The best leader I ever worked for made his team worse

Years ago, I was a Vice President at a top Wall Street investment bank. Our Managing Director was a guy I’ll call Derek.

Derek was brilliant. Engineering mind, deep technical knowledge, the kind of person who could look at a broken system and just see the problem. When someone on the team got stuck, Derek didn’t schedule a meeting. He walked over, sat down at their desk, opened the code, and debugged it himself. Line by line.

And the bank rewarded it. Derek was the model. Hands-on. In the trenches. A leader who “gets it.”

In fact many banks followed the model of the hands-on leader and celebrated it.

But there was a downside. His team had stopped thinking!

Why? Because every problem eventually landed on Derek’s keyboard. The fastest path to done was waiting for him. So they waited. Smart, capable people, waiting.

I want to tell you I saw it clearly at the time. I didn’t. Because for years, I led the same way. I thought being the person with the answer was the job. It took me embarrassingly long to notice that the more useful I felt, the less my team grew.

Bill Joiner has a name for this. He spent decades researching leaders and found they operate at five distinct levels. Derek and I were both at level one. Experts.

Level 1 is the Expert. You lead through knowledge. You’re the answer. Steve Ballmer’s Microsoft was this at company scale. all the talent, all the technology, and a culture where information flowed up to one brain at the top. When mobile exploded, Microsoft had the teams, the expertise except a way to think together and they failed.

Consider this. If your team stopped bringing you problems and started bringing you finished decisions, would that feel like relief or like losing your job?

Mine was “losing my job,” and I didn’t like admitting it.

Now imagine Derek had a leadership coach. A coach wouldn’t tell him he’s wrong to know his stuff. A coach would ask, after the third time he personally debugged someone’s code: “What did that analyst learn from watching you fix it versus what would they have learned if you’d asked three questions instead?” A coach sees the cost you can’t: every fast answer today buys a more dependent team tomorrow, and eventually your own growth caps out because you can’t scale into bigger problems while every small one still needs your hands on the keyboard.

Many of us are so busy to look for a good leadership coach. So how can AI help?

Here’s the AI version. Tonight, pick a real problem you solved today by giving someone the answer, and run this:

"I solved a work problem today by giving my team the answer directly, or by doing the work myself. Here's what happened: [describe it]. Ask me five questions that would have helped my team arrive at that answer themselves. Then ask me, one by one, why I didn't ask those questions in the moment."

Don’t just read the five questions. Answer the “why.” You’ll land on “it was faster” or “I wasn’t sure they’d get there” and that belief is the actual thing keeping you at this level.

Level 2 is the Achiever. This is where most successful leaders live, and it looks like winning.

Later in my career, at one of the largest global banks in the world, I watched a Technology Executive Director I’ll call Corey. The bank was behind on modern engineering practices, and Corey built a strong team that swooped in whenever another group hit a hard problem. Very visible. Very public. It worked. Corey and his team rose fast.

But the teams he rescued never got better. They just learned to call Corey next time.

That’s the Achiever’s blind spot. You’ve stopped solving everything yourself. You’ve built a machine. But you’re still the engine. Jack Welch’s GE ran this way for decades: the most valuable company on earth, right up until the world stopped cooperating with the plan and the organization had no way to adapt without the top telling it how.

The tell: do you walk into meetings with the outcome already decided, using the room to get buy-in for a call you made alone an hour earlier?

A coach watching Corey wouldn’t tell him to stop being ambitious. A coach would ask one question: “A year from now, is the team you helped still calling you every time this problem comes up OR can they handle it without you?” That question forces a measurement Corey never thought of “did we leave capability behind.”

How would a leadership coach help Corey would push him toward something that feels like giving away ground: Teaching the struggling team to fix it themselves, even if it’s slower, and letting their manager of the other team take the visible win.

How can AI become a thought partner for Corey?

"My team solved a hard problem for another part of the organization, and here's how we made sure leadership knew: [describe it]. First, tell me honestly whether the other team walked away more capable, or more dependent on us. Second, was my primary goal building their capability, or building our reputation? Don't soften this."

