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Why your best salespeople quit (and it’s not about money)

ChatGPT Image Jul 31, 2025, 10_03_51 AM

NOTES FROM NORTHWOOD 

Hey there…

Last week, a CEO called me frustrated. His top performer just gave notice.

“I don’t get it, Adam. We pay him well. He’s got great territory. He was killing it.”

Then he told me the real story.

This rep had been asking for coaching. Wanted help on bigger deals. Kept getting told “you’re doing fine, just keep doing what you’re doing.”

Meanwhile, the B and C players were getting all the attention because they were struggling.

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Here’s what most leaders miss about top performers

Your A-players don’t want to be left alone. They want to get better.

Think about it: Would Tiger Woods tell his coach “thanks, but I’m good” just because he was winning tournaments?

Of course not. The best performers are often the hungriest for improvement.

But here’s what happens in most sales organizations:

  • Top performers get ignored (they’re “self-sufficient”)
  • Struggling reps get all the coaching time
  • Management focuses on problems instead of excellence
  •  A-players start feeling undervalued and unchallenged

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The real cost of losing your best people

When your top performer leaves, you don’t just lose their production. You lose:

Revenue Impact: That 20% producer who drives 40% of your results

Knowledge Transfer: Years of relationship building and market intelligence
Team Morale: Other high performers start questioning their future

Replacement Cost: 6-18 months to get someone to that level (if ever)

I’ve seen companies lose $2-3 million in pipeline when their star player walks out the door.

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What great sales leaders do differently

The best sales managers I work with flip the script entirely.

They spend MORE time with their top performers, not less. Here’s how:

Strategy Sessions: Monthly deep dives on their biggest opportunities

Skill Building: Advanced training on complex deal navigation
Challenge Creation: Stretch assignments and bigger territories

Recognition: Public acknowledgment of specific achievements

Career Pathing: Clear discussions about their next level

One client started doing quarterly “A-Player Summits” where top performers share strategies and get advanced training. Retention went from 60% to 95%.

The bottom line? Your best people don’t want to coast. They want to grow.

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A simple test for your sales organization

Ask yourself: In the last month, how much quality time did I spend developing my top performers?

If the answer is “not much,” don’t be surprised if they start looking elsewhere.

High performers go where they can grow. If that’s not with you, it’ll be with your competitor.

Adam Boyd