Execution trap

Why you’re getting this: I'm Cat. 20+ years in Design, currently at Amazon. This newsletter is honest advice on design, influence, and career growth in big tech.

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I recorded a podcast back in May with Beyond UX Design. The episode is called “The Execution Trap Nobody Warns You About,” and it’s the most direct I’ve been about the years I spent doing beautiful work that nobody noticed.

On the podcast, I walked through a real example: a $7.8 billion opportunity that sat in plain sight for years because everyone assumed it wasn’t worth the trouble. It wasn’t. It was worth almost everything. I’ll let the episode tell you how we found it, and what it took to convince a room full of people who’d already written it off.

If you’ve ever built something excellent and watched it disappear into a system that never asked what you thought, this conversation is for you.

The better you get at delivering, the more delivery you're handed. Eventually you’re so busy building things well that no one thinks to ask whether they should be built at all. The way out wasn’t being a better builder.

It was five tenets I built, mostly by trial and error, to force my way back into the decisions that mattered.

The 5 Tenets

1. Smallest testable truth over comprehensive plans.
   When facing ambiguity, resist the urge to map everything before moving. Find the smallest version of your idea that can generate real signal, a concept, a conversation, a prototype and let evidence build conviction. Comprehensive planning in uncertain spaces is often procrastination disguised as rigor.
2. Customer truth is the only tiebreaker.
   Opinions in a room are just louder opinions. Data settles what conviction alone can’t.
3. Achievable now beats perfect later.
   When new technologies, expanded scope, or “dream state” visions threaten to stall progress, ruthlessly descope to what’s shippable. Momentum creates clarity; waiting for perfect conditions creates drift. You can always iterate toward the vision, you can’t iterate on something that never launched.
4. Alignment is shared problem definition, not shared solution agreement.
   Don’t try to get everyone to agree on how to solve something—that’s often impossible across orgs. Instead, invest in aligning on what problem you’re solving and for whom. Once stakeholders share a problem definition, multiple solutions can coexist and compete on merit.
5. Invisible problems are the biggest opportunities.
   The most valuable work often looks like questioning assumptions everyone else has accepted. If a problem feels “normal” or “just how things are,” that’s a signal to investigate. The billion-dollar opportunities aren’t hidden—they’re sitting in plain sight, unexamined.

How the Tenets Create Tension

The reason tenets work is they tiebreak, forcing you to choose. Tenets tell you what to prioritize. But you also need to know where to focus and that requires knowing which altitude the current problem requires.

Tenet 1 vs. Tenet 2: ‘Should I ship fast or research more?’ Ship something that generates customer truth, not just internal opinions.

Tenet 3 vs. Tenet 5: ‘Should I execute on the known problem or explore the invisible one?’ Depends on your leverage. If you have momentum, ship. If you’re between initiatives, investigate.

Tenet 4 vs. Tenet 1: ‘Should I align stakeholders or just start testing?’ Start testing if alignment is stalled; use the results to create alignment.”

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Have a great week ahead,