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...
7 days ago • 3 min read
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...
14 days ago • 2 min read
Your Portfolio Is Shaping How Your Team Thinks Issue #384-minute read Hi Reader, Last week, I asked why board connections stall. A — They don't know the prospect well enough and won't admit it. B — They know them, but the ask feels too risky. Here's what those of you who replied said: mostly A. Board connections stall for the same reason portfolios stall. Wrong design. Not wrong people. Let's start with a question. What is your portfolio actually built to produce? Revenue - of course. But, is...
21 days ago • 3 min read
System Nine: Board Leverage Issue #374-minute read Hi Reader, Last week, I asked whether you absorb the CEO's mid-quarter requests or stall for time. I only heard back from one person — and that tells me something. Either the question didn't land, or the answer felt too uncomfortable to put in writing. I've been in both places. So I'll answer it myself. My default used to be absorb. Every time. And it cost me before I built a system that gave ideas somewhere to land. That's what last week's...
28 days ago • 3 min read
The Monday Email That Breaks Good Plans Issue #364-minute read Hi Reader, Your Rocks are set. Your team is aligned. Then Monday happens. Your CEO emails about a donor she met Saturday night. She wants to move on it this week. It feels urgent. You know what’s at stake if you say yes. You also know what’s at stake if you hesitate. This isn’t a CEO problem. It’s a systems problem. And it’s the most common reason well-planned quarters fall apart. The Gap Nobody Talks About Most chief fundraisers...
about 1 month ago • 3 min read
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 —...
about 1 month ago • 2 min read
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...
about 2 months ago • 3 min read
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...
about 2 months ago • 3 min read
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...
2 months ago • 2 min read