The Strategic Plan Post-Mortem: Your Most Important Pre-Planning Work

Your strategic planning cycle is ending. The board kick-off retreat for your next plan is scheduled. A strategic planning committee is being formed. A consultant may be hired. The community is about to be mobilized for another round of visioning sessions, listening tours, and surveys.

But before you launch into all of that, stop.

There's critical work you need to do first – work that most schools skip entirely. You need a rigorous retrospective of your current strategic plan – what some might call a post-mortem. This isn't a celebratory recap of accomplishments or a polite summary of "areas for continued growth." It’s a genuine, unflinching examination of what you said you'd do, what actually happened, and why.

Here is why this matters: Most schools complete their strategic planning cycles with only partial delivery. Of five to seven strategic priorities, schools may execute two or three thoroughly, make modest progress on another one or two, and leave the rest largely unrealized. Then they move directly into the next planning cycle without understanding why some initiatives succeeded while others failed.

This pattern doesn't just waste the previous cycle's efforts, it sabotages the next one. Until you understand what enabled success and what prevented it, you're likely to repeat the same planning and execution mistakes, just with different initiatives.

The Patterns Schools Miss

Over the years, I’ve had many conversations with heads of school as to how their last strategic plan fared. Familiar patterns emerged:

Group A had five strategic priorities. Two were fully realized, two showed modest progress, and one barely moved forward. The board celebrated the wins and quietly acknowledged "ongoing work" on the rest.

Group B's plans included ambitious new academic programs meant to be their signature differentiator. Five years later, the programs exist more or less in name only, a paragraph on the website with vague descriptions and no clear identity. Faculty assigned to lead them were given neither resources nor direction. In some cases, a new building or space was built with corresponding specialized equipment, but the institutional focus and effort went into facilities, not program.

Group C developed comprehensive plans to address declining enrollment through enhanced programming and improved marketing. The enhanced programming was never adequately defined, designed, resourced, or staffed. The marketing improvements focused on telling better stories about programs that never evolved. Enrollment continued its decline.

What these schools have in common is not simply failed execution, it's failed learning. In many cases, they too often moved from one planning cycle to the next without examining why some elements of their strategy worked while others didn't. They repeated planning processes that produced similar results: some success, significant drift, and unclear accountability.

Why the Retrospective Matters

Strategic planning asks a lot of your community. Done well, the process should be energizing and inspiring, but it's undeniably time-intensive and requires genuine investment from multiple constituencies. Everyone commits significant time as well as intellectual and emotional energy to defining the school's next chapter.

Given this investment, you owe it to your community to learn everything possible from your last strategic cycle before launching the next one. The retrospective isn't about blame or judgment; it's about building institutional wisdom that makes your next plan more likely to succeed.

Consider what you're trying to accomplish with a new strategic plan. You want to set direction, allocate resources, focus effort, and ultimately move the institution toward greater impact and sustainability. But if your planning process consistently produces priorities that do not get realized, you're not creating strategy, you're creating elaborate to-do lists that can demoralize the community when they remain incomplete.

The Seven Critical Questions

A genuine retrospective requires examination of seven questions. Answering them is essential if you want your next plan to be a success.

1. What did we say we would accomplish?

Start by documenting every strategic priority from your plan. Be specific. Don't summarize or soften. If your plan said "Launch a signature interdisciplinary program serving 60 students by Year 3," write that down. If it said "Achieve an employee Net Promoter Score of 55," document that target.

This seems obvious, but many schools skip this step. They move into the retrospective with fuzzy recollections of what they committed to rather than precise documentation. Precision matters because vague goals enable vague assessments of progress. (Of course, if you never defined what you would do with any specificity, that’s another issue.)

2. What actually happened?

For each priority, document what was actually delivered. Again, be specific. Don't describe effort or intentions, describe outcomes. Did the program launch? Does it serve 60 students? What does it actually look like? Who leads it? What resources does it have?

This is where many retrospectives break down. Too often activity is confused with accomplishment. Schools point to committees formed, proposals written, or pilot programs attempted as evidence of progress. But strategic priorities aren't about activity, they're about results. If you said you would launch something and it didn't launch, name that clearly.

3. For priorities that were fully realized, what enabled that success?

When strategic priorities succeed, it's rarely accidental. Specific conditions and actions made success possible.

Did those initiatives have dedicated leadership with clear authority? Adequate resources? Senior leadership attention? Clear success metrics? Ongoing board oversight? Alignment with capabilities the school already possessed?

Document the enabling factors with specificity. "Strong leadership" isn't specific enough. Was it a senior administrator who made this their primary focus? Was it a faculty member given release time and a clear mandate? Was it a new hire brought in specifically for this purpose?

The point is to identify what worked so you can replicate those conditions for your next strategic priorities.

