Making the Ask: The Most Human Moment in Major Gifts

Why practice—and discomfort—are your best fundraising tools

There’s a moment in every major gift journey where strategy meets vulnerability.

It’s the ask.

No matter how long you’ve been cultivating a donor, how well you’ve mapped their passions to your mission, or how confident you are in your cause—there’s always a flicker of nerves before you ask for a significant gift.

That’s because major gift fundraising isn’t transactional. It’s deeply human.

The Ask Isn’t a Performance—It’s a Conversation

Too often, fundraisers treat “the ask” like a scene they have to nail in one take.
But the truth is, it’s not a pitch. It’s a partnership-building moment.

The most successful major gift solicitations are grounded in trust, mutual understanding, and a clear invitation—not pressure.

Your goal isn’t to impress.
It’s to connect.
To invite.
To co-create a vision for impact, together.

Objections Aren’t Rejections

One of the biggest myths in major gifts is that objections = failure.

In reality, objections are progress. They mean the donor is thinking critically. They’re engaging. They care enough to voice a concern rather than silently disengage.

Whether it’s:

• “I’m not ready to commit at that level.”

• “I need to talk to my partner.”

• “We’re prioritizing a different issue this year.”

…your job is to listen, stay curious, and keep the relationship open—not shut down.

Why You Must Practice the Ask

If you’re waiting to feel fully confident before you ask, you’ll wait forever.

The only way to build confidence is to practice. Not just writing out what you’d say—but saying it out loud, with a coach or colleague, and inviting feedback.

Practice helps you:

• Get comfortable hearing yourself speak the ask

• Stay steady when a donor surprises you

• Hear your tone, pacing, and language clearly

• Normalize objections so you’re not rattled when they arise

What I Recommend to Fundraisers

Whether you’re new to major gifts or a seasoned pro, here are three things you can start doing now:

1. Script the invitation (not the conversation)
   Prepare a clear, confident invitation to give—but leave room for dialogue.

2. Role-play the objection you fear most
   What’s the “worst-case” response you dread? Practice hearing it and staying grounded.

3. Debrief every ask
   Whether the answer is yes, no, or maybe—reflect on what went well and what you’d adjust. Every ask makes the next one stronger.

Fundraising Is a Skill—Not a Trait

You don’t have to be extroverted. You don’t have to be perfect.
You just have to show up prepared, practiced, and open to learning.

Major gift fundraising isn’t about having all the answers. It’s about building trust, navigating complexity, and staying in relationship—even when things get uncertain.

So don’t avoid the ask.
Prepare for it.
Practice it.
And when the time comes—make it with heart.

Want help practicing your next ask—or working through a donor scenario you’re unsure how to navigate? I offer coaching for fundraisers and teams who want to strengthen their major gift strategy, confidence, and conversations.

Contact me to sign up!

Balancing Acts: Connecting Annual Fund Strategies with Major Gift Success

In the world of fundraising, finding the right balance can feel like walking a tightrope. Recently, I received a message from a follower that perfectly captured what many organizations struggle with: too many special events, unclear connections between annual fund and major gifts, and plateauing annual fund results.

The Special Events Trap

Many nonprofits fall into the "event trap" - hosting numerous special events that consume significant resources while delivering diminishing returns. While events can create meaningful engagement opportunities, they often:

• Drain staff time and energy

• Require substantial upfront investment

• Yield unpredictable net revenue

• Distract from more strategic fundraising activities

Strategic Solution: Evaluate your events portfolio annually. For each event, assess:

1. Net revenue (after ALL costs, including staff time)

2. Donor acquisition/retention impact

3. Major gift pipeline development

4. Mission advancement

Consider replacing lower-performing events with targeted cultivation activities that serve both annual fund and major gift objectives.

Breaking Through Annual Fund Plateaus

When annual fund results stagnate, it's often because we're:

• Relying on the same donor segments

• Using identical messaging year after year

• Missing opportunities to segment and personalize

• Failing to clearly articulate impact

Strategic Solution: Revitalize your annual fund by:

1. Implementing strategic segmentation based on giving history and engagement

2. Refreshing messaging to highlight specific, tangible impacts

3. Testing new channels (like SMS) alongside traditional approaches

4. Creating clear pathways for donors to increase their giving over time

Building the Annual Fund to Major Gift Bridge

Perhaps the most critical challenge is connecting annual fund strategies with major gift success. Without this connection, organizations miss opportunities to develop their most promising donors.

