Andy Skipper is Founder and Chief CTO Coach, CTO Craft, and Lee-Jon has been a CTO for 14 years, with vast experience in Strategy, Technology & Product and is our day one conference chair on 23 May 2023.

CTO Craft Con
Hi Andy and Lee-Jon and welcome to an in-conversation chat about the CTO Craft Con: The Strategic CTO!
Andy, the conference is only weeks away, and the tagline is ‘CTO Craft Con: The Strategic CTO. Stop Firefighting, Start Leading.’ Can you tell us why you chose this area of tech leadership for the May conference?

Andy: Hi Sarah! The idea to focus on strategic awareness and planning came from the Community, as all topics CTO Craft covers do. Whether it’s in Circles, coaching sessions or just in the Slack Community itself, it’s very plain to see that technology leaders commonly start to struggle when they’re caught in the weeds of day-to-day demands and firefighting.

That’s so common in startups that are just starting to scale and all the more so for new leaders who don’t have the resources, experience or the headspace to manage everything being thrown at them. It’s also a major cause of burnout, which is still a really big issue among CTOs.

By learning to manage priorities, build plans, and focus on the future beyond this week, leaders can start to develop tools and the mindset to step away from the grind and give themselves more room to breathe.

Lee-Jon, you have hosted (either in-person on online) numerous – if not all! – CTO Craft conferences in some capacity. So, why would you recommend that individuals attend?

Lee-Jon: Before we became a leader, we could rely on our teams and our company’s support in our life and career – but a lot of us found that when we hit the top technology job, we lost this. Being a tech leader can be a lonely experience, especially when new to the role. Seeing other leaders discuss their challenges and their ways to overcome them is our pill against this.

One thing CTO Craft does well is get together a mixture of industries and backgrounds to discuss their role, their problems and challenges and how they overcame them. The conference is the core focal point for us to get this benefit from our peers and not feel overwhelmed by what we do.

We’re back in person for this two-day conference! What do you think are the benefits of conferences being in person rather than virtual?

Andy: While the online CTO Craft Cons have been a massive success, it’s clear that the networking and socialising elements that so many people attend conferences for just isn’t there yet.

It’s more typical for attendees to simply log off or go and do something else during breaks or at the end of the day when they’re at home, instead of building new connections, seeing familiar faces, and getting new perspectives. Maybe we’ll find a way to make that possible in the future, but for now, meeting face-to-face is the only way to achieve it. 

Lee-Jon: Oh, I hadn’t thought about the focus element Andy. That’s a good point, especially if you’re travelling to London for it.

For me, conferences are all about networking. It took me years to realise that networking isn’t this gross sales-like thing where you force a business card (do we still have these?) on someone. I think having the ability to chat with other technology leaders face-to-face is the main reason I’d attend any conference now. 

What are you most looking forward to about this May conference?

Andy: There are so, so many members of the CTO Craft Community whose names and faces I’ve seen, and many I’ve been speaking to online for the last few years, but who I’ve never met – I’m really looking forward to saying hello in person!

I’m also looking forward to all the amazing panels – we have some brilliant topics lined up, and the panellists we’ve invited are all incredible.

Lee-Jon: The problem with the online conferences is I’d see or introduce many great speakers and have limited ways to engage with them after. If I had a pointed question, I’d often send a Slack message in the community. But I want to chat with a group about their topic and see others’ thoughts. 

What would you say is one of the most valuable lessons you’ve learned relating to CTO strategy during your career?

Andy: In my first CTO role, I learned that strategy exists! Prior to that, each of the businesses I’d worked in, many of which were agencies, didn’t have any kind of real technology strategy, and the priority was always whatever was going on that week.

It took a long time in that first CTO role to understand that I did need to plan beyond a week, both for the sake of aligning with the rest of the organisation and for my own well-being, to avoid overwhelming myself with last-minute stuff. As a natural people-pleaser and workaholic, that was a tough mental shift, but it was the most important change I made while I was there.

Lee-Jon: The key difference between someone with a C in their title and someone who doesn’t is the former works on the whole business, whereas the latter works within a division.

Strategy is about working on the whole business. The hardest lesson for any executive is to break out of the divisional trap. It’s why CTOs in particular, get hit pretty hard, as we’ve honed our craft in a certain technology and running teams who develop on that technology.

Strategy is where we have to consider all departments – how does marketing a product or service change as we develop new capabilities in the operation or the technology or the product? How does that affect revenue? Strategy is about considering this whole, not just about ‘IT/tech part’.

To be a good C-suite, you have to have an idea of how a business runs, not just the technology and technology teams. 

What advice would you give someone who hasn’t attended one of our conferences before and doesn’t necessarily know anyone else attending?

Andy: Come with an open mind, and be ready to ask questions – very few of the attendees will have met at an in-person CTO Craft event before, this being our first live conference, but the success of the online conferences definitely came from the audience participation. It’s also a great way to make connections and join in the conversation.

Lee-Jon: Yeah, this is different to say a Java, Ruby or AWS conference where you’d bring your team, in that you may be attending by yourself.

Firstly call out in the CTO Craft slack channel to see if anyone fancies a coffee or is coming from your location.

Secondly, don’t discount the pre-coffee and lunch sessions as a great place to chat about your ideas and challenges and learn to your own agenda – they’re not there so you can catch up on email or Slack – they’re there to meet people in our field.

Finally, ask the hosts; we’re there not just to do introductions but can facilitate getting a question to a speaker, making an introduction, or just hang out with us.

Andy, do attendees have to attend every talk or session, and what would you recommend?

Andy: No, absolutely not – we’ll be releasing the full agenda well in advance of the conference, so you can plan which sessions are most important for you to attend. 

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

Andy: Strike up some conversations! Everyone is getting back into the swing of in-person events, and nobody is judgmental – come with an open mindset, and you’re likely to be met with one.

Lee-Jon: It sounds like homework but preparation. Research the attendees, research the speakers and think about what they could answer for you or what you could ask. If you’re shy or not used to networking (remember: it is a learned skill – not a natural one), maybe rehearse a question or an introduction.

A mistake I used to make is not thinking about what I wanted out of a conference and relying on what the conference wanted to give me. Think about that and use that to know what connections to build and what conversations you want to have. And if you’re not having those conversations, ask other attendees who may know who to speak to!

After the conference, it’s easy to get back into daily life and potentially fail to act on what you’ve learnt at the conference. What suggestions do you have for following through on actions/learning and taking them into your role?

Andy: Everybody has different approaches to learning – it’s worth having some visibility over what works best for you. That said, there are some typical steps you can take to cement some of the things you take away:

  • Write about it, either for internal use, a blog, or just for yourself.
  • Tell others about it – brown bag sessions, discussion groups, and Circles are all good places to do this.
  • Get an accountability partner – there are probably lots of others at the conference who’ll want to do the same, but if not, there will be plenty of people in the CTO Craft Community who will.

Lee-Jon: Follow-up is important. Keep a record of people you met and what you talked about, and what was an interesting topic or point or challenge, and make a point to connect with people about this to increase the productivity of the connection.

Also, do the same for the sessions – keep notes on ideas you felt important and add them to your ‘list of things to learn‘ so you can internalise these.


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