Let's Talk Fundraising

Have you ever left a donor meeting wondering, “Why did I say it like that?”
Or felt that quiet pressure to be more agreeable, more polished, more… perfect?

In this episode, Keith shares a story fresh from the road—an alumni reception that turned into a powerful reminder: you don’t have to be everyone’s favorite to be an exceptional fundraiser.

If you’ve ever struggled with people-pleasing, felt the weight of performance, or questioned your unique style in this work, this episode is your permission slip to stop contorting and start connecting.

Because people give to support the work… but they give through people.
And the only way your people can find you—is if they can see you.

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

Ever poured hours into a project only to watch it get worse, not better? That frustrating cycle of diminishing returns might be fueled by a deeply-held belief that's actually holding you back.

Growing up, I absorbed my father's working-class ethos that hard work—defined by time spent, effort exerted, and suffering endured—was the only path to success. This belief followed me through school and into my career, where I'd routinely second-guess myself, redo perfectly good work until it deteriorated, and eventually develop unhealthy procrastination habits. The breaking point came when I witnessed a colleague working 70-hour weeks with additional staff and still falling behind. That's when I realized I was trapped in the same pattern.

The transformation began when I started trusting my instincts, setting shorter timelines, and evaluating work at the halfway mark. Surprisingly, 95% of the time, my initial work needed no changes. This wasn't just about working smarter—it was about recognizing that our limiting beliefs often protect us in some way, even as they sabotage our success. My belief about hard work made me feel worthy and shielded me from the fear of not being enough.

This mindset shift extends beyond personal productivity to how we approach tools like artificial intelligence. Many fundraisers resist AI because they value human connection, but what if technology isn't the barrier between you and your donors? What if it's actually the solution that clears away administrative burdens so you can be more present in those relationships?

Ready to identify which beliefs are holding you back? Download our free "AI for Major Gift Fundraisers" cheat sheet with five simple prompts to help you reclaim your time and focus on what truly matters. Visit downloads.letstalkfundraising.com/AIprompts to get started today.

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

Have you ever left a donor meeting, recorded quick thoughts on your phone, then spent hours translating those scattered notes into a proper contact report? There's a better way.

At AFP Icon in Seattle last month, I watched a room full of fundraisers experience a collective "aha" moment. It wasn't sparked by fancy tech demos or pie-in-the-sky AI promises. It happened when they realized that tools like ChatGPT could immediately solve real problems they face every day. One fundraiser's words particularly resonated: "I always thought this stuff was for the tech team. I had no idea I could do it myself, like today."

That's the disconnect we need to bridge. AI has become an overwhelming buzzword, with too many platforms and not enough practical guidance. You've likely tried AI tools only to receive content that sounds like it came from a corporate handbook rather than your authentic voice. Maybe you've spent more time fixing AI-generated content than you would have spent just writing it yourself. The frustration is real — every minute wrestling with technology is a minute you're not deepening donor relationships.

Let me walk you through three game-changing tactics that are already helping fundraisers reclaim hours each week: First, "persona prompting" ensures AI understands your authentic voice before generating content. Second, turning voice notes into polished contact reports with a single prompt can save hours of documentation time. Third, building custom dashboards becomes simple when AI guides you through the process. These aren't theoretical possibilities — they're practical tools you can implement tomorrow.

Imagine saving eight hours this week, not by skipping meetings or working through lunch, but because your tools actually worked for you. What would you do with that time? Call that lapsed donor? Feel prepared for your next meeting? Or simply go home on time?

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

The journey from behind-the-scenes prospect researcher to frontline major gift officer can feel like jumping into the deep end without a life vest. In this illuminating conversation, Matt Stokes, Leadership Giving Officer at Yale University, shares his experience making this challenging career transition and the lessons he's learned along the way.

Matt brings a unique perspective, having spent years analyzing data and identifying prospects before stepping across the table to build relationships with donors directly. He reveals how his background in research has shaped his approach to cultivation and solicitation, providing him with valuable insights that many fundraisers never develop. Most importantly, he discusses the mindset shifts required when moving from data analysis to relationship building – particularly the realization that donors genuinely want to make meaningful impacts through their philanthropy.

