James is the Director of Engineering at Shopify. He is also the author of Become an Effective Software Manager and Effective Remote Work. He holds a Ph.D. in computer science and runs www.theengineeringmanager.com.
At our CTO Craft Conference, he’ll join a panel discussion about, ‘Building your management roster – Training the next generation of leaders.’
Hi James, welcome to the CTO Craft Spotlight Q & A. You’re a day 2 speaker at the CTO Craft Con and Director of Engineering at Shopify. Can you give us a teaser about what you might share with our audience at the conference?
We’re putting together a panel discussion that focuses on a common leadership challenge: succession planning. Almost as soon as you enter a senior leadership role, you need to start thinking about levelling up your leadership bench and who might be best placed to take your own role in the future!
Despite sounding a bit like you’re already out before you’re in, it’s a great lens to focus your direction for coaching and mentorship of those who report to you.
The conference theme is Culture and the CTO: Unleashing the Power of People. What methods do you use to ensure team morale and productivity during difficult times?
If only there was a prescriptive list of methods! From experience, the two main things that matter are meaningful work and great people that you trust to do it with.
No matter the difficulties — which recently have been the economic downturn and layoffs — the thing that keeps people motivated is knowing that they’re working together with others on things that really matter. A terrible week can be diffused by having a conversation with a user who is absolutely stoked by what you’re working on. Serving others is always the path forward.
In your experience, how do you know if an individual contributor is ready to move into a leadership role?
If by leadership we mean management, then there are a lot of shared leadership characteristics between managers and senior individual contributors that you can detect.
Selflessness, the ability to mentor and coach others, a mindset focussed on getting the job done and maintaining high trust with others — they’re all the same regardless of the role. Then, it’s a case of identifying these individuals and working with them to unlock where they would like to go next.
What tips do you have for building ongoing resilience for new leaders?
As with everything in life, nothing beats experience. Volunteering to lead challenging projects, vying for ownership of important areas, and then executing and seeing it through is more than enough to build resilience. If you gravitate towards being the person with whom the buck stops through your competency and your ambition to do greater things, you’ll build resilience along the way.
As a leader, what approaches do you use to create a culture of psychological safety for new or aspiring leaders?
Giving people the space to fail — which is essential for learning — is the key. For example, if someone wants to lead a project, or a team, or a department, then giving them a chance with a safety net for them to go back to what they were doing previously if it isn’t working out — rather than suffering the usual ramifications of poor performance — is a great way of opening the door to new leaders.
Also, encouraging peer groups of new and existing leaders to meet regularly under the Chatham House Rule can build community and connection.
How do you practice open communication with new leaders to ensure they receive the support they need?
I wrote about this before in an exercise called Contracting. This is one of the questions that you ask in your first one-to-one meeting: just have this conversation right at the start!
Changing the subject completely, please tell us an interesting fact we don’t know about you.
I live in what used to be a village pub in Cumbria.
In your opinion, why should someone come to CTO Craft Con?
It’s a great chance to get inspired, build some new connections with peers in the industry, and then take that back to your day-to-day.
What talk are you most interested in hearing?
I’m looking forward to Michael Lopp’s keynote.
Finally, can you recommend a book or a podcast that every technology leader should read or listen to either in the space of strategy, development or leadership in general?
I guess I can’t recommend my own books… however, as a slightly off-piste recommendation, I’d say The Great Work of Your Life by Stephen Cope. It’s a practical example-led exploration of the themes in the Bhagavad Gita.
We’re thrilled to announce that some of the most exciting tech leaders will be joining us at the CTO Craft Con on 7-8 November 2023 at the Tobacco Dock in London.
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