Strategic Planning the Goldilocks Way Part 2 — Building a Plan That’s Just Right

In Part 1 of this series, we looked at how to recognize when it’s time to start thinking about a strategic plan. From outdated roadmaps to shifting environments, leadership transitions, and board/staff misalignment, the signs are often clear — and if you’re seeing them, it’s probably time to act.

But here’s the catch: the biggest mistake I see is organizations jumping straight into hiring a consultant or scheduling a retreat before they’ve had the right conversations internally. That’s like asking a builder to design your house before you’ve even decided whether you want a cottage, a farmhouse, or a brownstone.

That’s where the Goldilocks principle comes in. Before you begin, you need to think carefully about what kind of plan is “just right” for your organization — not so elaborate that it drains energy, not so bare-bones that it provides no real guidance, but balanced to fit your size, capacity, and goals.

What to Discuss Before You Start

A strategic plan that fits begins with conversation. Before you bring in a consultant or map out a process, gather your board and senior staff and work through these key elements:

1. Why now?⏰

Every organization has a story behind why strategic planning is on the table. Are you coming out of a period of drift and need to re-center around your mission? Are you about to welcome a new executive director or board chair and want to give them a clear roadmap? Are you preparing for a major campaign or expansion? Being able to clearly say why now gives purpose and urgency to the process — and helps prevent the plan from becoming a generic exercise.

2. What’s in and out?📋

Without boundaries, strategic planning can become a catch-all for every wish, frustration, or idea that surfaces. That’s how plans balloon into 60-page documents that no one reads. Talk as a leadership group about what needs to be included — for example, fundraising strategy, program focus, or leadership transitions — and what can be set aside for another forum. A plan with clear scope is much more likely to be used.

3. Who is it for?🎯

Strategic plans can have different audiences. Some are written mainly for staff and board to guide daily decision-making. Others are crafted to demonstrate vision and credibility to funders and partners. Many are meant to serve both roles, but if you don’t decide up front, you risk producing something that pleases neither. Clarify your primary audience, and you’ll also clarify the tone, length, and level of detail that’s needed.

4. What questions must be answered?❓

The best plans don’t try to solve everything. Instead, they address the three to five essential questions that will shape the organization’s future. Naming these big questions early ensures the plan has a clear focus and avoids getting lost in minutiae.

5. What does success look like? 🌟

This is where the Goldilocks principle comes alive. Instead of leaving it vague, ask your board and staff to picture three scenarios:

• Superlative Vision ✨
  What would it look like if this plan exceeded all expectations?
  Example prompts: Would it inspire donors? Become a model in your field? Set a bold, game-changing direction?

• Minimal Profile 📄
  What is the least acceptable outcome that would still count as “success”?
  Example prompts: Would a short 3-page roadmap be enough? Would checking the box for funders do the job? What’s the floor below which this process isn’t worth doing?

• Goldilocks (Just Right) ⚖️
  What’s the balanced outcome we’re truly aiming for?
  Example prompts: Is it practical and energizing? Short enough to use, but detailed enough to guide decisions? Something you’ll revisit at board meetings, not just file away?

Talking about these three versions out loud helps your team set shared expectations — and protects you from ending up with a plan that’s either overbuilt or underwhelming.

6. What will it take?🛠️

This is the honest conversation most groups skip. Strategic planning requires bandwidth. Will your board actively participate, or will it default to staff? Do staff have the time to engage meaningfully, or are they already stretched too thin? Are there potential friction points — such as differing board/staff expectations or limited resources — that could derail the process? Surfacing these issues early allows you to design a process that’s realistic, not aspirational.

Wrapping the Two Together

In Part 1, we explored how to know when it’s time to start strategic planning. In Part 2, we’ve focused on the first steps — the conversations about purpose, scope, audience, and success that need to happen before the work begins.

Taken together, these steps help you avoid two common traps: the dreaded black hole of endless planning and the useless paper tiger that sits on a shelf. Instead, they set you up for something in between — a Goldilocks strategic plan that’s practical, energizing, and just right for your organization.