Professional development emerges as a crucial theme throughout our conversation. Matt credits scholarships from organizations like AFP and CASE with providing essential learning opportunities when organizational budgets might have limited his growth. He emphasizes the transformative power of mentorship, sharing how two influential leaders in the fundraising community have shaped his career trajectory through their guidance and wisdom. For those early in their fundraising careers, he offers practical advice on finding mentors and accessing professional development, even with limited resources.

Perhaps most valuable is Matt's advice on building confidence in donor conversations, particularly for those new to making solicitations. He reframes these potentially intimidating encounters as opportunities to help donors achieve their philanthropic goals – a perspective that transforms the entire relationship dynamic. His insights on handling donor criticism demonstrate emotional intelligence that fundraisers at any career stage can learn from.

Whether you're considering making the leap into major gifts, are new to frontline fundraising, or are looking to build stronger bridges between your research and development teams, this conversation offers practical wisdom from someone who has successfully navigated this critical career transition.

Connect with us to continue the conversation and subscribe for more insights on advancing your fundraising career!

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

When you picture a successful fundraiser, do you imagine someone who commands the room, speaks eloquently without hesitation, and thrives in crowds of donors? That stereotype has dominated our field for decades—but what if the most powerful fundraising superpower isn't being heard, but truly hearing others?

Carissa Konesky, CFRE and advancement officer at Simon Fraser University, challenges this outdated notion through her remarkable career journey. Recognized as a Top 30 Under 30 by BC Business and Woman of the Year rising star, she's built meaningful donor relationships not by dominating conversations, but through the quiet strength of deep listening and genuine connection.

This eye-opening conversation explores how fundraising environments often favor extroverts—from rapid-fire brainstorming sessions to expectations around networking—and offers practical strategies for both introverts navigating these spaces and organizations wanting to support them. Discover the critical distinction between introversion and shyness, and why assuming quiet team members can't handle donor relationships might mean you're overlooking your most effective relationship builders.

Carissa shares powerful examples of how listening transformed challenging donor interactions, built lasting trust, and ultimately secured significant gifts. For introverted fundraisers who've wondered if they belong in this field, her message resonates with validating clarity: your quieter approach isn't just valid—it might be exactly what today's donors are seeking.

Whether you identify as an introvert seeking strategies, an extrovert wanting to better support colleagues, or a leader building a balanced team, this conversation offers invaluable insights about embracing diverse fundraising styles. Connect with Carissa on LinkedIn to continue this important conversation about making space for all voices in our profession.

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

Fundraising shouldn’t feel like manipulation. It shouldn’t leave donors feeling drained, guilty, or pressured into giving. Yet, so much of our industry—especially certain political campaigns—leans into fear as a motivator. And while fear might work once, it doesn’t build relationships. It doesn’t make donors want to come back.

You know what does? Joy.

In this episode, I’m sharing two unforgettable stories from my time in hospice fundraising—one about a 102-year-old who became the town’s most eligible bachelor, and another about a baby boy who taught his family the power of love in the smallest of moments. These stories prove that when we lead with joy, we don’t just raise money—we create connection, community, and generosity that lasts.

If you’re tired of fear-based fundraising… if you want donors who love giving… if you’re ready to build a mission that feels good—this episode is for you.

Let’s talk about why joy wins.

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

Can AI really enhance human connection in fundraising, or is it just a high-tech distraction? Let's tackle this question head-on, revealing how AI can be a transformative force in the nonprofit sector. This episode isn't about replacing the personal touch — it's about using AI to deepen it. As I prepare for my upcoming session at the AFP Icon conference in Seattle, I'll guide you through the ethical integration of AI, showing how it can streamline repetitive tasks and allow us to focus on what truly matters: building genuine relationships and crafting compelling stories that resonate with donors. 

This isn't just tech-talk; it's a hands-on challenge to experiment with AI. Whether you're drafting emails or summarizing reports, I encourage you to explore its potential in your fundraising efforts. And remember, it's not about being perfect — it's about understanding and leveraging AI as a strategic assistant. Together, we'll discuss how AI aligns with organizational values and enhances our capacity to make meaningful impacts. With curiosity and strategic intent, let's embrace AI and transform the way we connect with our communities, making our work smarter and more human than ever before.

