A Change in Strategy for Strategic Planning

Have you ever watched or participated in nonprofit strategic planning? Did you check back a couple of years later and see what was accomplished? How accurate was the plan? Did everything get accomplished on the timeline?

Listen, I like a strong plan as much as the next person, and those are the first kinds of documents I ask for when I am jumping into an organization's grant work, but I also watch the “plan” fall off the radar or sit untouched more times than not.

You know what I think might be the problem? We set goals and track their impact using a calendar. I think the calendar is the problem.

Calendars fill with timelines that feel like hopeful guesses rather than informed commitments. People lump things into “Year 1” or “Year 2” goals, then scramble when those goals aren’t met “on time” or abandon them altogether. Not because the ideas were flawed, but because life, funding, and reality didn't match the schedule written a year or more ago.

I've watched this play out again and again. Leaders spend so much time trying to plan for the years ahead and then pull everyone along through a timed plan, and when one element slips because reality happens, the rest is left hanging. The work isn’t less important. It’s just misaligned with the calendar we tried to fit it into.

What if our measure of strategic progress wasn't time at all?

Why do we only tie nonprofit strategy to a linear timeline? The issues these plans address are complex and deeply rooted in imperfect systems that resist change. Things rarely work in a straightforward, uninterrupted way. And yet, we keep tacking dates to the work.

We default to timelines because they feel tangible and are easy to communicate. Funders ask for them. Boards expect them. Timelines give the illusion of control. But they can also become cages. The reality for many organizations is that their complex work doesn’t neatly map to 12-month increments and certainly doesn’t always fit into a funder’s grant award window.

When progress doesn’t happen according to schedule, it feels like failure. Even if something is moving forward, if it doesn’t hit the artificial milestone on the calendar, it can be dropped or deprioritized while we spend time and effort justifying its delay to boards and funders.

BoardSource has noted an interesting shift, writing that “the idea of a five-year strategic plan is becoming outdated. More and more, nonprofit boards are turning to adaptive planning strategies that account for ever-changing realities.” Yeah! Realities like pandemics, recessions, federal funding freezes, and the cutting of major social safety net programs.

What if we measured strategic progress by resources instead?

Instead of asking, “What can we get done by next year?” what if we asked, “What can we do with an extra $50,000?”, “What changes when we hit $250,000 in available funding?”, What can we accomplish with the building that we need?”

It’s all about being resource-responsive. Strategic planning can become a process of defining what matters most and then building modular, flexible paths toward those goals, aligned with what is realistically resourced.

This model is echoed in the concept of discovery-driven planning, introduced by McGrath and MacMillan in the Harvard Business Review. It advocates for releasing funds in stages, based on validated assumptions and milestone learning, instead of rigid timelines.

It also aligns with ideas from The Alford Group, who describe real-time planning as an adaptive strategy that helps nonprofits “pivot and respond quickly while maintaining a clear vision and strategic direction.”

In all these cases, time is not the driver. Readiness and resourcing are what truly propel us.

So, what does this look like in practice?

Some organizations embrace versions of this approach, even if they don’t call it “resource-based planning.” A few examples:

  • A youth-serving organization that launches one new classroom each time $75,000 is secured. No timeline pressure. Just a clear, costed-out expansion model.

  • A coalition with scenario-based funding: with $100K they sustain current efforts, with $250K they deepen partnerships, with $500K they go regional.

  • A healing-centered nonprofit that refuses to tie trauma recovery to a timeline. They fund and scale based on staff capacity, participant readiness, and resourcing instead of grant report deadlines.

  • An innovation lab with an idea bank and tiered budget triggers. Each idea activates only when sufficient funding and alignment are present.

These aren’t theoretical models. They’re grounded, practical, and in many cases, more sustainable than traditional timeline-based plans.

This model is especially useful for:

  • Small and mid-sized nonprofits that don’t have predictable revenue or dedicated strategy staff

  • Newer organizations still building infrastructure and relationships

  • Community-led and justice-oriented groups that prioritize trust, participation, and healing over speed

  • Organizations with “lumpy” funding cycles that need flexibility to move when the money (and staff) are there

  • Any organization that has weathered a global pandemic and upheaval of federal funding!

The Bridgespan Group calls this “strategy as resource allocation”, emphasizing that strategy must guide how an organization spends time, money, and energy. When those things are limited, a resource-responsive strategy might be the only viable one.

Why don’t more organizations take this approach? 

Because it’s not how we’re taught to plan.

We’re taught to use logic models, timelines, and fixed deliverables. Many funders still expect this format. Boards often want to see a calendar. And it’s easier to fill in a template than to build something from the ground up.

But more than that, this kind of planning requires vulnerability. It means saying, “We’re not going to make promises we can’t keep. We’re going to act when we’re resourced to act, not before. We are going to admit when we aren’t sure.”

That feels risky. But in my experience, I actually think people aren’t looking for certainty. They are looking for clarity, and we have just slapped a timeline on it all these years. Clarity lives in a model that says, “Here’s what we will do with the next $25K, and the $100K after that, no matter how long it takes to get there.”

But what if things really do need to be measured by time?

It’s true. Sometimes, time does matter. Sometimes the nature of the work or the external environment requires us to pay attention to dates, deadlines, or time-sensitive outcomes. Not all strategic goals are timeless.

There are initiatives that need to align with other calendars, grants with strict expenditure windows, and hiring decisions that must be made before a new program year starts. There are also moments in our work, especially when we’re trying to prove feasibility, meet compliance requirements, or scale up services, that genuinely require time-bound metrics.

When those are present, let them be present. Design around them. Be honest about them. But don’t tack deadlines onto goals just because we have the urge to.

The danger isn’t in having a timeline. The danger is in feeling like every single thing must be bound to one.

Before assigning a date, ask:

  • Does this milestone truly need to happen by then?

  • What is the risk if it happens later?

  • Is this aligned with a community need, or just a calendar habit?

Here are a few examples where time-based strategy makes sense:

  • A plan to roll out seasonal programming or summer camps

  • A federally funded project with a spending deadline

  • A construction project tied to weather conditions or zoning approvals

And here are a few examples that usually don’t need dates (but often get them anyway):

  • “Establish partnerships with five schools by Q2”

  • “Build community trust in Year 1”

  • “Increase trauma-informed practices within the team by the end of next year”

  • “Buy a new van by the end of the year”

These are valuable goals. But they’re not always linear. They happen at the speed of relationship, readiness, and resourcing (not Outlook reminders).

If you’re already doing the work of aligning goals with time because the work demands it, great. But don’t wrap a clock around something just to make it look tidy in a strategic plan. You’re not failing if something takes longer than expected. You’re just telling the truth about how complex work really works.

What could change if we planned this way?

Instead of “falling behind,” we’d stay aligned.

Instead of shelving good ideas because they missed a deadline, we’d keep them warm until they’re ready.

Instead of rushing to check off Year 2 goals, we’d make decisions based on capacity, community, and care.

And instead of asking staff and leaders to stretch themselves thin to meet artificial timelines, we’d give them space to do the work well…when it’s possible to do it well.

That’s the invitation: Step out of the calendar box. Step into resource-based clarity. Ask yourself what’s possible now, what’s worth waiting for, and how you want to pace the future.


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