Five Important Questions for New Sales Leaders

For those of us who’ve been promoted or newly hired to lead a sales organization or part of one, there are some common and weighty questions we all find we need to address. By my count, there are at least five important questions for new sales leaders to address if they hope to succeed in their role and deliver great sales results.

Depending on whose research you trust, the average tenure for a head of sales today is in the 17 to 24 month range. The reasons for why a new sales leader might not last very long in her or his role run the gamut from poor fit to incompetence to misaligned expectations to exhaustion to a myriad of other, specific contributing factors. For our purposes here, let’s just agree among ourselves that a new sales leader’s goal should be to deliver outstanding sales results, to exceed his or her financial and other business objectives, and to last in the job longer than 17 months.

As is the case with sellers and athletes, getting a fast start as a new sales leader is critical to achieving the goal. The sales leader who does not have a handle on the biggest and most common issues will be ill-equipped to lead and incapable of addressing the eventual curve balls that the market, clients, and her own sales organization will throw at her. A slow start or a series of missteps shortly after the start are the clearest path that I’ve seen failed new sales leaders go down… and they went down hard.

Getting a fast start requires considering the common barriers to success and making haste to address them. You don’t need to have all the answers right away, but knowing the right questions to ask and starting your diagnosis on day one are critical.

In my own experience working as a head of enterprise sales and as an interim Chief Revenue Officer, I’ve learned that knowing which questions to ask is maybe ninety percent of the battle. There are far more than just five questions that you’ll need to consider, Miss or Mister Head of Sales, but this list of questions for heads of sales can give you a great head start.

  1. Will my new team understand my strategy? First of all, is my strategy clear? Do I have a clear vision of success and how to achieve it? Am I articulating that vision well and helping my new team see what is in it for them to execute the strategy with gusto? Have they or will they have the chance to ask me clarifying questions about the strategy?
  2. Will my team be able to execute the strategy? Do they have the skill to execute the strategy? Have they done this before, or will they need a lot of practice at the new skills required to deliver on our vision of success? Do I have the right coaches and support system in the organization? Will my team make time to do things differently and as effectively as I need them to?
  3. How will I empower my team to execute the way I need them to? What issues will the team have to address as they execute the strategy? How can I help them address those issues? Which tools or additional resources will they need to do what we need them to do? What role will I play along the way? What role will my staff and key functions like sales operations and marketing play in setting expectations and following through?
  4. How will I establish the kind of sales culture that I want? What kind of culture do I want to establish in the first place? What steps will I take to really understand and diagnose the current culture and identify the steps and and changes required to build the culture we want? Where will I need help? Who are my internal allies and champions who can help lead the change?
  5. Who can I trust? Who are my truth-tellers, diagnosticians, humble leaders, learners, and most candid members of the team? Who can I bring onto my core team to give me feedback and help me answer these first few, important questions? Who trusts me?

How we go about processing these questions is as important as the answers themselves. Rather than asking these questions simply of ourselves or asking them in an echo chamber full of like-minded individuals and fans, we can derive huge value from posing these questions of people who don’t necessarily share our perspective. How would the CEO who hired or promoted you answer some of these questions? How about the head of HR or your counterpart in Operations or Engineering or Sales Ops? What about your frontline sales managers and sales people? Would the perspective of a core group of sellers and other client-facing folks help as you consider your answers to the big five questions?

If your answer is “yes” or “maybe,” then I think you know what to do next.

Transformation starts with one simple action by a bold leader. You’re armed with the most important questions. Now go ask them! And let me know if the answers change your thinking and impact your approach to leading and coaching the team from this point forward.

As always, we are at your service for ideas on how to plan and execute the right strategy for your environment and lead your team to victory. You can contact us by clicking here.

Matt McDarby is a Managing Director at Specialized Sales Systems and can be reached at