August 24, 2025
“I’ve got disappointing news”, I said.
“We’re going with someone else for the Head of Product role.”
I felt Seth’s heartbreak. Seven years at the company. He wanted it bad.
Seth was gifted technically. More studied in the craft than anyone. He excelled in every product role.
But people didn’t like being on Seth’s team.
It started fine, but he’d lose them eventually. Confidence eroded. His team wanted out.
We couldn’t risk this with our Head of Product role. It was too damn important.
So we went external. Hired someone with more experience than Seth. A stronger resume.
They failed within a year.
The role became a revolving door. A joke internally. Then the inevitable happened… Seth quit the company.
This created a huge hole on the product team. Performance tanked.
How did we fuck this up so badly?
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The greatest skill of any leader is developing other leaders.
Yes, we failed Seth. But not because we didn’t promote him.
We failed him because he wasn’t ready to be promoted in the first place.
We never showed him how to manage. We never developed him into the leader he would eventually become (elsewhere).
This pattern kept emerging across our 200+ person team. Internal folks not ready. Hire external. Internal folks quit.
All of a sudden we had a massive leadership development problem on our hands.
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High performance isn’t just about hiring the right people. You also need the right conditions to get the most out of your team.
High Performance = Right People + Right Conditions
Without the right conditions, an A-player at one company will become B or C player at another. And, surprise surprise, one of the top 5 conditions for success is… leadership development. The very roadblock Seth and others ran into at my company.
Last week in Highland I laid out the 5 conditions for success during a Masterclass. Here’s a clip and summary below.
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I. Shared Purpose
Well-defined mission & values set the foundation
But people need to connect their personal ‘why’ to the company’s
This connection gets them through tough spots and hard pivots
And makes them stay when competitors offer more money
Your job? Create opportunities to strengthen this connection!
II. Clear Direction
Clear direction starts with vision, strategy, and annual goals
Then a reliable operating rhythm keeps everyone on the rails
When direction is clear, people stop asking permission
They take ownership & make more decisions themselves
They become mini-CEOs, not followers
III. Aligned Incentives
Misaligned incentives create internal competition, not collaboration
Create a “one team, one dream” mentality
But don’t penalize top performers
Company-wide bonus plans are great tool to do both
50% based on company-performance
50% based on individual performance
IV. Earned Recognition
Undeserved recognition destroys high-performance culture
Your team watches who gets pay raises, promoted early, etc.
Recognition should stem from work and leadership excellence
Not peanut buttered across the company like last place trophies
Individual goals help you measure a person’s work outcomes
Standards help you define & identify top leaders across company
This will bite them in the ass.
V. Leadership Development
Every 12-24 months, your org has completely different needs
Develop the bench-strength so you can promote internally
Build tomorrow’s leaders, today, through training & opportunity
Create succession plans for every critical role, including yours
Accept that some early favorites won’t be right for the next phase
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Yes, hire great people. But don’t ignore your company’s conditions.
It’s the difference between a group of talented individuals and a championship team.
Till next time,
Never say die 🏴☠️