In Our Toolkit I am not interested in using AI to produce more content. I am interested in using it to produce better work. In fundraising, the writing has consequences, so I treat AI like a collaborator that needs direction, not a machine that gets to run on autopilot. Before we write, I set a
Annalisa Unfiltered I planned to write a quick January note about AI in fundraising. I thought I would sit down, pull up a clean draft, and tell you what I have learned in the last year and a half about using AI to write faster without sacrificing rigor. I expected it to be easy because
In Our Toolkit This time of year, I receive a lot of thank-you notes. I write a lot of them, too. And to be honest, most of them blur together. They’re polite. Appreciative. They hit the expected tone. But they don’t linger. Then every once in a while, I get one that does linger. Just
by Annalisa Holcombe, Founder & Principal Consultant Last week, I joined about a hundred people in silence as we walked through the dark forest at Bloedel. Each of us carried a small lantern. There was no talking, no narration, no instruction—just the light we held and the path in front of us. We were strangers.
Connection Collaborative Annual Report 2024-2025 This year, we celebrated our first full year as Connection Collaborative. We often tell our clients that annual reports are more than a record of impact — they are a chance to reflect, to celebrate, and to plan for what comes next. One day it occurred to us: we should
Taking time off should be simple. But for a lot of high-performing professionals, it isn’t. You’re not just managing your schedule, you’re managing guilt. You’re not just prepping your out-of-office, you’re navigating identity. You want the break, but you also want to feel indispensable. I’ve been there. Early in my career, I measured my worth
by Annalisa Holcombe, Founder & Principal Consultant I’ve been fundraising for a long time. And I’ve seen a lot of job descriptions over the years. But there’s one type of line that still stops me cold. It usually goes something like this: “Ideal candidate has access to 7- and 8-figure donors.” That one sentence tells
Everyone asks me about a pitch deck. And every time, I bristle just a little. We’re not pitching a product. We’re building belief. The word “pitch” feels transactional to me, like we’re trying to sell something instead of inviting someone into a shared vision. Fundraising isn’t sales. It’s not about convincing someone to buy. It’s
Too often, fundraising language centers the organization—its needs, its plans, its budget gaps. But when we position ourselves as the destination, we miss the deeper truth: donors don’t give to organizations. They give through them. Donors are driven by belief. They give because they want to create equity. Because they care about education. Because they
These days, it seems like every headline brings new grief: genocide, climate disasters, injustice, displacement, rising extremism. We’re all moving through some version of sorrow, anxiety, or disorientation—and it’s easy to lose sight of the fact that your donors are, too. In seasons like this, it can feel awkward—or even inappropriate—to keep asking for support.
