Your Organization Evolved. Has Your Fundraising?

The year was 1999. The event: Dakota Rubin's Bar Mitzvah. The shoes: magenta hot pink platform strappy heels from the DSW sale rack.

Those shoes were perfect for seventh-grade me—exactly what I needed to figure out who I was. Fast forward to my early fundraising career, and I was still chasing the "perfect" professional shoe, convinced that looking the part meant suffering through galas in stilettos. It wasn't until my late thirties that I realized: I could wear sneakers to an event and no one would give a damn.

Here's what I've learned about growth, whether it's personal or organizational: what fit perfectly three years ago might not fit at all today. And recognizing that isn't failure—it's evolution.

I wrote about this recently in my newsletter about stepping into new shoes, exploring how individual roles and careers need to evolve as we grow. But here's what I want to dig into today: this same principle applies to your fundraising strategies.

Your organization isn't the same as it was three years ago. Your programs have matured. Your team has changed. Your community impact has deepened. So why are you using the same grant language, the same donor templates, the same systems you implemented back then?

When you're working so hard and so focused on mission, it's easy to lose sight of the fact that you might be working harder than you need to. If we can just pause to find our fit—to assess what's still serving us and what's holding us back—we might be able to work more impactfully.

Key Takeaways:

• Your organization isn't static—your fundraising shouldn't be either. What worked brilliantly three years ago may need refreshing today.

• Templates become generic without intentional evolution. Copy/paste convenience can cost you your organizational voice and donor connection.

• There's a difference between learning curve discomfort and true misfit. Not every struggling system needs replacement, but some genuinely don't serve your needs.

• Annual reassessment prevents autopilot fundraising. Building regular review into your rhythm keeps strategies fresh and aligned with current reality.

• You have permission to change what's not working. Even if you invested time, money, or ego into it—staying in uncomfortable shoes causes more pain than change.

From Individual Growth to Organizational Evolution

In my previous post about moving from scarcity to frugality, I explored how nonprofit sustainability doesn't require constant growth—it requires intentional stewardship of what we have. That same principle applies to how we approach our fundraising strategies over time.

We get comfortable with what works. A grant proposal that landed significant funding becomes our template. A donor appeal that performed well gets recycled year after year. A CRM we spent months implementing becomes "just how we do things," even when it's creating more work than it saves.

This comfort makes sense. You're busy. You're understaffed. You're focused on mission delivery, not constant fundraising innovation. Why fix what isn't broken?

But here's the thing: it might actually be broken, just slowly enough that you haven't noticed.

The danger of fundraising on autopilot isn't dramatic failure—it's diminishing returns. Your grant proposals still get funded, but at slightly lower amounts. Your donor communications still generate gifts, but maybe fewer than before. Your systems still function, but they require constant workarounds that eat up staff time.

The cost compounds over time: generic language that fails to capture what makes your work special, stale messaging that doesn't inspire action, and systems that create friction instead of flow.

Three Areas Where Fundraising Strategies Outgrow Themselves

Let's look at the most common places where organizations need to pause and reassess whether their fundraising strategies still fit.

Grant Writing and Program Positioning

Your programs evolve constantly. You refine your approach based on what works. You serve more people, or serve them differently. You gather data that proves impact in ways you couldn't have measured three years ago.

But your grant language? Often, it stays frozen in time.

Here's what happens: You write a compelling narrative for a major grant. It works beautifully—you get funded. So the next time you apply for something similar, you copy that language. And the next time. And the next. Before you know it, you're describing programs from three years ago using data from five years ago, completely missing the opportunity to tell the story of who you are now.

Signs your grant language needs refreshing:

• You're using program descriptions from your last strategic plan (which ended two years ago)

• Your case for support doesn't reflect current world context—you're not acknowledging how your community's needs have shifted

• You're citing data that's accurate but outdated, missing newer and more compelling evidence of impact

• You're using generic national statistics when you could use hyperlocal research that builds credibility and demonstrates deep community knowledge

• Your language hasn't evolved to reflect how you talk about your work internally—you still say "clients" in grants but "community members" everywhere else

What to reassess annually:

The most effective grant writers I know treat their core program narratives like living documents. Every year, they:

• Update program data and outcomes with the most recent information available

• Refresh how they position impact to reflect current organizational priorities

• Review their case for support to ensure it speaks to today's context, not last year's reality

• Add new examples, stories, and evidence that didn't exist when they first wrote the narrative

• Ensure their language reflects their organization's current values and voice

This isn't about rewriting everything from scratch every year. It's about intentional evolution—keeping what works while updating what's stale.

