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The Center for Sales Strategy Blog

24 Ways to Effectively Coach Millennial Salespeople

Effectively coach millennial salespeopleDo Millennials simply have less sales talent than prior generations?

After conducting tens of thousands of sales talent assessments, we here at The Center for Sales Strategy can assure you that’s not the case.

In part one of this two-part series, we shared four key differences in how the Millennial generation was raised, insight that was gained from Brad Karsh in an never-ending quest to learn more about how to activate Millennials. These differences explain much of the enormous disconnect between many Millennial workers and their managers today.

Infographic: Top 15 Reasons Your Employees StayClosing the Gap Between Generations

Karsh provided an example that we can all relate to: a Gen X or Baby Boomer appreciates greater freedom in their work, so when they assign projects to their Millennial employee, they generously say something like, “Here is a project, you have two weeks to complete it, and you can put your own stamp on it.” They walk away feeling like a hero! The Millennial, on the other hand, is freaking out because that's is not how they work.

It often feels like managers and Millennials are speaking two different languages. But don’t panic: There are ways to close that gap between you and your younger employee!

Below are 24 ways to effectively coach your Millennial seller. Some of these are straight from Karsh's webinar, others are tried-and-true strategies that have been recommended for years by our Talent Analysts while working with sales managers struggling with 20-somethings.

24 Ways to Effectively Coach Millennial Salespeople

  1. Schedule time to discuss their personal goals and how they want to be managed.

  2. Position yourself as a partner in their learning and success.

  3. Share your thoughts on their career path with them to increase retention and keep them from bouncing from job to job.

  4. Get their input on the kinds of rewards they want when they are successful.

  5. Teach them by demonstrating and doing the work with them, side-by-side.

  6. Provide variety in their work by allowing for cross-training opportunities that help them to know the entire business inside and out.

  7. Allow them to work in teams of two or in small groups when possible.

  8. Personalize it. They want to like where they work and the people they work with. Get to know them and their lives outside of work.

  9. Manage their expectations. Happiness = Reality – Expectations. In other words, happiness at work happens when the outcome exceeds the expectations—and unhappiness occurs when the outcome falls below expectations. Make sure they don’t think they're going to be your Zuckerberg in the next 6 months.

  10. Invest in them by providing training on the things they really need right now—business etiquette, leadership, conflict resolution, etc.

  11. Provide flexibility in their work. They're not going to give up everything just because they have a job; adjust your style when possible and meet them in the middle.

  12. Create a highly collaborative environment with peer mentors, group brainstorming, and group projects.

  13. Challenge them—but give them the structure they expect and need. Provide a detailed timeline and an outline of the steps to success.

  14. Have the “try versus results” conversation. You know they are the trophy generation, raised to believe that all you have to do is “try.” But now, at work, it’s about the results. This is a hard transition—help them make it.

  15. Schedule in-field days and weekly focus meetings with them—and stick to your schedule.

  16. Set milestone goals—so they can feel as though they have achieved success more frequently. Give immediate feedback on their performance.

  17. Check in with them often to show them you care and help them to feel on-track.

  18. Let them know you’re available to help. Invite them to bounce things off you whenever they like.

  19. Tell them why—never “because I said so.”

  20. Be generous with praise and recognition—it’s the number one driver of this generation.

  21. Don’t forget the simple thank you.If they don’t hear positive feedback from their boss, they assume they are doing something wrong.

  22. Make the work—or the workplace—fun to the extent possible.

  23. Celebrate successes as a team.

  24. Include their family and friends in after-hours events.

What are some of your best strategies for coaching and working with millennials?

5 Min, On-Demand Webinar: Manager Tips for Working with a Remote Sales Team


Editor's Note: This post was originally published on February 24, 2014, and has been updated.

Topics: company culture