The Sales Leadership Pyramid
- Heather Tenuto
- Nov 3, 2025
- 1 min read
I told a struggling VP of Sales: "You used to be Michael Jordan. Now you need to be Phil Jackson."
If you remember the Chicago Bulls Dream Team, you know exactly what I mean.
Here is the trap I see over and over again in sales organizations:
→ The best salesperson gets promoted to manager.
→ They thrive… until the team grows past 8 or 9 people.
→ Suddenly everything breaks.
The reason for that is…
Role confusion.
Selling and leading are not the same job.
You have to move from "I do, you help" to "you do, I watch."
Most never make that transition.
→ They keep trying to be the star player instead of the coach.
→ They jump in to close deals instead of teaching others how to close.
→ They know HOW to sell, but they never learned how to teach it.
That is when you need to sit down with your Michael Jordan and have an honest conversation.
You can be the best salesperson and a solid coach for a small team. But you might not be the person to manage an entire franchise.
And that is perfectly fine.
Promotions in sales don't work like anywhere else. You don't just get better at the same thing - you have to be better at something completely different.
The best individual performers aren't always the best leaders. And the best leaders aren't always the best at doing the work.
Figure out which one you are, and what skills you need to work if something else is what you want.





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