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Tom

Do you have a burning leadership question? You can book a call with me, or start with AskTom, my curated AI, built on the over 1,000,000 words and 2,000 articles I’ve published on #OpenLeadership

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Massive

Impact

You are already a visionary, successful and making a difference, yet you remain hungry to make an even bigger “dent in the universe” for yourself and your organisation.

Actionable

Insight

You need authentic, creative, relevant and “cut through” actionable insights. Tom delivers this through deep listening allied with decades of business experience. That’s why his clients are clients for life.

Tom McCallum

Elevating

Leadership

Unlock and realise your potential by enhancing your leadership with wisdom and advanced decision-making. Call Tom today to discuss your “what’s next”.

I thoroughly enjoyed working with Tom. I still remember, just after COVID, sitting outside a café on a cold, wet Manchester day talking through the very real challenges of leading teams and staying connected with clients when travel and face to face meetings weren’t possible. That conversation was incredibly valuable and spurred me on to think harder and be better. That’s what Tom does so well. He listens deeply, then offers thoughtful perspectives that gently but effectively challenge your thinking. Our sessions consistently lifted me out of the day to day and into more strategic, reflective conversations—space you rarely get elsewhere. We often walked while we chatted…Tom is an excellent sounding board, a great listener, and someone whose insights stayed with me long after each discussion. I would highly recommend Tom to anyone who wants to be stretched, challenged, and supported to become a better leader.

Cath Schefer
EVP and Chief Operating Officer Global
Stantec

What I value most about Tom’s coaching is how quickly he creates clarity. I often left our conversations thinking I was simply “checking in,” only to realize afterwards that my perspective had shifted in a meaningful way. Tom has a gift for listening deeply, challenging gently, and helping you articulate what you already know, but have not quite said out loud yet.

He is great at navigating complexity and transition. He doesn’t offer answers, but helps leaders sharpen their thinking, strengthen their presence, and lead with greater intention and confidence.

His commitment to helping leaders realize their full potential is genuine and consistent with how he shows up. He is thoughtful, insightful, and grounded in real leadership experience. I would strongly recommend Tom to senior leaders who are serious about making a more meaningful impact and navigating what comes next with clarity and purpose.

(He can’t help that he is an Arsenal fan)

Bjorn Morisbak
Executive Vice President & Chief Corporate Development Officer
Stantec

I enjoyed having the opportunity to work with Tom McCallum; his impact on my thinking was immediate and lasting. Tom has a rare ability to elevate the conversation—helping you step back from day-to-day complexity and see the broader strategic landscape with greater clarity. Our work together sharpened how I frame challenges, make decisions, and communicate direction at the executive level. What truly sets Tom apart is his communication and storytelling capability. He has an exceptional gift for distilling complex, often ambiguous ideas into clear, compelling narratives that resonate with senior leaders. Whether exploring an issue out to its boundaries, pressure-testing a strategy or helping shape a message, Tom consistently brought insight, structure, and perspective that made the thinking stronger and the outcomes more effective. I would highly recommend Tom to any leader looking to strengthen their strategic perspective and communicate with greater impact and purpose.

John Take
Executive Vice President, Chief Growth & Innovation Officer
Stantec

Tom has been a fantastic sounding board over several years, with wonderful recommendations for practical action, as well as intellectual challenge and rigour. I always leave our conversations feeling invigorated and inspired!

Dr Wanda Wyporska, FRHistS
Chief Executive Officer
Black Cultural Archives

Many thanks to Tom McCallum for mentoring me during my transition into starting my company. Definitely one of the most interesting people leaders can hope to encounter on their journey and an amazing human being overall! If you’re ready to make a massive impact with your business or organisation, don’t miss your chance to connect.