4. For priorities that failed or stalled, what prevented success?

This question requires genuine honesty and a willingness to examine both the strategy itself and the execution systems that were supposed to deliver it.

In my experience, strategic priorities fail for predictable reasons that schools could prevent if they examined them systematically:

A strategic initiative was not treated as a hypothesis. Sometimes schools make strategic bets based on assumptions that turn out to be false. They assume demand exists for a program when it doesn't. They believe a certain positioning will attract families when it actually doesn't resonate. They think a capability is achievable when it requires expertise or resources the school can't access.

My EXPLO Elevate colleagues and I advocate for approaching strategy as hypothesis – a well-reasoned bet about the future that requires testing and iteration. When schools treat strategy as a fixed plan to be executed rather than a hypothesis to be tested, they often persist with initiatives long after evidence suggests the underlying assumptions are wrong. They double down on flawed premises rather than acknowledging the hypothesis needs revision. 

The initiative was never adequately resourced. A board approves an ambitious priority but doesn't commit the budget, staffing, or infrastructure needed to deliver it. It’s not unusual that a faculty member gets told to "get it running" with no release time, no dedicated budget, and no support. 

This isn't execution failure, it's planning failure. If you genuinely want something to happen, you have to resource it proportionate to its ambition. When schools announce strategic priorities without committing resources, they're setting up their people to fail.

There was no clear tactical plan or ownership. Strategic priorities need to be translated into specific initiatives, with clear ownership, timelines, and success metrics. Too many strategic plans stop at the aspirational level: "Enhance student engagement." "Strengthen community partnerships." "Develop innovative programming."

Without conversion to tactical plans and operational plans – who does what by when, with what resources, measured how – strategic priorities remain perpetually "in progress" but never completed.

No one knew what success looked like. If you can't define what the realized version of your strategic priority looks like, how will you know when you've achieved it? How will you measure progress? How will you hold anyone accountable?

Vague goals enable vague execution. "Improve faculty retention" means nothing without specificity. Is the goal 90% retention? 95%? Reducing three-year turnover from 38% to 22%? Until you define success precisely, you can't design systems to achieve it.

Progress wasn't monitored or managed. Some strategic priorities fail simply because no one was consistently checking on them. The board approved them, leadership nodded, and everyone assumed they were happening. No regular reviews. No milestone check-ins. No data collection to assess progress.

Without systematic monitoring, strategic priorities drift. Small obstacles become insurmountable barriers. Early warning signs go unnoticed. By the time anyone realizes the initiative is stalled, it's too late to course-correct.

The plan never converted to organizational goals. The most common execution gap is the failure to translate strategic priorities into board goals, head of school goals, and senior leadership goals. The strategic plan exists as a separate document from the performance expectations for the people who are supposed to deliver it.

If your head of school's annual goals don't directly reflect strategic priorities, those priorities will compete with everything else on their plate and the strategic priorities will lose. If your senior leaders aren't explicitly accountable for specific strategic initiatives, those initiatives will always be secondary to their operational responsibilities.

The community moved on. Sometimes strategic plans get completed, celebrated, and then essentially forgotten. The board meeting that approved the plan was the plan's high-water mark. Trustees return their attention to governance basics. Faculty focus on the academic year ahead. Parents never fully understood the plan in the first place. The creation of the plan is only the first step. Keeping strategy alive means regularly talking about it, finding stories and examples of how it is coming to fruition, and making it part and parcel of the daily conversation of the School.  

Strategic priorities require sustained attention, ongoing communication, and visible commitment from leadership. When that attention wanes, execution wanes with it.

5. Did you identify the assumptions on which the strategy was built?

Here's where Roger Martin's What Would Have To Be True framework becomes invaluable. Every strategic priority rests on assumptions. For those assumptions to be more than hopeful guesses, you need to identify what would have to be true for your strategy to succeed, and then actively test whether those conditions exist.

If your strategic priority was launching a new academic program, what would have had to be true? Sufficient family demand? Faculty expertise in the relevant areas? Ability to deliver it without degrading existing programs? Competitive differentiation from what's already available locally?

Did you articulate these conditions explicitly? Did you test them rigorously? Did you gather data that validated or challenged your assumptions? Or did you simply assume your hypothesis was correct and move to implementation?

When strategic priorities fail, it's often because the underlying hypothesis was flawed and no one caught it early enough because they weren't actively testing it. Approaching strategy as hypothesis means building in mechanisms to detect when you're wrong and being willing to pivot when evidence suggests your bet isn't working.

6. What did we learn about our leadership metabolism?

Strategic execution depends on your leadership team's capacity to absorb complexity, make decisions, convert strategy to action, and sustain momentum. Some priorities fail not because the strategy was wrong but because your leadership system couldn't effectively process what you asked it to handle.

