The pressure, the team, the decisions that keep you up at night — that's not in any development newsletter.

The Judgment Calls We Make Alone Issue #513-minute read Hi Reader, There’s a category of decision in this work that doesn’t have a good home. Not the strategic calls. Those we can think through with our CEO and our leadership team. Not the operational calls. Those live inside our systems and our staff. I’m talking about the judgment calls. The ones that require a read on people and pipeline that only someone sitting in our seat can make. And the ones where being wrong has real consequences. I...

The Board Member Who Changes Everything Issue #564-minute read Hi Reader, I didn't pick her. The nominating committee did, years before I ever sat across from her. By the time she joined our board, the decision was already made. I just inherited it. She was a successful corporate executive. She held a high position, had strong connections, and didn't have time for unnecessary tasks. I gave her one goal for our annual event: help us find sponsors. I explained it once and gave her everything...

Quiet Systems Issue #533-minute read Hi Reader, The systems that hold aren’t just the ones that work. They’re the ones your organization believes in. The sequence we built to vet corporate prospects was never the problem. The process was rigorous. The logic was sound. The criteria held up under scrutiny. What wasn’t ready was the culture around it. That’s what this issue is about. What Makes a System Quiet A quiet system doesn’t announce itself. It doesn’t require you to defend it under...

Issue #523-minute read Why Growth Makes Fundraising Worse Hi Reader, When people started questioning one of our biggest sources of charitable giving, my team didn't see it as just a question about how things work. They felt like it was an attack on their integrity and the way they do their jobs. I wasn't ready for that reaction. Our corporate partnerships team works carefully. We make sure companies truly help children’s health before working with them. There is a rigorous process to assess...

The Thing That Got Me Fired Issue #503-minute read Fourteen years ago, I was fired from a CEO role at a nonprofit I loved. It was painful. It still is, though it gets easier to hold with time. I’d been their CDO for years. I was promoted to CEO. And then I was let go. I’ve been hearing from CDOs lately. People who’ve been let go, or who are watching their relationship with leadership deteriorate, can feel what’s coming. And I keep finding myself wanting to tell them the same thing I wish...

The Opportunity I Killed Issue #493-minute read Hi Reader, We had prospects, but nowhere to put them. Tech companies. Startups interested in supporting the mission. But our existing partnership model wasn’t built for them. I hated saying no - especially in this market. So I tried to build something new. A fee-for-service model that would create a pathway where none existed. I spent three months on it. Consulted with people who do this work. Built toward something I genuinely believed could...

The Strategy That Has to Wait Issue #483-minute read Hi Reader, I found an AI vendor to build something perfect. Not a chatbot. A real AI tool that could tell me how mid-tier donors were engaging with our content — in real time — and customize communication based on behavior signals, not just gift history. We have thousands of prospects in that segment. The lifetime value implications are huge. I wanted to run a cost-benefit analysis on whether to hire the vendor. I couldn’t. Because we don’t...

The Ask You Should Not Make (Yet) Issue #473-minute read Hi Reader, Jerold Panas spent decades studying why major gifts succeed and why they don't. His framework was deceptively simple: Ask the right person, for the right amount, at the right time, for the right purpose. People often compress it to three variables. Panas was intentional about the fourth. Purpose is what separates technique from judgment. The real signal isn't just getting all four variables right. It's knowing when one of...

The Donor You Should Not Chase Issue #463-minute read We have a prospect who can't decide. Not because they aren't interested. Not because the mission doesn't resonate. But every time we come back with a program idea, it's not quite right. Too broad. Too specific. Not the right population. Not the right geography. We've generated four or five compelling options. Each one grounded in real need. Each one a genuine fit for what they told us mattered to them. Still not quite right. At some point,...