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Coding Chats · October 8 · 53 min

I took CTO title not knowing what I was getting into

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.

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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.

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