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

The Chief Fundraiser Operating System Issue #424-minute read Hi Reader, Fourteen weeks ago, I set out to build an operating system for the Chief Fundraiser role. I thought I knew what it would look like. Twelve clean systems. A logical sequence. A framework you could install and run. Here's what I actually built: something messier and more honest than that. The systems are real. But what surprised me — writing each one, testing the language against what we actually do at my organization — is...

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,...

A KPI System People Can Stand Inside Issue #453-minute read Hi Reader, My management team pushed back. Not hard. Not angrily. But clearly. I'd brought them the final piece of a two-year EOS journey: setting our department's One Number. The structure works in three layers: company, department, and individual. The ask was to pick one number that defines development's contribution to the organization. They couldn't do it. Not because they didn't understand. Because one number couldn't hold a...

When the Problem Isn’t Performance Issue #443-minute read Hi Reader, Last week, I wrote about developing your team one level deep — and promised to come back to what happens when a direct report isn’t doing it. Here’s what I’ve learned: the conversation you think you need to have is rarely the one that moves things. Two patterns show up most often when a direct report isn’t developing their team. The first: a fundraising generalist I promoted to lead a team of specialists. Smart. Committed....

One Level Deep Issue #434-minute read Hi Reader, A CFW reader inspired me with the idea for today's newsletter after we met recently. She said it’s something CDOs wrestle with but rarely talk about. You can be available to everyone. You cannot develop everyone. Those are two different jobs. Confusing them will exhaust you and quietly undermine the people who report to you. Here's the framework I use. Open door. Full stop. My entire team of 16 knows they can come to me. Any time. That's not a...

You Can't Systematize This One Issue #414-minute read Hi Reader, Last April, budget season handed me a gut punch. My CEO and CFO have watched us grow 69% without adding a single frontline fundraiser. They believe in the model. And then the revenue goal for the new fiscal year landed. Revenue target: up. Headcount: same. Strategy conversation: not on the agenda. They didn’t do it to be dismissive. They did it because that’s how budget math works. Revenue must grow. Expenses need to stay flat....

The System That Keeps Strategy Alive Issue #404-minute read Hi Reader, I realized something uncomfortable. If I stepped away, our execution would soften. The team would keep working. Meetings would still happen. Revenue would come in. But the strategy would drift because it lived in my head. Not in the system. We didn't have a scorecard. We didn't have a planning rhythm that the whole team could see. We had instinct. That's how a lot of development operations run. The leader isn't weak. The...

Your Forecast Won't Warn You Issue #394-minute read Hi Reader, Two years ago, we learned something the hard way. A corporate donor surprised us by deciding not to renew a seven-figure partnership. By the time it hit the dashboard, the window for recovery was already closing. The system wasn’t broken. It just didn’t warn us. Most fundraising dashboards are built to measure what happened. Very few are built to surface where you’re exposed. That difference matters when conditions change. Why...