Look at the pattern of what succeeded and what didn't. Did your realized priorities share common characteristics – maybe they were led by particular individuals or didn't require significant operational changes? Did your stalled initiatives all have something in common – perhaps they required cross-departmental collaboration that your structure doesn't support, or they needed rapid decision-making in an organization that defaults to consensus?

Your retrospective should surface whether you have leadership metabolic constraints that will sabotage certain types of strategic priorities regardless of how good the strategy is. If your leadership team struggles with decisive action, complex projects requiring coordination across divisions, or sustaining multiple priorities simultaneously, you need to acknowledge that before loading up your next plan with initiatives that require exactly those capabilities.

7. What patterns keep appearing across cycles?

If this isn't your first strategic planning cycle, look for patterns across multiple plans. Do you consistently overcommit? Do certain types of priorities reliably succeed while others reliably stall? Do you have specific organizational constraints – funding models, scheduling structures, leadership capabilities – that repeatedly prevent certain types of strategic work?

These patterns reveal your institutional tendencies. They tell you what kinds of strategic priorities your school is actually capable of executing versus what kinds require capabilities you don't yet have.

The Altitude Agreement Your Board Needs

The retrospective requires an explicit altitude agreement between your board and head of school. This isn't about assigning blame – it's about understanding what happened at different levels of the organization so you can plan more effectively next time.

At the strategic level: Did we make the right bets about the future? Were our assumptions about market demand, competitive positioning, and educational needs correct? Did our strategic priorities actually align with our mission and values, or did we drift toward what seemed popular or fundable?

At the tactical level: Did we convert strategy into clear initiatives with proper resourcing, ownership, and success metrics? Did we establish the policies and resource allocations needed to support our priorities?

At the operational level: Did our leadership team have the capacity to execute? Were the right people in the right roles? Did we have the systems to monitor progress and course-correct?

These are different questions requiring different kinds of analysis. Your board needs operational details to understand what happened, but it should focus its governance attention on the strategic and tactical levels – on whether the strategy was sound and whether the board fulfilled its responsibilities for resourcing and oversight.

From Retrospective to Readiness

The retrospective should produce more than a report; it should create a shared understanding that shapes how you approach your next planning cycle.

Before you begin your next strategic plan, you should be able to answer these readiness questions:

Do we know what enabled our previous successes? Can you articulate the specific conditions – leadership, resourcing, governance attention, organizational capabilities – that allowed certain priorities to succeed? Are you prepared to create those conditions again for your next priorities?

Do we understand what prevented previous progress? Have you identified whether failures were strategy problems or execution problems? Do you know which organizational constraints need to be addressed before you commit to ambitious new priorities?

Have we built institutional learning into our planning process? Are you approaching your next plan as a hypothesis to be tested rather than a fixed blueprint to be executed? Have you identified what success looks like for each potential priority? Have you determined how you'll monitor progress and adapt when evidence suggests you need to?

Is our leadership system ready? Does your senior team have the metabolic capacity to handle what you're about to ask of them? Have you addressed any leadership constraints that undermined your previous plan? Have you protected senior leaders' time for strategic priorities rather than assuming they'll add strategy work on top of everything else?

Have we established the conversion mechanisms? Are you prepared to translate strategic priorities into board goals, head goals, and senior leadership goals? Will you create the feedback loops and accountability structures that keep strategic priorities visible and active throughout the planning cycle?

If you can't answer these readiness questions confidently, you're not ready to begin your next strategic planning cycle even if the calendar says it's time.

The Gift You Give Your Next Plan

Your community is about to invest enormous energy in defining your school's future. Trustees will clear calendars for retreats. Faculty will serve on committees. Parents will attend focus groups. Alumni will complete surveys. Consultants will facilitate conversations. Everyone will bring their hopes, concerns, and ideas to the process.

That investment deserves to be built on learning from your last cycle, not on institutional amnesia that dooms you to repeat the same planning mistakes. The retrospective is how you honor that investment. It's how you ensure the next strategic plan is informed by wisdom about what your school can actually deliver and what conditions enable that delivery.

Before you begin your next strategic planning cycle, do the retrospective. Make it rigorous. Make it honest. Make it learning-focused rather than blame-focused. Document what happened, understand why, and use that understanding to shape a next plan that's grounded in reality about your school's capabilities and constraints.

Your next strategic plan will be better for it. More importantly, your school will be better for it – stronger in its self-knowledge, clearer about its capabilities, more honest about what it can deliver. The retrospective doesn't just improve your next plan. It builds the institutional muscle for honest assessment and adaptive learning that every school needs to thrive in an uncertain future. And that muscle matters far more than any single strategic plan ever will.