I say this from a place of love and experience, with the understanding that it’s an aspiration for some publishers, but something everyone should keep in mind when at all possible:
You're always in a better negotiating position when you ask for money you don't need.
“Trying to raise money on the basis of an organization’s needs will work just about as well as trying to obtain a bank loan by pleading poverty,” wrote Jim Lord in “The Raising of Money.”
When you're desperate—when your cash flow is tight, and you're scrambling to make payroll in two weeks—every conversation with a potential donor becomes a panic. You're not pitching quality solutions that will make that donor a partner in improving your community and your constituents' lives. You're asking for a lifeline, and most donors will feel it, especially if they make a lot of donations or grants, because they've seen it all before.
The moment they sense urgency driven by need rather than opportunity, the dynamic shifts. You've gone from partner to panhandler.
One part of the answer is planning ahead. Even if it sounds impossible—and, again, I get it—try to build a cash flow cushion before you need it. Have a second bank account and allocate 10-20% of your collections as a buffer. Budget to spend less than you bring it and bank the difference.
Identify your slower revenue months and plan for them, both with your buffer and by allowing longer lead times for your campaigns and promotions. Ask major donors for commitments when you're solid, not when you're bleeding. This takes discipline, but it can also lead to better outcomes—more unrestricted dollars, larger, longer-term commitments. When you're not panicking, you can actually have a real conversation about impact.
The second part of the answer is building relationships. Most of the philanthropic dollars you'll ever get—from major donors, big-dollar individuals, family foundations, even national philanthropy—will come through relationships you've built, not grant applications you've written.
I'm not saying good grant apps don't matter. I'm saying that the decisions that truly sustain your organization—the commitments that move the needle on longevity—are made by humans. Those people need to believe in you, trust you, enjoy your company and appreciate you.
Sales trainer Brent Weaver once taught me that “relationships equal interactions over time.” I love that it’s both nerdy and profoundly human at the same time. What it means is that your best relationships will be built over multiple “touches” at different times and durations, with the bonus tip that more short interactions are better than fewer, longer ones.
But, either way you slice it, that means that some of your most important relationships for the future of your organization will take time to develop.
The playbook is simple. (Not easy, but simple.)
Build relationships before you need them.
Salt away some cash (or, worst case, a short-term line of credit) so you can ask from a position of strength, not desperation.
Feel freer to make bigger, boldest asks—since you don't need the money.
Don’t wait until you're in crisis mode—start now!
