What I’ve Learned from 20 Years in Strategy

... and what I’d do differently

As I reflect on the last two decades of working in strategy, from my early days in corporate communications to now running my own consulting business, there’s much I’ve learned—and even more that I would do differently with the benefit of hindsight. In this blog, I’ll share the key lessons I’ve picked up over the years and some reflections on what I wish I’d known earlier.

1. The Power of Clarity

One of the most fundamental lessons I’ve learned is the importance of clarity. A clear direction is the backbone of success, whether a business strategy, marketing approach, or internal communications plan. Early on, I saw how a lack of clarity can create confusion, misalignment, and wasted resources.

What I’d Do Differently: I would spend more time upfront, ensuring that all stakeholders—clients, team members, or partners—have a shared understanding of the strategy and its objectives. In the past, I sometimes rushed the planning phase, assuming everyone was aligned, only to realise later that assumptions weren’t enough. Now, I prioritise clear, transparent communication from the outset.

2. The Importance of Emotional Intelligence

Strategy isn’t just about numbers and metrics. It’s also about understanding people—clients, customers, and teams. Over the years, I’ve recognised how crucial emotional intelligence (EQ) is when developing strategies that resonate and inspire action. EQ helps build relationships, foster collaboration, and create a culture of trust—all vital to any strategy’s success.

What I’d Do Differently: I would have emphasised EQ earlier in my career. I was overly focused on data and results in my earlier days, sometimes overlooking the human element. Now, I approach strategy holistically, recognising that connecting with people emotionally leads to a more profound, more sustainable impact.

3. The Need for Flexibility

One thing I’ve learned time and time again is that no strategy is set in stone. Markets evolve, customer behaviour shifts and even the best-laid plans can face unexpected challenges. While having a clear strategy is essential, it’s equally important to remain flexible and agile in response to new information and changing circumstances.

What I’d Do Differently: Early in my career, I was often too rigid in my approach to strategy. I believed in executing the plan as it was developed, even when circumstances changed. I’ve learned that flexibility is just as necessary as the strategy itself. I would have embraced a more agile mindset much sooner.

4. Data Is Crucial, But Insight Is Key

In today’s data-driven world, analytics and insights often shape strategy. However, I’ve come to realise that while data is crucial, it’s the insight you draw from it that truly matters. The ability to interpret and apply data to inform decision-making is what separates good strategies from great ones.

What I’d Do Differently: In the past, I was sometimes too focused on the volume of data rather than on the quality of the insights it provided. Today, I approach data analysis more discerningly, focusing on actionable insights that drive tangible business outcomes. I would have prioritised this shift in mindset earlier in my career.

5. Stakeholder Engagement is a Strategy, Not an Afterthought

When I started working in strategy, I often viewed stakeholder engagement as something that happened after the plan was developed. It wasn’t until later that I realised how integral it is to the strategy. Engaging the right stakeholders at every stage of the strategy development process ensures better buy-in and leads to more innovative, well-rounded strategies.

What I’d Do Differently: Looking back, I would have made stakeholder engagement a central part of my strategic thinking. Early engagement with stakeholders leads to better insights, stronger collaboration, and, ultimately, more successful strategies.

6. The Importance of Taking Risks

Strategy requires courage. It involves making decisions with limited information, challenging the status quo, and taking calculated risks. Over the years, I’ve seen how businesses willing to take strategic risks often appear ahead. The most successful strategies push boundaries and embrace new opportunities, even when the path forward isn’t entirely clear.

What I’d Do Differently: I used to play it safe more often than I should have. Looking back, I would have been more comfortable taking risks in my strategies, knowing it’s okay to fail as long as you learn from it and adapt. Risk-taking is essential for innovation and growth, and I would have embraced it more confidently earlier.

7. Continuous Learning is Key to Growth

The world of strategy is constantly evolving. New technologies, shifting customer preferences, and emerging business models mean that what worked yesterday might not work today. Staying ahead of the curve requires a commitment to lifelong learning and personal development.

What I’d Do Differently: While I always valued learning, I now recognise that it’s not enough to stay current with industry trends. I would have invested more in developing my leadership and strategic thinking skills throughout my career, attending more training sessions, and seeking out mentors who could challenge my thinking.

8. Trust Your Instincts

Finally, one of my most valuable lessons is trusting my instincts. Strategy often involves uncertainty, and there are times when the data doesn’t provide clear answers or when the "safe” path isn’t the best option. In those moments, trusting my intuition and experience has often led me to the right decisions.

What I’d Do Differently: I sometimes doubted my instincts earlier in my career, relying more heavily on others’ opinions or conventional wisdom. Over time, I’ve learned that my intuition is a valuable tool in strategic decision-making. I now trust my instincts more and encourage others to do the same.

Final Thoughts on 20 Years in Strategy

As I move into the next phase of my career, these lessons continue to shape the way I approach strategy, both in my consulting work and the businesses I am building. Strategy is more than just planning; it’s about agility, emotional intelligence, and a willingness to take risks. Looking back, I see how much I’ve grown and how much I would have done differently. But that’s the beauty of strategy—it’s not just about getting it right the first time; it’s about learning, adapting, and evolving along the way.

If you’re a business leader looking for clarity and insight into your strategy, I’d love to help. Let’s make your business vision as crystal clear as possible with a well-planned, adaptable, and people-centred approach.