I’ve been thinking lately about what makes generosity truly generous.

Since maybe forever, I’ve understood generosity as an expression of giving. A way to spread abundance and a signal to others that they mattered. That their happiness was important. While these things may still be true, I’m realizing there’s something more nuanced at play.

Lately I’m thinking the distinction between giving and generosity isn’t about the size of the gesture or even the intention behind it. 

It’s about resonance. 

It’s about showing up for others in ways that land deeply for them, in moments that truly matter to them and within the context of their lived experience. It’s about knowing another person’s love language and dedicating ourselves to learning to speak it. 

A Reminder from the Past 

Years ago, I received a hand-written thank you note from a woman who had worked for me nearly a decade earlier. Someone I hadn’t seen or spoken with in ages. Out of the blue, she wrote to thank me for all I had taught her about strategy during our time working together way back when. It was truly a gift to receive it. 

But here’s what made it remarkable: She shared that while she had valued the learning at the time, she had only come to fully appreciate it now, years later, as she was bringing those insights to bear in an entirely different job and industry. She was writing not just to acknowledge the past, but to let me know how that early foundation was serving her in ways neither of us could have anticipated.

The generosity of that moment wasn’t lost on me. Taking the time to reach back across years and industries to connect dots I would never have connected myself. She recognized something that mattered—not just to her, but to me—and acted on it.

Reconsidering the Grand Gesture

The most generous leaders I know aren’t necessarily the ones out there performing grand gestures. They’re the ones who notice the people around them. They pay attention to what energizes them and matters to them. They get curious about what challenges them and what they might be wrestling with beneath the surface. 

They understand that sometimes the most generous thing we can offer others is our full attention and presence. Other times, it’s stepping back and creating space for others to shine. Or quietly advocating for them behind closed doors. Sometimes it’s a willingness to have the hard conversation everyone else is avoiding.

The Multiplier Effect

When we show up generously in ways that resonate, we don’t just impact the recipient. We model something powerful about what it means to truly see and value another person. We tap into our capacity to create meaningful change in the lives of others.

The woman who wrote to me? Her note wasn’t just generous to me. It was generous to everyone whose life she’ll touch as she continues to lead with that same spirit of recognition and appreciation. The generosity she offered in writing that note reflects the generosity she likely brings to her daily leadership.

This is how generous leadership multiplies. 

Not through grand gestures that make a profound but momentary statement, but through authentic moments of connection that remind people how they’ve touched us and why they matter. 

Through small acts that echo long after the moment has passed, in ways and places we could never have planned.