8 Critical Decisions for Strategy Facilitators
Hey Luck Hackers,
In today's issue, I'm sharing eight critical decisions strategy facilitators need to address before launching into a strategy development process.
Facilitating a strategy process isnât about throwing ideas on the wall and seeing what sticks. Itâs about asking the right questions, making informed decisions, and setting a clear path forward. Without clarity on key issues, a strategy risks being irrelevant, fragmented, or impossible to execute.
***************
New Training: The Strategy Accelerator Program
Elevate your career with this transformational 8-10 week program designed for consultants, internal strategy leaders, and strategy professionals.
Master the art of strategy facilitation, strategic planning, and strategic execution with advanced facilitation techniques, coaching strategies, and powerful tools.
Gain the expertise to deliver actionable, embraced, and executed strategy.
- Get Certified as a Strategy Facilitator
- Leverage proven frameworks and methodologies
- Start realizing your full potential as a Strategic Advisor
Elevate your career. Expand your influence. Accelerate your impact.
Click here -> join the waitlist for the program
***************
The 8 decisions outlined here are not just arbitrary checkpointsâtheyâre the foundational for effective strategy facilitation. Each decision reflects a core aspect of strategy development that must be addressed for the process to succeed. Below, we explore these decisions, why they are essential, and how to approach them.
1. Does the Organization Have a Clear Strategy?
Why This Question Is Important:
Many organizations operate without a clearly defined strategy. Instead, they rely on vague goals, disconnected plans, or outdated assumptions. A lack of clarity at this stage often leads to wasted time and resources on processes that solve the wrong problems.
What This Question Uncovers:
- Whether the organization has a strategy or just a collection of tactics.
- The degree to which leadership and employees are aligned on the current strategy.
- Areas of ambiguity or inconsistency that need resolution.
How to Approach This Decision:
- Audit the Existing Strategy: Review strategic documents and ask leaders to articulate the strategy in one sentence.
- Facilitate Alignment: Identify where leadership views diverge and address discrepancies early.
Key Consideration: Without clarity on the organizationâs current strategy, itâs impossible to determine whether to refine it, rethink it, or start from scratch.
2. Is It Time to Rethink Strategy?
Why This Question Is Important:
Even a strong strategy can become obsolete when markets shift, customer needs evolve, or competitors innovate. Recognizing the need for a strategy refresh is crucial to staying relevant and competitive.
What This Question Uncovers:
- External triggers (e.g., new competition, regulatory changes) or internal challenges (e.g., declining performance, cultural misalignment) that may warrant a strategic reset.
- Whether the organization is clinging to an outdated strategy out of inertia.
How to Approach This Decision:
- Identify Triggers: Look for signs like declining market share, customer dissatisfaction, or employee disengagement.
- Engage Leadership: Ask, âWhat has changed externally or internally that might affect our strategyâs relevance?â
Key Consideration: Rethinking strategy isnât always necessary. Sometimes, the issue lies in execution rather than the strategy itself.
3. How Do You Define Business Success?
Why This Question Is Important:
Strategy must have a clear purpose. In too many organizations, the leadership team has never gone through the hard work of identifying and codifying the central objectives of the organization. Without a shared definition of success, teams may focus on conflicting priorities, leading to inefficiency and misalignment.
What This Question Uncovers:
- The degree of alignment about what success looks like.
- The organizationâs ultimate goals, whether they are growth, throughput, responsiveness, efficiency, innovation, or impact.
- Key metrics for success and whether they align with the organizationâs mission.
How to Approach This Decision:
- Clarify Goals: Ask leaders, âWhat does success look like?"
- Identify Metrics: Ensure that success is measurable and tied to meaningful outcomes.
Key Consideration: Defining success creates a north star for the strategy process, ensuring all efforts are focused on achieving the same vision.
4. What Is the Primary Challenge the Business Faces?
Why This Question Is Important:
Strategy exists to solve problems or overcome obstacles. Without understanding the organizationâs primary challenge, the strategy risks being irrelevant or overly broad.
What This Question Uncovers:
- External challenges, such as market volatility or competitive pressure.
