Twelve Things to Know About the Chair of the Planned Giving Round Table

When Baltimore native Craig Lestner first got involved with The Associated, he wasn’t thinking about leadership titles or long-term strategy. He was saying yes to conversations, relationships and opportunities to learn.

Here are 12 things to know about the Chair of the Planned Giving Round Table, Craig Lestner.

1. His leadership journey started at Towson University Hillel.

Craig spent more than a decade involved with Towson University Hillel, including three years as board chair. The work shaped how he thinks about engagement and identity.

“Our biggest focus was always engagement,” he explains. “How do you help students feel comfortable showing up and building relationships that last beyond college? How do we help these young people transition to Jewish life beyond what their parents or what their family instilled in them to create their own identity.”

2. His involvement with The Associated started through networking.

Craig’s path to The Associated was not strategic. It began with conversations and encouragement from people already involved, including his wife, Allyson, who worked at the time for The Associated.

“One thing led to another,” he says. “I said yes to an opportunity, and it opened the door to more meaningful involvement.”

3. Planned giving aligns naturally with his professional life.

A financial planner for more than 20 years, Craig was drawn to the Planned Giving Round Table (PGRT) because the conversations were relevant, thoughtful and practical.

“It fit with the work I do,” he says. “The speakers were strong, the topics mattered and the people in the room were engaged.”

4. He believes philanthropy should start with genuine interest.

Craig often advises younger professionals to begin with curiosity rather than obligation.

“You have to find something you care about,” he says. “You don’t have to be passionate yet, but you do have to care. You start small, you show up and you learn.”

5. Engaging the next generation is his top priority as chair.

As chair of PGRT, Craig is focused on how philanthropy looks different for younger donors, who often support multiple causes and want to see clear impact.

6. The February PGRT event reflects that focus.

The February 24 program — Millennial Philanthropy: The Next Generation of Philanthropy — will explore how professionals can better engage millennials in philanthropy. Craig hopes attendees leave with ideas they can actually use.

“They don’t necessarily want to give to just one place,” he says. “Part of our role is helping them understand how giving works and why it matters without sounding salesy. And explain why giving back is important and how it can benefit them personally, professionally, but also the community that they’re trying to support.”

“How do we engage the next generation in a way that feels comfortable and authentic?” he asks. “That’s the question we’re trying to answer.”

7. For him, planned giving is about continuity and responsibility.

Craig believes planned giving helps ensure that Jewish life and institutions remain strong in the future, especially during uncertain times.

“There aren’t a lot of us,” he says. “Having places where we can come together, learn from one another and plan for the future is more important than ever.”

And now, a few fast facts to get to know Craig beyond the boardroom…

8. What mentor does he seek advice from professionally?

“I used to work with my father-in-law who retired a couple years ago, so he’s always a good source of guidance on this end. I have other peers who I’ve been doing this with for 26 years with who I reach out to. I try to look to lots of different places.”

9. How does he unplug after a long day at work?

“I go home and ride my Peloton.”

10. Early bird or night owl?

“Early bird. I probably would be in bed at nine if I could.”

11. Spontaneous or carefully planned?

“Don’t tell my wife, but I’m usually more carefully planned than spontaneous.”

12. Two things on his bucket list?

“Used to be running a marathon but my back doctor made me take that off the list. I would say going to Switzerland – trying to plan that for my 50^th.”