News and analysis
August 31, 2017

What It Takes to Be a Leader: Advice From People at the Top

Credits l to r: Chronicle photo by Julia Schmalz; Independent Sector; Eve Edelheit for The Chronicle

Left to right: Patty Stonesifer; Dan Cardinali; Diana Aviv.

Recent Chronicle profiles of top charity and foundation executives offer insights into effective leadership — and a few pieces of advice.

Think Big

In 2013, Patty Stonesifer (profiled in August) left her post as CEO of the Gates Foundation, the world’s largest grant maker, to run Martha’s Table, a small charity in Washington, D.C. At Gates, she says, the challenge was to think broadly while tying the work to the real world. At Martha’s Table, she says, "we are so embedded in the real world that our challenge is to stop a minute, pull back, and think big."

Ms. Stonesifer has a gift for looking at issues from all angles, says Melinda Gates, who has known her for decades. "She’s going to get close to the problem, but she’s always going to be thinking about scale."

Keep Your Cool

Dan Cardinali (July) took the reins at Independent Sector just before Donald Trump’s election as president. Though he’s rallying the nonprofit world to fight on Capitol Hill, he’s not leading a pell-mell charge to the barricades. "He’s not reactionary in a time when it seems like everybody wants to be reactionary," says Brian Gallagher, chief executive of United Way Worldwide and a former Independent Sector board member.

Listen Well

Annemarie Reilly, an executive with Catholic Relief Services, describes working with Sean Callahan (March), the organization’s new leader, in Pakistan soon after the September 11, 2001, terrorist attacks. The U.S. government was mobilizing to attack the Taliban and hunt down Osama bin Laden, and the organization was readying for a wave of Afghan refugees to spill over the border into Pakistan. "I remember meeting with Sean several times and [seeing] just how supportive he was of his staff" as they tried to decide how to respond, Ms. Reilly says.

"He cares deeply and listens deeply to people. He wants to hear different perspectives and hear about real experiences that people are having."

Stand Firm

Though Sixto Cancel (July) is only 25 years old, he is wielding enormous influence as head of Think of Us, a nonprofit using technology to help young people as they age out of the foster system. "He’s like the Mark Zuckerberg of child welfare," says Sandra Gasca-Gonzalez, director of the Jim Casey Youth Opportunities Initiative and a Think of Us board member.

As a Casey fellow, Mr. Cancel spoke to lawmakers about the importance of extending foster care beyond age 18 and changing regulations to allow young people in that system to do things other youths take for granted, like attending sleepovers and learning how to drive. "He’s not afraid to push back, very firmly but very appropriately, when something is incorrect or he doesn’t agree," Ms. Gasca-Gonzalez says. "I’ve seen him in some high-stakes situations, and he manages really well."

Be Transparent

Rajiv Shah (April), former director of the U.S. Agency for International Development, took over as president of the Rockefeller Foundation with a few ideas about how to set to rest fears about philanthropy’s influence abroad.

"It’s important for philanthropy in particular to be transparent and clear about their operations and the results they seek to deliver. That’s just a good business practice for a sector that otherwise might not always prioritize such transparency."

Take Risks

The United Way of Metropolitan Dallas, like many legacy organizations, fights to demonstrate that it’s more than a century-old group with a tired brand. In recent years, its CEO, Jennifer Sampson (May), has been bundling for-profit ideas and philanthropy innovations into United Way’s traditional formula.

"She understands that we’re going to take a chance on some things, and we’ll fail. And then we’ll pick up and run from that failure," says the organization’s chief digital officer, Dan Aptor, recently hired from the private-equity world and stints with NBCUniversal and Disney.

Know Their Pain

Luma Mufleh (July) started Fugees Academy, a private, nonprofit school and soccer program for child refugees who have escaped violence and depravation in their home countries. She’s lived in the United States since college — in part because her family in Jordan cut her off after she told them she was a lesbian — and she applied for political asylum because there are few protections for gay people in her homeland.

"There’s a trauma that comes with not being able to be in your country," she says. "I feel that pain."

Connect With Others

Feeding America CEO Diana Aviv (February) has the ability to connect with and value every voice she hears, says Kate Maehr, head of the Greater Chicago Food Depository. She suspects the skill might be the result of Ms. Aviv’s years as a social worker.

"It doesn’t matter if you are the CEO of the food bank, somebody who runs a food pantry, somebody who operates a forklift, or somebody in line to get food," Ms. Maehr says. "When she’s talking to you, she’s listening, and she’s so thoroughly appreciative of the feedback that she’s getting."

Pick Up the Phone

Maya Winkelstein (April) leads the Open Road Alliance, which makes grants and low-interest loans to nonprofits in the middle of projects that encounter roadblocks. She got her start in the nonprofit world writing grant proposals for Lift, an antipoverty charity. She hasn’t forgotten what it was like to be a grant seeker, and she has set up her organization’s systems with nonprofits’ needs in mind. Open Road accepts applications on a rolling basis; the first step is a telephone call.

"It is amazing how much easier and faster it is to build the trust and transparency necessary to get at the heart of the issue," she says of the phone discussions.

Send an e-mail to Drew Lindsay.