It stings the first time you see the answer written back plainly. The sting is the signal it’s working.

Level 3 is the Catalyst. About one in ten leaders gets here.

At that same global bank, an Executive Director I’ll call Guru was handed cloud adoption for the entire organization. Every geography. Every product team. He could have built an elite squad to do every migration personally: Consider the Corey playbook, at scale.

He didn’t. He handed ownership to local teams in each region and kept asking one question: what do you need to solve this yourselves? He structured the change using Kotter’s 8 steps and then got out of the way. Cloud adoption succeeded at a scale no hero team could have touched.

Satya Nadella did the same thing with all of Microsoft in 2014. No bold ten-year plan. He killed the stack ranking that made colleagues compete with each other, rewired the culture around learning over knowing, and pushed decisions down. Market cap went from $300 billion to over $3 trillion.

The shift is one sentence: your job is not the answer. Your job is to build capability around you.

Even Guru would benefit from a leadership coach because Catalysts have their own trap. A coach would ask: “Where are you still the single point of failure, at a higher altitude?” You can stop fixing code and still become the person who has to personally rally every region, which means the transformation still depends on you showing up in every room.

A leadership coach would help Guru map which geographies had genuinely internalized ownership versus which were just complying because he kept pushing and redirect his energy to the stuck ones. The coach would also name the quiet cost of this level: Catalysts often feel invisible, because the credit lands on the local teams. The moment you start craving the credit back is the moment you slide toward hero mode again.

The AI version, before your next initiative that spans teams you don’t control:

"I'm leading an initiative that requires several teams outside my direct control to succeed. My instinct is to [describe what you'd naturally do send in experts, take over the hard parts]. Instead, give me four ways to structure this so those teams build genuine ownership, even if it's slower and messier than me handling it directly."

Then, mid-project, go back and ask: “Where did I genuinely hand over ownership and where did I say I was handing it over, but quietly stepped back in anyway?” That second question catches the backslide while you can still correct it.

Level 4 is the Co-Creator. Rare enough that you’ve probably never worked for one. Other leaders treat your problems as their own without being asked, because the ownership is genuinely shared.

Think about this: If you disappeared for six months, which of your relationships would hold, and which would quietly fray? The frayed ones were never great partnerships.

A coach at this level stops teaching and starts pressure-testing: is the shared ownership you’ve built durable, or does it secretly depend on your presence to hold together?

The AI version:

"I lead a team that collaborates closely with three other departments. [Describe what it would look like, in concrete behavior], if those departments felt full ownership over our shared outcomes. Then tell me which relationship I'm managing transactionally that I should be treating as a genuine long-term partnership."

Run it monthly. Track whether the relationships are deepening or just staying politely functional.

Level 5 is the Synergist. Joiner found it so rare it’s barely worth chasing. I mention it so you know the ceiling exists. Catalyst is the real target, and it’s hard enough.

Now, the uncomfortable part.

Under pressure, everyone slides down. The Achiever starts micromanaging. The Catalyst starts controlling. Tight deadline, real stakes, and the old version of you shows up — and your team notices faster than you do. They always do.

Almost everyone rates themselves a level higher than their behavior shows. I did. The gap is nearly impossible to see from inside, because Expert feels like competence and Achiever feels like leadership.

So I built a way for you to self rate yourself. It’s a free 10-question free assessment. It will take two minutes, tells you which level your actual behavior points to, and gives you the coaching moves and the AI prompt matched to your level. I was surprised when I tried it.

Take it, then reply and tell me where you landed. I read every response, and I’m collecting the results for a future issue.

P.S. The prompts above are a mirror, not a coach. A mirror shows you the gap; it can’t practice closing it with you. If your result stings and you want live support real scenarios, people in the room who catch your Expert habits as they happen then join my Certified Agile Leadership workshop (CAL-1, certified through Scrum Alliance)

Reference:

Leadership Agility by Bill Joiner and Stephen Josephs