Every major gift fundraiser has experienced “stuck” moments. You’ve sought meetings, reached out, sent notes, extended invitations … and nothing seems to move. At times like these, silence can be discouraging.

In major gifts work, a pause in communication does not always signal a lack of interest. We all know relationships develop over time. These in-between times call for perspective, patience and disciplined strategy.

When prospect movement slows, consider these three approaches:

Evaluate the Messenger

Peer-to-peer relationships remain one of the most effective tools in fundraising. Sometimes the opportunity for progress can be as simple as a different messenger.

Would the prospective donor respond more readily to a board member, volunteer leader, CEO or another donor? Is there someone with shared experiences, greater credibility or a stronger personal connection who could reach out instead?

Change the Strategy

When outreach slows, resist the urge to use the same approach through different channels: another email, another meeting request or another invitation. Instead, shift the type of engagement. Ask for advice on an initiative. Share a meaningful impact story or book connected to their interests. Introduce them to a program leader or beneficiary. Thoughtful engagement keeps the relationship grounded in mission, curiosity and shared purpose.

Assume the Best

Sometimes, people are simply busy. Maybe they aren’t uninterested or intentionally disrespectful. Maybe life is simply happening—vacation, illnesses, caring for children or elderly adults, celebrations with friends and family. Give them the benefit of the doubt and assume they still care about your mission. Remain thoughtful, consistent and mission-focused; when the timing is right, you’ll be positioned to move the relationship forward.

When you’re stuck, control what you can, which is quite a lot. Major gift fundraising requires long-term relationship thinking. Continue cultivating other prospects, stewarding active donors and building future opportunities. This steady, forward movement across a portfolio may put “gas in your tank” and position you to return to slower-moving relationships with renewed focus and energy.

“Marley was dead: to begin with.”

Copy-paste it into an AI platform, ask for improvements, and the options are virtually limitless: “From the very start, Marley was dead.” “Marley was, from the outset, quite dead.”

A classic opening … dead: to begin with.

AI is astounding and an invaluable tool for innovation. Used well, it can take you where you want to go at lightning speed. For a deep dive from AI experts speaking at Kinetic’s 6th Annual Power of Philanthropy Summit, explore the summit recap.

For tips from a novice in the trenches, here you go:

Asking AI for help is fun and functional, but it’s a tool for inspiration and accuracy, not dependency.

Mull, imagine, gather information, move things around, think deeply. Then, ask AI. Like relying only on navigation apps to drive, losing the ability to discern north from south or retain situational awareness might be a bug or a feature. Either way, good instincts are priceless. Don’t let them atrophy. Start with human intelligence and use artificial tools as a means to an end, not an end in itself.

Sharing options with others is easy, but options aren’t answers.

Rule of thumb: If someone else can plug it into AI and generate a list (they can), don’t send that list. Yes, it’s speedy—with a hit of dopamine after hitting send—but it’s neither creative nor helpful. Look over the options, use critical thinking (head), trust what feels right (heart), envision the end audience (empathy), imagine the desired outcome (aspiration), make the call (leadership). Then, share good ideas or act on them.

Accepting everything at once is fast, but not always better: The A is still artificial.

Finish as you begin: with a human point of view. Don’t accept paragraphs out of whole cloth. Use discretion to retain authenticity. AI will give feedback indefinitely, so consider diminishing returns. Is the product improving or simply changing? And always guard the mission and style guide or the nonprofit’s culture will drift over time. Stay thinky: “Do we even use serial commas? Are so many em dashes really necessary?”

AI’s incredible, especially when it’s coupled with human intelligence and intuition. Less A, more I.

Preparation, not solicitation, is what makes the difference between a nonprofit reaching its fundraising goals or falling short.

Assessing an organization’s internal readiness is fundamental to ensuring a positive outcome. Evaluating your readiness prior to a campaign also instills confidence in your leadership, knowing that the proper structure, strategy and leadership is already in place, right from the start.

Drawing on several benchmarks, an objective evaluator is able to access a nonprofit’s readiness to not only ask for gifts, but receive them and maintain good relationships for the long term. Some essential benchmarks include a strategic plan, case statement, donor base, leadership engagement and systems for tracking data and communicating with donors and prospects.

Here are just a few benchmarks used to help determine a nonprofit’s campaign readiness:

Strong Strategic Foundation

A clear strategic plan and compelling case statement are critical. Your board as well as donors need to understand what your nonprofit does and why it matters. Once you have a clear vision and a path for moving it forward, aligning the fundraising plan with the campaign goals ensures consistency and credibility.

Solid Relationships and Infrastructure

Major gifts are developed through relationships. They are not transactional. A measure of readiness includes evaluating your donor constituency, identifying prospects and engaging them meaningfully. We look at your in-house systems, including record keeping, communications and research to ensure they are efficient and data-driven to support personalized donor cultivation.

Support From Leadership and Board Members

Successful campaigns require active involvement from leadership and board members. Their participation not only provides meaningful support, but it signals confidence and commitment to potential donors. Strong fundraising leadership and a fully engaged board can open doors, validate the mission and help secure transformational gifts.

Major gift fundraising begins with readiness. An honest assessment by an outside evaluator is a solid first step on a long and  rewarding journey. By evaluating the organization against benchmarks and strengthening key areas in advance, you can position your nonprofit for sustainable success and deeper donor partnerships.

