Uncertainty and Bull Markets | Questions Every CEO Should Ask The Sales Leader

70% of sales leaders express low confidence in their ability to translate strategy into action.

  • Ignore strategic planning
  • Let expenses balloon
  • Neglect talent management
  • What happens if we lose one or more of our top accounts?
  • How are we evaluating the position of our offering to ensure it’s more than competitive in the market?
  • 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 a potential acquisition?
  • What else could we be offering our customers that they currently buy from other sources?
  • How are you planning 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?
  • How have expenses per sales rep trended over the last six months?
  • What % of our discretionary spending is allocated to closing new business vs. maintaining existing business?
  • How do we measure the ROI on certain expenses? Travel? Conferences? Tools in the sales stack?
  • If you had to eliminate 20%+ of discretionary spending tomorrow, what would you eliminate and 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 the money?
  • What happens if tomorrow we ask you to reduce the sales force by 10%? To whom do you reassign the accounts?
  • How would losing your top two reps change the way you’ve currently structured the team? How long would it take you to replace them?
  • Have we structured the team so that we have them focused on the right activities? Are we asking too much of the team? 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 are craving and prepared for more responsibility?

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