There’s probably a good chance that you have been involved in a strategic planning process that didn’t work. One that resulted in a beautiful list of goals and objectives—but sat on a shelf, unopened. Or one that was so detailed, staff was too paralyzed to proceed.
At the Winkler Group, we know the best plans strike a balance: they’re visionary enough to inspire, but simple enough to implement. They bring people together, spark donor confidence, and provide a clear roadmap for action and accountability. This guide draws on more than two decades of experience helping organizations avoid the common pitfalls that derail even the best intentions.
More importantly, this guide offers proven strategies to make sure your next strategic plan delivers on what it’s meant to do: move your mission forward.
Mistake No. 1: Creating a Plan That Is Not Realistic or Measurable
A plan that is pages and pages of tasks and strategies is okay if you have the staff size and complexity to divide and conquer. If not, and there are no plans to hire additional staff, your strategic plan will fail.
We have seen organizations spend months gathering data and information. They review other organizations for ideas and intel. Then they get caught up thinking about the grand future. “What if…” becomes their mantra as they try to tackle all of society’s challenges. And in chasing every possibility, they lose sight of what’s actually achievable with current staffing and resources. A beautiful plan that can’t be implemented isn’t a success—it’s a stalled opportunity.
Without clear metrics or defined capacity, there’s no way to know if progress is being made. And without realistic pacing, staff default to the day-to-day instead of advancing long-term goals. When no one knows who’s in charge of what, accountability disappears and momentum fades.
If a plan asks more than an institution is equipped to deliver, it won’t just gather dust, it will undermine confidence and erode trust in the process itself.
Solution No. 1: Develop a Plan That Moves from Vision to Action
Start with outcomes. What does success look like for your museum three years from now? Increased membership? New interpretive themes? Stronger community partnerships? Let those outcomes shape your goals.
From there, define strategies and build a path to implementation. Use tools like GANTT charts or visual dashboards to track progress across departments. Most importantly, assign responsibility: someone needs to drive the plan forward—whether it’s your executive director, chief operations officer, or a cross-functional staff task force.
And don’t forget to measure what matters. Whether it’s attendance growth, exhibit impact, or donor retention, tie your plan to measurable progress that leadership and funders can rally behind.
If you can’t measure it, you can’t manage it—and if you can’t manage it, you can’t expect results.
Mistake No. 2: Creating a Plan That Is Too Complicated to Execute
If you’re like most nonprofit professionals, you’ve been part of a strategic planning process that ended with a document resembling a corporate annual report. Powerful graphics, professionally written text, and pages and pages of goals, objectives, strategies, and tactics. It looked good, but nothing much came from it.
30,000-foot View
Think of your strategic plan as a pyramid. The board helps shape the top tier—your long-term goals and high-level strategies. From there, staff take the lead in building out the base: objectives and tasks that bring those strategies to life.
Everyone has a role to play, but the roles are different. A strong plan honors those differences and stays anchored in your museum’s mission. If an initiative doesn’t move the mission forward, it doesn’t belong in the plan.
If a strategic plan is buried at the bottom of a drawer, it’s worthless. No matter how many staff hours were spent on it.
We would rather see a final strategic plan that looks like a war map—its pages dog-eared and worn. Notes in every margin. Highlighted areas lighting up the page. That is a strategic plan that can…and is being executed.
A good strategic plan is a shift in mindset.
Strategy shouldn’t be limited to a single-day retreat or an annual part of one board meeting. Strategy needs to be a habit, part of your daily work. If you have a plan that’s too complicated or one that isn’t clear on roles and responsibilities, you’ve lost the game even before kickoff.
Solution No. 2: Stay on the Same Page
A strategic plan only works when everyone understands it.
Start by getting aligned on language. Define what you mean by goal, strategy, objective, and task—and stay consistent throughout the document.
Your plan doesn’t need to include every great idea. It needs to prioritize what’s most essential and most achievable in the next three to five years. Keep your strategies broad enough to provide direction and your objectives narrow enough to create traction.
When the marketing team, the curator, and the facilities manager can all see where they fit into the larger picture—and know what success looks like—you’ve moved from vision to action.
Your plan should be the most dog-eared document in the building, not the most polished.
Mistake No. 3: Creating a Plan with No Consensus
Museums are deeply relational institutions. They hold the public’s trust, often stewarding histories and identities far beyond their walls. That’s why consensus is everything. When strategic planning is confined to the boardroom or managed by only the executive team, it misses the depth and breadth of perspective that makes a plan relevant and resilient.