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

Have you ever felt like fundraising was just begging for money? Like you were throwing out asks and hoping someone would say yes? If so, you’re not alone—but there’s a reason it feels that way. And it’s not just you.

In this episode of Let’s Talk Fundraising, I break down the difference between real fundraising and what I call panhandling. It all started with a phone call that should’ve been about speaking at a conference—but instead turned into a hard sales pitch for sponsorship. And when the other fundraiser shrugged and said, “Well, we have to ask everybody”, it hit me like a brick.

No. We don’t.

Fundraising isn’t about throwing out asks to anyone with a checkbook. It’s about building real relationships, aligning passions with purpose, and guiding donors on a hero’s journey—where they see themselves as part of the change.

In this episode, we dive into:
🎙️ The huge mistake that makes donors run the other way
🎙️ Why real fundraisers never feel like salespeople
🎙️ The key to making donors excited to give (without pressure)
🎙️ How to stop “panhandling” and start inspiring generosity

If you’re tired of making asks that feel transactional, if you want to build real donor relationships that last, this episode is for you.

🚀 Let’s raise money the right way.

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

Join us for an enlightening conversation with Bri Gerzevske, an expert in nonprofit fundraising leadership, as she shares her transformative approach to creating high-functioning teams. Ever wondered how to step into a new leadership role and immediately start building trust and a positive team culture? Bri’s strategy centers around joy and belonging, and she shares how one-on-one meetings can help set expectations and understand team dynamics, all while maintaining healthy work-life boundaries. She also tackles the thorny issue of micromanagement and the importance of fostering a trust-based work environment.

The episode takes a deep dive into the challenging waters of hiring without bias. We explore the critical need for self-awareness and environmental analysis before recruitment, using approaches like SWOT analyses to ensure a well-rounded and diverse team. Bri shares her firsthand experiences balancing the emotional demands of fundraising in social services, particularly at St. Patrick's Center, where the administrative duties often intersect with the harsh realities faced by program staff. Through thoughtful strategies, she demonstrates how managing expectations is crucial for effective fundraising, while also highlighting the emotional resilience required in this field.

Finally, we delve into empowering teams through sustainable growth and support. Discover how to create a safe environment that encourages personal and professional development for each team member. Bri emphasizes the importance of recognizing what drives individuals and being a strong advocate for their aspirations, even when it means preparing them for opportunities beyond the current organization. We wrap up with practical advice on celebrating wins, integrating new team members, and maintaining a cohesive, motivated team dynamic that not only meets but exceeds fundraising goals.

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

What if holiday generosity could transform lives beyond the festive season? Leanne Baumel, Chief Development Officer at Casa de Esperanza de los Niños, joins us to share her insights from the frontline of holiday fundraising. We'll unravel the complexities and joys of orchestrating campaigns like "Triple the Hope," which has successfully raised over $550,000, and explore the heartfelt process of bringing Christmas cheer to 350 children. Leanne's stories shed light on the power of donor support in changing lives while also navigating the well-meaning chaos that often accompanies it.

The holiday season brings unique challenges for nonprofits, and Leanne doesn’t shy away from discussing them. With vivid anecdotes, she illustrates how Casa de Esperanza aligns donor intentions with organizational needs, ensuring the dignity and personal touch in family celebrations. We also discuss how setting boundaries and maintaining donor engagement throughout the year is crucial for sustained success. The essence of year-round support, the significance of unrestricted giving, and the importance of strong relationships with corporate donors are pivotal themes that surface throughout our discussion.

Cross-team collaboration and empowering leadership are vital for nonprofits, especially during the bustling holiday months. Leanne shares her journey from a hands-on "doer" to a strategic leader who trusts her team to make impactful decisions. We also touch on creative strategies, such as utilizing Amazon wishlists and engaging corporate partners in unique ways, to streamline operations and maximize donations. Leanne's experience offers a blueprint for nonprofit professionals eager to harness the spirit of the season while ensuring long-term support and growth.

Sign up for the June 24, 2026 webinar on leading your organization in developing an AI policy that works for your development office. 

👉 www.LetsTalkFundraising.com/AIPolicy

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite