How to Use AI for the Right Ask (Without Being Creepy)

We’ve all received cringe-worthy fundraising messages that just don’t feel quite human. They’re vague, don’t explain the impact of the donation, and ask for an arbitrary amount of money. If an appeal feels like it was written by a robot, it likely was generated by AI.

Such subpar messages may be the reason that 63% of fundraisers feel uncomfortable using AI for personalized donor communications. While AI is often touted as a way to hyper-personalize fundraising efforts, to many fundraisers, AI can make communications seem less personal, less authentic.

But here’s the thing: AI doesn’t have to feel creepily robotic or impersonal. When used thoughtfully, AI can actually help you be more human and strengthen your authentic connections with donors. Its value lies in solving complex, role-specific problems—like assisting a fundraiser in making the right ask.  

In this article, we’ll explore the power in aligning AI technologies and methodologies by showing you how AI can support every stage of the ask, ultimately helping you raise more dollars for your organization, without being creepy.

Starting with the End in Mind: The Perfect Ask

Before we jump into AI’s capabilities, let’s cover the elements of the perfect ask.

• Right timing: When to make an ask depends on a variety of factors like the donor’s interest, engagement, and giving history.
• Real relationships: Making an ask for a donation immediately after meeting someone is like asking to borrow a car from someone you just met—there isn’t enough trust built to warrant the interaction. Instead, fundraisers should create a series of touchpoints, building the foundation of the relationship before making the ask.
• Genuine interactions: When you make the ask, you don’t want it to feel like a one-to-many communication. You should know the donor well enough that you can reference personal facts, and interests, and make the request for a donation as if you’re speaking to a friend or colleague.
• Resonates with donor interests: Understanding what aligns (and what doesn’t) with your donors’ interests can guide when to and what to ask for.
• Appropriate amount: Deciding on the right amount is one of the more challenging aspects of the ask. Request too much and you risk donors feeling overwhelmed or pressured. Ask for too little and you miss out on opportunities for your organization. Using donor and prospect data, such as giving history and capacity, can help you determine the appropriate amount.

Setting the Foundation: Pre-Ask Due Diligence

There are many steps in the donor lifecycle before an ask is made. Fortunately, AI can give you a leg up with each stage and, we promise, it won’t come off as creepy (if you don’t let it).

Smart Donor Research

Instead of spending hours Googling prospects, hunting down LinkedIn profiles, and scanning your CRM for every ounce of information, let AI be your research assistant. AI can:

• Flag relevant news articles about donors’ interests that you can use in your outreach
• Identify potential relationships between donors, such as family, friendships, or colleagues
• Highlight significant life events that might affect giving
• Track engagement patterns across your communications
• Use donor location to help you determine who to set up meetings with when traveling and optimize routes for multiple donor visits

Pro Tip: Use fundraising-specific AI models to help with your research. For example, Momentum’s free Chat-GPT is geared specifically toward major gift fundraisers.

The Art of Timing

Because AI can analyze vast amounts of data very quickly, it excels at identifying patterns that people might miss. Use AI to:

• Analyze past giving history to predict optimal ask timing—this can include developing dynamic donor plans so you know the best cadence of communications prior to making the ask
• Track engagement metrics to identify when donors are most receptive
• Monitor donor behavior patterns to suggest the best contact times
• Flag potential concerns, such as slipping engagement or possible churn

Pro Tip: Use AI to track seasonal giving patterns alongside personal donor milestones. If a donor typically gives in Q4 but also makes special gifts around their birthday, you can plan your outreach accordingly.

Personalization That Feels Authentic

Try using AI to add personal touches to your communications at scale for all donors within your portfolio:

• Create detailed donor profiles based on interactions and interests
• Suggest conversation topics aligned with donor passions
• Draft customized communication points
• Generate personalized impact stories relevant to each donor

Pro tip: When using AI to draft communications, prompt it with examples of your best-performing donor messages. Say, “Write in the style of this successful appeal…” rather than starting from scratch.

Learn why AI is a game-changer for major gift officers

Making the Ask: AI as Your Strategic Partner

Finding the Right Number

One of AI’s superpowers is its ability to process staggering quantities of data to suggest optimal ask amounts. When you prompt AI for its recommendation on the best amount to ask for, it gives you an estimate based on a variety of data points:

• Past giving patterns
• Engagement level
• Response to previous asks
• Current involvement with your organization
• Recent life events
• Giving to similar organizations

Pro tip: Look at the AI-generated number first. People tend to rely heavily on the first piece of information they receive when making decisions (also known as anchoring bias). In this case, the first donation amount you see acts as an anchor and influences how much you will ask for. By asking AI first, your bias is geared toward a data-informed answer.

Crafting the Perfect Pitch

AI can help you prep the ask by reviewing what worked in the past. Use AI to:

• Analyze successful past pitches for commonalities and tips
• Identify language that resonates with similar donor groups
• Suggest talking points based on donor interests
• Prepare responses to potential objections

Pro tip: Record your practice pitches and use AI to analyze your delivery and pacing. You can also have AI analyze recordings of past pitches to review metrics like listening ratio, speaker engagement, and overall emotional tone of the meeting.

Adding the Human Touch to Reduce the Cringe

We’d be remiss to not address how to avoid being creepy when using AI. A lot of the creepiness stems from either a lack of oversight of AI-related use cases or forgetting to incorporate the human touch.

1. Add context. Don’t just accept AI suggestions blindly. Always ask yourself:

• Does this align with what I know about the donor?
• Would I say this in a face-to-face conversation?
• Does this reflect our organization’s voice and values?

And if the answer isn’t yes, let AI know. You could provide examples of what you’re looking for or give specific feedback on how AI’s response does not fit your needs. AI learns through feedback and adjusts as it learns more about your organization. Use this ability to learn to your advantage.

2. Train your AI tool. In the same vein, you can train your AI tools with information specific to your organization. This will help AI provide high-quality responses from the get-go. Give AI access to:

• Your organization’s unique voice
• Successful past communications
• Donor feedback and preferences
• Your mission-specific language

3. Don’t use AI for everything. Just because AI can do many things doesn’t mean it should. Remember, AI is not a replacement for your job but a powerful tool to help you streamline your workflow and better engage donors.

Two examples: you could use AI to create a word-for-word script of what to say on your next call with a major donor, or you could use AI to create a one-page brief.

If you recite the script—cringe alert—you will sound unnatural, even robotic. But, if you use the one-page brief outlining recent interactions, giving history, the donor’s interests, and talking points, you walk into the call prepared, not scripted, not creepy.

Let AI handle critical background info:

• Data analysis and pattern recognition
• Initial research and draft content
• Meeting summaries and follow-up tasks
• Engagement tracking

But keep human control over the human elements:

• Final communication approval
• Relationship strategy
• Personal interactions
• The actual ask

The Ask: Give AI a Try

The goal isn’t to automate the entire fundraising process. It’s to use AI strategically and with intention to make every interaction more meaningful, more personal, and more effective.

Now it’s our turn to make the ask—are you ready to take AI for a whirl? Explore AI solutions, like Momentum’s AI-powered Donor Engagement Platform. It helps you improve your ask and reach the right donor at the right time with the right message. Plus, it seamlessly connects with Blackbaud fundraising solutions to help you make the most of your donor data with Blackbaud’s Intelligence for Good.