Too often, the same voices are always at the table.
Instead of seeking out varying perspectives, planning teams often default to the familiar: senior staff, trusted board members, and maybe a major donor or two. But a lack of diversity in perspective leads to narrow priorities and missed opportunities. Plans made by a few rarely resonate with the many.
Dissent is avoided rather than engaged.
When discomfort arises in the planning process, it’s often avoided instead of embraced. Organizations miss out on honest feedback, especially from staff, community members, or stakeholders who may feel marginalized. Rather than creating space for constructive tension, the process favors politeness over progress.
There’s no clear rationale for who gets included.
Planning often begins and ends with those closest to an organization’s power structure: the board, the CEO, select department heads. Without intentionally reaching further, toward staff, educators, docents, emerging donors, or community leaders, the plan reflects internal priorities but lacks external relevance.
Stakeholder engagement is seen as a checkbox.
When broader stakeholders are engaged, it’s sometimes too little or too late, such as a survey sent after major decisions have been made or a single listening session with no follow-up. Without genuine opportunities to influence direction, constituents know they’ve been asked for input—not given a voice.
Solution No. 3: Turn Planning into a Tool for Engagement
The more people help shape the plan, the more they’ll help implement it.
Start with the full ecosystem, not just the boardroom.
Map out who your key stakeholders are. This might include board members, curators, educators, funders, front-line staff, docents, municipal partners, and even community members who see the museum as a public resource. The mix will look different for a large, city-funded art museum than it will for a regional history museum with a tight-knit donor base—but the principle remains the same: your planning process should reflect the ecosystem that supports and sustains your work.
Look for meaningful opportunities for others to have a voice. You don’t have to bring everyone into every conversation to build consensus. Create a structure for input that makes sense. A working group can be established to lead the process, while surveys, interviews, or listening sessions can invite broader participation. Keep the process simple, respectful of time, and clear about how input will be used.
Mistake No. 4: Not Hiring an Outside Facilitator
At the risk of sounding self-serving, we cannot overstate the importance of working with someone from the outside. An effective strategic plan simply cannot be achieved in-house. Here’s why:
Internal dynamics go unspoken.
Staff often hesitate to speak openly when their supervisor is leading the conversation. Sensitive topics—like broken systems, leadership gaps, or strained team dynamics—go unspoken. Even trusted board members can unintentionally shut down candor when they control the process. The result? A plan shaped more by what’s easy to say than by what’s true.
Familiarity limits perspective.
Even the most well-meaning leaders bring personal bias to the table. It’s nearly impossible to step back far enough to see institutional blind spots, especially when navigating internal priorities, staff politics, or legacy programs.
The process becomes harder, not easier.
What starts as a cost-saving move often creates more work. Planning meetings get postponed, discussions go in circles, and decision-making stalls. Leaders are pulled in two directions—trying to facilitate and contribute at the same time. It slows momentum and wears teams down, and what should be a moment of institutional focus turns into a side project with no real ownership.
Implementation often falters without external accountability.
Without someone to follow up and measure progress, the plan loses traction. There’s no neutral voice to check in, no external accountability to ensure goals are being met. The plan fizzles—not because it wasn’t good, but because no one was responsible for keeping it alive.
Solution No. 4: Don't Do It Alone
Ready to take the next step?
You don’t need all the answers to get started—you just need a place to begin. Our team of strategic planning consultants works with museums every day to help clarify next steps, avoid common pitfalls, and build plans that lead to real change.
In a free, 15-minute conversation, we’ll ask a few questions and offer tailored recommendations based on your goals and challenges. No pressure. No pitch. Just thoughtful guidance to help you move forward with confidence.
Contact us to schedule your consultation.
Hire a professional to help.
An experienced facilitator brings clarity, structure, and a fresh perspective. They’re not bound by your politics or assumptions. They can ask hard questions, synthesize input, and keep the process moving. They free up your leadership team to be active participants, not referees. And, critically, they help ensure the plan stays on track long after the initial sessions end.
When museums invest in outside expertise, it sends a signal to staff and donors alike: this plan matters. We’re not just checking a box. We’re building a future.
About the Winkler Group
Arts and cultural institutions preserve what matters. The best ones move their communities forward. We help make both possible.
For over two decades, the Winkler Group has specialized in guiding organizations from vision to action through strategic planning, capital campaigns, and fundraising counsel that delivers results.
A national firm headquartered in Charleston, South Carolina, with offices across the country, the Winkler Group proudly partners with organizations that steward history, elevate creativity, and serve the public good.