📖 Read More: The Tooth Fairy is Not a Viable Development Strategy - On the importance of realistic projections vs. aspirational budgeting in your fundraising planning.

Donor Communications and Storytelling

Templates are lifesavers. I'm not here to tell you to stop using them. But here's the hard truth: templates that worked brilliantly the first five times can become generic and lifeless through repeated use.

When you're in the thick of campaign season, it's so tempting to pull up last year's appeal letter, swap out the numbers, maybe update a story, and call it done. You're busy. The template worked before. Why reinvent the wheel?

But what gets lost in that efficiency is the very thing that makes your organization special—your voice, your specificity, your authentic connection to the work.

Signs your donor communications need evolution:

• You can't remember the last time you wrote a donor letter from scratch

• Your appeals could apply to any organization in your sector if you removed your name

• You're telling the same donor stories over and over—your audience might not realize it, but you do, and you've lost connection to the actual current work

• Your thank-you letters feel like they're on autopilot (because they are)

• You use the same opening line in every email: "We hope this finds you well" or "As you know..."

• Generic impact language dominates: "Your support makes a difference" instead of specific, tangible outcomes

Here's what I see happen: Organizations work incredibly hard on their mission, but their donor communications don't reflect the richness and evolution of that work. The passion that drives the team every day doesn't come through in the fundraising copy—because the copy hasn't been refreshed to match where the organization actually is.

The template audit exercise:

Set aside an hour. Pull up your most-used templates: year-end appeal, thank you letters, major donor outreach, event invitations.

Read them as if you're seeing them for the first time. Ask yourself:

• Does this sound like how we actually talk about our work today?

• Would a donor who received this three years ago notice any difference if they received it again today?

• What's missing? What new programs, insights, or impact aren't reflected here?

• Where have we used generic nonprofit language instead of our specific organizational voice?

Then give yourself permission to refresh. Not necessarily rewrite everything—but breathe new life into the pieces that have gone stale.

For more on making your donor communications more targeted and effective, check out How Segmenting Donor Data Can Make Your Fundraising Soar.

Systems and Tools (CRMs, Databases, Processes)

This one's tough because we invest real resources—time, money, training, emotional energy—into our systems. When a CRM isn't working well, the sunk cost fallacy kicks in hard: "We paid for this. We spent months implementing it. We trained everyone. We have to make it work."

But sometimes, a system genuinely doesn't fit your needs. And staying in those metaphorical uncomfortable shoes causes more pain than making a change.

The critical question: Is this a learning curve issue, or is this a true misfit?

Signs it's a learning curve issue (stick with it):

• You haven't been using the system long enough to build muscle memory (less than 6 months)

• Staff haven't completed available training or explored key features

• You're comparing it to your old system instead of assessing it on its own merits

• The problems are mostly about habit/preference, not actual functionality gaps

• Other organizations similar to yours use it successfully

Signs it's a true misfit (consider changing):

• You've been using it for over a year and still need constant workarounds

• It requires 10 manual steps to do something that should be simple

• Your donors or volunteers complain about the user experience

• It doesn't integrate with other essential tools, creating duplicate data entry

• You're only using 20% of its features and paying for functionality you'll never need

• Staff actively avoid using it because it's so cumbersome

• It was built for a different organization size/type and doesn't scale to your needs

Changing systems is hard. It feels like more work to change than to just bobble around in something that's not quite right. But here's the truth: staying in those hypothetical uncomfortable shoes compounds the pain over time. The friction adds up. The workarounds eat staff capacity. The frustration builds.

You have permission to make a change, even if you invested in the original decision.

📖 Read More: Before You Automate: Audit - A framework for assessing your systems and processes before making changes.

The Evolution Assessment Framework

So how do you know what needs attention? Here's a simple framework for assessing whether your fundraising strategies need a refresh, overhaul, or replacement.

