Lessons from the Field: Facilitating a High-Stakes Strategy Alignment Workshop
- Jentz Tan
- Sep 30, 2024
- 4 min read
Recently, I facilitated an offsite strategy workshop for a group of senior leaders representing different regions. Their goal was to align on their strategy for 2025—an objective they had been struggling with for months. The stakes were high, with a week-long retreat organized for leaders from across the globe and a pressing need to leave with a clear, actionable strategy.
The team had been working with the Theory of Change framework, while my approach leans heavily on Roger Martin’s Strategy Choice Cascade (SCC) and Strategy Process Map (SPM). Rather than introducing an entirely new framework, I chose to bridge the familiar with a strategy-driven process, which guided the team toward alignment. The result? Success. The leadership team walked away with an actionable strategy that already positioned them for a strong start in 2025. Here are some key reflections from that experience.
Why Practical Experience Outweighs Theory
There’s a world of difference between knowing theoretical frameworks and applying them in real-world situations. You can read all the books or watch as many tutorials as you want, but true expertise is forged in the field—especially when navigating the nuances of a high-stakes discussion.
As one of the directors told me afterward:
We’ve worked with other facilitators, but you did much better. Despite all the technical and scienticific discussion, you managed to asked the right questions, knew when to push and when to step back.
This feedback underscores a vital point: facilitation isn’t just about guiding the room; it’s about understanding the dynamics and navigating them with precision. And that level of understanding only comes from practice.
Lesson 1: Mastery Beats Quantity
Bruce Lee once said,
“I fear not the man who has practiced 10,000 kicks once, but the man who has practiced one kick 10,000 times.”
This couldn’t be truer in the world of facilitation.
Rather than trying to learn every new framework that comes along, it’s far more valuable to master a few and apply them effectively. That’s Roger Martin’s Strategy Choice Cascade (SCC). I’ve used these a couple of times, refining my understanding of how to apply them to different teams and challenges. It’s this focused mastery, rather than having a vast toolkit, that delivers results in real-world situations.
Lesson 2: Be Over-Prepared But Ready to Improvise
I spend about twice as much time preparing for every workshop I facilitate as I do delivering the actual session. For a three-day session, six full days of prep is required. I planned the agenda meticulously, considered different scenarios, and designed activities to foster productive discussion. However, as is often the case, only about 10% of my original plan was actually used.
By the second hour, the team’s conversation had diverged from the agenda. That’s when improvisation came into play. But the ability to pivot and adapt in real-time comes from thorough preparation. Even though I had to discard my plan, the preparation was critical because it allowed me to stay sharp and responsive to the team’s needs as they arose.
On the right is an example of a decision tree map I created to simulate different scenarios and determine which methods and frameworks to use for each possibility.
Facilitation requires flexibility. It’s not about adhering rigidly to a plan—it’s about being prepared enough to guide the conversation in the right direction, even when the path changes.
Lesson 3: You Get What You Pay For
Some organizations hesitate to invest in external facilitators, especially when they see the preparation-to-workshop time ratio. In my case, it often takes twice as long to prepare as it does to deliver the workshop. So, a 3-day session might involve 6 days of preparation.
But think of it this way:
Would you rather spend months attempting to align internally with no clear outcome, or make an investment to ensure you leave the session with an actionable, focused strategy?
In this case, our client is poised to use the last quarter of the year to start laying the groundwork for 2025, giving them a head start on their competitors.
It’s true that high-quality facilitation is an investment, but the cost of indecision and misalignment is far greater.
Final Thoughts
If you’re finding it difficult to align your leadership team on your 2025 strategy, or if you simply want an external perspective to guide the process, feel free to reach out. I’m happy to discuss how I can help you align your team and create an actionable roadmap for the future. And even if we don’t end up working together, I’d be glad to share some insights to help you move forward.
Ready to talk?
Let’s connect and ensure your strategy is built to succeed in 2025 and beyond.
[About the Author]
Jentz has a deep background in innovation and design across Europe and Malaysia. Committed to enhancing design practices, Jentz aims to help position Malaysia as a hub for creative and impactful solutions. Join him in exploring the potential of design thinking to tackle immediate challenges and inspire transformative change and innovation.
