You’ve done everything right. You’ve researched your prospect, built the relationship, and scheduled the perfect meeting. You deliver what you think is a compelling case for support, make your ask, and then… the donor says they need to think about it. Two weeks later, they decline.
What went wrong?
Most major gift asks fail not because of bad timing or insufficient relationship building, but because of critical mistakes made during the actual request. These errors are so common that most fundraisers don’t even realize they’re making them. But once you understand these fatal mistakes – and more importantly, how to fix them – your close rate will improve dramatically. (The 5 Minute Major Donor Ask Might Help!)
Here are the five mistakes that kill major gift asks, with specific examples of what not to say and exactly how to fix each one.
Mistake #1: Talking After You Make the Ask
This is the most common and most deadly mistake. You make your request, and then you keep talking. You fill the silence with additional information, alternative suggestions, or nervous chatter. Every word you say after making the ask gives the donor a reason to say no.
What It Sounds Like: “I’m hoping you’ll consider a gift of $50,000 for our new program. This would really help us serve more families, and I know it’s a big amount, but we could also break it into payments if that works better, or maybe start with something smaller if you prefer. We’re also looking at other funding sources, so this wouldn’t be the only gift we need…”
Why It Kills Your Ask: When you keep talking, you signal uncertainty about your request. You’re essentially arguing against your own ask. The donor hears hesitation and starts to doubt whether the gift is really necessary or if you’re confident in what you’re requesting.
How to Fix It: Make your specific ask, then stop talking completely. Let the donor think. Let them respond. Silence feels uncomfortable, but it’s your friend. Practice this: “I’m hoping you’ll consider a leadership gift of $50,000 to fund our new program.” Then count to ten in your head before saying anything else.
The Right Way: “I’m hoping you’ll consider a gift of $50,000 for our new program. This investment would allow us to serve 200 additional families this year and create lasting change in our community.” [STOP. Wait for their response.]
Mistake #2: Being Vague About the Amount
Fuzzy language around gift amounts kills momentum and forces donors to guess what you really need. When you’re not specific, donors default to giving less than you hoped, or they get confused about what level of support you’re actually seeking.
What It Sounds Like:
- “We’re hoping for a significant gift”
- “Any amount would be helpful”
- “We need substantial support”
- “Perhaps you could consider a major gift”
- “Whatever you feel comfortable with”
Why It Kills Your Ask: Vague requests put the burden on the donor to figure out what constitutes an appropriate gift. Most donors will guess low because they don’t want to seem presumptuous. You’re also missing the opportunity to anchor their thinking at a higher level.
How to Fix It: Always request a specific dollar amount based on your prospect research. If you’ve done your homework on their capacity and interests, you should know what range makes sense. Pick one number and ask for it confidently.
The Right Way: Instead of: “We’re hoping you might consider a substantial gift for this project.” Say: “I’m requesting a gift of $75,000, which would fund our entire youth program expansion for the first year.”
Amount Selection Guidelines:
- Research their previous largest gifts to any organization
- Look at their business success and lifestyle indicators
- Consider their stated interests and connection to your cause
- Ask for an amount that’s meaningful but achievable
- When in doubt, err slightly higher – they can negotiate down
Mistake #3: Presenting Multiple Options During Your Ask
This seems helpful – giving donors choices should make it easier to say yes, right? Wrong. Multiple options during the ask create confusion and weaken your request. Instead of focusing on one compelling opportunity, you’re forcing them to choose between different levels of support.
What It Sounds Like: “You could give $25,000 to fund scholarships, or $50,000 to support our facility improvements, or maybe $100,000 for a combination of both. We also have naming opportunities at different levels, so there are really several ways you could get involved.”
Why It Kills Your Ask: Choice paralysis is real. When you present multiple options, donors spend mental energy comparing alternatives instead of focusing on the impact of their gift. You also dilute the power of your specific request and make it seem like you’re not sure what you really need.
How to Fix It: Make one specific ask for one specific amount for one specific purpose. If they want to discuss alternatives, they’ll bring it up. Your job is to present the most compelling opportunity you have and request their support for that.
The Right Way: Instead of: “You could support our programs at several levels – $25,000, $50,000, or $100,000, depending on what feels right to you.” Say: “I’m asking you to consider a leadership gift of $75,000 to fund our new community outreach coordinator position for two years.”
