May 11, 2026
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Microsoft just spent millions proving the bottleneck is culture. Here’s what to do about it.
Microsoft’s 2026 Work Trend Index dropped this week with a finding that should make every AI vendor uncomfortable:
The biggest barrier to getting value from AI isn’t the technology. It’s not the workers. It’s the organizational culture around them.
They call it the “Transformation Paradox.”
Sixty-five percent of AI users fear falling behind if they don’t adopt fast. But forty-five percent say it feels safer to just focus on current goals. And only thirteen percent say their company rewards reinvention with AI — even when it works.
Every culture is a game.
Not metaphorically.
Structurally.
A game has four properties:
Now run your company’s AI adoption through that filter.
What is it?
“Use AI more” isn’t a goal.
“Become AI-native” isn’t a goal.
Those are vibes.
A real goal looks like this:
Reduce time-to-first-draft on client proposals from three days to three hours.
That’s a game worth playing.
Do your people know what’s allowed?
Can they experiment with customer data?
Can they use AI to draft external communications?
Can they build their own workflows?
In most companies, the answer is some version of:
We’re still figuring that out.
Which means the rules are vague.
And vague rules produce the same result every time: people default to what’s safe and familiar.
How does anyone know if their AI experiment worked?
Microsoft found that only thirteen percent of workers are rewarded for reinvention. That means eighty-seven percent are playing a game with no scoreboard.
Imagine a basketball game with no score display.
You’d stop playing hard pretty fast.
Are people choosing to engage with AI, or are they being told to?
There’s a massive difference.
Mandated adoption creates compliance.
Voluntary adoption — fueled by genuine curiosity and a visible upside — creates momentum.
Microsoft’s data shows that the highest-performing AI users, the “Frontier Professionals,” aren’t just skilled. They’re in environments where they chose to experiment and were supported when they did.
Before you buy another platform, design a better game.
August 29, 2025
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You must try out his amazing social / party game: Casting Call the Game.
October 14, 2024
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I learned a lot about how to create WOW experiences during my tenure at Zappos. And now I’m applying them to the sales experience (specifically for outbound sales calls with a complex sale).
I’ve developed this sales game (below) that can be used in:
a) Training / Role play
b) On live calls
c) During coaching / mentoring
The game dynamics work so that:
1. The win isn’t just closing the sale. You get a point score at the end of it to track progress over time.
2. The player can see what stage of the process they get stuck on (when they collect the coins at the end of the day), so they know how to ask for coaching help.
3. You see you’re in the sales flow vs when you’re in pure rapport building or objections smashing.
4. You learn how to rapidly smash objections through the additional card game
5. It takes what can be a long and boring sales script and turns it into a fun and engaging game.
Have you thought about creating a game out of your process.
I’d love to help you. Let’s talk (click here)
April 22, 2024
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Here’s my opener for Zendesk…
