⚙️ Ops Playbook #69

Why most leadership training is just expensive theater

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⚙️ Hi Operator,

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As we wrap up the year, let’s talk about how to develop your leaders.

P.S. Knock knock, are you there? Don’t be afraid to say hi!

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  • There’s an alternative to leadership development (Chief Learning Officer)

  • 8 outdated leadership styles to avoid (The Hub)

  • Five reasons leadership training fails (Forbes)

  • Leadership Development is failing us. Here’s how to fix it (MIT)

  • The plague of mediocre leadership (Time)

Why most leadership training is just expensive theater

Insight from Jessica Kriegel

Last year, I sat through a leadership training that made me want to bang my head against the wall.

You know the type - some consultant with perfect hair flipping through slides about "emotional intelligence" while everyone pretends to take notes on their laptops (but are actually checking email).

We spend billions on leadership training every year. And what do we get? A bunch of managers who can recite frameworks, but freeze up when real problems hit their desk.

I've been on both sides of this - I've attended the fancy workshops and I've run teams where theory meets reality.

Here's what I've learned: real leadership has nothing to do with what happens in training rooms.

Take what happened at Microsoft under Nadella.

Instead of making managers sit through another death-by-PowerPoint session about "cross-functional collaboration," they created hack teams. Teams tackled actual business problems, from cloud infrastructure to new product development.

Some of these teams crashed and burned. Others cracked problems that had stumped the company for years. But every single person came out the other side as a real leader.

Want to build real leaders? Stop with the theoretical BS. Find the ugliest, scariest problem in your company - the one that keeps your executives up at night:

  • That market shift that could kill your core product

  • The culture mess from your latest acquisition

  • That digital transformation everyone keeps talking about but nobody wants to touch

Now hand that problem to your rising stars. But here's the key - you need to:

  1. Give them real power to make decisions: Not just suggestions, but actual authority to implement changes

  2. Back them with actual resources: Budget, team members, and tools to get the job done

  3. Connect them with senior leaders: Mentors who guide but don't take over

  4. Set clear boundaries: Define what success looks like, but let them figure out how to get there

  5. Create timeline pressure: Set ambitious but achievable deadlines

Some of these projects will fail. When Intuit launched their "Innovation Catalysts" program, they celebrated failed experiments as much as successes.

Because a leader who's never failed is just someone who's never tried anything hard.

After each project, gather your team and ask three essential questions:

  • What worked and what didn't?

  • Which assumptions proved wrong?

  • What would you do differently next time?

Real leadership is about having the guts to make real decisions when you're not sure what's going to happen next.

So please, stop with the corporate theater. Take your biggest problems and turn them into leadership bootcamps.

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