Making the Bold Ask

Bold Asks Start Here

Early Fall is prime time to tune up your major gift portfolio: set each donor’s high/low Ask and put the estimated Ask week 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 amount? Here’s one case study.

Background:

• "Charity A" is U.S. human services nonprofit. My clients were the development director (DD) and the executive director (ED).

• Donors “Samuel” (introvert) and “Samantha” (extrovert), steady 12-year supporters.

• Samantha served on the board and prodded them to launch a development committee; together Samuel and Samantha helped fund the first DD position ten years ago.

• Giving pattern: the donors have made several "special” gifts at $20,000; other years $1,000 to $10,000. They have strong affinity and deep trust with Charity A. 

• New signals: Samantha is “ready to get more involved,” and ready to make a "lead gift." She expressed that they are frustrated that their alma mater isn’t asking them to give.  

So what should the Ask be?

Often, I find that 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 DD was leaning toward a request of $40,000 to $50,000, partly because a favorite program experienced a $40,000 cut in funding and this couple were the first people he thought of.

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,” or

• Reference last year’s gift and a gap, then ask for 50% or 100% (or some other percentage) more.

Given these donors’ signals, a desire to engage more, improved financial situation, frustration at not being asked by the university, and deep trust in the nonprofit's work, I recommended framing this as a Bold Ask. 

How to Set High/Low Amounts (and Read the Room)

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 use now, and lets donors right-size from there if they feel the need.

For Samuel and Samantha, the bold Ask is $50,000 (framed by them as "lead gift", which does not have a precise level at this nonprofit). It communicates significance without apology and invites them to meet you there.

The High/Low Framework (and Why Anchoring Matters)

• High (Bold) Ask: $50,000
  Lead-level gift to power a core priority for Charity A, with the option to split across two areas.
• Middle Options: $25,000 or $40,000
  Less risk of saying or showing that $50,000 is too much, but it is likely they can do more.
• Low: $20,000 or $25,000 
  This is a safe option, which I see some fundraisers do when they want a "sure thing" and don't want to think about how to inspire donors to greater impact.

Avoid negative anchoring. Don't lead with their past gift amount of $20,000 or the last gift of $1,000. The first number you say sets the frame.

How to Guide the Conversation

• Lead with transformation, not "holes"
  You can reference the program that has experienced cuts (in this case, a hotline) by talking about the impact it has in the community, but don’t make the conversation about plugging a budget gap. Instead: “Your gift will ensure more survivors reach help as soon as they need it.”
• Offer two resonant lanes:
1. The Hotline (immediate, tangible outcomes)
2. Leadership Development (education/mentorship aligns with their education identities)
• Be flexible: If they love both programs, acknowledge that Samuel and Samantha could direct a gift to each program.
• Remind (lightly) of giving vehicles: Some past gifts have come from a family foundation, but that is no longer a giving option. I suggested that the DD may mention various giving vehicles lightly as a reminder, "You may already be giving through a DAF" or securities or other options if relevant - after the Ask.
• Come prepared for conversation: Have the discussion first. Follow up after with a one-page recap, a proposal, or other materials the next day.

The suggested convo flow

1. Warm welcome and gratitude
   They are meeting at a coffee shop, at the donors' request, and outside as they are bringing their dog. DD and ED will attend the meeting. Begin with personal touch points: recent organizational milestones, her board service, impact of earlier leadership gifts, long-time support - without naming dollar amounts.
2. Open with values and what resonates
   “What’s resonating most with you in our work right now?”  (Samantha will likely respond. Watch Samuel’s body language; loop him in with low-pressure check-ins: “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 requested this meeting is that we have a bold ask for you both. Would you consider a gift of $50,000 this year?" 
5. Be quiet
   I usually pause here.Would a consider Let their first reaction guide you. They may wish to hear more about a program, but I usually find that the body language tells you most. Reactions might be nodding or it may be, "That's too rich for my blood!" or something in between.
• Carry on with the ask, in most cases - explain the program or areas of support, ask the donors if they would like to know more or have any questions. 
• Right-size the request, if needed - In this case, we know the donors are disposed to a gift. I find that experienced philanthropists often come to meetings with a range that they are considering in their heads, and will often want to have time to consider the request away from you. However, If the donors say the gift isn't aligned with their thinking:
  >> "Would you consider a gift of $50,000 over two years?" (This is just above their highest gifts of $20,000).
  >> "Would you consider support for the hotline at $40,000 " Samantha will likely know this is the budget cut. Be quiet and listen to what they say. This is better than saying, "Well, what do you want to give?"
  >> Some donors might say, "We will certainly consider your request" and short circuit further conversation.
6. Close with agency and next step
   Depending on how the conversation and Ask goes, you may close the gift during the meeting. Often, I find donors want the space to think about this gift in amongst their other giving priorities. Thank them for their time, and maybe you brought a treat for the dog. Offer to follow up on any questions that arose and to send along details (or a proposal, if they have requested one). Then say, "Might we reconnect in 2–3 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 (not ‘fill the gap’):
  “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 our Leadership Development program are tugging at you, you could direct the gift between the two. We will put your generosity straight to work across both.”
• Two-year pathway:
  “If timing is the issue, would making a gift of $25,000 now and $25,000 next year work better for you?”
• Vehicle nudge (post-amount): “Given market gains, a stock gift could be tax-smart, I'd be happy to share simple instructions.”

This is the time of year for you to review your major gift portfolio, your high/low Ask amounts and estimated timing. Start reconnecting and building rapport with current and lapsed donors right now.

Need support or inspo? Download my Portfolio Case Study to help you find more gifts in your major gift portfolio.