Strategic Solution: Create intentional pathways by:

1. Identifying annual fund donors with major gift potential through wealth screening and engagement analysis

2. Developing mid-level donor programs that provide special recognition and engagement

3. Including major gift officers in annual fund strategy discussions

4. Creating shared metrics that incentivize collaboration between teams

Resource Alignment for Maximum Impact

Success requires aligning your resources - both human and financial - with your strategic priorities. This means:

• Evaluating staff capacity realistically

• Investing in systems that support integrated fundraising

• Creating clear processes for moving donors between programs

• Developing shared goals and metrics across fundraising teams

Moving Forward Together

The organizations that thrive are those that view fundraising holistically - understanding that annual giving, mid-level programs, and major gifts are all part of one donor journey. By breaking down silos and creating intentional pathways between these areas, you can maximize both current revenue and long-term sustainability.

Strategic Shift: From Events to Major Gifts: Maximizing Fundraising ROI

Nonprofit organizations are increasingly challenged to deploy limited resources in ways that yield the greatest fundraising return. Although data consistently demonstrate that major gift programs deliver substantially higher returns than special events, many nonprofits continue to disproportionately invest in event-based strategies. This white paper explores the data underlying this paradox, outlines the opportunity cost of current practices, and provides a roadmap for optimizing fundraising return on investment (ROI) through a strategic rebalancing toward relationship-centered major gift development.

The Fundraising ROI Paradox

A growing body of research reveals a fundamental misalignment between how nonprofit organizations allocate fundraising resources and how revenue is generated:

• Special events yield a median return of approximately $0.50 per dollar spent.

• Major gift programs, by contrast, return $5 to $10 per dollar invested.

• Yet, nonprofits spend 63% of fundraising time on events that produce only 27% of total revenue.

• Major gifts account for up to 80% of revenue, while receiving just 20% of staff time.

• Organizations that strategically shift resources from events to major gift initiatives report an average 34% increase in net revenue.

This disconnect suggests a substantial opportunity cost—and underscores the need for a data-informed realignment of fundraising strategy.

The Risk of Event-Centric Models

Overreliance on events not only produces a lower financial return, but also exposes organizations to strategic and operational risk. Events are highly susceptible to external disruptions such as economic downturns, inclement weather, or public health crises. The COVID-19 pandemic starkly revealed the fragility of event-dependent fundraising strategies. Organizations with established major gift pipelines proved more resilient and adapted more quickly to virtual or relationship-driven fundraising environments.

Opportunity Cost and Resource Misallocation

Event-based strategies carry significant opportunity costs. Staff time spent coordinating logistics, securing auction items, and managing vendor relationships is time diverted from high-impact donor cultivation activities. While these tasks are visible and often celebrated internally, their actual fundraising ROI is often poor compared to relationship-focused work. This misallocation limits an organization’s ability to build lasting donor partnerships and secure transformational gifts.

Beyond Direct ROI: The Enduring Strategic Value of Events

While the financial ROI of major gifts far exceeds that of events, events continue to serve meaningful strategic purposes when integrated intentionally into a broader fundraising portfolio.

Community Building and Belonging

Events create space for supporters to experience a sense of connection—both with each other and with the organization’s mission. This "return on belonging" can deepen emotional ties and foster loyalty, laying the groundwork for future philanthropic engagement.

Cultivation Pipeline

Strategically designed events can serve as soft entry points for prospective major donors. The immersive experience of an event often sparks curiosity and connection, which can be converted into deeper involvement through thoughtful follow-up.

Visibility and Social Proof

Public-facing events enhance organizational visibility and generate goodwill. When well-executed, they demonstrate community momentum and endorsement—key psychological motivators for major gift prospects.

Strategic Rebalancing: Optimizing the Fundraising Portfolio

Rather than eliminating events, organizations should adopt a portfolio approach that maximizes both short-term returns and long-term relationship value. Key strategies include:

1. Selective Event Strategy

Concentrate resources on fewer, high-impact events that are purpose-built for cultivation or stewardship. This approach maintains engagement opportunities while reducing staff burnout and opportunity costs.

2. Post-Event Activation

Events are only as valuable as the follow-up that comes after them. Organizations should design tailored post-event strategies to move attendees through the donor pipeline—especially those showing signs of major gift potential.

