Living Strategic Thinking: The Misunderstood Role of Strategists in Transformation

There is a lot written about Strategic Thinking and recently I noticed that discussions about it are increasing. Thus, it is not surprising that it is often hailed as a critical leadership skill. But in my experience, it’s not just a skill—it’s a behaviour, a mindset that guides how you navigate complexity, inspire change, and lead transformation.

Yet, strategists are often misunderstood. They’re seen as disconnected visionaries, overly theoretical planners, or individuals lost in the big picture without grounding their ideas in reality. Nothing could be further from the truth.

Strategists play a critical role in driving transformation. They don’t just design the roadmap—they help the organization navigate it, ensuring that change is actionable, sustainable, and meaningful.

Through my work, I’ve identified five golden behaviours that can help leaders embody strategic thinking and demonstrate how strategists genuinely authentically contribute to transformation.

1. Be Proactively Forward-Thinking

Strategists look ahead and ask, What’s next? What could we do today to position ourselves for success tomorrow? They anticipate trends, prepare for challenges, and ensure the organization is one step ahead of the curve.

This mindset helped my team identify and address future skills gaps in one transformation project I worked on. Instead of reacting to market demands, we proactively invested in employee development, ensuring we were ready before the competition.

Advice: Build the habit of looking beyond the immediate horizon. Ask forward-looking questions in every meeting to prepare your team for what’s coming.

2. Simplify Complexity and Think Critically

Transformation is messy. Strategists thrive in this complexity by breaking it down into manageable parts and identifying what matters most. They analyze challenges critically, question assumptions, and turn complexity into clarity.

For example, during a restructuring initiative, I encouraged my team to step back and focus on the root cause of delays rather than quick fixes. This critical thinking approach revealed misaligned priorities across departments—a discovery that reshaped how we approached collaboration moving forward.

Advice: Don’t be afraid to pause and dig deeper. When faced with complexity, focus on clarity and objectivity to help others see the bigger picture.

3. Ask Provocative, Thoughtful Questions

Strategists don’t just provide answers—they ask questions that spark innovation and deeper thinking. Questions like What are we missing? or How does this align with our broader goals? push teams to think beyond the obvious and explore new possibilities.

When I started framing conversations with open-ended questions, I noticed a significant shift. My team began offering ideas and solutions I hadn’t even considered, creating a more collaborative and innovative environment.

Advice: Make it a habit to ask thought-provoking questions. This behaviour not only fosters strategic dialogue but also empowers your team to think strategically themselves.

4. Connect the Dots Across Silos

Strategists are master connectors. They see patterns where others see chaos and align disparate efforts to achieve larger goals. This ability is critical during transformation, where alignment between teams is often the deciding factor for success.

In one merger I supported, aligning the priorities of two very different teams was pivotal. By facilitating conversations that focused on shared goals, I helped bridge gaps and create a unified vision—turning potential conflict into collaboration.

Advice: Look for relationships others might miss. Help your team see how their work fits into the broader strategy to build alignment and momentum.

5. Anticipate Ripple Effects and Drive Sustainable Change

Every decision has consequences—some immediate, others long-term. Strategists think through the ripple effects of their actions, ensuring that transformation is sustainable and impactful over time.

One piece of advice I often share with leaders is this: Transformation isn’t a one-time event—it’s a journey. In a policy change initiative I led, mapping out how the change would impact every level of the organization helped us avoid unnecessary disruptions and ensured smoother implementation.

Advice: Think beyond the first step. Consider how your decisions will affect the organization in the weeks, months, and years to come.

Why Strategists Matter

Strategists don’t just live in their heads—they make transformation possible. They create clarity in complexity, connect ideas to execution, and align stakeholders around a shared vision.

The biggest lesson I’ve learned is that strategy is most impactful when it’s demonstrated daily. It’s not just about what you think but how you show up:

• Are you connecting ideas to action?
• Are you helping others see the bigger picture?
• Are you leading your team through uncertainty with purpose and clarity?

Strategic thinking is no longer just a skill to master—it’s a behaviour to live.

Which of these golden behaviours resonates most with you? How are you demonstrating your strategic mindset in your organization?