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Strategic Agility: A New Routine

Shane Evans • December 27, 2024

Practice Bi-Weekly Scenario Planning for Strategic Fitness

Thought Experiment: Brainstorm risks, uncertainties, and threatening dynamics relevant to your business and industry. Identify the top three most likely to change or materialize. Identify the top three in terms of potential impact. Are any high likelihood and high impact?



Introduction: Strategy as a Weekly Habit

Strategy is often viewed as an annual event—a dedicated retreat where senior leaders spend days crafting plans for the future. While these sessions are vital, they shouldn't be the only time an organization engages in strategic thinking. In a world that’s fast-moving and unpredictable, organizations need a way to keep their strategies agile, relevant, and actionable.


Imagine strategy as a muscle—it requires regular exercise to stay strong. By incorporating strategic thinking into weekly or bi-weekly practices across all levels of the organization, leaders can make smarter decisions, faster, and remain ahead of emerging trends. We previously explored various strategic thinking exercises you can use to bulletproof your strategy, but one of the most powerful, accessible tools to achieve this is scenario planning.


What Is Scenario Planning?

Scenario planning is a structured method of envisioning and evaluating different possible futures. Unlike forecasting, which tries to predict the most likely outcome, scenario planning explores a range of plausible outcomes to stress-test current plans, challenge assumptions, and uncover opportunities.


At its core, the process invites you to ask, “What if?” For example:

  • What if a key supplier suddenly goes out of business?
  • What if customer preferences shift dramatically toward sustainability?
  • What if new technology disrupts our industry?
  • What if new regulation were introduced or the pace of regulation accelerated?
  • What if there is a recession?


The goal isn’t to predict the future—it’s to build readiness for a variety of plausible futures.


Why Make It a Weekly Habit?

Imagine if you only exercised once a year. You might feel accomplished after an intense session, but would it make you healthier? Experts in fitness and health recommend consistent exercise—just 30 minutes a day or a few hours each week—for lasting benefits. Regularity builds strength, endurance, and mental clarity, ensuring each session is more effective and less daunting because you’re already "in shape."


The same principle applies to strategy. Many organizations approach strategy as a once-a-year event, a marathon of brainstorming and planning. But just like physical health, strategic health thrives on consistent practice. Here are the benefits to staying 'strategically fit':

  1. Fast, Easy & Inclusive: Anyone & everyone can do it, alone and in a group, in 10 minutes or an hour, with nothing more than their mind, a whiteboard, or paper and pen. Analyze just one quadrant of a single scenario planning exercise, or complete a few exercises assessing various uncertainties. And, the more you do it, the faster and easier it becomes.
  2. Increased Organizational Agility: Frequent scenario planning keeps strategy nimble, allowing teams to pivot as new challenges or opportunities emerge.
  3. Cross-Organizational Insight: By involving different departments or teams, you surface diverse perspectives and ensure strategy is informed by on-the-ground realities.
  4. Black Swan Events: By conducting strategic planning frequently, you move past the obvious uncertainties and become much more thorough in examining seemingly remote and unlikely risks. 
  5. Decision-Making Confidence: Practicing “what if” scenarios regularly reduces the paralysis that comes with uncertainty, empowering leaders to act decisively. Leaders and teams grow more confident and competent in their strategic thinking.
  6. Skill Development: Like any discipline, strategy improves with practice. Regular scenario planning sharpens critical thinking, collaboration, and decision-making skills across the organization.
  7. Improved Annual Planning: Frequent analysis of strategy not only provides great input to the annual exercise involving senior leaders, but allows the organization to conduct more complex or meaningful strategic analysis.
  8. Collective Intelligence: Cataloging the output of scenario analysis exercises from across the organization and over time produces a robust library of intelligence as well as insight into specific and trending issues/concerns that management may be unaware of, fascilitating new insights and learning.

How to Practice Scenario Planning: A Step-by-Step Guide

Here’s how you can start scenario planning in your organization today:

  1. Define the Focus Area:
    Decide on the specific topic, decision, or challenge you want to explore. For example: “How might our market change over the next 12 months?” Keep it relevant and actionable.
  2. Identify Driving Forces:
    List the key external factors or trends that could shape the future in your focus area. These could include technological innovations, regulatory changes, economic conditions, or customer behavior. Example: A healthcare company might identify aging populations, telemedicine adoption, and shifting government policies as key drivers.
  3. Map Critical Uncertainties:
    Select two uncertainties that are both high-impact and high-uncertainty. Plot them on a 2x2 matrix to create four distinct quadrants, each representing a possible future. Example: A software firm might choose “speed of AI adoption” (fast vs. slow) and “regulatory environment” (strict vs. lenient) as critical uncertainties.
  4. Build Scenarios:
    Develop a brief narrative for each quadrant, describing what that future might look like. Be creative but grounded in reality. Give each scenario a name that captures its essence.Example: For the software firm, scenarios could include:
  5. “AI Gold Rush” (fast adoption, lenient regulation)
  6. “Regulated Innovation” (fast adoption, strict regulation)
  7. “Slow Progress” (slow adoption, lenient regulation)
  8. “Bureaucratic Bottleneck” (slow adoption, strict regulation)
  9. Stress-Test Your Strategy:
    Evaluate how well your current strategy holds up in each scenario. Identify vulnerabilities, opportunities, and areas for adjustment.
  10. Develop Contingency Plans:
    For high-impact scenarios, outline specific actions your organization could take. These contingency plans don’t need to be exhaustive—they’re starting points for rapid decision-making. Example: In the “AI Gold Rush” scenario, the software firm might prioritize hiring AI specialists, while in the “Regulated Innovation” scenario, they’d focus on compliance capabilities.
  11. Review and Adapt Regularly:
    Revisit your scenarios weekly or bi-weekly to assess their relevance and update them as new information emerges.

Conclusion: Small Time Investment, Big Strategic Payoff

Making strategy a weekly or bi-weekly habit transforms it from a static plan into a dynamic process. Scenario planning, in particular, equips organizations with the tools to anticipate change, navigate uncertainty, and seize opportunities. Whether you’re a senior executive charting corporate direction or a middle manager driving team initiatives, practicing strategy regularly fosters resilience and ensures you’re always ready for what’s next.


It’s time to rethink strategy not as an annual event but as an ongoing conversation—one where everyone in the organization can participate and contribute. With frequent scenario planning, you can. After all, the future doesn’t wait for annual meetings, and neither should your strategy.



Thought Experiment:  Pick two uncertainties relevant to your business and industry. Consider the high/low or good/bad of each uncertainty. Think through just one of the four permutations and what that future looks like. How your enterprise & strategy would fare?



If you'd like to teach your organization how to do this or run a workshop with your team, we can help!

Let's Talk
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