- Internal challenges, such as resource constraints or cultural resistance.
How to Approach This Decision:
- External Environment: Assess whether the market is stable or unpredictable and whether the organization is shaping or reacting to its environment.
- Internal Dynamics: Identify resource limitations, growth constraints, or operational inefficiencies.
Key Consideration: A clearly defined challenge ensures the strategy is focused on solving the right problems.
5. Who Needs to Be Involved in the Process?
Why This Question Is Important:
Strategy development requires input from the right people. Too few voices can lead to blind spots, while too many can create decision paralysis.
What This Question Uncovers:
- The stakeholders who must be involved to provide expertise, ensure alignment, and drive implementation.
- The level of engagement required for effective participation without unnecessary complexity.
How to Approach This Decision:
- Map Stakeholders: Identify who has influence, expertise, and responsibility for the strategyâs success.
- Tailor Engagement: Determine whether the process should involve just the leadership team or a broader group of employees.
Key Consideration: Engaging the right people builds alignment and ownership, making the strategy more actionable.
6. What Gaps in Data or Understanding Must Be Addressed?
Why This Question Is Important:
Good strategy relies on good data. Without accurate insights, decisions may be based on assumptions, leading to flawed outcomes. While executive intuition is powerful, it tends to be based on widely shared beliefs, not necessarily hard facts. Many of the most potent strategic insights have come from disaggregating averages to look at customer needs by segment and product and customer segment profitability.
What This Question Uncovers:
- Areas where the organization lacks critical information, such as customer segmentation, competitor behavior, customer profitability, or product profitability.
- Whether the organization has the tools and processes to gather and analyze data effectively.
How to Approach This Decision:
- Audit Knowledge: Identify gaps in understanding about customers, products, markets, and operations.
- Conduct Pre-Strategy Analysis: Address these gaps before the strategy process begins.
Key Consideration: Filling data gaps early ensures the strategy is built on a solid foundation.
7. What is the likely source of competitive advantage?
Why This Question Is Important:
A strategy worth having must create an advantage. Without a clear understanding of what sets the organization apart, the strategy risks being generic and uncompetitive. The strategy facilitator must know the answer to this question if they want to be an effective guide to management.
What This Question Uncovers:
- The unique resources, capabilities, or relationships that differentiate the organization.
- The competitive factors such as scale, branding, or network effects will separate the winners from the also-rans.
- What customers will miss if the organization disappears
How to Approach This Decision:
- Assess Differentiators: Ask, âWhat does the organization bring to the world? Does that difference matter? Is something about it scarce and difficult to imitate??â
- Evaluate Market Position: Identify how the organization delivers value relative to competitors.
Key Consideration: Understanding competitive advantage ensures the strategy focuses on building and protecting strengths.
8. Is the Organization Ready to Execute the Strategy?
Why This Question Is Important:
Even the best strategy is useless if it canât be executed. Assessing readiness ensures the organization has the processes, systems, and tools to turn plans into action.
What This Question Uncovers:
- Whether management processes and communication systems are robust enough to support execution.
- Areas where additional resources, tools, or training may be needed.
How to Approach This Decision:
- Evaluate Processes: Ask, âDo we have the management processes and systems to manage execution effectively?â
- Identify Barriers: Pinpoint cultural or structural obstacles to implementation.
Key Consideration: Addressing execution barriers upfront ensures the strategy is actionable.
Conclusion
These 8 critical decisions are the foundation of effective strategy facilitation. They ensure the process is aligned with the organizationâs goals, focused on solving the right problems, and supported by actionable insights.
By addressing these questions before starting the process, facilitators can guide organizations toward strategies that deliver real results.
Great strategies donât start with answersâthey start with the right questions.

Until next time, be somebody who happens to the world.
Stay lucky,
Alex
Alex Nesbitt
Founder, Strategy Academy
PS - Here are three ways we can work together:
(1) Contact me for 1:1 CEO coaching and advisory services
(2) Level up your Strategic Thinking for Advantage here.
(3) Join the Strategy Accelerator program for consultants, internal strategy leaders, and professionals who want to be more effective Strategy Facilitators.
Responses