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Three Common Sales Management Challenges—and How to Approach Them

Learn how to approach challenges leading yourself, your direct reports, and your boss with proven methods from the instructors of Strategic Sales Management.

6/20/2017 | Leadership and Management | 4 minute read

Written By:
John Westman & Michael McCarthy

The success of a sales organization depends on the quality of its leadership. Sales managers often need to juggle competing demands from supervisors, staff, and customers—while also meeting their own career needs.

According to John Westman and Michael McCarthy, the instructors of Strategic Sales Management, success depends on your capacity to help your direct reports, stakeholders—and yourself—meet important goals.

Here, Westman and McCarthy explore three common challenges sales managers face and offer advice on how to approach them.


Challenge: Creating a sales career advancement plan


Solution: Lead yourself

When you “lead yourself,” you become the CEO of your assets. You are at the helm, guiding your career. To develop a career strategy, you must be certain of your professional purpose. Begin by asking yourself these questions:

  • Why do you do what you do?
  • What motivates you about your work?
  • What gives you energy?
  • What impact are you trying to have in the world?

Your answers should help you understand your motivation. Use this to identify your career aspirations, assess your strengths, and create a roadmap of your sales career strategy.

Take time to define and physically write down your one, three, and five-year career aspirations.

Detail the actions you will take to achieve them. Consult your supervisor to find opportunities for them to support you.

Here’s an example: “In one year, I want to build my capacity to manage a sales team that doubles in size. I will gain leadership skills by attending sales manager training this year and getting specific monthly feedback from our director.”

Challenge: Developing a high-performing sales team


Solution: Lead down

“Leading down” means inspiring your sales team to achieve above-target results. As a sales leader, you must be able to energize and retain star performers. Through coaching and motivation programs, you can help your staff members realize their potential.

To start, create a professional development plan for each direct report that identifies opportunities for them to develop skills and prepare for advancement. Then, review the document monthly to ensure the plan is advancing.

Ask every Monday, “What else can I do to make you even more successful?”

Challenge: Meeting your supervisor's needs


Solution: Lead up

To effectively “lead up,” create a plan that helps you understand and meet the needs of your manager.

Do the basics: regular reporting of sales, pipeline, and other key metrics. If sales are down, provide an explanation and present strategies for increasing performance.

Most importantly, meet with your boss to define and agree upon a plan that increases your boss’s (and your) contributions to your organization.

Request to set up a monthly debrief meeting to discuss what is going well, identify what activities to continue, and ask for feedback on areas that could be improved. Additionally, agree to hold quarterly discussions with home office personnel in areas such as Finance, Human Resources, and Legal to thank them, and learn ideas to improve cross-departmental collaboration.

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