Make the Bold Ask

The Ask is where many fundraisers hesitate longest. Here's how to do it with confidence.

Early fall is prime time to tune up your major gift portfolio: set each donor's High/Low Ask amount and put the estimated Ask timing on the calendar.

Recently I coached two teams wrestling with the same question: how do we ask for a larger gift — and how do we determine the right amount? Here's one case study.

Background

• "Nonprofit A" is a U.S. human services nonprofit. My clients were the Development Director and the Executive Director.
• Donors "Samuel" (introvert) and "Samantha" (extrovert) are steady 12-year supporters.
• Samantha served on the board and helped launch a development committee; together, Samuel and Samantha helped fund the first DD position ten years ago.
• Giving pattern: several "special" gifts at $20,000; other years $1,000 to $10,000. Strong affinity and deep trust with Nonprofit A.
• New signals: Samantha is "ready to get more involved" and ready to make a "lead gift." She mentioned they are frustrated their alma mater isn't asking them to give.

So What Should the Ask Be?

Often, I find there's a gut sense — followed by second-guessing. What if we scare them? What if we leave money on the table?

In this case, the Development Director was leaning toward a request of $40,000 to $50,000, partly because a favorite program had experienced a $40,000 funding cut — and this couple were the first people she thought of.

I find that when fundraisers get nervous, the instinct is to:

• Skip naming an amount and just "see what the donors say"
• Recite program costs so the donor can "do the math in their heads"
• Reference last year's gift and a gap, then ask for 50% or 100% more

Given Samuel and Samantha's signals — their desire to engage more deeply, their frustration at not being asked by their alma mater, and their 12 years of deepening trust in this mission — I recommended framing this as A Bold Ask.

How to Set High/Low Amounts

A Bold Ask is an intentional stretch — rooted in relationship and timing — that anchors the conversation at the true level of impact your organization can put to work right now. It lets donors right-size from there if they feel the need.

For Samuel and Samantha, the Bold Ask is $50,000, framed as a "lead gift." It communicates significance without apology and invites them to meet you there.

The High/Low Framework

• High (Bold) Ask: $50,000 — A lead-level gift to power a core priority for Nonprofit A, with the option to direct across two areas.
• Middle Options: $25,000 or $40,000 — These reduce the risk of the donor feeling stretched, but given what we know about this couple, they are likely capable of more.
• Low: $20,000 or $25,000 — A safe option — but one that doesn't invite them into their full potential as partners.

Avoid negative anchoring. Don't lead with their past gift of $20,000 or last year's gift of $1,000. The first number you name sets the frame for the entire conversation.

How to Guide the Conversation

• Lead with transformation, not "holes" — Reference the program that experienced cuts by talking about its impact in the community, not the budget gap. Instead of "we lost funding," try: "Your gift will ensure more survivors reach help at the moment they need it."
• Offer two resonant lanes:
  1. The Hotline — immediate, tangible outcomes
  2. Leadership Development — education and mentorship align naturally with their identities as alumni
• Be flexible — If they love both programs, let them know they can direct a gift across each.
• Mention giving vehicles lightly — after the Ask — A gentle reminder works well once the amount is on the table: "You may already be giving through a DAF — or securities might make sense given market gains."
• Come prepared for conversation, not a presentation — Have the discussion first. Follow up the next day with a one-page recap or proposal if requested.

The Suggested Conversation Flow

1. Warm welcome and gratitude — They're meeting at a coffee shop, outdoors, and the donors are bringing their dog. Both Development Director and Executive Director attend. Open with personal touch points: recent milestones, Samantha's board service, the impact of their earlier leadership gifts — without naming dollar amounts.
2. Open with values — "What's resonating most with you in our work right now?" Samantha will likely respond first. Watch Samuel's body language and loop him in gently: "Does that fit how you're thinking, Sam?"
3. Name the stakes in human terms — One succinct story or snapshot about why this program changes lives this year and next.
4. Pivot to the Bold Ask — anchor early — "Part of why we wanted to meet today is that we have a bold ask for you both. Would you consider a gift of $50,000 this year?"
5. Be quiet. Let their first reaction guide you. Body language tells you most. They may nod, ask questions, or say "That's too rich for our blood!" — or something in between.
   • Carry on in most cases — Explain the programs, invite questions, let the conversation breathe.
   • Right-size if needed — "Would you consider $50,000 over two years?" Or: "Would you consider supporting the hotline at $40,000?" Then be quiet and listen. This is better than asking, "Well, what do you want to give?"
   • Some donors will say "We'll certainly consider your request" and gracefully close the conversation there. That's a fine outcome.
6. Close with agency and a next step — Thank them, maybe slip the dog a treat, offer to follow up on any questions, and close warmly: "Might we reconnect in two to three weeks?"

Scripts You Can Steal

• Bold pivot: "We came today with a bold ask — because you're among a small group of supporters who can move the needle right now."
• Impact framing: "Your gift will ensure more survivors reach the help they need at the moment they need it — with a text or a phone call."
• Two-lane option: "If both the Hotline and Leadership Development are pulling at you, you could direct the gift across both. We'll put your generosity straight to work."
• Two-year pathway: "If timing is the issue, would $25,000 now and $25,000 next year work better for you?"
• Giving vehicle nudge (post-Ask): "Given market gains, a stock gift could be tax-smart — I'd be happy to share simple instructions."

This is the season to review your major gift portfolio, set your High/Low Ask amounts, and put your Ask timing on the calendar. Start reconnecting with current and lapsed donors now.

Q: How do I determine how much to ask a major donor for?

Start with what you know — then let the relationship inform the stretch.

Look at the giving history, but don't let past gifts set your ceiling. A donor who's given $10,000 several times isn't a "$10,000 donor." They're a donor whose relationship with your organization has been calibrated to that level so far.

Then look at the signals. Are they expressing deeper interest? Stepping into leadership? Frustrated that other organizations aren't asking them for more? Those signals tell you more than last year's check amount.

I use a High/Low framework: a Bold Ask at the true level of impact you could put to work right now, a middle option if they need to right-size, and a lower option if timing is the issue. Anchor early at the high end — the first number you name sets the frame for the entire conversation. Don't lead with last year's gift. Lead with possibility.

Q: What is a "bold ask" in major gift fundraising?

A bold ask is an intentional stretch — rooted in relationship and timing — that anchors the conversation at the true level of impact your organization can put to work right now.

It's not about guessing high and hoping for the best. It's about reading the signals: depth of relationship, expressions of interest, capacity, and timing — and making an ask that honors what you believe this donor is motivated and able to do.

The key is to lead with transformation, not transaction. Don't frame the ask around a budget gap or a program cut. Frame it around what becomes possible: "Your gift will ensure more survivors reach help at the moment they need it."

Then be quiet. Give the donor room to respond. The discomfort of silence belongs to you, not them.

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Beth Ann Locke is the founder of The Fundraiser Coach and has been raising major gifts since 1991. She coaches major gift fundraisers and nonprofit leaders to build genuine donor relationships and secure transformational gifts. Learn more at thefundraisercoach.com.