Strategic Planning the Goldilocks Way Part 1 — Knowing When the Time Is Right
Strategic planning has become one of those topics that makes nonprofit leaders groan. Too often, it’s associated with expensive consulting engagements, endless meetings, and a glossy binder that gets shelved and forgotten. At the same time, most leaders feel a nagging sense that they should be doing it — like the gym membership you know you ought to use.
The truth is, strategic planning can be powerful and energizing when it’s the right time and approached in the right way. But it can also become a drain if it’s too much, too little, or simply not the right fit for your organization.
That’s why I’ve framed this short two-part series around the idea of the Goldilocks strategic plan — not too big, not too small, but just right.
Part 1 looks at how to know when it’s time to begin.
Part 2 explores the first steps you should take — and why hiring a consultant too early is like asking a builder to construct a house before you’ve even decided what kind of home you want.
My hope is that these pieces give you and your board a clear, practical way to approach strategic planning so it becomes a tool you’ll actually use — not a dreaded “paper tiger.”
Part 1: Is It Time for a Strategic Plan?
So how do you know when the moment has come? Strategic planning isn’t something to tackle just because you feel you should — it’s most effective when the timing is right. There are signals that tell you an organization is ready, and that a plan would provide real value rather than drain energy.
✅ Signs It’s Time to Start a Strategic Plan
Your current plan is outdated or irrelevant: If your last plan is more than 3–5 years old, or no one even remembers what’s in it, you’re likely operating without a shared roadmap.
Your external environment has shifted: New funding realities, changing community needs, shifting policies, or new competitors/collaborators are often a trigger to re-evaluate your direction.
Leadership transitions are underway: A new executive director, CEO, or board chair is an ideal moment to align around priorities and vision.
Your team is stuck in reactive mode: If staff and board are constantly firefighting without clarity about longer-term priorities, a plan helps re-center around mission and focus energy.
You’re about to launch a major initiative: Whether it’s a capital campaign, a new program, or expanding into a new community, a strategic plan provides the scaffolding for sustainable growth.
There is a lack of alignment between board and staff: If you hear competing versions of “what we do” and “where we’re going,” it’s a sign the organization needs to get everyone on the same page.
Funders or partners are asking questions you can’t answer: “What’s your five-year vision?” “How do you measure success?” If those answers are fuzzy, it’s time to clarify them.
You need a tool for accountability and learning: A strong strategic plan doesn’t just sit on a shelf — it becomes the framework for measurement, evaluation, and learning.
🤔 Ask Yourself (and Others)
Beyond the checklist, it helps to pause and ask a few deeper questions. These aren’t meant to be yes/no answers but conversation starters. If the answers feel vague, inconsistent, or uneasy, that’s usually a sign it’s time to plan.
As a leader:
Am I making big decisions without a clear framework for priorities?
Do I feel like we’re constantly reacting rather than steering?
Have I inherited (or am I about to hand off) a leadership role without a roadmap?
Do I struggle when funders ask, “What’s your long-term vision?”
With your board and senior team:
Are we aligned on our most important goals for the next 3–5 years?
Do we agree on what success looks like — and how we’ll measure it?
Are we investing our resources in the right places?
Are we energized by where we’re headed, or losing steam?
With your stakeholders:
Are we meeting the needs of the people we serve today?
What do you most value about our work — and what gaps do you see?
What role should we play in the community five years from now?
⚖️ Don’t Forget the Cost of Not Acting
Timing isn’t just about looking for signs that you should plan—it’s also about weighing the risks of not planning. Sometimes the greater risk isn’t the cost of doing a plan—it’s the cost of not doing it when the signals are clear. Here are a few common costs of delay:
Lost opportunities: New partnerships, funding streams, or initiatives may pass you by without a clear strategy to guide quick decisions.
Erosion of alignment: The longer you wait, the more staff, board members, and stakeholders may drift into competing versions of your mission and priorities.
Funding disadvantages: Donors and grant-makers often want to see a clear, written plan. Without one, you may be leaving money on the table.
Burnout from firefighting. Operating without a roadmap keeps everyone in reactive mode—leading to wasted energy, frustration, and eventual turnover.
✨ Conclusion
Strategic planning doesn’t have to be the dreaded, resource-draining exercise leaders fear. When the timing is right, it can be one of the most energizing tools your organization has—clarifying direction, aligning people, and opening doors to funding and opportunity. The key is to pay attention to the signals, weigh the risks of waiting, and be honest about whether now is the “just right” moment.
👉 In Part 2, we’ll look at what to do once you’ve decided the timing is right—so your planning process is focused, practical, and built to last.