We built what looked like the perfect new team.

Small. Cross‑functional. Smart people from across the company.

They were asked to create a brand‑new service the company wanted to offer.

We thought, “This is how we transform the business.”

It didn’t work.

The team was shut down.

I was sick to my stomach for letting them down as their coach.

Looking back, the biggest lessons were not about the approach or framework we used.

They were about leadership.

Here’s what happened, and what you can use in your own company.


The “Dream Team” We Built

We pulled the best people from:

·      Engineering
·      Sales
·      Marketing
·      Business development
·      IT

We made one small, cross‑functional team with clear roles and responsibilities.

We set a clear vision and goal.

We created a list of work.

We planned in short cycles (sprints).

We reviewed results often.

We held regular retrospectives to improve how the team worked.

On paper, this was everything a “modern” team should be.

It still failed.


What Went Wrong

Three big things killed this effort.

None of them were about effort.

All of them were about leadership.


1. “You’re Empowered”… But We Don’t Really Trust You

Senior leaders said they wanted to empower the team.

But they never set clear outcomes.

The team would move forward, thinking they were doing the right thing.

Then leadership would swing back in and say:

“Nope, that’s not what we want.”

This created a false sense of empowerment.

The team felt:

·      “We own this”… until someone above changed the rules.

·      “We’re trusted”… until a surprise “No” appeared.

Over time, they got confused and discouraged.


Leadership lesson:
​
You can’t just say, “You’re empowered.”

You must:
·      Define clear, simple outcomes in business terms
·      Agree on what success looks like and what will not change
·      Give the team room to make decisions inside those guardrails

Empowerment without clarity is not empowerment. It’s a trap.


2. A Hard Conversation… Then “Kill It Now”

After several months, pressure was high:
·      Leadership was unhappy with progress.
·      The board was asking, “Where are the results?”
·      The team felt like they were failing.

We held a retrospective with leadership in the room to ask:
·      What’s working?
·      What’s not working?
·      What should we change?

The team finally spoke openly:
·      The goals were unclear.
·      Priorities kept changing.
·      They lacked a proper support from a specific business unit.

This was a golden moment.

It could have been the turning point.

Instead, leadership listened… and decided:

“Disband the team. Kill it and kill it now.”

The team was crushed.

(Many of them even told me later they planned to keep working as if they were still a team.)

But once leadership pulled the plug, the energy died.

The structure that was helping them improve was gone.


Leadership lesson:
​
When a team finally tells you the truth, that is not a sign to kill it.

That is a sign to listen and adjust, not abandon.

Better questions at that moment would have been:
·      “We hear you. What would you change?”
·      “If you could fix one thing that would unlock progress, what is it?”
·      “What do you need from us to succeed?”

Instead of making a business‑model change, we made a team‑execution change.

We fixed the wrong thing.


3. The Personal Side: As a Leader, I Felt Like a Failure

When the team was shut down, I was wrecked.

I felt like:
·      I had let the company down
·      I had let the team down
·      I had failed as their coach

My heart hurt. My pride took a hit.

But that pain became one of my most useful lessons.

Here’s what I now do differently with CEOs and business owners:
·      I set clear expectations with leaders up front
·      I warn them that these tensions will show up
·      I explain that saying “We empower teams” means changing how you lead, not just changing how teams work
·      I push leaders to stay with the team when it gets hard, not pull the rug out

That failed team taught me more than any success story.


4 Questions to Ask Before You “Kill” a Team

When you’re under pressure from boards, customers, and your own doubts, slowing down feels risky.

But shutting down a team too soon often costs more.

Before you make that call, ask yourself:

1.    Have we given them clear, fixed outcomes to hit?

Or are we changing our minds every few weeks?


2.    Are we solving the real bottleneck?

Is this a product, delivery, or sales problem?


3.    Have we truly listened to the team’s view from the ground?

Or are we reacting from the boardroom only?


4.    Have we asked, “What would you change?” before saying, “We’re done”?

The best ideas to fix the system often come from the people in it.


The Principle That Matters Most

Frameworks, methodologies, processes – these are just tools.

The core principle is simple:

If you say you empower people, you must actually trust them, support them, and listen when they tell you the truth.

Your legacy as a CEO or owner won’t come from one “perfect” team.

It will come from how you respond when a good team struggles.

That’s where real culture is built.

​That’s where real leadership shows up.