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For many of us, planned giving seems intimidating—all those complex financial instruments and legal terminology. But here's the thing: the donors you need to reach, especially those born between 1965 and 1980, don't want to hear about charitable remainder trusts on your first conversation either. They want to know how they can make a real difference while being smart about their finances.

Gen X donors are hitting their peak earning years right now, and they will be the primary recipients of the Boomer estates. So, they’re thinking about legacy in ways that might surprise you. Let's break down how to reset your planned giving approach to connect with this unique generation.

Some call it storytelling; others call it an elevator pitch. Either is fine, and elevator pitches are good as long as you know that most people want to get off on the 2nd floor.

Developing a concise, compelling, and succinct message that clearly states the societal problem you’re working to address, how you will solve it, and what differentiates your work is a key factor in fundraising campaign success. Your case must be made clearly, quickly, be externally focused, and demonstrate urgency.

Summer’s erratic schedules—donors on vacation, staff taking time off, board members and volunteers unavailable—can disrupt traditional fundraising efforts. But this quieter season offers a powerful opportunity for fundraising leaders, whether they manage teams or work as individual contributors, to reset their approach by leaning into authentic, one-on-one connections. By focusing on building genuine relationships with colleagues, donors, volunteers, and board members, leaders can foster trust, inspire collaboration, and fuel long-term success in ways no strategy or tactic can match. Here’s how to use summer’s lull to cultivate meaningful connections that transform your leadership and organization.

Can you believe we’re already halfway through the year? If you’re like most nonprofit leaders, you kicked off the year with ambitious fundraising goals, detailed plans, and a whole lot of motivation to have “the best year yet!”

Now, with six months behind us, it's time to step back and ask: How are we really doing?

Remember, fundraising isn't just about year-end campaigns, online appeals, or event seasons; it’s a year-round effort that begins on day one of your new fiscal year. Taking time now to evaluate your progress can be the difference between scrambling in Q4 or finishing strong.

A mid-year review gives you a chance to:

• Assess the first six months of the year
• Identify gaps
• Re-engage and realign
• Plan ahead with purpose

Maybe you've felt it before. That moment when you're face-to-face with a potential major donor, or standing before your board, or speaking to a community group, and despite your preparation, passion and expertise, you can see their attention drifting. You know your organization's work is transformative. You can recite the statistics. You understand the impact. But somehow, in that moment, the magic of your mission isn't communicated as vividly as you hoped it would be.

I've been there and that is why I’m excited to share some reflections from a book I have read that has helped shape my approach to storytelling. Karen Eber's book, The Perfect Story: How to Tell Stories That Inspire Action and Get Results offers science-based frameworks that are easy to apply to how you tell stories about your organization’s impact and mission in action.

In The Anxious Generation, social psychologist Jonathan Haidt presents a compelling case for how smartphones and social media have transformed childhood—from active, play-based experiences to phone-based, screen-dominated ones. While much of the conversation around the book has focused on youth mental health, Haidt’s research holds deeper relevance for all of us living in an increasingly distracted, hyper-connected world.

As I read, I found myself reflecting not just on childhood, but on adulthood and on how we connect with one another as family members, neighbors, colleagues, and members of a shared community. Haidt’s analysis of how technology rewires our brains and behaviors applies just as powerfully to adults as it does to kids. And in the nonprofit sector, where our work depends on meaningful relationships and shared purpose, those insights feel especially critical.

I’ve been spending an increased amount of time in The Bible over the last couple of years and continue to be struck by how much practical application to donor relations there is in the teaching of Jesus. “Ask and you shall receive” encourages us to approach a fulfiller of needs with faith and diligence. The “parable of the talents” shows the benefit of being good stewards with what has been entrusted to us, namely that more will be entrusted.

Early in my career, I was given a copy of a book which my experienced colleague at the time said would “be the basis for your success.” The book was Designs for Fund-Raising by Harold J. Seymour. Harold (Si) Seymour is considered one of the founding fathers of modern fundraising. His book, originally published in 1966, established many fundamental concepts that still form the backbone of fundraising practice today.

For me, these are the key aspects that remain relevant:

1. The emphasis on relationship-building rather than simply asking for money
2. The importance of thorough planning and strategic campaign design
3. Understanding donor psychology and motivation
4. The cultivation cycle for major gifts
5. The concept of donor stewardship

As we move through the year, nonprofit leaders need to ask themselves: Are we where we hoped to be? These check-ins are about more than forecasting—they are a strategic opportunity.

These are opportunities to not just to evaluate results, but to ask deeper questions about direction, adaptability, and mission alignment. As Tod Bolsinger writes in Canoeing the Mountains, leadership today is no longer about mastering well-worn paths. It’s about stepping into the unknown, “off the map,” where the old tools don’t work, and the terrain requires new vision, vulnerability, and innovation.

Whether you’re ahead of pace or navigating unexpected challenges, this is your opportunity to drop the oars, stop paddling harder in the wrong direction and begin adapting to the real terrain ahead.

The Headwinds

Turmoil and uncertainty leave nonprofit volunteers and staff at a loss. Should we launch our campaign? Should we pause our campaign? What about our annual fund? Where do we go from here where “here” keeps shifting?