If They Want Options: Let them ask. If a donor says, “What other giving levels do you have?” or “What if I can’t do $75,000?” then you can discuss alternatives. But start with one clear, specific request.
Mistake #4: Apologizing for Asking
Apologetic language undermines your entire ask. When you apologize for requesting support, you’re suggesting that asking for money is inappropriate or that your cause isn’t worthy of investment. Confident donors give to confident organizations.
What It Sounds Like:
- “I hate to ask, but…”
- “I know money is tight, but…”
- “I’m sorry to put you on the spot…”
- “I don’t want to pressure you, but…”
- “I know this is a lot to ask…”
Why It Kills Your Ask: Apologetic language makes donors uncomfortable and suggests you don’t believe in your own request. If you’re apologizing for asking, why should they feel good about giving? You’re also setting up the interaction as something negative they need to endure rather than a positive opportunity to make a difference.
How to Fix It: Reframe your mindset. You’re not asking for a favor – you’re offering an opportunity. You’re inviting them to be part of something meaningful. Approach the ask with confidence and gratitude for their consideration, not apologies for making the request.
The Right Way: Instead of: “I hate to ask, but we really need your help with this project.” Say: “I’m excited to share this opportunity with you because I believe it aligns perfectly with your passion for education reform.”
Confident Ask Language:
- “I’m pleased to invite you to consider…”
- “I believe you’re the right person to help us…”
- “I wanted to share this opportunity with you because…”
- “Given your commitment to [cause], I thought you’d be interested in…”
Mistake #5: Overwhelming Donors with Too Much Information
Information overload is the enemy of decision-making. When you spend 45 minutes covering your organization’s history, every program you offer, and seventeen different ways their gift could be used, you’re not building excitement – you’re creating confusion.
What It Sounds Like: A long presentation covering organizational history, multiple programs, various funding needs, board member backgrounds, accreditation details, administrative costs, volunteer opportunities, upcoming events, and general organizational challenges.
Why It Kills Your Ask: Too much information leads to analysis paralysis. Donors can’t process everything you’ve told them, so they default to saying they need time to think about it. You’ve also buried your specific request in a mountain of details, making it hard for them to focus on the decision at hand.
How to Fix It: Focus relentlessly on one opportunity. Everything in your presentation should relate directly to the specific project you’re requesting funding for. Save organizational background and other programs for follow-up conversations or written materials.
The Right Way: Structure your ask around one clear narrative:
- Here’s the specific problem or opportunity
- Here’s our proven solution
- Here’s what your investment will accomplish
- Here’s what I’m asking you to consider
Information Hierarchy:
- Essential: The specific project, why it matters, what their gift will accomplish
- Important: Brief evidence that your approach works, timeline for implementation
- Nice to have: Organizational background, other programs, general impact statistics
- Save for later: Detailed financials, staff biographies, accreditation information
Your Pre-Ask Checklist
Before your next major gift ask, review this checklist to avoid these fatal mistakes:
Amount and Specificity:
- [ ] I have researched this donor’s capacity and interests
- [ ] I am asking for one specific dollar amount
- [ ] I can explain exactly what their gift will fund
- [ ] I have practiced stating the amount confidently
Ask Structure:
- [ ] My ask focuses on one specific opportunity
- [ ] I can present this opportunity in 5 minutes or less
- [ ] I have identified the real urgency for this project
- [ ] I have prepared to stop talking after making my request
Language and Tone:
- [ ] I have eliminated apologetic language from my ask
- [ ] I am presenting this as an opportunity, not a burden
- [ ] I have practiced confident, specific language
- [ ] I am prepared to handle silence after my request
Content Focus:
- [ ] Everything in my presentation relates to this specific project
- [ ] I have removed unnecessary organizational background
- [ ] I can clearly articulate why this donor should care about this opportunity
- [ ] I have evidence that our approach works
The Bottom Line
Major gift asks fail because of what you do during the conversation, not what you do before it. Avoiding these five fatal mistakes will dramatically improve your success rate with major donor prospects.
Remember: donors want to make a difference, and they want to feel confident about their investment. When you make specific, focused requests with confidence and clarity, you give them exactly what they need to say yes.
Your next major gift ask is an opportunity to practice these principles. Make one specific request, state it confidently, and then give your donor the silence they need to consider your invitation. The results will speak for themselves.
