Interview with Sam Boswell, CTO @ WorkGaps

Published on Jan 3, 2018

2 min read

image for Interview with Sam Boswell, CTO @ WorkGaps

Location: Berkshire, UK
Current Role: CTO @ WorkGaps

What’s your background and how did you get into management?

My background was primarily technical – my first roles were in bespoke software, and from there shifted to web-app development. I was recommended a role with a start-up company that led to me building and leading a development team. I’ve been making the transition from senior / lead engineer to a management role over the last year.

What are the biggest challenges you face?

Personally, the shift away from coding into a focus on people and process is the biggest shift for me. As a manager, estimations, and communicating the associated risk to the business team.

What is your approach to hiring?

Hire for the person and attitude first – specific knowledge can be learned, but a person with a good work ethic and desire to grow and learn is much more valuable.

We run a 1st pass CV screen, a quick phone interview (can you hold a conversation, have you done some research on the company, are you who your CV says you are), followed by an in-person interview which where appropriate, includes some in-person programming! I put a lot of weight on people’s attitude to programming – open source work, home projects and a general drive for growth and improvement are such valuable markers of a good hire.

What’s your advice for managers who are just starting out?

Brace for the drop in your usual output, it’ll be more than you expect. Be ready to over-communicate, and let people tell you to tone it down rather than the other way around. Be ready to iterate and adapt your plans to the reactions you find.

What’s your workday like and how do you manage your time, emails, etc.?

Morning coffee and my first GTD loop, followed by team stand-ups.

If anything is timebound, it goes into my calendar, which is always as accurate as possible (including retrospectively updating for accuracy) This includes blocks for eating and sleeping!

Much of my time currently is spent in Jira, review and planning out for the team, looking for and removing as many obstacles as I can.

Playbooks and pre-planned mental models lift lots of cognitive load – if it breaks once, document for next time.

What’s a personal habit that contributes to your success?

Offloading my time management to my calendar, and information storage to digital, searchable systems!

Share an internet resource or tool that you can’t live without.

I love Notion (, after moving from Evernote and OneNote, this web app serves as my cabinet of useful snippets, my task list, and is used by the team here as the internal knowledge base. Along with this and Google Keep – I use a butchered variation of GTD ( ) to keep my tasks and information in order!

If you could recommend one book to managers, what would it be and why?

Meditations by Marcus Aurelius – it’s not specifically a management book but is a collection of thoughts from a Roman emperor on how to deal with people, life, and situations that he found himself in. So much of it still holds, and it makes for a nice book to dip into for inspiration or reassurance.

Where can we go to learn more about you? (LinkedIn, Twitter, GitHub, etc.)

I’m on LinkedIn at

Twitter at

My personal site is

This series asks engineering managers to share their experiences with the intent of helping other engineering managers learn and improve. Have someone you want to see featured or questions you think we should ask? Contact me.

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