Three Steps to Ensure Your Team is Ready
for a Successful Strategic Plan
Every week, I chat with CEOs and board members eager to dive into strategic planning. I’m all for that enthusiasm, but before jumping in headfirst, I like to ask a series of probing questions to gauge whether they’re truly prepared for the rollercoaster ride that is strategy development.
And guess what? Often, our conversations end with them deciding to hit the pause button.
Why? Because taking a step back and laying the groundwork before diving into strategy can be a real game-changer. That’s exactly what we’ll explore in this blog series on strategy readiness.
Are you ready for Strategy?
Before you take that first step, check out all three parts of this blog series on strategy readiness. We’ve outlined three pivotal questions to consider before launching into strategic planning:
WHAT "job" are you hiring a strategy to do for your organization?
HOW can you ready your team and board for this undertaking?
Parts one and two of this series help you clarify the purpose of your strategy and determine the right timing. In strategic planning, timing is everything—knowing when to take the leap can make all the difference.
Now, let’s dive into Strategy Readiness Question #3: HOW can you prepare your team and board for this critical work?
Strategic planning is a disciplined effort that allows organizations to define or reaffirm who they serve, what they do, and why they do it, all with an eye toward the future. It's a discipline, not an event. To create a strategic plan that reflects diverse perspectives and achieves strong alignment, be prepared to collaborate with a wide range of stakeholders.
Most teams dive deeply into strategy every five to ten years, typically in response to significant events such as the entry of a new competitor, market shifts, or growth expectations that demand clear plans. Time spent in preparation is time well spent.
Before you start chopping down the tree, take the time to sharpen your axe.
Three Key Steps to Ready Your Team for Strategic Planning
Asking the right questions can unlock valuable insights. As Warren Berger says it in A More Beautiful Question, "Ask the right questions, and good ideas will follow."
1. Decide What Question You Are Answering With This Plan
Most strategic planning propoals I receive include a list of objectives, deliverables and requests from the client - such as stakeholder interviews, surveys, SWOT analyses or workshops. However, before we build out how you'll approach this work it's crucial to begin with why.
Take a moment to draft a single, overarching question that frames the purpose of your strategic work. This question should strike a “goldilocks” balance—not too broad, yet not too narrow. To refine it, consider the following:
Is the question too narrow? For instance, “How should I reorganize my team?” leaves little room for creativity. Widen the lens to encourage broader thinking.
Is the question too broad? For example, "How can we transform our community?" may leave participants struggling to generate actionable options. To avoid this, narrow the focus to something that can be addressed within the project’s scope. Without clear boundaries and focus, the team may find it difficult to develop practical solutions.
Does the question imply a solution? For example, “What new programs or services should we launch?” might stifle expansive thinking. Pull the camera back and reframe so that the reader can use their own creativity to generate ideas or solutions.
Revisiting and refining the question will help you reach that “just right” level of focus. A useful template might be: How might we grow our impact on [audience] in a future environment of [context]?
Crafting a great question helps create a shared language and clear definitions within your team. When terms like “grow,” “impact,” “audience,” and “context” are well-defined, they become powerful tools to guide your strategy work.
2. Make Sure The Right Leaders Are At The Table
As a CEO, your most crucial role in preparing for strategic planning is to ensure the right leaders are at the table. The journey of building a strategy is intense and can involve challenging long-held practices and assumptions, engaging in difficult conversations, synthesizing research, and reaching consensus after lively debate.
One client paused their strategy work for two months so that they could complete a recruiting process for four key positions. They smartly decided that these new leaders needed to be in place to contribute to and influence the strategy.
Don’t overlook your board's role in this process. Most successful strategies are led in partnership between the the CEO and a dedicated strategic planning committee within the board of directors. Choose members who possess strategic agility and influence, as they will help carry the strategy to the larger board and facilitate buy-in.
At the end of a strategy engagement, you’ll have a team and board that have walked together on this journey to make tough choices and tradeoffs. Once hard questions—often debated for years—are finally resolved, the team can become champions for both the reasoning behind and the implementation of the final decision.
As Peter Drucker famously said, “Culture eats strategy for lunch.” Successfully launching a strategy is intrinsically linked to change management. If strategy answers the business questions of who, why, and how—change management addresses the human side of implementation.
By involving those who will implement the strategy in its creation—through interviews, workshops, and discussions—you increase the likelihood that the strategy will stick in the long term. Ultimately, strategy must become part of the culture and ethos of any organization.
3. Make Time For Strategic Conversations
Before starting work with clients, I “diagnose” their readiness for strategy. A key factor is understanding how aligned various stakeholders are around the major decisions facing the organization. As you plan your strategy, assess your organization's alignment on critical choices. On a scale of 1 to 5, how close is that alignment?
Given the life-stage of your organization: will this strategic plan be a moderate iteration of what you already do, or a more significant evolutionary change? Early in the process, I often ask, “Is this an evolution or a revolution?” There's no wrong answer, but the answer will guide the timeline and scope of your strategy.
For example, one client sought to deeply understand the evolving landscape of homelessness in Atlanta and incorporate these insights into significant changes in their services. As part of their strategy, they commissioned extensive research. This exploration took time, and the insights required careful consideration by both the teams and the board to fully grasp the implications for future strategy.
Effective strategy often brings long-standing behaviors, choices, and assumptions into the light for re-examination. These conversations can take weeks or even months to fully unfold. The first time a significant issue is raised might not be the right moment for a decision. But when it resurfaces weeks later, the team may be wiser and more prepared to make that choice.
Give your organization and board the time they need to make informed decisions. Allow space for insights to surface, time for information to be thoroughly processed, and ultimately, let these elements shape the choices that will define your future.
Are you getting ready for a strategic plan? We'd love to talk about your situation and help you prepare!
