3 Sales Leadership Challenges (and How to Fix Them)

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Being a leader is hard. When faced with a new sales leadership challenge, it can often feel like you are alone on an island. Turns out, finding a group of peers that both grasp your issue and can provide valuable insight into how they have handled a similar situation is like finding a needle in a haystack. Enter Factor 8’s Executive Open Bar, a place where we can speak openly about the challenges that often accompany a C-level position. Whether we are talking about the big picture or the daily struggle, we have created a safe space to share our challenges. 

This quarter our participating executives shared some timely issues. We want to share the insights we discovered; in case you find yourself facing these same quandaries! 

  • Question 1: The company will be shifting a portion of the team from live selling to online bots. During the transition, we will need the live team to assist our customers in making the switch to digital. We are struggling with the strategy for keeping the live team members motivated when there is a foreseeable end to their position. What advice can you share about a change in strategy that results in job loss? 
    • Communicate, communicate, communicate! If we do not talk with our team members about the elephant in the room, the elephant only gets bigger. 
    • Town Meetings with the executive team can help ease employees’ anxiety. This will work best if relevant and specific information about the process is provided.
    • Money talks. Offering a staying bonus to team members can be a great motivator.
  • Question 2: With the weather getting nicer and the world reopening, we are seeing a drastic drop in staff engagement and performance. We are still 3-6 months from returning the full team to the office. What advice can you share for keeping people motivated?
    • Change up your contests. Have the quantifier be the area that your team is struggling with. So, instead of awarding for the number of deals closed, maybe concentrate on the shortest deal closing window. Instead of just measuring the number of successful call connections, break it out into two games. Measure the number of successful connections both before and after lunch. 
    • Communicate! Have an all-team meeting. Acknowledge that you know the world is exciting again. You’ve let it slide for the last 2 weeks because we know the pandemic has been hard for everyone. However, it’s time to get back to work and crush those goals! We now have just 2 weeks to (insert goal here)
  • Question 3: We’ve reached our end-of-year goal early. The CEO is saying “sell, sell, sell” while the supervisors are sharing that we need to ease off because the workload is not sustainable. How do I have the conversation with the CEO that selling more might not be in the company’s best interest? 
    • Do your research! Before speaking with the CEO, have hard numbers on hand.
      1. What is the expense to the company of burnout? How much does turnover cost the company? 
      2. How much will it cost the company to hire/train new employees to execute additional sales? 
      3. Come prepared with a better option. For example, “If you give the team a 30% break on the new goal, here is what we will be able to do with the time ______ (train to up our game, upsell current customers, prospect larger accounts, etc.)
    • Ask the CEO to help you find the best solution AFTER you’ve presented your research. Make finding the solution a collaborative effort. Often the CEO is looking at the big picture, not necessarily the daily details you are facing. 

I always feel so invigorated after one of the Executive Open Bar sessions! I want to thank the leaders that joined us for their openness, insight, and assistance.

If our Executive Open Bar sessions would be helpful for you, please email us at info@factor8.com for an invitation! 

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