Hey Changemakers,
A question landed on me recently that I haven’t been able to shake:
Are you saying yes to all your no’s?
It sounds simple. Sit with it for a minute, and it gets uncomfortable fast. Because most of us, if we’re being honest, have a running list of things we’re quietly avoiding. Delegating the hard conversation. Asking the board member who’s been coasting to step up. And, perhaps most universally in this sector:
Fundraising.
A lot of nonprofit leaders loathe it. Not all of them, but enough that I’ve spent a good part of my career sitting across from brilliant, mission-driven people who will do almost anything to avoid the ask. They’ll plan the strategy. They’ll build the team. They’ll stare hopefully skyward, waiting for pennies from heaven.
Here’s the thing: Pennies from heaven are real. I’ve seen them land. But they only show up when you’ve done the upfront work. Humans aren’t ATM machines. There’s no magic pin code that unlocks someone’s generosity. What actually works is vision, commitment, discipline, follow-through, and connection. Meaning-making is the key.
I’ve come to think of fundraising as a faith-based initiative. You have to believe, and you have to act. The leaders I’ve watched do this well have stopped thinking about fundraising as a grind and started thinking about it as an invitation to join something worth joining. That reframe alone changes the conversation you have with a donor, with your board, and with yourself.
They’ve given philanthropy a big hug.
Giving philanthropy a big hug is a choice to stop bracing against the ask and start leaning into it as the catalyst it actually is. For CEOs, yes. But also for CDOs, board members, and anyone whose job touches the mission and the money.
That shift in posture changes everything. And there’s a real discipline to it.
Two Things I See Get in the Way
On the CEO side: the pull to jump in and get something done rather than asking, what does my team need from me so they can lead well?
On the staff side: waiting for direction rather than managing up. (If you missed December’s piece on managing up, it’s worth a read.)
Both feel reasonable in the moment. Neither is actually leadership. And well-intentioned micromanagement just fills the hole where a system should be.
What Actually Changes Things
Structure. The kind that runs in the background so your team has room to do the deeper work: qualifying prospects, nurturing relationships, identifying the big bets, and having the conversations that make donors feel like true partners rather than funding sources.
Three frameworks and a mantra I come back to again and again:
PAL: Performance, Activity, and Learning Goals. Most development teams are only measured on performance: dollars raised. Money is always a lagging indicator. You need leading indicators, or Activity Goals, to ensure you’re focused on doing the right things right. No one comes with everything they need to be effective. Building in Learning Goals helps upskill. Without these, it’s like reading the final score without tracking any of the plays.
The Asking Matrix. A framework that puts the donor at the center and clarifies who does what at every stage of the cultivation cycle—the CEO, the CDO, the board connector. It covers how you spark a donor’s interest, how you prepare everyone before the conversation, and how you present the opportunity with clear roles. It solves the “we had a lovely lunch, and nothing happened” problem.
CPR = A. Certain inputs, properly sequenced, produce an ask. This formula helps you separate your operating budget needs from your fundraising goals—two things that are constantly conflated and create enormous anxiety at year’s end.
Always Be Teaming
The CEO stops grinding out gifts alone. They initiate relationships and bring their team with them. The CDO runs the system. Board members open doors. Donors feel like partners, not prospects. Think of it as three levels: staff managing the cultivation cycle, board engaged as connectors, and donors invited in as stakeholders. Not a pyramid with the CEO doing all the heavy lifting. A network, humming along because everyone knows their role.
Always Be Teaming. It’s the antidote to the grind. And it only works when the leader has done the internal work first: given philanthropy the hug and decided to lead at the level only they can.
Two things worth sitting with: When was the last time you stepped in to do something a direct report should have handled? And what would it look like for your CDO to bring you into donor conversations fully prepared, with a clear role and a clear ask?
That’s the hug. And it’s a trade worth making.
Cheers,
K
A note on sourcing: The patterns described here are drawn from many years of client conversations. Details have been changed, and stories composited to protect the privacy of the leaders who’ve trusted me with them. But the dynamics and the work are very real.
