Stop Guessing, Start Co-Creating: A Better Way to Ask

If you’ve ever walked into a donor conversation thinking, “I hope I guess the right number… the right timing… the right project…”—you’re not alone.

A lot of fundraising “training” teaches us to perform: memorize the case, rehearse the pitch, anticipate every objection. And then we wonder why we feel anxious, tight in our chest, and disconnected from the actual human sitting across from us.

There’s a better way.

Instead of guessing what donors want, you can co-create the gift with them.

This post is about making that shift in real time—using small, practical head-to-heart pivots that move you out of performance mode and back into relationship, curiosity, and courage.

What “Guessing” Looks Like (and Why It Burns You Out)

When we’re in guessing mode, conversations often sound like this:

• “I think they might be a $100,000 donor? At least that's what they gave somewhere else.”

• “They said they’re ‘interested’… does that mean $20,000? $1,000? A monthly gift?”

• "The wealth screen said they had capacity to make a gift of $500,000. Maybe we just make a proposal for that amount."

Underneath that guessing are some very human fears:

• Fear of offending someone by asking “too high”

• Fear of missing out by asking “too low”

• Fear of hearing no after you’ve put yourself out there

So we overthink the math and underuse the best tool we have: a real, two-way conversation.

Co-creating a gift doesn’t mean being vague or apologetic. It means this:

You’re honest about the need, and you invite the donor to help shape what their best “yes” looks like.

You still prepare. You can still have a thoughtful goal or range. You just stop pretending you already know the exact answer—and let the donor help you find it.

Head-to-Heart Pivot #1: From Pitch to Partnership

Default mode: “I need to nail this pitch and persuade them.”

Co-creating mode: “We’re exploring together whether this is the right fit and what it could look like.”

Instead of launching into a monologue, set a collaborative tone from the start.

Try:

• “I’d love to share what we’re working on and then hear what resonates for you.”

• “As we look at this together, I’m curious where you feel most drawn.”

Mini example

Instead of:

“The most important part of the project for us is making sure that can renovate our shelter.”

Try:

“Now that I've shared a little more about the project, what parts feel like a homerun to you?”

These types of phrases subtly tell the donor: You're not being sold something. We're shaping this together.

Head-to-Heart Pivot #2: From “Perfect Number” to Honest Range

Default mode: “I have to pick the exact right number.”

Co-creating mode: “I’ll offer a thoughtful range and invite a real reaction.”

You still do your homework on capacity, past giving, and relationship. You can still be clear and bold—you’re just not treating it like a one-way announcement.

Script you can steal:

“Given your long-time support and your passion for [X], we’re hoping you might consider a leadership gift in the $150,000-$200,000 range, possibly over multiple years. Does that feel like something you’d want to explore, or would a different level or timing be a better fit?”

If they say, “That’s more than we can do,” pivot without panic:

“Thank you for telling me—that’s really helpful. If we thought about a gift that feels both meaningful and comfortable for you, where do you think that might land—either in amount or in how it’s structured?”

Now you’re not guessing; you’re designing together.

Head-to-Heart Pivot #3: From Presentation to Conversation

Default mode: You talk for 20 minutes, blurt out the number... and then rush to justify it or quickly move on before it can be awkward.

Co-creating mode: You share a bit, make a clear ask, pause, and then have real conversation about the request.

What this sounds like in practice

Share the case briefly:

“That's why we are raising $28M over three years—to triple our capacity at our current site and add a new child care center.”

Make the ask clearly:

“Given your long history with this work and our past conversations, I'd love to invite you to consider a leadership gift of $500,000 structured in a way that works for you.”

Pause and check in:

“Does this feel in the realm of possibility, or is it higher or lower than you were imagining?"

You’re shifting from “presenting at” to “processing together”—giving them space to react, be honest, and think out loud with you.

Start Small: One Pivot Per Conversation

You don’t have to overhaul your entire asking style overnight.

For your next donor conversation, pick one of these:

• Share a clear range instead of silently agonizing over a single number.

• Ask, “What part of this connects most with what you care about?” and really listen.

• Try the line, “I don’t want to guess at what might be right for you—can we explore that together?”

Then debrief with yourself:

• What did I learn when I stopped guessing?

• What felt surprisingly easy?

• Where did I feel more connected to the donor?

That’s how you move from head-spinning guesswork to grounded, heart-forward, co-created gifts.

Want the Simple 5-Step Framework?

This post focused on the micro-shifts you can make in the moment.

If you’d like my simple 5-step framework for structuring a co-created ask—from the first hello to the follow-up:

👉 Email hello@solfullfundraising.com with “5-steps” in the subject line, and I’ll send it your way.

One pivot at a time. 💛

Frances Roen: Frances Roen is a Georgia girl at heart, and has been graciously adopted by beautiful, snowy Minnesota. She is a forty-something daughter, friend, mom, wife, and entrepreneur, and is always on the look-out for a perfectly fried piece of chicken.

Frances is a Certified Fundraising Executive (CFRE) with nearly 20 years of experience fundraising and has raised over $200M for nonprofits. She has held fundraising positions at The Bakken Museum, Augustana Care Corporation, and YouthLink and consulted with dozens of nonprofits clients across the globe. In these roles she has been responsible for all aspects of fundraising including capital campaigns, major and planned gifts, annual funds, events, communications, corporate partnerships and volunteers.