Helping Tech Leaders Grow Through Conversation
When I announced my transition into independent work in Spring 2024, one of the first people to get in touch was Martin Baker, someone I’d first worked with back in the early 2000s during my days at Epic. At the time, Martin had brought my team in to build a Moodle site for the Charity Learning Consortium. Two decades on, he reached out again, this time with a different kind of request: would I mentor his Head of Technology, the brilliant and fast-rising Josh Wilcock?
Josh was a talented web developer who had stepped into a technology management role in a small but ambitious organisation. He had a few developers reporting to him, multiple internal stakeholders to support, and some significant technology decisions to steer. It’s a role that demands equal parts technical understanding, leadership, communication, and confidence, and often, you’re expected to develop those skills on the job.
A sounding board when it matters most
For someone leading technology in a growing business, having access to an external sounding board can be really useful. Josh and I met for about an hour every couple of weeks. Our conversations ranged from architectural direction and product planning to team dynamics, prioritisation, and how to effectively communicate decisions to the wider organisation.
What I offered wasn’t prescriptive “do this, not that” advice, but a space to explore options to test ideas, challenge assumptions, and bring perspective from someone who has been through similar transitions. After 20 years managing software teams, building products, and leading learning-technology services, these conversations felt natural and energising. And, judging by Josh’s feedback, they genuinely helped him navigate the role with more clarity and confidence.
The impact
The mentoring didn’t need to be time-intensive to be valuable. Just a regular cadence of conversations provided momentum and structure. Josh used the sessions to reflect, plan, and troubleshoot. I learned lots too – not just about Josh’s passion for home automation and solar technology or the latest Moodle product improvements – but I was reminded how much I enjoy supporting people with talent and ambition to accelerate their growth, and to play a small part in that development.
An unexpected but welcome direction
I hadn’t originally set out to offer mentoring as part of my independent work. But this experience reminded me how much I enjoy coaching emerging technology leaders, especially in mission-driven organisations like those in the learning and nonprofit sectors. Helping others navigate leadership, technical strategy, and team challenges is something I’ve done throughout my career, and doing it more intentionally now feels like a natural evolution.
Long story short, I’m up for working with more people like Josh. If you’re moving into a tech leadership role in the learning or social-impact space and want to engage a trusted outsider to talk to, I’d be delighted to help…