What if “strategic planning” is actually the reason your strategy isn’t working?  

In this episode, Bonny and Nora unpack one of the most widely accepted, and rarely questioned, concepts in business: strategic planning. In this episode, they challenge the assumption that strategy and planning are one and the same and explore how confusing the two can lead to false progress, endless motion, and teams that are busy but not actually winning. Through a candid, real-time conversation, they explore the tension between strategy-first and emergent strategy, and land on a modern approach: treating strategy as a set of intentional, testable hypotheses that evolve through disciplined execution and reflection. 

Key Takeaways:  

➡️ Strategy is not the plan: Strategy defines how you believe you’ll win; it’s an intentional set of choices and trade-offs. Planning is a set of activities that gain momentum and test those choices. 

➡️ False progress feels productive: Without clear strategic choices, even the best plans can create motion without direction and success becomes accidental.  

➡️ Emergence requires intention: Strategy can be set upfront or emerge through action, but only becomes real when leaders stop, reflect and choose.  

➡️ Agility is disciplined learning: Adapting isn’t about constant change; it’s about building a cadence to reflect and evolve with intention.  

Strategy + Planning + Cadence = Momentum 

Listener Challenge: 

Before your next planning session, pause and ask: 

1️⃣ How do we believe we win?  If it sounds like a list of initiatives, you’re planning not strategizing 

2️⃣ What needs to be true for this strategy to work? If you don’t know, you can’t learn 

3️⃣ What would make you intentionally change direction? You might pivot too soon, or too late.  

 
This week, don’t start with the plan. Start with the choice. 

Resources / Tools:

➡️ Define your winning strategy with Roger Martin’s Choice Cascade  

➡️ Roger Martin on Strategy is not Planning  

➡️ Browse EOS Worldwide for tools like Vision/Traction Organizer (V/TO), and the 90 day world 

➡️ Download your OKR or OGSM Template to help you plan.  

➡️ Assess your Why, How, What with Simon Sinek’s Golden Circle 

Our Co-Hosts:

Bonny van Rest 

Strategic Thinker. Bold Challenger. Grounded Visionary.  

Bonny is a strategist, facilitator, and co-founder of Sidekick Consulting who believes momentum is built in the middle of the mess. With a background as a CMO and over a decade of experience across startup and corporate environments, she’s known for her sharp thinking, no-nonsense mindset, and ability to turn big ideas into grounded action. Bonny brings a calm presence, clear direction, and just the right amount of edge to move things forward—with intention. 

Nora Griffiths 

People-Centered Leader. Strategic Integrator. Dynamic Optimist.  

Nora is a purpose-driven leader, facilitator, and co-founder of Sidekick Consulting who believes that bold and meaningful impact is accomplished when done together. With deep roots in business development and operations, she’s known for her people-first lens and her talent for uncovering insights and ideas that translate swiftly into action, driving both people and performance. Nora brings a rare blend of energy, empathy, and clarity to build momentum that truly matters. 

Production by PRCPRN Studio. 

Directed by Giuliana DiBonaventura