APPLE PODCASTS | SPOTIFY
In today’s rapidly changing nonprofit landscape, strategic planning might seem like a luxury your organization can’t afford—or worse, an exercise in futility given the constant uncertainty we’re facing. But as we discussed in our recent Changemaker Conversations podcast episode, strategic planning isn’t just important—it’s essential, especially during turbulent times.
One of the worst things an organization can do in a moment like this is just ride the waves without being proactive or having a plan. But any plan developed today absolutely needs to be nimble and agile, with the ability to pivot as conditions change.
Without the foundation of a strategic plan, it becomes far too easy for nonprofits to get swept up in the news of the moment or current events, losing sight of their mission and impact priorities. A thoughtful strategic plan provides the steadfast commitment and clarity your organization needs to weather any storm.
But not all strategic planning processes are created equal. After more than a decade facilitating strategic planning for nonprofits of all sizes, we’ve identified three critical mistakes that cause most strategic plans to fail—and practical solutions to avoid them.
Mistake #1: Choosing the Wrong Facilitator (or None at All)
Most strategic planning processes begin with an RFP. The nonprofit issues a request for proposals, evaluates written submissions, and selects a consultant or facilitator based largely on documents. This transactional approach often leads to a poor fit between the organization and consultant.
Strategic planning is one of the most consultative, in-depth, relationship-oriented engagements your organization will undertake. It requires deep collaboration between your leadership team and the consultant. Yet the traditional RFP process provides minimal opportunity to assess whether you have the right rapport with a potential facilitator.
At Prosper Strategies, we prioritize conversations over presentations and proposals. We take time getting to know organizations we might work with before we ever put anything in front of them regarding approach or pricing. We believe the sale is the sample, working with potential partners to shape different options for collaboration rather than presenting a one-size-fits-all approach.
While some organizations attempt to facilitate strategic planning internally to save costs, this approach comes with significant downsides, as well. You can’t see the label from within the jar. An outside facilitator brings crucial perspective on sector trends, helps navigate power dynamics, and creates an environment where difficult conversations can happen productively.
If budget is truly a constraint, we recommend bringing in a facilitator just for key moments in the process, such as the strategic planning retreat, rather than skipping outside facilitation entirely.
Mistake #2: Inadequate Stakeholder Engagement
The second critical mistake we see in nonprofit strategic planning is limited stakeholder engagement—particularly when it comes to involving the people and communities your organization serves.
While most strategic planning processes include staff and board input, they often completely overlook constituent voices. This would be like developing a strategy for a for-profit business without ever asking what your customers want.
Even when organizations recognize the need to include constituent voices, many do so in limited, one-off ways, such as sending out a single survey and considering the box checked.
For strategic planning that truly drives impact, constituents should be engaged throughout the entire process:
-
- During initial research through surveys and interviews
-
- As participants in strategic planning retreats when appropriate
-
- Through listening sessions where constituents can provide feedback on draft priorities
-
- In ongoing feedback loops during plan implementation
We’ve seen transformative results when organizations meaningfully involve their constituents in strategic planning. In one recent example, an organization serving women in a specific career field discovered that their members didn’t value expensive national conferences nearly as much as regular, informal regional gatherings. This insight completely shifted their strategic priorities and helped resolve budget challenges simultaneously.
When constituents see an organization taking their feedback and actually implementing it, they understand they’re truly valued. They recognize this is an organization that cares about them—not just one that asks for feedback and then does what they were going to do all along anyway.
Mistake #3: Creating a Plan That Isn’t Actionable
The third major pitfall happens after the planning process concludes. Too often, strategic plans become beautiful dust collectors—inspirational documents that fail to drive day-to-day action.
At the end of many strategic planning processes, organizations have really nice documents that are visionary and inspiring. The board signs off, and people are pumped up for a little while. But then inevitably, life happens, other demands come up, and that strategic plan just dies in the water or gathers dust on the shelf.
At Prosper Strategies, we combat this with what we call the “Progress Element” of our process:
-
- We build key components of the strategic plan (pillars and objectives) into a living, breathing dashboard
-
- Each element has a clear owner, target metrics, and requires ongoing tracking
-
- We establish a regular meeting cadence for teams to assess progress and make adjustments
-
- We break down high-level objectives into concrete monthly and weekly action items via action planning
This approach transforms a strategic plan from a static document into an active management tool that drives daily decisions. When circumstances change—as they inevitably will—this system allows organizations to quickly identify what’s off track and make targeted adjustments without abandoning the overall strategy.
Only if we make the plan a living, breathing document that people actually work in every single day can we achieve the agility needed for today’s environment.
What About The Board’s Role in Strategic Planning?
A common question we receive is how to appropriately involve the board in strategic planning—both during development and implementation.
From our experience working with numerous boards and serving as board members ourselves, we’ve found the board’s role should focus on setting the overall vision, mission, and big picture priorities. The board should help determine the three or four things the organization will focus on in the next three years to achieve its mission.
During strategic planning, we recommend:
-
- Creating a dedicated board strategic planning committee with executive team representation
-
- Involving the full board in mission/vision work and final plan approval
-
- Keeping the board focused on high-level strategy while staff manages implementation details
-
- Ensuring regular progress updates that focus on results rather than tactics
Put simply, the board provides high-level strategy and guidance, while staff focuses on implementation and day-to-day work on the strategic plan. Staff and board should collaborate on developing the strategic vision, but board members should almost never be involved in the day-to-day minutiae of implementation.
Moving Forward After an Unsuccessful Strategic Plan
What if your organization completed a previous strategic plan but didn’t achieve what you set out to accomplish? Should you just update the dates and try again?
The answer is usually no. There is a reason you didn’t achieve the things in your last strategic plan. You need to go back to the drawing board and assess: were these really the right priorities? Did we really have the right goals in mind? What happened that made us go off track?
Organizations that struggled with their previous plan often missed the Progress Element that makes a plan actionable and measurable. The next planning cycle is an opportunity to build in those critical accountability mechanisms.
Strategic planning isn’t just something you do because your bylaws require it. When done thoughtfully, it’s what makes an organization effective and resilient, even in uncertain times.
By avoiding these three critical mistakes—choosing the wrong facilitator, inadequate stakeholder engagement, and creating plans that aren’t actionable—you can develop a strategic plan that genuinely drives your mission forward rather than gathering dust on a shelf.
Resources Mentioned in This Episode:
The Progress element of the Nonprofit Strategy System
101 Guide: Strategic Planning for Nonprofit Organizations
About Changemaker Conversations
Changemaker Conversations is a podcast for nonprofit leaders who are ready to build smarter, more strategic organizations with less friction and more joy. Join hosts Alyssa Conrardy and Lindsay Mullen, Principals at Prosper Strategies, every other week as they pull you out of the day-to-day grind and refocus your attention on the big picture through candid conversations about the challenges facing nonprofit leaders today.
Subscribe wherever you get your podcasts and visit changemakerconversations.com for show notes and additional resources. If you have ideas for future episode topics or guests, email us at hello@changemakerconversations.com.
