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The Executive Sales Leader Who Couldn’t Sell His Boss

As an executive sales leader of your organization, is there any greater joy than seeing your team thrive?

In the ideal version of your company, everyone would be thriving.  So what’s stopping them?  Could it be you?

For most of us, there is only one thing preventing us from living a life that is truly inspired, and having a company that is full of inspired people.  I call that one thing “being dense.”  We are so busy running the business that we don’t notice how dense we are, and the impact that has on everyone around us.  So what can we do to be less dense, and create more of a clearing for living a great life?


One thing we can do is take the time to properly cultivate our most valuable asset; the talent of our people.  Having the right people in the right roles can release the creativity and power needed to win in a competitive marketplace. This is especially true with regard to the executive team.

Take Jack and Bert.  Jack is leading a division of a Fortune 500 beauty products maker, and he has many skills and talents, but sales forecasting is not one of them.  In fact, Jack has no sales experience at all.  To make up for this deficiency, Jack hired Bert as his sales VP to be an executive sales leader.

I started executive coaching sessions with Bert to help him achieve a breakthrough in his new position.  It became clear to me right away that there was a disconnect between Bert’s talents and his ability to share those talents with the company.  Specifically, Bert was very good at forecasting.  Unfortunately, this didn’t translate to success for the company.  Because Bert’s boss, Jack, lacked of sales experience, the forecast for the division was always inaccurate.  Consequently the division always missed their numbers, and Bert ended up losing his bonus.

This was deeply frustrating to Bert.  Here he was, an expert at putting together an accurate forecast, so good that he never failed to hit his number, but it wasn’t translating to success for himself or his company.  But rather than share his frustration, Bert kept it bottled up, until one day in a forecasting meeting, he blew up at Jack.  He pounded on the conference table and said, “Your forecasts are so bad they are literally taking money out of my pocket!  When are you going to learn to do it my way?”

Not surprisingly, Jack did not take this harsh accusation as a constructive offer to help.  So he did nothing.  Time went by, Bert found that still no one would listen to him.  As a result, he got even more frustrated.  He became even angrier, but rather than act out again, he withdrew.

I pointed out in our coaching session that it looked as though he’d given up.

Bert said, “I don’t know what else to do!”

I suggested that his first order of business was to stop being so dense.

“Me?  How am I dense?” he asked.  “Jack’s the one that won’t listen to reason.”

I showed Bert that the way he was dense was he was not asking himself an important question.  He should have been asking himself, “What is it about me that causes people not to listen to me?”  There must have been something Bert was doing, or not doing, that was getting in the way of his desire to help people.

“You mean the way I talk to people?” Bert said.  “The way I yelled at Jack?”

“Exactly,” I said.  “If I think you are going to yell at me whenever you are frustrated, it will be hard for me to trust you.  And if I don’t trust you, I won’t take your advice.”

Then I showed Bert that there are four parts to trust.  First is truth.  Do I trust that you are telling me the truth?  Yes, we have to assume that everyone knows Bert is telling the truth that he can help the division get better at forecasting.

After truthfulness comes competence.  Do I think you are capable of doing what you say you can do?  In other words, are you competent?  In Bert’s case, again, the answer is “Yes.”  Competency is not his problem.

Third is reliability – can I count on you to do what you will say you will do?  Some people have to be checked on all the time.  But everyone knows Bill is the kind of guy who will take it and run.  He’s very reliable.

This leaves just one component of trust: sincerity.  Do I trust that Bert will have my back?  Do I really think he has my interests at heart?  I told Bert that by talking about his own bonus, rather than how much the company can be helped by improving the division’s forecasting, he was giving the impression that he was just in it for himself.  If he could figure out a way to craft a win-win, Bert could overcome this deficiency.

Bert was ultimately successful.  Once he realized that his dense behavior was making him untrustworthy, it was as though rays of light penetrated his blind spots, and he was able to see clearly what to do.  He dropped his frustration, anger and bitterness, and approached Jack with an open mind – and without rancor or discord.

Do you have a “Bert” on your team?  If so, how are you developing him to be an effective manager?  As the leader, it’s vitally important that you overcome your own dense areas, so you can develop your team for management.


About Jack Skeen

Jack Skeen
Jack Skeen, founder of Skeen Leadership, has been coaching bright and successful leaders for close to two decades, spending thousands of hours addressing every imaginable leadership, business and life issue with wisdom and professionalism.

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