Scenario Planning Beats a Perfect Plan
“Plans are worthless, but planning is everything.” — Dwight D. Eisenhower
That quote seems dismissive and overly simple. However, anyone that has been forced to make decisions in high-stress high-stakes situations will know it is true. Scenario planning emerged from military experience, where leaders like Eisenhower anticipated battlefield chaos by running through multiple “what-ifs.” The process of scenario planning is something any leadership team should use as a way to prepare to make hard decisions.
Scenario planning isn’t about building a perfect blueprint. It’s about training your team to act fast, remain objective, adapt quickly, and avoid getting blindsided.
Why Use Scenario Planning?
Manage high uncertainty: Team face shifting markets, emerging tech, and sudden constraints
Explore action plans ahead of time: When time is short there is often not time to fully brainstorm and interrogate many different tactical schemes
Remove emotion: By picturing difficult outcomes leaders can have an easier time remaining objective
Plans rarely survive contact with reality: Like von Moltke’s century‑old advice or modern battlefield lessons, no strategy survives contact with the enemy.
When to Use Scenario Planning?
The best time to scenario plan is well ahead of when you would actually need to make the difficult decisions or execute the strategy. However, you also want to be close enough to the event that you can have a reasonable understanding of the context and circumstance around the decisions that the team will need to make.
I have found scenario planning to be most valuable about 1-3 months before a major event like a product release or the start of a fundraising process. It can also be helpful to do on regular intervals as you pull your head up to take stock of your current strategy.
Scenario Planning Process
1. Choose your key uncertainties
Review the potential variables that will impact your decision-making. Ideally these are measurable and objective.
Product launch example:
Number of Users
Conversion (First Time User Experience funnel)
Retention
2. Create distinct scenarios
Choose the number of scenarios that make sense given the variables. I have found it to be helpful to start with four and then expand as needed.
Best Case: what if everything goes right?
Base Case: what do we think is most likely to happen?
Worst Case: what if everything goes wrong?
Absolute Worst Case: what if absolutely everything goes wrong? (in my experience most teams do not actually think about a true disaster scenario but they should)
Product Launch example:
Best Case: More users than expect with high conversion and high retention
Base Case: Expected number of users with expected conversion and retention
Worst Case - Users: Low number of users with expected conversion and retention
Worst Case - Conversion: Expected number of users with low conversion and expected retention
Worst Case - Retention: Expected number of users with expected conversion and low retention
Absolute Worst Case: Extremely low number of users with Extremely low conversion and retention
3. Map decisions and plans
For each scenario, think through what to do. I like to get extremely specific on the details while discussing the key decision points to fully explore the right trigger for the team to use to execute a plan. There is some value in preparing the core parts of several of these plans but most likely none of these scenarios will play out exactly as you describe them.
Spend additional time talking through the true worst case. Be ready to make hard choices when needed and know exactly where you will draw the line so that if it happens you can move quickly and unemotionally to the right decision.
Product Launch example:
Best Case: Pour more fuel on the fire and accelerate! Hire faster, spend on marketing, raise more capital, etc.
Base Case: Stay the course and keep executing on the current product roadmap
Worst Case - Users: Increase marketing spend or shift the marketing message
Worst Case - Conversion: Shift the product roadmap to focus more on conversion
Worst Case - Retention: Shift the product roadmap to focus more on retention
Absolute Worst Case: Hard pivot, do layoffs, make major changes
4. Review and update
As you gather more information or as other variables change it is useful to revisit the scenarios and triggers. Allowing the team to get comfortable with all the possible outcomes can make it much easier to execute quickly and improvise when needed.
Final Thoughts
Scenario planning isn’t about predicting the future, it’s about being ready for it.
There is tremendous value in practicing making a decision and talking through potential outcomes well ahead of time. Not only can the team take additional time to discuss decision triggers and plans, but they can also spend time building out the infrastructure needed to execute on those plans.
Remember that even the best improvisers practice constantly. And do not underestimate the value of premeditatio malorum.