• Name: Douglas Squirrel
  • Age: 45
  • Current position: Startup Consultant
  • Bio: Left my maths doctoral programme at UC Berkeley for the startup world, first in San Francisco and then in London. 15 years of tech leadership followed at TIM Group (fintech), Secretsales (e-commerce), and Osper (banking for kids) before becoming a consultant in 2015 for London-based startups including Geckoboard, Arachnys, Wonderbly (Lost My Name), Bookingbug, DueDil, and MarketInvoice.

Tell us about your life before leadership — what kind of roles and projects did you work on?

I was a grad student, heading for a PhD and eventually a job as a maths professor — teaching calculus was (unusually) my favourite part of grad school. I took a break for a year to work in ‘the industry’ and earn money to pay for my wedding, but I enjoyed coding so much I never went back. I spent just over a year working as a developer, then took some project leadership roles.

How did your first leadership position come about, and was it intentional on your part?

Entirely unintentional — I was the senior technical person in the company (TIM Group) and when we started our first technology product the founder designated me CTO without warning or even my permission!

How did you manage the transition? What came easily / what was difficult?

Luckily, I had a green field to work with, and none of us knew what a startup tech team looked like, so we felt okay about making mistakes. Joel Spolsky was a light in the dark offering helpful advice when there was very little available.

What was your biggest failure in that first leadership role?

I didn’t delegate enough or soon enough.

What made you keep doing it?

It was a lot like teaching so I enjoyed it!

Tell us a fun fact that nobody knows about you?

Despite my strong American accent, I am a proud Englishman and have even become a cricket umpire to cement my Anglophilic credentials!

What are the three key skills you think every lead needs?

In the organisations I specialise in (series A, high-growth startups), the key skills are delegation (to allow personal scaling), communicating a vision (to enable team scaling), and managing upward (to enable company scaling).

What have you learned about acquiring and retaining talent?

Use professionals — I am definitely not a recruiter. Internal recruiters are a recent and very welcome innovation; I wish I’d had one when I was hiring myself. Work samples are also crucial at all levels, because only an example of real work verifies that the candidate can actually do the job. Ensure that during interviews, you have developers writing code, PMs planning work, and CFOs analysing financial models.

How do you motivate your team and manage their stress levels?

I usually work with teams that are (or should be) scaling fast, which means they are under enormous pressure. I teach them techniques for simplifying and speeding up their work like ‘elephant carpaccio’, and ensure they are working on the right things first. The latter is almost always the first problem I have to address with any client.

How do you manage your own stress levels and productivity?

Management by exception is the only method that’s ever worked for me; briefly, you ensure that you have solid information flow, identify problem areas and then work exclusively on the most important, highest-leverage item first to the exclusion of others (I’d recommend Andrew Grove’s High Output Management, for a detailed introduction). Sleep really does help too!

How do you stay in sync with other parts of the business?

With six clients at once, I have to structure meticulously to make sure I’m on top of relevant people and news at each one. I plan information flow carefully so I receive reports and hold check-ins regularly with those around the people I’m coaching.

Where do you see yourself in 5 years’ time?

Author of one or more books on agile development and startups, and an active consultant and speaker.

What product do you wish you’d invented?


If you, or your CTO / technology lead would benefit from any of the services offered by the CTO Craft community, visit: www.ctocraft.com or contact us via email at: info@ctocraft.com.

Subscribe here to Tech Manager Weekly for a free weekly dose of tech culture, hiring, development, process and more…