How to Engage your Top Performers—So You Don’t Lose Them

By: Phil Stern  |  July 16, 2020

Are your top performers fully engaged? Are they going to be with you in 12 months?

I’ve lost strong performers a few times, but I vividly remember the day I lost my top performer. We were on a ski trip with a few other team members in Colorado and I was using his laptop to plan our route. I happened to see a message pop up on his computer asking him for final confirmation that he was going to accept an offer he had received at another company.


We addressed it while hiking up the mountain that morning, and I can honestly say, it didn’t ruin our weekend. In fact, we remain friends to this day. But I couldn’t help but ask: Why didn’t he tell me? How could I have kept him on my team?

I hope you get the opportunity to have a top performer on your team. Not just the person who crushes their numbers, but someone who leads your team in ways that are difficult to measure—someone who consistently breaks records and sets new standards of high performance while also generously sharing best practices and leading your team culturally.

These top performers are invaluable because they’re a multiplier of the people around them, coaching and inspiring others to do better. Losing a person like this is the equivalent of losing two solid performers or an entire team of average sellers.

So, what do you do when you have a team member like this? You work your butt off to keep them.

My friend, and top performer, still says there was nothing I could have done to keep him. I’m still not sure that’s true.

Nine ways to engage a top performer

  1. Talk about career aspirations often. Make their aspirations a focal point of your 1:1s. Talk to them more about their growth and less about their results.
  2. Create development plans. Don’t just talk about aspirations—write down goals and timelines in a shared document and check in on that document at least twice a month. Since their sales performance is on point, focus almost exclusively on helping them continue to find work that gets them excited. And don’t commit to anything you can’t deliver.
  3. Increase their visibility. Depending on the size of your company, this could mean getting them a 1:1 with the CEO, dinner with your Head of Sales, time with a cross-functional executive, or even lunch with a board member. They know you value them—help them see their impact on the company as a whole.
  4. Send them to industry conferences or events. Apart from these typically being fun trips, it’s a simple way to show you are invested in their development. Ask them to report back with insights and to share their findings with the team.
  5. Grow them into leadership. Some (and I truly mean some) top performers will make your next great leaders. When you recognize that potential, start giving them chances to lead. Make them your official coverage plan when you’re out of office. Have them mentor new team members or up-and-comers from other departments. You might even slice off a few reps and create a pod that they can lead in a player-coach format.
  6. Find ways to tap into their skills to improve the performance of the entire team. Not all top performers are destined for leadership; some just want to sell and enjoy being an individual contributor. Don’t force it! You can still find ways to increase their influence and show that you value their contributions simply by giving them more chances to showcase their talents and ideas. This could mean leading team trainings, being the sales team representative with one of your cross-functional partners, or helping you to refine your talk tracks. In the end, your top sellers will get to begin and end each day doing what they love—selling.
  7. Bring them into decision-making. Give them a seat at the table for key decisions like designing comp plans, setting territories and working on cadences and tests. Having their insights included in some of these projects will make your work stronger and make it clear that their opinion matters.
  8. Don’t punish them for their success. It can be easy to ask more and more from your top performers. They have the capacity, they deliver great work and they never let you down. But make sure you’re not punishing them for their success by piling on more work. If they start carrying the weight of the team (or you), they will come to resent it. Instead, find ways to give them more recognition and compensation to reward them for their amazing work.
  9. Encourage them to go after a new market or new target customer. To help avoid burnout or stagnation, continually identify new challenges that your top performer might want to tackle. In the process of pursuing new growth opportunities for your business, their skills will be challenged, they’ll grow, and because they’re so good, they’ll probably deliver.

Engagement that leads to retention

Don’t try all nine of these angles on one person. You should know your team well enough to understand which will resonate with them, so pick and choose.

Be open. Be vulnerable. And with a little luck, your efforts to engage will result in your top performers sticking around.

Phil is a Operating Principal at Mainsail Partners. He leads the firm’s Center of Excellence for Sales and is responsible for helping Mainsail’s portfolio companies optimize their growth strategies and deploy sales practices.
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