The Feedback You Don't Notice You're Getting

From the Travel Tech Podcast newsletter for episode 28, The Feedback You Don't Notice You're Getting.

This week I handed the microphone to the two people who know exactly where the bodies are buried: Adrian McKenzie and Oli Deakin, my leadership team colleagues from Snowflake Software (in its second phase). I'm the one answering questions this time, in front of those of you who read this newsletter every week. I wanted that discomfort on the show.

The two people asking the questions spent years building a UK software company with me from scratch, then went their own ways not just post acquisition but after the subsequent handful of years in corporate life. One now runs a leadership practice built on the idea that you should be kind, not nice. The other advises heads of technology on building strategies that outlast next quarter's roadmap. Apple Podcasts, also streaming on Spotify and YouTube.

The conversation kept circling back to the same fault line: the discipline that gets you through a corporate career is not the same discipline that lets you build something from nothing outside of it.

Closer to the edge

That tension has a structural cause. Big organizations layer review gates, sign-offs, and stage checks between any individual and a costly mistake, the same kind of process that might route a single system change through several review boards before it ships at a large aviation or travel enterprise. Strip those layers away and every decision, good or bad, lands on you directly.

AI is adding a new pressure to that equation. Alex pointed out that a solo operator can now do in weeks what would have taken a funded team two and a half years ago, and he expects a wave of new founders to test that math over the next few years. It's working well for scoping, drafting, and shipping software fast. It's working less well, so far, for the judgment calls and difficult conversations that still need a human close to the edge.

Adrian McKenzie and Oli Deakin join Alex Brooker, founder of Airside Labs, for a conversation covering the difference between being kind and being nice, the book Alex is writing about his early days of Snowflake Software, why most CTOs lack a real multi-year technology strategy, and what changes once you trade a corporation's safety net for direct exposure to every decision.

Key Takeaways

• Kind, not nice: Conflict avoidance is a poison in any organization, and real kindness sometimes means having the conversation you'd rather skip.
• The feedback you don't notice: The most effective feedback often doesn't register as criticism until you look back on the conversation later.
• The coding ceiling: Every founder hits a point where the problem is too big to solve alone, no matter how good the code is.
• Missing tech strategy: Most technology leaders spend their time on what's in front of them rather than building a plan tied to where the business needs to be in three to five years.
• Proximity to risk: Leaving a large corporation swaps procedural protection for direct exposure to every decision, and some people find that trade energizing rather than stressful.

Talk soon,
Alex Brooker, Host of the Travel Tech Podcast, Founder of Airside Labs