Ask These Questions:

For Grant Language:

• When was the last time I read our standard program narratives with fresh eyes?

• Does our case for support reflect current world context and community needs?

• Are we using the most recent, most compelling data available?

• Would someone who funded us three years ago see clear evolution in our impact?

For Donor Communications:

• If I remove our organization's name, could this template apply to anyone else in our sector?

• When did we last tell a new story or share a fresh example?

• Do these communications reflect how we actually talk about our work today?

• Would our most engaged donors notice if we sent the same thing we sent last year?

For Systems:

• How much time do we spend on workarounds versus the system working as intended?

• Are we using this tool to make our work easier, or has it become another task to manage?

• What would we need to be true for this system to actually serve us?

• Is there a different tool that would better match our current needs and size?

Then Decide:

Minor Refresh Needed:

• Update data and examples

• Add current context

• Tighten language

• Remove outdated references

• Time investment: 2-4 hours

Major Overhaul Needed:

• Rewrite from scratch with fresh perspective

• Develop new templates or narratives

• Conduct stakeholder input process

• Time investment: 1-2 days

Complete Replacement Needed:

• Different system or tool required

• New strategic approach

• Significant change management

• Time investment: Varies significantly

Practical Steps: Refreshing Without Starting from Scratch

The goal isn't to blow everything up and start over. The goal is intentional evolution—keeping what works while updating what's stale.

For Grant Language:

• Schedule a quarterly "narrative refresh" where you update your core program descriptions with recent data and examples

• Keep a running "impact stories" document so you always have fresh material to pull from

• Review your case for support annually, asking: "What's changed in our community/world that we should acknowledge?"

For Donor Communications:

• Create a "template refresh calendar"—plan to update your most-used templates on a rotating basis (e.g., year-end appeal in August, thank you letters in January, event invites in March)

• Build a practice of writing one thing from scratch each quarter, even if you have a template—it keeps your muscles strong

• Ask a trusted colleague or board member to read your donor communications and tell you where they sound generic

For Systems:

• Conduct an annual "systems satisfaction survey" with your team—what's working? What's creating friction?

• Track the workarounds you're using—if you're consistently going around the system, that's valuable data

• Build in evaluation checkpoints when implementing new tools (30 days, 90 days, 6 months) to assess fit before you're too deep

Building a Culture of Continuous Evolution

The organizations that do this well don't treat it as a one-time project. They build reassessment into their annual rhythm.

What this looks like in practice:

• End-of-year debrief: After your biggest fundraising push, gather the team and ask: "What worked? What felt stale? What do we need to update for next year?"

• Quarterly check-ins: Brief conversations about whether your tools and templates are still serving you

• Annual narrative refresh: Dedicated time to update core program descriptions and case for support

• Permission to experiment: Create space for trying new approaches alongside proven ones

This isn't about constant change for change's sake. It's about being intentional instead of being on autopilot.

The most sustainable organizations I know are the ones that can hold two truths at once: consistency builds donor trust AND evolution keeps your work fresh. You can honor what's working while also giving yourself permission to let go of what's not.

Remember those magenta platform heels? They had their purpose—they were exactly what seventh-grade Cat needed to figure out who she was. The black stilettos I threw in the dumpster after that painful gala? They reminded me I could stop doing something that hurt. And the sparkly sneakers I wear now? They're perfect for where I am and what I'm building.

Your fundraising strategies deserve that same grace.

Your organization is growing and changing. Your community needs are evolving. Your impact is deepening. Your fundraising gets to grow too.

You're not failing if the grant language that worked three years ago feels stale now. You're not doing it wrong if your donor templates need refreshing. You're not being wasteful if the system you invested in doesn't fit anymore.

You're evolving. And your fundraising strategies can evolve with you.

The alternative—stale templates, outdated narratives, systems that create more work than they solve—that's actually harder than the discomfort of change. Staying in uncomfortable shoes compounds the pain. Making the shift to what actually fits? That's where the relief comes.

So pause. Assess. Ask yourself: Has my organization evolved faster than my fundraising strategies?

If the answer is yes, you know what to do. It's time to find shoes that fit where you are now, not where you were three years ago.