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The Sales Leadership Dilemma

The vast majority of sales leaders were high-performing salespeople who got promoted. The logic is that if they were successful, they should be able to help others be successful. But it's not that simple.

The job of a sales leader is vastly different from that of a salesperson. Good salespeople have some combination of the following traits:

  • Prospecting/opening doors
  • Networking and generating partners that can refer business to you
  • Great Discovery: asking questions that uncover customer needs and providing value by introducing things they may not have thought of yet.
  • Connecting your product/service to the customer's needs so they can see how you can solve their issues.
  • Negotiating
  • Closing/getting commitments
  • Having a plan for themselves and sticking to it
  • Maintaining customer relationships
  • Account Planning
  • Deal strategy
  • Driven to achieve goals

If you were a CEO or owner with a salesperson with most of those skills, you would be extremely happy. What do most senior leaders in this situation do? They take that person out of the field and make them the sales leader. 
Let's take a look at their new role as a sales leader.  In order to succeed, what do they need to be good at?

  • Hiring
  • Training/Onboarding
  • Coaching and teaching (capable of observing and providing feedback).
  • Driving accountability
  • Forecasting
  • Time management
  • Setting team strategy – looking for new opportunities for the company
  • Developing systems and processes that allow the company to scale
  • Communicating up, down and sideways (good and bad news).
  • Developing comp plans that drive the right behavior
  • Sales planning for the entire team: goals, territories, structure
  • Setting the tone/culture for the team
  • Maintaining a balance between what is best for the company and the customer


Most owners and CEOs would kill for a sales leader who could do all of these things. But take a look at these two lists. What do they have in common? Not a lot.

There’s the dilemma. We've taken a great performer out of the field and put them in a job where they don’t have the right skill set. The big question is, “What do you do about it?”

It can work out if you give that new sales leader the training and coaching they need to develop these new skills. Unfortunately, that doesn't happen often. I have talked to hundreds of sales leaders and asked them what kind of coaching they received in those critical sales leader skills.  No matter how long they’ve been a sales leader, I typically get a crooked, knowing smile that seems to communicate, “Probably the same as you – very little!”

To compound the problem, in most organizations, there isn't anyone who can teach them. Could the CEO or owner do it? Very few people in those roles came up through sales. They may have good general leadership, but sales presents a whole new set of issues that they don’t have experience with. They simply don’t know how to help their sales leader.

What usually happens in this situation? Typically, the owner gets frustrated with lack of results and their solultion is to fire the sales leader and hire a new one. The problem is that the new leader you just hired came from the same lack of training system. So the cycle continues.

A better solution is to get your sales leader a coach, mentor, or peer group where they can learn the essential skills of being a sales leader. These employees are promoted for a reason, their generally pretty sharp people. They're struggling because nobody has shown them what good looks like in their new job. They can become outstanding sales leaders when they can make critical changes such as:

  • Understanding how to be an effective coach rather than just telling people what to do
  • Learning how to delegate and implement systems where people can be successful without them.
  • Proactively managing from systems and data rather than just reacting to the deal or fire of the day
  • Understanding growth strategy and how to make a plan to execute vs. just executing the day to day business.

When your sales leader can grow in these areas, your business becomes much more scalable and efficient.

What are you doing to help your sales leader?

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