In this episode, we’re joined by Keita Demming, Partner at The Covenant Group, award-winning author of Strategy to Action, and trusted advisor in strategy, design, and innovation. We explore how strategy becomes a lived practice through intentional behaviour, personal development, and the quality of our conversations. Keita shares his approach to coaching leaders through conflict avoidance, curating effective inner circles, and aligning day-to-day actions with long-term vision. He introduces a powerful shift in thinking from chasing outcomes to asking better questions and what it means to lead with clarity and courage.

We talk about what strategy really looks like when it's practiced daily, why organizations often struggle to face hard truths, and how self-awareness, team dynamics, and sector alignment can either accelerate or stall transformation. Keita brings practical insight and honest reflection on what it takes to build something meaningful, starting with the conversations we choose to have. Whether you're growing a business, refining your leadership, or rethinking your goals, this episode offers a grounded framework for becoming the kind of leader your future needs.

About Keita Demming

Keita is an award-winning author, educator, and coach focused on transforming companies into idea-driven, people-centred environments. His book Strategy to Action offers a practical approach for turning bold ideas into tangible results, helping close the often-frustrating gap between strategy and execution.

As a trusted advisor in design, strategy, and innovation, Keita also hosts the podcast Conversations with Keita Demming, where he explores insights from leaders across disciplines. He believes learning from others lightens our own journey. Among his proudest achievements is building the TEDxPortofSpain community, one of the most successful TEDx events globally.

Resources discussed in this episode:

• Strategy to Action
• Erykah Badu
• The Selfish Gene by Richard Dawkins
• CS Lewis
• Brene Brown

Contact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd. 

• Website: BeaconFamilyOffice.com
• LinkedIn: Cory Gagnon
• LinkedIn: Beacon Family Office
• Email: [email protected]

Contact Keita Demming | The Covenant Group 

• Website: keitademming.com
• LinkedIn: Keita Demming
• YouTube: @KeitaDemming
• Instagram: kdemming
• Facebook: keitademmingconversations
• Email: [email protected]

We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises.

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