Today's guest is Joel Chippindale!
Joel is a full-time CTO Coach and one of the coaches-in-residence in the Refactoring community, where he runs monthly mastermind sessions and other community events.
With Joel we dived into what coaching is, the difference with mentoring, one-on-one versus group coaching, and what are the top challenges that CTO faces today.
🎙️ Episode
You can watch the full episode on Youtube:
Or listen to it on Spotify, Apple, Overcast, or your podcast app of choice.
🥇 Interview Summary
If you are a 🔒 paid subscriber 🔒 you will find my own summary of the interview below.
It’s the 10-minute, handcrafted takeaways of what we talked about, with timestamps to the relevant video moments, for those who don’t have time to sit through the 1-hour chat.
Here is the agenda for today:
🧠 Coaching vs. Mentoring (05:22)
👥 Individual vs. Group Coaching (10:10)
🏢 The CTO's Relationship with the Executive Team (21:44)
💬 Advocating for Technical Work (25:44)
🔄 Delegation and Team Development (39:14)
And links to the things Joel mentioned:
Let's dive in 👇
1) 🧠 Coaching vs. mentoring (05:22)
Joel begins by making an important distinction between mentoring and coaching – two approaches often confused but fundamentally different in their philosophy and execution.
Mentoring is based on learning from someone with different experiences than yours, leveraging their knowledge to accelerate your learning. In contrast, coaching starts from the assumption that you're already capable and resourceful.
"Coaching comes from a place of assuming that you're a capable and resourceful person. And therefore, most of the answers to your challenges are already in your head somewhere. They just need help getting out."
As a coach, Joel creates a thinking partnership to help CTOs become clearer about themselves and their situations, challenge self-limiting beliefs, and examine available options for change.
🤝 Trust-based partnership — Unlike mentoring, coaching isn't about giving advice but helping clients discover their own answers.
🔍 Self-discovery process — The coach guides clients to uncover solutions that are already within them, making outcomes more sustainable.
🌱 External perspective — Senior leaders like CTOs often lack peers within their organization who can provide unbiased support without evaluation.
2) 👥 Individual vs. group coaching (10:10)
Joel outlines the key differences between one-on-one coaching and group coaching, each offering distinct benefits for CTOs. One-on-one coaching provides personalized attention and deep focus on individual needs:
