Show Notes
Coding Chats Episode 81 - Ben Howdle talks to John Crickett about being a first time CTO in a start-up. Ben, author of The First CTO, shares what changes when you move from building technology to leading a technical team: the pressure, the trade-offs, and the realization that writing code is only part of the job.Drawing on startup experience and lessons learned the hard way, Ben discusses how to balance quality against runway, manage people, and communicate technical decisions in terms that founders and other non-technical stakeholders can understand. He also explores why resourcefulness, resilience, and comfort with ambiguity matter so much—and why CTOs often spend more time selling ideas than they expect.Whether you’re stepping into your first CTO role or leading a technical team at an early-stage company, this conversation offers candid insights into the realities of technical leadership.
Chapters 00:45 The Loneliness of the CTO 16:57 Essential Skills for a First-Time CTO 22:53 Understanding the Hierarchy: Who is the Boss? 30:14 The Importance of Advisory Network 38:06 Transitioning to People Management 44:27 Understanding the 40% Rule 52:54 Exploring Related Content
Ben's Links: https://www.linkedin.com/in/ben-howdle/
John's Links: John's LinkedIn: https://www.linkedin.com/in/johncrickett/ John’s YouTube: https://www.youtube.com/@johncrickett John's Twitter: https://x.com/johncrickett John's Bluesky: https://bsky.app/profile/johncrickett.bsky.social
Check out John's software engineering related newsletters: Coding Challenges: https://codingchallenges.substack.com/ which shares real-world project ideas that you can use to level up your coding skills.
Developing Skills: https://read.developingskills.fyi/ covering everything from system design to soft skills, helping them progress their career from junior to staff+ or for those that want onto a management track.
Takeaways Taking on the CTO title without experience can be the thing that forces the growth you wouldn't have sought otherwise. At a startup, runway isn't just a finance metric — it should be the lens every technical decision gets filtered through. The tension between building things well and building things fast enough to survive is one of the defining challenges of being a first-time CTO. The most chaotic, uncertain period of your career might also be the one where you're most alive. A first-time CTO needs resourcefulness, comfort with ownership, and resilience more than any specific technical skill. When you have no one to bounce ideas off internally, build an informal council from your network — it can double as a recruiting pipeline. The quicker you can identify your own blind spots and weaknesses, the quicker you can plug the gaps. Early-career engineers often drown non-technical stakeholders in jargon to mask imposter syndrome — the real skill is meeting people where they are and speaking to business outcomes.
More from Coding Chats
Coding Chats Episode 83 - In this episode, VB from OpenAI’s developer experience team explains why he thinks plan mode is obsolete and how coding agents have shifted from step-by-step instructions to outcome-driven, long-running work. We cover how to write a good agents.md, why tests still matter when agents write the code, spec-driven development, and why cloud agents may be the future of dev tooling.
Coding Chats Episode 82 - John talks with Dave Westgarth, head of delivery at a Databricks consultancy. Dave shares his path from a psychology degree and McDonald's into tech, and they discuss why the Scrum Master role is so misunderstood, how it differs from a delivery manager, and whether either needs to be technical.They also look at how AI is changing delivery work. Faster code just moves the bottleneck upstream, John argues there's no AI-specific skill you can't learn in a day, and engineering fundamentals are what make AI useful.
Coding Chats Episode 80 - start-up advisor Alexander Berkovich shares his expertise on building successful start-ups, hiring strategies, CTO roles, and the importance of communication between technical and business teams. Discover practical tips for navigating the challenges of early-stage companies and how to align technical excellence with business goals.
Coding Chats Episode 79 - Richmond Alake, Director of AI Developer Experience at Oracle, joins John to discuss agent memory — how AI agents store, retrieve, and adapt to information. He argues that developers building memory on flat files are naively reinventing the database, and that once you factor in concurrency, security, and scalability, a proper database is inevitable. The conversation covers the full memory stack and how Oracle's AI database keeps embeddings and data together without shipping sensitive information to external providers.
Coding Chats Episode 78 - John Crickett talks to Robert Harris, an experienced engineering leader. Robert shares hard-won lessons from years of leading software teams, drawing on a distinctive "human systems" lens to explain why so many engineering organisations struggle — not because of bad people, but because of broken systems, misaligned leadership, and invisible cultural forces.