10 Mistakes Enterprises Make When Scaling Agile — and How to Avoid Them

When I walk into a Fortune 500 boardroom and hear, “We’ve adopted Agile,” I brace myself. Usually, what follows is a whirlwind of rebranded status meetings, overwhelmed middle managers, and teams confused about whether they’re sprinting or slowly marching in circles.

Enterprise Agile transformations are rarely short on ambition. But too often, the reality is a mismatched combination of frameworks, tool obsession, and unclear intent. Over the past decade, I’ve led Agile rollouts in healthcare, finance, and tech. These are the ten recurring mistakes I see — paired with practical remedies rooted in experience.

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If You Want Better Stories, Stop Writing Them All Yourself

I’ve talked to a lot of product owners who are drowning in tickets, trying to “get ahead” by writing every single user story themselves.
I used to be one of them. And every sprint, we’d slip. Morale tanked. The team blamed the process, and I blamed myself.

But after one conversation — and one uncomfortable realization — I found a single thread running through every success story I’ve seen since.

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Velocity = The Most Abused Agile Metric Ever

Welcome to the dark side of velocity — the number that started as a planning aid and ended up as a weaponized performance metric, often wielded by people who’ve never touched a user story in their lives.

In this episode, we’ll break down:

• What velocity is supposed to do
• How it gets misunderstood and misused
• Why chasing it kills team health
• And how to bring it back from the dead

Let’s sprint into it. (Pun 100% intended.)

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