars, It Doesn’t Make Sense

Expense management requires sales leaders to closely examine each month’s P&L for opportunities to improve ROI. Pre-pandemic, sales leaders enjoyed healthy discretionary spending like travel and entertainment, but not so much anymore. Make sure your candidates know how to effectively redeploy discretionary spending.

Recently I’ve focused on my clients’ sales technology stack. They all seem to have a tool for everything, and that’s fine. As long as the tools are being used, I support adding tools over adding people. However, don’t assume the sales team regularly uses them.

Good Talent Eventually Leaves

Eventually, all your top reps will move on to pursue new opportunities. Bull markets expose sales leaders in two distinct ways: 1) they stop recruiting and over-rely on recruiters to fill the few open vacancies, depleting the team’s overall “bench strength”; 2) they assume top producers are happy with their current earnings (most reps enjoy healthy commission checks), and they neglect their reps’ career needs.

CEOs Should Ask Candidates These Questions 

To uncover whether the sales leader you’re interviewing can excel today, ask candidates these questions.

Questions Every CEO Should Ask on Sales Strategy

  • What happens if we lose one or more of our top accounts?
  • How do we evaluate our offering’s position to ensure it’s more than competitive?
  • Does our current go-to-market strategy really support the company’s strategic objectives over the next 1-3 years?
  • Have we identified the right strategic partners to explore joint ventures, collaboration, or potential acquisitions?
  • What could we offer our customers that they currently buy from other sources?
  • How do you plan to replace yourself? Are you doing work that only you can do?
  • How much of your time is spent on low-value activity vs. uniquely helping us grow the business?

Questions Every CEO Should Ask on Expense Management

  • How have expenses per sales rep trended over six months?
  • What percentage of our discretionary spending is allocated to closing new business vs. maintaining existing business?
  • How do we measure the ROI on certain expenses, like travel, conferences, and tools?
  • If you had to eliminate 20%+ of discretionary spending, what would you eliminate? Why?
  • What is the optimal cost per sales rep? How do we realize incremental decreases in cost per sales rep month-over-month?
  • If we were to increase your expense budget by 20%+, how would you spend it?

Questions Every CEO Should Ask on Sales Talent Management

  • What happens if tomorrow we ask you to reduce the sales force by 10%? To whom do you reassign accounts?
  • How would losing your top two reps change your team’s current structure? How long would replacing them take?
  • Have we structured the sales team so it focuses on the right activities? Are we asking too much of them? Do you see opportunities for specialization or more generalization within the team?
  • If we asked you to double the size of the sales team in 120 days, could you?
  • How many of the current sales reps crave and are prepared for more responsibility?

The most successful leaders differ from their less successful peers in how they remain hypervigilant in good and bad times.

Do your sales leader candidates have what it takes to succeed in today’s market?

Grab a copy of Revenue Harvest for $5 at

Headshot of Nigel Green

Nigel Green is Sales Team Architect and Author of Revenue Harvest.