Written by a practicing Chief Fundraiser

How to Complete Your Strategic Priorities Issue #353-minute read Hi Reader, Your annual plan is solid. You know which systems to build. You have the budget and the team buy-in. And then Q2 ends. Only half of your priorities shipped. You were buried. Urgent donor calls. Board prep. Event planning. Forty-seven other things that felt critical in the moment. This is the gap between annual planning and actual completion. The fix isn’t better time management. It’s System Seven: Quarterly Planning —...

Which System Do You Build When You Can Only Build One? Issue #343-minute read I could build five systems right now. Each one would add $2M-$5M or more in revenue capacity over the next three years. But I can’t build them all at once. Between staff capacity, training requirements, budget approvals, and my own bandwidth, doing everything is a recipe for doing nothing. So the real question isn’t what we should build. It’s what do we build first. This is System Six: Systems Investment — deciding...

The Delegation Framework That Lets You Grow Issue #333-minute read You built the team structure. Your strategic operators are in place. But you’re still the person everyone needs to say yes. That’s not a people problem. It’s a decision system problem. The Approval Trap Delegation isn’t assigning work. It’s assigning decisions. When I joined my current team, I thought I’d set clear boundaries. The Director of Individual Giving owned prospects under $50K. The Director of Corporate and...

The Team Structure That Scales Issue #323-minute read Running into people and system problems? That’s not unusual. The wrong team structure turns good people into bottlenecks. The $15M Inflection Point Below ~$12M, a flat structure works. You stay close to everything. Decisions move fast. Past ~$15M, that model breaks. I hit this with five direct reports. My calendar was filled with decision meetings. Strategic work moved to nights and weekends. The structure that got us to $14M could not get...

Hi Reader, Every Sunday I send you one deep-dive executive brief. Once a month, you'll also get something different: the Chief Fundraiser Field Guide — a short, midweek edition featuring insights from my LinkedIn posts this month. Think of it as the best of what I've been working through in real-time. It’s what's landing right now. 1. The $100M Secret to Trust St. Jude isn't the most trusted nonprofit in America by accident. They spend over $100 million a year on marketing. Meanwhile, the...

When Good Forecasts Still Miss Issue #313-minute read We keep missing our individual giving targets. Not dramatically or catastrophically, but consistently. Major gifts and principal gifts—the parts of our revenue mix expected to do the heavy lifting—are falling short. The annual fund exceeds goals. Foundation grants are skyrocketing and corporate giving is steady. Big individual gifts keep coming in under plan. Each miss can be explained by factors like a delayed decision, a timing shift, or...

Your Team Already Knows the Answer Issue #303-minute read At our Thursday Level 10 meeting, a direct report raised an important prospect strategy question. “How should we move forward with this relationship?” he asked. I almost answered. The strategy felt obvious. We’d navigated similar situations before. Instead, I asked, “What’s your recommendation?” He paused, then outlined a thoughtful approach. Relationship timeline. Cultivation steps. Ask strategy. It was impressive. I turned to the...

Why Rhythm Matters More Than Intensity Issue #293-minute read For three months, my Level 10 meetings ran smoothly. Every Thursday at 1:00 p.m., we stuck to the same agenda. We tracked our rocks, solved problems, and made decisions. Then I canceled two weeks in a row. The first week, I had a donor prospect meeting that couldn’t be moved. The second week, vacation. When I came back, things had drifted. Gift officers were waiting for decisions I thought we'd already made. Rocks had stalled. The...

System Zero: The Hidden Constraint No One Wants to Name Issue #283-minute read My team recently spent hours on a six-figure grant for a program that is not a top priority. If you’ve led a fundraising team, this probably sounds familiar. The issue wasn’t a shortage of good ideas. Every idea had a case to make.The problem was choosing. Every conversation ended the same way: If we say yes to this, what are we saying no to? We weren’t struggling with fundraising.We were running into something...