3. Relationship-Centered Metrics

Beyond revenue, evaluate events based on their ability to drive relationship outcomes:

• Number of qualified prospects identified

• Strategic conversations with existing donors

• Movement within the cultivation or solicitation pipeline

• Long-term giving trends among event participants

4. Strategic Time Allocation

Because staff time represents a major hidden cost, organizations should proactively budget and monitor how time is invested in event planning vs. relationship development, ensuring alignment with strategic goals.

Leadership as a Lever: Driving Cultural and Strategic Change

Successful realignment requires more than programmatic change; it demands leadership vision and cultural shift. Boards and executive leaders must champion the transition toward major gift development. Board members can serve as powerful ambassadors by opening doors, making introductions, and modeling philanthropic commitment. Leadership support signals to staff that major gifts are a strategic priority and helps embed a long-term, relationship-centered mindset throughout the organization.

Theoretical Framing: Applying the Pareto Principle

The well-known Pareto Principle—where 80% of outcomes stem from 20% of inputs—is particularly salient in fundraising. Major gifts frequently comprise 80% or more of total revenue yet often receive disproportionately low organizational investment. Aligning staff time, leadership focus, and strategic planning with this principle enables organizations to more effectively drive revenue growth and deepen donor engagement.

Prioritizing major gifts also reflects a broader philosophical shift in the sector: from transactional fundraising to transformational, donor-centric engagement. This shift emphasizes understanding donor motivations, aligning giving opportunities with personal values, and building long-term partnerships based on trust and shared purpose.

Implementation Framework: Transitioning to a Major Gifts Focus

To effectively rebalance toward major gift development, nonprofits can adopt a phased implementation model:

Phase 1: Assessment

• Conduct a comprehensive ROI analysis of all fundraising activities.

• Evaluate events for both financial performance and relational outcomes.

• Identify untapped major gift potential within existing donor and event attendee pools.

Phase 2: Strategic Planning

• Curate a focused event calendar aligned with cultivation goals.

• Build out a post-event engagement plan tailored by audience segment.

• Establish a robust qualification and stewardship process for major donors.

• Set realistic and measurable targets for major gift growth.

Phase 3: Capacity Building

• Train development staff in major gift fundraising, including discovery, cultivation, and solicitation.

• Develop compelling giving opportunities that align with donors’ values and interests.

• Implement tools and systems for tracking pipeline progress and donor engagement.

Phase 4: Execution and Refinement

• Launch and monitor execution with close attention to key performance indicators.

• Regularly review outcomes and refine strategies based on real-time feedback.

• Celebrate progress internally and externally to build confidence and momentum.

Conclusion

The future of sustainable fundraising lies not in hosting more events, but in building deeper relationships. Nonprofits that strategically shift their focus from event-centric tactics to major gift development are better positioned to realize both higher ROI and stronger mission alignment.

Events should no longer be viewed as standalone fundraising solutions, but rather as part of a multi-channel, relationship-driven strategy. By aligning resources with what the data clearly supports—major gift cultivation—organizations can unlock significant new revenue and deepen the impact of their work.

Recommended Reading & Resources

For those seeking further insights into optimizing fundraising performance, the following resources offer practical tools and evidence-based guidance:

1. Dataro. (2023). How to Calculate Fundraising ROI: Quick Guide for Nonprofits.

2. DonorSearch. (2024). Nonprofit Fundraising Metrics: 30+ KPIs to Measure Success.

3. CFO Selections. (2023). Calculating Nonprofit ROI.

4. Classy. (2024). Nonprofit Marketing Metrics for ROI: What to Track.

5. Nonprofits Source. (2024). 2024 Charitable Giving Statistics, Trends & Data.

6. Dataro. (2024). Fundraising Analytics: 20 Critical Metrics & How to Use Them.

From Fundraisers to Ambassadors

It all begins with an idea. Maybe you want to launch a business. Maybe you want to turn a hobby into something more. Or maybe you have a creative project to share with the world. Whatever it is, the way you tell your story online can make all the difference.

Don’t worry about sounding professional. Sound like you. There are over 1.5 billion websites out there, but your story is what’s going to separate this one from the rest. If you read the words back and don’t hear your own voice in your head, that’s a good sign you still have more work to do.

Be clear, be confident and don’t overthink it. The beauty of your story is that it’s going to continue to evolve and your site can evolve with it. Your goal should be to make it feel right for right now. Later will take care of itself. It always does.