Views From “the Other Side”: How My Nonprofit Career Shapes the Way I Lead Today

This reflection comes from my transition from nonprofit leadership—where my work focused on fund development—to my current role as Executive Director of the Lawson Charitable Foundation. Having worked on both sides of philanthropy, the perspective I gained as a nonprofit leader now directly informs how I lead, how we communicate, and how we approach grantmaking today.

Life on the Nonprofit Side

For more than two decades, my professional life was spent on what I now call—fondly—“the other side” of philanthropy: the nonprofit side.

I led development teams working relentlessly to meet daunting, often multi-million-dollar fundraising goals. Our teams were lean. Our timelines were tight. And the pressure to keep programs running—for those in need—was constant.

There was no luxury of time.
No room for inefficiency.
And certainly no margin for wasted effort.

Yet, a significant portion of our work required exactly that.

We spent countless hours researching foundations (both private and corporate), trying to determine alignment from websites that were vague, outdated, or overly aspirational. We pored over Form 990s like IRS auditors, searching for clues that might help us decide whether an application was worth the time. We made cold calls. We followed up. We tried to find clever ways to stand out (leaving a Dunkin’ gift card at an office in exchange for 15 minutes of coffee talk was not above me). We wrote lengthy grant proposals—some rivaled the research and rigor of my graduate comprehensive exams (only half joking).

And all too often, that time-consuming effort fell flat—but thanks for the coffee!

That’s where the real issue comes into focus —not competition, not rejections, not dislike of Dunkin’ (I mean, who really dislikes Dunkin’), but misalignment.

The Real Issue: Misalignment

To be clear, I understand that not every grant application can be approved. The need far outweighs available philanthropic dollars, and foundations must make difficult choices each year—and trust me, those choices are tough.

But many times, the issue wasn’t competition—it was misalignment.

Despite doing our homework, the information available simply didn’t make it clear that our mission wasn’t the right fit. For nonprofit development staff, that realization—after hours or weeks of work—is deflating, exhausting, and sometimes infuriating. Time is money in the nonprofit world, and time spent chasing the wrong opportunity is time taken away from serving the community.

Too often, funders unintentionally force nonprofit teams into a scavenger hunt—searching for clues, reading between the lines, and trying to unlock an invisible door just to determine whether they should even apply.

Now, I Sit on the Other Side – as a Funder

As Executive Director of the Lawson Charitable Foundation, I no longer raise critical dollars to sustain operations. We are family-funded and do not accept donations. In many ways, I now hold what I often called an “endgame role” in the philanthropic ecosystem—and I say that with humility and respect, because I earned my perspective through years on “the other side.”
One guiding principle I brought with me is to respect the time of those hustling to keep their programs running.

How can we do this? Simple: if a nonprofit organization visits our website, they should be able to determine alignment within five minutes.

What clarity looks like in practice:

  • Clear giving areas
  • Examples of what we support through Impact Stories
  • Plain language
  • No guessing

Together with our trustee, we designed an application that asks only for information we truly use in decision-making—and that is required for compliance. Nothing more. Nothing performative. Nothing designed to “test” an organization’s ability to jump through hoops. This approach is intentional—not to make the process easier, but to make it more meaningful by focusing on alignment, clarity, and compliance rather than unnecessary complexity.

That same commitment to clarity extends to how we communicate beyond our website. Whether we are sharing an impact story or announcing a grant opportunity, we intentionally connect each post back to our giving priorities. When a grant opportunity is available, we link directly to our eligibility requirements so organizations can quickly assess alignment before investing time in an application. Social media should reduce confusion—not create more of it.

Transparency Matters.

Another pain point I carried with me from my nonprofit days was uncertainty around timelines. When funding decisions stretch on without clarity, nonprofit leaders are left managing real consequences—paused programs, delayed hiring, uncertain budgets, and difficult conversations with boards and staff. Silence does not exist in a vacuum; it creates ripple effects that reach far beyond a single application.

So we made our grant cycle transparent from the start. Application opening and closing dates, decision timelines, and award distribution dates are clearly outlined on our website. There is little room for question—and that’s intentional.

This clarity not only helps nonprofit partners plan responsibly, it also allows me, as a one-person foundation team, to manage my time effectively and reduce unnecessary inquiries. Transparency benefits everyone.

And while misalignment surfaced earlier in this reflection, it’s worth returning to—because it was so often the hidden reason behind rejected proposals, stalled conversations, and wasted effort. More times than not, the issue wasn’t competition or capacity; it was that the information available simply didn’t make it clear that the work we were doing wasn’t the right fit.

Despite doing our homework, nonprofit teams were left piecing together clues—trying to read between the lines and justify alignment that wasn’t fully there. That realization, after hours or weeks of work, is deflating, exhausting, and avoidable. Time is money in the nonprofit world, and time spent chasing the wrong opportunity is time taken away from fulfilling mission.

Philanthropy Rooted in Respect

nicole-anderson

Philanthropy works best when it is rooted in mutual respect.

My years on “the other side” continue to shape how I lead today—how we communicate, how we design our processes, and how we show up as a funding partner. Foundations hold power, whether we acknowledge it or not. With that power comes responsibility: to be clear, to be accessible, and to recognize the very real human cost of inefficiency.

When systems are designed without the nonprofit perspective in mind, the burden is quietly shifted onto already stretched teams. But when clarity is prioritized—when expectations are transparent, timelines are known, and alignment is easy to assess—time is returned to where it matters most.

My hope in sharing this reflection is that more funders pause to consider what it actually takes for nonprofits to do their work and intentionally design their systems accordingly.

Because every hour saved on process is an hour returned to mission. And at the end of the day, that is what we are all here for.

Nicole Anderson – Executive Director, Lawson Charitable Foundation

The Lawson Charitable Foundation was created in 2021 by Cathy and Tom Lawson. The mission of the Foundation is to help those that are working hard to help themselves and others.

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