So You Think Philanthropy Is Easy?

The day after the Kehinde Wiley exhibition opened at the de Young Museum, my phone lit up. A Google policy lead needed to talk—now. A senior San Francisco official had pulled her aside for a take down: one of our Oakland organizers had criticized the administration in a recent speech. We'd brought that group into the program. Funded them at a significant level.

“Fix this,” was the subtext. “Make it go away.”

Welcome to the kitchen of philanthropy, where everyone sitting in your dining room has different tastes.

The check is easy. The change is hard.

Live in the Tension

To understand that phone call, you need to understand the night before.

March 2023. I'm at the de Young Museum with Darren Walker and Kehinde Wiley to open his An Archaeology of Silence exhibit—25 monumental works of fallen Black figures. In the main gallery, Googlers beam, proud to be part of the largest corporate foundation grant in the museum's history. Wine flows. Executives shake hands with museum board members.

Thomas Campbell (FAMSF CEO), Kehinde Wiley (artist), Darren Walker (Ford Foundation President), and Justin Steele (author) at the opening of An Archaeology of Silence, March 2023

In an adjacent room, Oakland organizers prepare healing circles for communities who've lost loved ones to violence. Same building, different worlds.

This is the setup we’d carefully orchestrated with Abram Jackson, bringing both constituencies to the same table. The museum got its blockbuster exhibit and free-admission weekends. The community got grief workshops and a speaker series. Google got to stand at the intersection, claiming we could hold both.

For one glittering evening, it worked. The contradictions held. The tension felt productive, even beautiful.

Then morning came, and with it, that phone call.

The Dining Room Is Full

Philanthropy is a twelve-course tasting menu with a crowded dining room.

Your principals —board members, executives, family offices—control the resources. They want familiar flavors. A glass of cabernet and a filet.

The community facing the deepest challenges sits at another table. They need something real. The soul food gumbo that actually sustains—not always pretty or plated right, but the thing that nourishes.

Add the media table. The staff table. The political players who weren't invited but somehow have opinions about your menu.

Your job? Cook something real that travels between tables—that works in the boardroom and the community center.

The Kehinde Wiley Course

Months before that March evening, Adrian Schurr and I walked into the de Young Museum having rehearsed a polite decline. Then we heard Wiley’s vision: a body of work confronting systemic violence against Black bodies, brought to millions through the Google Arts & Culture team, turning a museum exhibition into digital narrative change.

The museum asked for free‑admission weekends, grief workshops, a respite room. We knew the exhibition needed community voices, too. So we funded healing circles and a speaker series.

The policy team wanted the community grant removed. Keep it simple. Keep it safe.

Had we pulled the community grant, the museum would have had its carefully curated experience. Google would have had a brand moment. And the communities actually living with the violence Wiley's art depicted? They would have remained what they've always been in these spaces—subjects to be discussed rather than partners to be heard.

What Good Chefs Actually Do

After a decade cooking these impossible meals, here's what I found works:

1. Balance what you serve

Treat your portfolio like a tasting menu with three movements.

The opening courses: Light, accessible, beautifully plated. Nothing challenging. In corporate philanthropy, that's computer classes for kids, disaster relief, veterans programs.

The bridge courses: The dishes everyone knows, transformed. In corporate philanthropy, that's cybersecurity clinics at HBCUs, job training that quietly includes returning citizens, mental health programs in schools that happen to center immigrant families.

The brave courses: What separates brave chefs from conventional ones—serving what makes diners pause, then realize this is what they've been missing. In philanthropy, that's programs that challenge accepted narratives that underpin our social hierarchy, proposals that aim to redistribute concentrated wealth.

2. Time your service

Don’t bring out the hardest dishes first. Your first 90 days? Start with the inventory. What ingredients are actually in your pantry? Who's been burned by the last chef? Which dinner guests have the CEO's ear, and what did they last complain about? Map the real kitchen, not the one in the brochure. Then cook one small, perfect dish that everyone can taste. Build from there.

3. Learn what nobody will tell you

No one hands you Things That Will Get You Fired. Watch for what tightens your CEO’s jaw. Notice which words make legal perk up. Stay close to the exec who hired you—they’re your thermometer; if they start sweating, you’ve turned up the heat too high. Build a mental map of no‑go zones.

4. Bring dishes to the table

A meal nobody sees might as well not exist. Don’t hide your best dishes in the kitchen. Bring grantees into the room. Document with photos, stories, and impact metrics—not for the menu, but to prove the cuisine transforms lives.

Why Most Kitchens Serve Forgettable Meals

The money exists. The intent exists. The need is urgent.

What's missing? The bridgers. Chefs who cook across cultures. Who can take that unfamiliar ingredient from the community's garden and make it sing on the principal's plate.

They’re the chefs who’ve earned their stripes in both worlds: maybe they've run a nonprofit AND closed deals, organized communities AND read P&Ls, or lived the problems AND speak the language of solutions. They know when to say “ROI” and when to say “justice”—and understand these aren't always different things.

Most kitchens serve safe, forgettable meals. Principals get their steak. Community gets something. Boxes checked. Little transformed.

After Service

The Wiley exhibition opened to 35,000 visitors during free weekends. The grief workshops filled. Oakland organizers and the San Francisco museum found common ground.

We notched real wins. But not everyone saw them that way.

That tension never fully resolves. Serving company interests and serving community needs don't always align perfectly. Someone has to hold that complexity.

My team learned to cook in the tension. They saw that the best work happens precisely in that uncomfortable space between safe and right.

Your Kitchen Awaits

So you're stepping into your first giving portfolio. The dining room is full. Orders conflict. The heat is rising.

Good.

Live in the tension. If you ever stop feeling it, you’re probably not doing the work. This isn’t about writing checks. It’s about feeding people across impossible divides—making trust travel farther than suspicion—cooking meals that transform both the fed and the feeder.

Welcome, chef. Now cook something that matters.

Justin Steele is co-founder and CEO of Kindora, a Public Benefit Corporation using AI to help social-sector organizations find and win funding. He previously directed nearly $700 million in philanthropy at Google.org over a decade and serves as a trustee at The San Francisco Foundation. This piece was originally published on LinkedIn.