Strategic Planning

Knowledge Base

Strategic Thinking: A Skill You Can Craft and Use to Create the Future

Execution & Implementation, Vision & Goal Setting

Strategic thinking isn’t an art reserved for prodigies. It’s not a gift bestowed on the few who seem to intuitively see the bigger picture. It’s a skill, and like any skill, it can be learned, sharpened, and applied. What separates strategic thinkers from the rest isn’t talent – it’s the deliberate practice of stepping back, connecting dots, and playing the long game.

Why does strategic thinking matter so much? It elevates people from following the status quo to shaping it. It turns problems into opportunities and positions you not just to respond to change but to drive it. The ability to think strategically isn’t just about being reactive or tactical; it’s about envisioning a future worth pursuing and building the roadmap to get there.

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Rethinking the Status Quo: How to Mine for Dissent to Drive Strategy

Adaptability & Resilience, Evaluation & Continuous Improvement, Execution & Implementation, Innovation & Growth, Leadership & Culture

There’s a certain kind of comfort in the status quo. It doesn’t demand much of us; it lets us settle into well-worn patterns and predictable outcomes. Yet comfort, as seductive as it is, rarely breeds progress. To lead strategically, whether in life, business, or any pursuit that calls for vision, we must ask: Where can I reason differently and overcome biases to change the status quo?

It’s a question that feels deceptively simple – after all, don’t we already strive to be objective, logical, and open-minded? Yet, when we pause to examine our decisions, we often find a subtle thread of familiarity running through them. We make choices based on what has worked before, who agrees with us, or what feels safest. Changing the status quo requires not only the courage to challenge our assumptions but also the discipline to actively mine for perspectives that oppose or stretch our thinking.

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The Symphony of Project Preparation: Planning, Cadence, and the Power of Communication

Execution & Implementation, Leadership & Culture, Vision & Goal Setting

Over the past three years, since taking on the Corporate Service responsibilities at the Ottawa Community Foundation, I’ve been at the helm of an ongoing cycle of major projects. These initiatives are part of a broader effort to evaluate and refine our systems and processes, ensuring we are best prepared to support the community in addressing some of the most complex challenges we collectively face. In this journey, I’ve found myself repeatedly returning to the first principles of project management – revisiting, relearning, and reaffirming the fundamentals that drive successful outcomes.

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The Overlooked Voices: Unlocking Strategic Success Through Inclusive Strategy

Adaptability & Resilience, Evaluation & Continuous Improvement, Execution & Implementation, Innovation & Growth, Leadership & Culture, Vision & Goal Setting

In the relentless pursuit of progress, it’s easy to fall into the trap of listening only to the loudest voices – the executives in boardrooms, the strategists with polished presentations, the data points that seem to scream their conclusions. But there’s a powerful question that leaders often overlook, one that carries the potential to reshape not just decisions but outcomes:

Who have we left out of the loop?

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Strategy Unboxed: Embracing the Chaos to Build Resilience

Adaptability & Resilience, Execution & Implementation

In boardrooms and brainstorming sessions, strategy often gets boxed into a predictable process: analyze, plan, execute, repeat. This neat, linear approach promises order and control. But the moment these plans meet reality – markets shift, competitors pivot, customers evolve – that structured strategy can feel like a house of cards.

A single change can bring it all down.

The issue isn’t strategy itself but how we frame it. Most approaches assume that business decisions unfold in a controlled, predictable environment. But we know that’s rarely the case. Real strategy isn’t a fixed staircase; it’s a living, shifting puzzle – a framework that adapts rather than stacks. It embraces complexity, values agility, and navigates ambiguity.

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The Power of Strategic Connections: Expanding Perspectives to Enrich Decisions

Adaptability & Resilience, Evaluation & Continuous Improvement, Innovation & Growth, Leadership & Culture

Strategic thinking isn’t a solitary act.

It’s a dynamic interplay of curiosity, ambition, and connection. At its core lies a simple but profound question: Whom can I connect with who might have an important perspective for me to consider? This isn’t merely about networking; it’s about building relationships that stretch your thinking, challenge your assumptions, and inspire your choices. It’s about recognizing that no matter how sharp our instincts or thorough our research, the clarity we seek often comes through others.

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