Author: Katherine Sprissler-Klein, Senior Consultant[/caption]
If you’ve been in major gifts long enough, you’ve felt it: the slow drag of a relationship that won’t advance, the weight of an ask you’ve over-prepared for, or the gnawing doubt that maybe your donor just doesn’t “get” it. At the senior level, it’s rarely about knowing the textbook steps of cultivation. It’s about the nuance—the art of reading timing, shifting your mindset, and turning complexity into clarity.
Here are five beyond-the-basics tactics for seasoned professionals who want to move from “stuck” to strategic:
1. Nervous about an upcoming ask?
Shift your mindset from their dollars to your senses
When nerves spike before an ask, remember—you’re not selling. You’re curating an experience that allows the donor to live their values. Get out of your head and into your body. Also if you are nervous (which we all can be) spend some time visualizing the impact of their gift and review all your past contact reports. Trust your preparation!
Too many of us default to waiting for the “perfect moment” to ask—or push forward too soon because of internal pressure. You are offering someone an opportunity to live into their values.
2. Donors aren’t clear about what your organization does?
Clarity beats complexity
Donors don’t always “get it” because we don’t always make it easy! First of all, throw your organization and sector’s jargon out the window. Keep explanations of programming or pillars simple. If the donor is in a similar field, or you understand they value expertise, then you can go into deeper specifics. Another tip is to find your own why within an organization’s “why”. What pulls you personally is a key to connecting.
3. Struggling to get the meeting?
Stop chasing and start listening
When you’re struggling to get a meeting, resist the chase. Instead, shift into curiosity. What’s happening in their world right now that makes them unavailable? What signals can you pick up from the gatekeeper, their public engagements, or their own language in emails? This not only reframes persistence from pressure to insight—it makes your outreach smarter and your eventual touchpoints more welcome.
4. Pushing for a gift too soon, or waiting too long to ask?
Remember timing is strategy, not serendipity
Too many of us default to waiting for the “perfect moment” to ask—or push forward too soon because of internal pressure. Honest and open conversations are crucial. Make sure you are obtaining consent for the entire process and make it clear why you are engaging them. No deleting titles on your emails!
We’ve also noticed that gift amounts are coming up earlier in cultivation than before. Have a line in your back pocket about not planning on an ask, but that you want to show them everything they need to know to feel good about an investment of “x”.
5. Paralyzed by pressure?
Progress over perfection
Perfectionism paralyzes even the most seasoned among us. The best fundraisers adopt a mantra of equanimity, which is not reading into anything as being “good” or “bad”. Quit rewriting emails, fussing with a proposal, and give yourself some grace. Human beings are deeply flawed and our profession often expects perfection when we are not in control of the entire equation.
Final thought
You are not “Fundraiserbot 3000.” You are a human being, working with other human beings, on behalf of humankind. The goal is not flawless performance—it’s forward movement. Sometimes that means leaning on a board member. Sometimes it means swapping stories with your colleagues. Those who thrive in major gifts aren’t those who avoid getting stuck, they know how to get unstuck themselves.