What To Do About The Sales Rep You Shouldn’t Have Promoted

BY C. Lee Smith
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Carter Cast, a professor at the Northwestern University Kellogg School of Management Venture Partner, and author of The Right and Wrong Stuff, knows what it takes to succeed as a leader. He has studied and uncovered the key reasons that good people — talented, motivated, got-​game people — run into trouble when they move from contributing to managerial roles. This is fascinating research, especially in the context of a sales organization where so many great reps fail to make the leap to successful managers. He explained what you can do about this problem in a recent Manage Smarter podcast.

In researching about 100 people, ages 25 to 45, who failed as managers, Cast identified troublesome behavioral patterns. His conclusions weren’t based on the new managers’ insights alone. He also interviewed their bosses. He came up with several managerial archetypes you might be dealing with in your sales managers. Here are three particularly interesting types.

Captain Fantastic

We probably all know about this kind of manager. Now that they have the title, they feel entitled. Their ego is in the driver’s seat. Every action they take is about themselves and their career. In the long run, their lack of empathy for team members will bring them down. During their reign, captain fantastic managers will damage your organizational culture and send reps running for the exits.

Solo Flyer  

We all appreciate the star performer who delivers on time, every time. This person arrives early to meetings, thinks ahead about what must be done, and then delivers. It’s easy to get tricked into promoting this person. It’s not easy to realize this person will need significant coaching to change their ways. Otherwise, they will be doing all the work themselves and hover over every detail of every sale their team members are trying to close.

Whirling Dervish

These people will have no end of fantastic ideas. They play a critical role on your team. If your reps are having a tough time deciding how to approach a difficult prospect, leave it to the dervish to come up with ten ideas. Just don’t ask your dervish to sit down and implement the ideas in any kind of a logical fashion. They can’t do it, and for that reason, they don’t make the best managers for employees who crave structure, discipline and development.


If you’ve got a sales manager who's failing to set an example or develop their team members, you’ll need to address the problem. Feedback can work wonders. Carter breaks feedback into three categories. 

You’re probably used to coaching people on what they need to do to develop a specific skill in order to improve their performance. Something like learning to master Power Point falls into this category. 

Positive reinforcement is another feedback category. Encourage your struggling managers to work on an area where they excel. 

It’s the last category of feedback that difficult to deliver: That’s when you talk to the new manager about how they need to change a basic part of their personality or style. Deliver this kind of news in the most positive way. Explain how their tendency — such as whirling dervish — is holding them back from advancing in their career. If your budget allows for it, hire a coach for a few sessions. But, only do this if your manager agrees to work on their problem area.

If they’re successful in changing, they’ll excel and your organization will reap the rewards.