From BorrowMyDoggy to Healthcare CTO: Les Cochrane on Asking for Help and Cognitive Offload

Season 1, Episode 23 • 58:50

From BorrowMyDoggy to Healthcare CTO: Les Cochrane on Asking for Help and Cognitive Offload

Welcome back to I'm a Software Engineer ~ What Next? The podcast for devs figuring out their next move. Hosted by James Wilson and Matt Sinclair, we talk honestly about what it takes to build a meaningful career in tech.

This week we're joined by Les Cochrane, CTO at Practice Toolkit, building software for GPs inside the NHS. Les started in hardware, networks and second-line IT support, switched to interactive media at uni, did UX before anyone called it UX, taught himself the backend on a Rails app he built to replace the FTP site at a marketing agency, and then co-founded BorrowMyDoggy on the back of a weekend hackathon. After that: contracting, leading 24 engineers in sports data at IMG Arena (including being the employee rep when they had to let go of about 180 of them), and now CTO at a healthcare startup learning what compliance means for the first time.

In this episode, we cover:

  • Validating his startup that he co-founded (BorrowMyDoggy) by sticking posters up on Hampstead Heath and having someone in Exeter sign up within 24 hours
  • What happens when 4,500 people sign up in an hour to a landing page that doesn't have a working search yet
  • Why "I need help" is the wrong way to ask for help, and what to say instead
  • Product engineer vs T-shaped vs Kent Beck's paint-drip people, and why time matters in the metaphor
  • Going from leading 24 engineers to being the employee rep during a 180-person redundancy
  • AI as a force multiplier "for good or evil" — and why introducing it into a six-month-release shop won't help
  • The LLM-generated PR quiz that makes you answer 10 questions about your own checked-in code before it merges
  • Centaur chess, supertanker captains, and Kahneman's type-3 thinking: cognitive offload and what we lose

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