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Motivating Your Millennial Sales Leader

If you choose to buy into all the Millennial stereotypes, you have already lost the battle.  Forget about the labels and get to know the individual in front of you and their potential. Then you are in a stronger position to discuss the development of your millennial sales leader.

Who encouraged you when you were starting out in business?

One morning, during my early Xerox days, I walked confidently into a prospect meeting. I’d mapped out excellent questions on my pre-call worksheet. The conversation started out well, but then I saw my prospect losing interest.

I doubled down by asking even more questions; I tried as hard as I could. So I was shocked when I was asked to leave— immediately.

I felt devastated and deeply embarrassed. Plus, I was certain I would get fired. I drove back to the office, sobbing uncontrollably in the car and all the way into my manager’s office.

Through my sobs, my manager empathetically helped me debrief my failed sales call. He praised my determination to master the questions. However, he pointed out that I had focused too much on the questions and not enough on listening to the answers.

Like any great sales manager, he ended the coaching conversation by sending me back out into the field, with these encouraging words, “You can do it, Danita. You know we only hire the best.”

Have you had an opportunity recently to help your young mentee over a hump? How did you encourage them?

Encouragement Reveals Potential

Our RESPECT acronym (react, encourage, sensitivity, politeness, extraordinary kindness, considerate, timeliness) is a useful guide to model respect and collaboration to your Millennial sales leader.

Encouraging them is the second action step to help you develop Respecting Others as part of your Relationship Wiring.

Here are 6 action steps to help you positively encourage your young mentee:

Identify your millennial’s preferred communication mode.

We all use sight, sound, and touch to communicate. However, we are unique and one of these modes of communication might be more dominant than the others.

When you identify the dominant communication mode of your millenial sales leader and deliver your encouragement in the way they want to receive it, you’ll establish greater rapport.

Invite respectful listening.

Respectful listening happens when you create a safe atmosphere where your sales mentee confidently shares ideas – even the wacky ones.

Model good questioning skills.

You have the opportunity to model how to ask deeper-level questions. These questions help you understand your young sales leader’s differing perspectives.

Eliminate negative labeling.

If you choose to buy into all the Millennial stereotypes, you have already lost the battle.  Forget about the labels and get to know the individual in front of you. Then you are in a stronger position to discuss the development of their potential.

Find the gem in their failure.

Help your mentee find the gem in their failure. Many of the millennial sales leaders I mentor, fall prey to negative self-talk and become despondent or even depressed when they don’t succeed immediately.

Do this by changing their perspective on what they see as a black or white scenario only.  Here are helpful questions to ask when you have this discussion with your mentee. What did you do well? What did you learn and can use moving forward? Did you learn something about yourself?  How will this experience change what you do next time?

Emphasize the value of the uniqueness factor.

Encourage your next-gen leader to begin a lifelong habit of valuing his own uniqueness, as well as the uniqueness of others. As you’re coaching your young mentee, you can list the different strengths that you have identified in your sales team.

Highlight the fact that it’s only because of the combination of those talents and the collaboration that exists, that your business is able to achieve sustainable growth.

Your young up-and-coming sales leader needs to know that you want him or her on your team.  Even when they are still learning – even when they are failing.

By modeling respectful encouragement, you’re helping your millennial sales leader to see their value to the team, even if they’re the newest employee in the workplace.


Great sales leadership begins with a great team. Download our FREE Sales Manager’s Ultimate Interview Guide to make better sales hiring decisions that ultimately lead to the development of a high performance sales team.

About the author

Danita Bye

Danita Bye, M.A. is a leadership and sales development expert. She has successful sales…

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