Strategy: The Simple Roadmap You Might Not Know You Need

Hey friends — finishing up season one of the podcast had me thinking about one word I didn’t say enough when I was starting out: strategy. It sounds big and sometimes people overuse it until it feels meaningless. But strategy is simply a practical, honest way to get from where you are to where you want to be.

If the word has felt intimidating, let me strip it down: strategy = looking back, looking at where you are now, and clearly deciding where you’re going — then writing a realistic, prioritized plan to get there.

A tiny example you know — the restaurant

Imagine someone wants to open an Italian restaurant. They don’t need a 50-page strategic plan to be strategic. What they do do (or should) is:

• Look around: Are there other Italian restaurants? Are they good?

• Check themselves: Do they have the skill, money, time?

• Look ahead: What is the first goal given the resources and situation?

• Prioritize tasks: Find property → get loan → buy equipment → hire chef → open.

• Do things in the right order and with a realistic assessment of resources (you don’t hire the manager before you have a location).

That’s strategy. It increases the odds of success because it fills gaps instead of hoping everything works out.

Why strategy matters for hybrid schools and nonprofits

For a solo business owner — like our restaurant owner — strategic thinking often happens naturally. For nonprofits (including hybrid schools operating as a nonprofit), strategy must be shared work: the board is responsible for ensuring the organization can sustain its mission. That adds complexity:

• No single owner decides everything — the board governs.

• The goal is mission-driven sustainability, not owner profit.

• Board members must be trained to understand and do strategic planning.

So the same basic process applies, but it needs structure, shared language, and accountability.

A practical process you can use

If you’re building a hybrid school or shaping a nonprofit board’s planning work, here’s a clear, friendly roadmap:

1. Agree on the goal(s).
   Maybe it’s simply: “build a sustainable, high-quality program where all operations are funded by tuition, teachers are fairly paid and well-trained, and a 3-year lease is negotiated with the building.” Keep early goals realistic and time-bound (e.g., 1 year).

2. Gather stakeholder input.
   Talk to staff, parents, donors, board members — surveys, focus groups, short interviews. Ask: What’s working? What’s missing? What would improve sustainability and quality?

3. Do a SWOT-style review.
   Map Strengths, Weaknesses, Opportunities, Threats across categories: curriculum, staffing, facilities, finances, culture, governance.

4. Identify the top 3–5 priorities.
   Don’t try to fix everything. Pinpoint the few things that will most improve sustainability. Maybe one top priority is increasing enrollment so that the budget balances

5. Make an action plan for each priority.
   For every priority, answer: What exactly will be done? Who will do it? By when? What resources are needed? Increasing enrollment might mean improving the admissions process and expanding marketing.

6. Assign responsibility and resources.
   Ensure the person/team has time, budget, and support. If not, adjust the scope or provide the resources. Identify the staff member who will be responsible for admissions and marketing (Will their hours increase? Do they need a raise? Is there money for that? Will their job description be updated? Who will do that? Who will make sure they understand the task and have support the may need?)

7. Build realistic timelines (possibly multi-year).
   Some changes take months or years. That’s okay — document it. A two- or three-year strategic timeline is often more realistic than trying to fix everything in 3 months. Does increasing enrollment have an actual number on it? Timeline? (“Fill each class to max next fall” is better than “Increase enrollment”)

8. Create accountability & check-ins.
   Regular progress checks (e.g., at each board meeting) keep momentum. The board should help remove barriers and hold people to agreed timelines.

Common pitfalls to avoid

• Stopping at “we should do this.” Don’t leave priorities vague. Convert them into specific tasks with owners and deadlines.

• Under-resourcing the work. If staff don’t have time, money, or clarity, the plan fails. Make sure it’s feasible!

• Letting personal preferences drive decisions. Prioritize organizational sustainability over individual requests.

• Trying to do everything at once. Scope and sequence matter — build stability first.

• Not speaking up. Anyone involved should have the opportunity to express concerns and the trust to do so.

Culture and leadership matter

Strategy works best when there’s healthy teamwork: educated leaders, clear roles, people willing to speak up, and leadership that listens. Strategic planning is a conversation — it’s not a top-down directive. Everyone should be honest about what’s feasible.

Final thought

Strategy isn’t a magic document; it’s a process. It’s about being realistic, intentional, and organized so your program can deliver its mission well — not just survive, but thrive. Start small if you need to: a one-year plan with clear priorities is better than no plan at all