Event Details

April 17, 2026
9:00 a.m. – 11:30 a.m. CDT (10:00 a.m. – 12:30 p.m. EDT)
Virtual | Free to Attend

Register now to reserve your spot

A Conversation About Curiosity and the Future of AI in Philanthropy

As artificial intelligence reshapes how we fundraise, govern and measure impact, the most important advantage may not be the tools we adopt, but the questions we are willing to ask.

The Power of Philanthropy Summit is a free virtual event designed for nonprofit professionals, board members, volunteer leaders and philanthropists navigating change and innovation. Hosted by Kinetic in partnership with the Bloch School of Management at the University of Missouri–Kansas City, the Summit brings together thought leadership and practical insight to explore how curiosity, discernment and responsible innovation can strengthen philanthropic impact.

Keynote Session

The Curiosity Code: Building a Culture of Curiosity to Thrive in the AI Era
with Nathan Chappell, MBA, MNA, CFRE, AIGP
Chief AI Officer, Virtuous

Nathan Chappell is a thought leader, public speaker, author and AI inventor recognized for his work at the intersection of artificial intelligence and generosity. He serves as Chief AI Officer at Virtuous, where he supports AI integration to help nonprofit organizations amplify mission at scale. In 2018, he founded Fundraising.AI, a global advocacy organization focused on responsible and beneficial AI in the nonprofit sector.

In this keynote, Nathan explores why curiosity, not just efficiency, is the essential skill nonprofit professionals need to thrive in a time of rapid technological change. As AI continues to reshape the way we work, the ability to think critically, challenge assumptions and seek new possibilities will determine who adapts and who falls behind.

Attendees will gain insight into:

• How a culture of curiosity leads to better decision-making, stronger donor relationships and more resilient organizations

• The science behind curiosity and why it fuels engagement, creativity and growth

• The role of AI as a curiosity amplifier and how to ensure it enhances rather than replaces human ingenuity

• Practical strategies for cultivating curiosity in daily work, from donor engagement to leadership

Nathan is the author of Nonprofit AI: A Comprehensive Guide to Implementing Artificial Intelligence for Social Good and The Generosity Crisis: The Case for Radical Connection to Solve Humanity’s Greatest Challenges. His work has been featured in NPR, The Chronicle of Philanthropy, Forbes and Fast Company. He also hosts the Fundraising AI podcast and serves as an advisor to the OpenAI Users Forum, the AI for Good Foundation, the International Committee for Information Technology Standards and the Forbes Technology Council.

“At a moment when technology is reshaping how we serve communities, the nonprofit sector needs more curiosity, creativity, and courage than ever. We’re excited to bring together thought leaders like Nathan Chappell to help nonprofit professionals explore how curiosity and responsible innovation can expand impact.” — Matt Beem, Chairman and CEO of Kinetic

Panel Conversation

Following Nathan’s keynote, the Summit will feature a dynamic panel of philanthropic leaders sharing candid perspectives on leadership and the evolving role of AI in shaping communities.

Rhodri Davies
Founder and Director, Why Philanthropy Matters
Rhodri is a leading voice on philanthropy and civil society, known for his work exploring the purpose and impact of giving. He brings a global perspective informed by research, policy and practice.

Donell Hammond
Chief Information Technology Officer, Ewing Marion Kauffman Foundation
Donell is a technology leader focused on using digital innovation to expand opportunity and impact. His work centers on aligning data, systems and strategy to support mission-driven outcomes.

Carla Meyer de Dumont
Executive Director, Rafael Meza Ayau Foundation
Carla is a social impact leader advancing initiatives that support vulnerable communities. Her work focuses on strengthening systems and driving sustainable change in El Salvador.

Reserve Your Spot Today

Join us for the Power of Philanthropy Summit, a free virtual event focused on curiosity and the future of AI in philanthropy.

Registration is required. We look forward to welcoming you on April 17.

You were invited to be part of a capital campaign team and, of course, you accepted, because you believe deeply in the cause you have been asked to support.

But, then, there is this: You have been assigned to ask potential donors for contributions. It feels uncomfortable, because: You worry about making the perfect ask; you dread being rejected and wonder how it will appear to your campaign peers; and/or you are concerned soliciting gifts could intrude upon relationships you have with potential donors. Guess what? Most everyone who has been part of a capital campaign has experienced similar emotions. Here are strategies to help you rest easy and embrace the ask:

Don’t Expect Perfection

Your role isn’t to deliver the perfect soliloquy or hit a giving threshold. It’s to invite people, genuinely and in your words, into the process of supporting something that has deep meaning to them and you.

You Aren’t Speaking With Strangers

Asks are expected and overwhelmingly welcomed. This isn’t a solicitation of strangers to contribute to a campaign. You’re making asks of others with a nexus to – or at least a positive knowledge of – the organization you are supporting.

Your Invitation Will Acknowledge Their Value

An ask is a sign of respect for the person’s belief in the organization and their standing in the community. Those who meet these qualifications would much rather be asked and listened to than be overlooked. You have already expressed your support for the campaign by being part of its volunteer team. Your ask allows others to express theirs.

Remember, always, that giving is a privilege, turning means into impact. You know this, and so do those of whom you ask. Your interaction is a precious moment to remind you both. Giving it its own reward – trust asking to offer nothing less.