Nik Grabacic
Founder
Spark + Matter

I have worked with Tom for around a decade, meeting him initially on a Leadership Development Programme he built and delivered in the Cayman Islands. He subsequently became my executive coach and business coach. I would recommend him to anyone who seeks to understand who they really are as a leader, wants to achieve full potential in their business and knows they have the potential to grow as a person. He knows the questions to ask, brings a fresh perspective and will quickly understand the challenges you are facing and the opportunities you are missing.

David Foster
Strategic Advisor & Investor
Etcho

Tom worked with me, my Chair and Board Directors during a pivotal time of growth for Canadian Pulmonary Fibrosis Foundation (CPFF). His role was centred around facilitating our annual board strategy meetings and virtually during the pandemic even thought he was 5 hours ahead of Toronto time!

What I love about Tom, is that he holds your feet to the fire and won’t let you leave the room (in person or virtually) until everyone comes to an agreement. This is so refreshing, as often, facilitators allow the participants to not come to a conclusion, which means you never move forward.

Sharon Lee
CEO
Canadian Pulmonary Fibrosis Foundation

Over the last 3 years Tom has been a wise and generous coach. I look forward to our conversations and always leave them thinking – and feeling – more clearly. Tom is an excellent active listener, and with a depth and breadth of insight from his own experience and his extensive reading, research and relationship, he is a man who can be relied upon for informed support in any circumstances.

Ben Brabyn
Business Development and Ecosystem Specialist

Working with Tom in 2020 and 2021, he helped identify, encourage and essentially unlock a positive strategic change in both my personal and entrepreneurial journey.

The shift since has been astounding, with little sign of slowing down. Things were good before and honestly we had little to complain about. But we were not fulfilling our potential, both personally and professionally.

I’ve now moved on from ‘working’ to finding and nurturing my ‘life’s work.’ The energy shift and increased positivity in both myself and those around me has been huge. I have a lot to thank Tom for in helping make that change by ultimately being more me.

Tom Ahmad
Co-Founder
Bailey Ahmad Business Recovery

Tom worked with me as a coach and advisor from mid 2017 through the end of 2019. He assisted myself and my team with strategic planning, was great as a sounding board, and was particularly helpful at simply keeping me on track! I would not hesitate to recommend Tom for a future assignment.

Kirk Morrison
EVP Stantec (retired) and Professional Engineer

Tom is an insightful forward thinker with over 30 years of management experience that moves business emotionally and exponentially towards their full potential.

Morgan Da Costa
Managing Director
Maedac Supply

My Shirlaws experience with Tom was an excellent one – he really helped my team come together and focus on our goals. His interest in our success was genuine, and the foundation for a great relationship.

Dax Basdeo
Chief Officer
Ministry of Financial Services, Cayman Islands Government

Tom was my coach for nearly two years. Working with him can be expressed for me most succinctly in three famous taglines: “Just Do It” “(Coaching) gives you wings” “You’re not yourself without your (Coaching)” Tom’s coaching provided me with a framework to develop my leadership skills, thankfully free of management-speak but full of practical steps to affect real change both within myself and within my organization. These seemingly small changes had led to a big change in how I see myself and how others see me as well as tangible impact where it matters most to businesses, i.e. the bottom line.

Charlotte Caulfield
Managing Director
Kalo

Through our engagement, Tom assisted the CUC executive team with bringing a greater sense of clarity and purpose to the leadership role. The impact down through the organization has been tremendously positive.

Richard Hew
CEO
Caribbean Utilities Company

Tom has been a mentor and a great source of support and inspiration to me for over a decade. Always willing to share his insight, perspective and wealth of experience, he has always challenged me to do better. Work with him if you get the chance!

Steve McIntosh
CEO
Cayman Finance

Tom is at his best one-on-one, in conversation, where he is an excellent listener, keen to understand what I am saying behind the words. He is sensitive to emotions and motivations, connecting personal journeys with the aspiration of the overall business. I always have the sense that Tom has time to care and that my opinion matters, which is a rare talent in such a busy world!

Mark Beaumont
Investor, Speaker, Author, Speaker, Global Adventurer