Eight Questions With Featured Grey Swan Guild Member: Tom McCallum

Grey Swan Guild
6 min readMar 3, 2022


Sounding Board to Leaders Ready to Make an Even Bigger “Dent in the Universe”

Our Eight Questions is part of our ongoing series profiling some of the amazingly talented members of our global Grey Swan Guild and get behind the curtain of what makes them think and sense the world differently and more effectively than others.

Tom McCallum — Caymanian and Scot based in London, U.K.

Bio: Tom is driven by his purpose of #MakingPotentialPossible and lives this in his work with leaders of organisations seeking to scale their impact. He believes in and operates from two models. The first is #OpenLeadership, the belief that the leaders of now and tomorrow are both Brave and Hungry and also Open and Humble. The second model is his “Scale for Impact Model”, a virtuous circle where leaders are driven by Purpose, People and Planet, using a focus on Profit as an outcome that then allows them to spin that “righteous flywheel” to scale their impact.

He is passionately curious about people and ideas and loves to meet new people and digest and learn from them, often sharing learnings in his daily posts and weekly live podcasts hosted on his website tommccallum.com

Tom McCallum— Member of the Grey Swan Guild

A Sensemaking Metaphorical Tool You Personify:

CONNECTING THE DOTS (pencil on a map).

What do I mean? First, deep listening then next, I gently allow pattern matching to provide me insights to share back that can also often be further questions, so a virtuous circle of listen, insights, listen, insights etc

1. Who are you/ what makes you tick?

People and Ideas.

2. What are some of the important questions that you are making sense of nowadays?

  • We live in what I call Unthinkable times, where things move so fast no leader can have all the answers, so how do we shift leadership so that organisations embrace and thrive. Hint, hierarchical and command and control won’t cut it anymore. The model I have developed is called #OpenLeadership and my main work focus is on applying this with clients internationally. Gratifying to see positive results and also how real world application is also a tool for learning and evolving application of the model
  • What is the purpose of the corporation? Milton Friedman has dominated thinking on this for decades, but it can no longer be that the “sole purpose of the corporation is to enrich the shareholders”. I developed the “Scale for Impact” model to create a “both/and” model that evolves the “triple bottom line to make Profit an Outcome rather than the Driver of business. Again this forms much of my work in the real world, supporting leaders seeking to have a massive impact to lead from purpose.

3. How are some of the ways you go about making sense of the world?

I listen then I connect the dots. I also consciously create space for serendipities by allowing for randomness and wide variety of people I meet and ideas I learn about, including being aware (as far as I can_ of my biases, going as far as to often make time for people and ideas I know I do not agree with and even strongly object to.

4. What is overhyped? What is underhyped?

Overhyped: The Metaverse / Crypto / ESG

Underhyped: The Singularity / Blockchain / Ethical investing

(Yes, I’m inferring that there is nuance here!)

5. Who is at your sensemaker last supper? Four people?

I’ll stick with the living, as I would love to manifest this one happening!

  • Paul Krugman — Noble Laureate Economist and SciFi fan, not necessarily in that order
  • Chris Van der Kuyl — Visionary Thinker, Entrepreneur, Philanthropist and fellow Scot
  • Arlan Hamilton — Inspirational in how she is changing the way the world thinks about VCs (in a good way!)
  • Marla Dukharan — Leading Caribbean Economist and passionate about reducing inequality and inequity through tools such as blockchain and economic policy

Why this group? They are all visionary thinkers and all believe that business can be a driver for change. I believe in business as a force for good. Oh, and I know all of them to varying degrees and feel that connecting these live and active “dots” can create something that can be actionable and tangible.

6. What big and small question would you love answered or solved?

Big Question: To shift the paradigm in the general populace (as well as MBA schools and leaders in general) that all CEOs only care about (and need to care about) “making money”

Small Question: How can I get the Cayman Island Government to get behind the relatively paltry investment of c$10m needed to change and save lives through building an Aquatic Centre?

7. When you are not thinking deeply about the world, what else are you passionate about in your day to day life?

Living a long and healthful life. I am absolutely focussed on physical, mental and spiritual wellbeing and, at 56, feel I am just getting started with the deepest impact I can have in and for the world. Being in great shape is key to that.

8. What do you enjoy about being part of the Guild, and being part of the F+S Expert Squad and being 1,000 Day Radar?

Being provoked to make sense of the world, not only the Grey Swans, but thinking small and large. These questions are a great example, they have helped me make a little more sense of me, my “why”, what I do, what makes me tick!

Find Tom at:

LinkedIn: https://www.linkedin.com/in/tommccallum/

Twitter: https://twitter.com/tomcayman

YouTube: https://www.youtube.com/channel/UCP9asYRiIKRTfg_vcVJ90Kg

Website : https://tommccallum.com/

Podcast: https://tommccallum.com/live/

Tom McCallum —Supporting Purpose-Led Leaders ready to make a Massive Impact

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Grey Swan Guild — Our Mission

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Grey Swan Guild

Making Sense of the World’s Biggest Challenges & Next Grey Swans — curating and creating knowledge through observation, informed futurism, and analysis🦢