“Enhanced visibility and awareness of who you are and what you do is a superpower that can be missed by leaders who are too insular and inward-focused.”

Andy Skipper
Hi Andy, welcome to the CTO Craft Spotlight Q & A. The conference is fast approaching, and although the three days will focus on several themes, the tagline is “Digging deep into relationships with other C-level leaders and building your network as an Engineering Leader.”. Can you give us an insight into why you chose these areas?

Hello there! Absolutely – throughout my own experience as a CTO, one of the most powerful strategies I’ve used is to take time to build strong relationships with others at my level in other functions within the company. It can be easy when moving from individual contributor to leadership to see the engineers you’re responsible for as your primary focus, especially if you’ve been a part of the team in the past, but that can be very damaging from an alignment and culture perspective.

As a senior leader, you’re expected to be the eyes and ears of the technical function in the business at large and be the eyes and ears of the other functions in the engineering team – you can’t be purely one or the other without isolating yourself and the team culturally.

Building a personal network is another very important strategy, not just in terms of building a support structure and knowledge-sharing group but in terms of career progression and highlighting the work your team does for the world at large. Enhanced visibility and awareness of who you are and what you do is, again, a superpower that can be missed by leaders who are too insular and inward-focused. It’s not a difficult issue to fix, and it can add massively to how your whole career and work-life play out.

What’s so special about the CTO Craft Conference, and why would you recommend that individuals attend?

As usual, we have dozens of CTOs from the best technology businesses in the world and other industry-best thought leaders who’ve very generously agreed to come and share their insights and wisdom. There’s a great cross-section of leaders from many verticals and company stages from around the world, who we’ve hand-picked to give the most useful and actionable information.

On top of that, we’re taking the professional networking theme of the conference to heart and adding a third day which will be completely focused on interacting with the several hundred other CTO Craft community members and attendees. You’ll be able to share your experiences in an Unconference and join a community-led roundtable.

What’s the most valuable lesson you’ve learned from working with other C-level leaders throughout your career?

As a first-time CTO back in 2006, I flailed about quite heavily because I expected myself to know the solution to every problem, be it technical or human. I think that was partly a severe case of impostor syndrome, partly a lack of understanding of how the role worked and partly a poorly-defined mandate in that company.

As I progressed through other CTO roles, I learnt that the role isn’t about having your finger on every pulse, or being able to fix any problem, either intuitively or through learning. I also learnt that psychological safety and the ability to make mistakes without the shadow of blame were as important for me as my team – I had to learn to give myself that same respect.

When I started coaching CTOs in 2016, I started noticing some very common patterns in CTOs and startups, such as the difficulties first-time leaders face when moving from development without explicitly making that choice and the poor level of support for leaders in early to mid-stage startups who are meant to just get on with it. Armed with those truths, I was able to help hundreds of leaders come to terms with both their roles and their trajectories within their companies and beyond. 

“As I progressed through other CTO roles, I learnt that the role isn’t about having your finger on every pulse.”

What would be your tip/s for successful networking at conferences?

Networking in virtual conferences is notoriously light-touch, and one of the main reasons we’re all dying to get back to in-person events, but having attended several over the pandemic, I’ve made some great connections simply by watching the conversation alongside the main stage and chiming in, and starting one-to-one chats with people whose comments had really stuck with me.

I think we’ve found a much better way to create the opportunity for connecting in the upcoming conference by holding lightning talks and having subject-specific video roundtables which enable attendees to mix with others who have the same interests as them. On top of that, all attendees will be invited to join the 4,500 or so members in our Slack community, which is an amazing place to build connections and learn from each other.

This year is the first CTO Craft Unconference. So why now, and what can attendees expect?

CTO Craft really exists to help engineering leaders learn and evolve by bringing them together and giving them a way to share their experiences, ask for help and talk about the difficulties they experience in a safe space. There’s an absolute wealth of experience among the many thousands of community members, and it only makes sense that we’d bring some of that culture of sharing to our conferences. The unconference is designed to help people both learn and give back.

We’ll shortly be opening a Call for Thoughts for a series of lightning talks on the final day of the conference. There will also be a number of open round tables on various leadership and engineering topics available for anyone to join and get into the conversation. 

Can you explain the Call for Thoughts and what this means for Unconference attendees?

Absolutely. The Unconference day is really exciting for me, having watched and taken part in so many amazing conversations in the CTO Craft Slack community – there are so many incredibly knowledgeable people willing to share their knowledge and experiences.

We’ll be opening the Call for Thoughts on day one of the conference itself, November 14th, and sharing a Google Form with all attendees, which they can use to submit their lightning talk ideas.

There will be two tracks of lightning talks on the final day, November 16th, with six 15-min slots open in each track, so attendees can jump between talks as they wish. After the lightning talks, we’ll open up a number of round tables with a facilitator from the CTO Craft crew, where you’ll be able to dig deeper into topics you’ll have heard about during the conference talks with other attendees.

What advice would you give someone if they’re unsure about putting themselves forwards to host a Lightning Talk at the Unconference?

Don’t worry – I’ve definitely been there before and struggled to build the confidence to get up in front of my peers and talk about a subject that I was passionate about. It’s natural to feel anxiety – but this will be a safe space, and everyone in attendance will be there to both learn and give back. The only prerequisite for applications will be a real interest in the topic you’ve chosen and in giving something back to the community. We won’t judge you on anything else. 

Will there be another CTO Craft Conference next year, and if so, what can we expect?

Of course there will! As usual, we’re planning two conferences for 2023 – plans are coming together at the moment. Who knows, we may even get to meet you all in person….

Why do you think individuals should join the CTO Craft Community?

Genuinely, and not just because I helped pull it together, I believe the CTO Craft Community is one of the best resources anywhere in the world for those in senior engineering leadership positions. Of the 4,500 or so members, there’s not one person who I believe would judge or withhold their knowledge or experience, and we ensure it’s kept a safe space by monitoring applications one by one to prevent salespeople, recruiters, marketers and other C-level leaders from joining. It’s a friendly, welcoming, sympathetic and supportive community, and I’m incredibly proud to be involved with it.

In terms of tangible, empirical benefits, there are a plethora, from having the ability to pose questions about the role and get near real-time answers from others, to the bi-weekly newsletter full of learning material, to conference ticket discounts, to regular events and get-togethers, and on it goes. And we’re just getting started – there’s a huge amount still to come that we’re pulling together.

We always ask our conference Spotlight Q&A interviewees to recommend a book or a podcast that every technology leader should read or listen to in the space of coaching, learning and development or leadership in general. What would you recommend?

One book I come back to time and again, which isn’t just for professional coaches, is the Coach’s Casebook by Geoff Watts and Kim Morgan. It includes a huge number of archetypes and situations, conversations and tools and techniques for helping team members plough through limitations and difficulties. I love it.

I’ll also always recommend the amazing Patrick Lencioni, especially the Advantage and the Five Dysfunctions of a Team. Absolute must-reads.


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