Why critical analysis in strategic planning matters
You have just exited a town hall with your organization where you delivered the first phase roll-out of your strategic plan. The executive team is energized, the questions were good, engagement was high in the room and online. You are confident about executing this plan because you have resourcing and communication lined up. Then later that evening, a comment from the Q&A sticks in your mind. “It is all good until Softyware offers 24/7 drone delivery.” Could they be right? It has been a year since you heard about Amazon’s interest in Softyware. Could drone delivery be real for your market? Why are you still thinking about this?
That feeling matters. Teams build positive momentum and single perspective planning can create blind spots. Critical analysis in strategic planning helps you surface assumptions before they become expensive lessons.
Cautionary tales, when plans miss the mark
Red Lobster rolled out all you can eat snow crab for $22.99, assuming no one would sit for six hours and eat crab. They did. The company lost millions and a substantial portion of its market capitalization. Blackberry went from dominant to irrelevant in mobile because it held to the full keyboard while the touchscreen improved. Did they actually test customer preferences once touchscreens worked well, or did they rely on old data?
Every company reviews decisions to some degree. With exponential technology change and instant information, the environment is complex for everyone. That makes critical analysis in strategic planning essential.
Three methods to strengthen critical analysis in strategic planning
1. Appoint a devil’s advocate
In a previous article we discussed the dangers of groupthink and how to avoid it. One practical step is to appoint a devil’s advocate who prepares and presents strong contrarian views. This is something you can implement in your next planning session. Read more: Alignment Versus Group Think, Avoid the False Harmony Trap.
2. Assign roles to all team members
Use a structured process like De Bono’s Six Thinking Hats. Have each participant wear a different colored hat that defines their perspective for the discussion.
- Yellow: Optimism, benefits and potential
- Blue: Organizing and process
- Red: Feelings, intuition and emotion
- Green: Creativity, possibilities and alternatives
- Black: Judgment and skepticism, risks and problems
- White: The facts, information and data
This deliberately diversifies viewpoints and reduces blind spots without slowing momentum.
3. Red Teaming
Red Teaming formalizes critical analysis. A red team is separate from the planning group and is tasked with evaluating the plan. Red team members adopt an adversarial perspective to challenge assumptions, premises, and strategic choices. By doing this, they identify potential flaws, biases, and alternative approaches that may have been overlooked during development.
Although the stance is contrarian, effective red teams are creative and collaborative. They engage planning team members to confirm facts and clarify assumptions. Assembling a red team is a significant commitment and requires a solid understanding of the process to be effective, yet it can become a capability that separates your organization and protects its future.
Make critical analysis a leadership habit
Regardless of your organization’s size or ambitions, put critical analysis in strategic planning at the top of your to-do list. We can help you implement simple practices like devil’s advocate and Six Thinking Hats, or develop full Red Teaming capability for high-stakes decisions. Connect with Sage & Summit to explore facilitation, leadership team coaching, and executive coaching that strengthen decision quality and execution.
