The Flak Jacket

The thing that kept my Microsoft team going during a brutal seven-month project wasn’t what you’d expect.

I was leading a digital marketing team responsible for a major launch.

The stakes were high.
The pressure felt relentless.

We spent way too many late nights eating bad pizza in Building 18 conference rooms.

A couple of months in, one of my team members suggested we create a rotating award—something fun, fast, and ideally free—to lift morale.

Everyone brought ideas.

The one we picked? A flak jacket.

Each month, it went to someone who had stepped up to take on a tough challenge.

(To be clear, this was not a participation trophy.)

The winner got to:

→ Add their own flair - a pin, a patch, whatever made it theirs
→ Nominate the next recipient

The jacket did its job and then some.

If this were today, it would probably have its own TikTok account.

Here’s what I learned:

When you’re leading through sustained pressure, you can’t expect people to hold their breath until the big finish.

Progress markers matter.

Each small win gives your brain a dopamine hit that says, “This matters. Keep going.”

That’s how you build teams with long-haul capacity.

The ability to keep showing up, even when the road is long and the goal feels far away.

That launch became one of dozens I worked on at Microsoft.

But I still remember the flak jacket.

So much that I’ve shared the idea with coaching clients ever since.

One Seattle team created the Whale Award—a stuffed orca.
A startup uses a vintage coffee mug.
A construction team passes around a tin monkey in a hard hat.

Different tokens. Same purpose.

They remind us that small moments of recognition create the fuel to keep going.

So, I’ll ask you this:
What’s your team’s flak jacket?

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When Your Help Stops Helping

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When Your Strength Becomes Your Stranglehold