How to Lead with Courage: A Conversation with Satonya Fair

According to Satonya Fair, the President and CEO of PEAK Grantmaking, leading in philanthropy takes courage and a good pair of track shoes.

Leading in a mission-oriented organization is difficult at any time. The problems you are trying to solve are complex and the potential organizations you can support are many. But modern grantmakers-ones intentionally incorporating both technology and community engagement-also must balance innovation with empathy. And that takes a new kind of courage, one where you share hurdles and pivots (hence the track shoes), you tell hard truths with kindness, and you bring other voices to your decision-making.

In our conversation with Satonya, she shared these five tips for leading with courage as the philanthropic industry continues to change.

1. Believe That You Can

Everyone at your organization has the power to lead change, no matter what seat they are in. But first, you have to see yourself as a change maker and a leader of change. Whether you manage programs or handle the database, you don't need "Executive" in your title to look for ways to do your job better.

Find time to think about what you have done well and what you have not tried yet. As Satonya said on the webinar, "Think first. Technological solutions come later." If you start with the solution, you might be addressing a symptom. If your application completion rate is low, you might jump to creating another webinar and flyer to walk people through the process, when it might be that your application is too long and requires bespoke data.

Organizations find their way to equity, change, and innovation through different routes. Just because one path worked well for a peer organization doesn't necessarily mean it's the right path for you. Gather resources from other grantmakers, but lean on what you know about your mission, community, and processes to find the right path for you.

2. Share Your Failures and Your Wins

Wins are exciting, especially for grantmakers. It means you made a difference, and people's lives are better because of the work you did. But courageous leadership is more than just wins. "If you are really courageous, you will tell us where you failed," Satonya said on the webinar.

Failures almost always come with knowledge. Don't hoard your knowledge. There will be examples of projects that were net neutral and programs that didn't turn out at all like you had hoped. Show the innovative courage of sharing your knowledge to help the next organization evolve and take the next step forward towards unraveling these complex problems. Satonya highlighted organizations that established a test kitchen for their projects, understanding that undergoing big changes means some things aren't going to work the first time.

3. Show Your Team Their Roles on the Other Side of Innovation

Technology, like generative AI, can be disruptive-in good ways and bad. Have a people-first approach and be clear about the important work people will be doing after the change.

Innovation is exciting. It's easy to lead with the big idea. But along with the big idea, you have to show people how they fit into that innovation. If people can't see their role on the other side of your big idea, whether that's generative AI adoption or a new grant management system, you will lose them. Satonya acknowledged the work of Trabian Shorters, noting that rarely are the laggards and naysayers dragging their feet because they can't learn the technology. Rather, they are frustrated because they can't see their role on the other side of it.

Before we think about what AI will do for your organization, think about what people will be doing during implementation and once it's ingrained in your processes. What are the important roles that they will be doing when they are no longer managing all the paper and check runs? This will likely involve your HR and communications teams, because job descriptions may have to change and the future competencies your organization needs may be different.

And if it does mean moving forward with fewer staff members, be honest and as clear as possible.

4. Develop Radical Partnerships

Leading with courage means recognizing that you can't solve the big, complex problems on your own. Look outside your traditional peer group to find partners who can bring new tools, ideas, and technology to your work. Yes, this will include vendors.

Model the change you want to see so everyone can move forward together. This includes community members, other funders, grantees, and organizations that care about progress towards your mission. Together, you have the knowledge and prowess to make sure people don't get lost in the technical changes, but you can't do it without each other. Each organization has a unique contribution they can make. Think about how you can weave this moment side by side instead of behind or in front of one another.

5. Put Your Track Shoes On

Leading in philanthropy requires you to constantly jump over hurdles and pivot to better support the changes in your community. Big changes can be very disruptive, but they can also be very grounding for an organization.

Change isn't a direct line, and you may not have an answer within six months or a year. It may not require a full 360-degree turn every time. It might just be a series of quarter turns to incorporate the change you need. Instead of focusing on how much money has been invested, think about whether you still are making progress toward the problem you are trying to solve.

Modern Grantmakers Must Be Ready for Change

Leading in philanthropy today means embracing adaptability and innovation. It's about recognizing that the path to progress is not a straight line, but a series of thoughtful, strategic pivots.

As grantmakers, our mission-driven work requires us to look beyond traditional boundaries, to forge radical partnerships, and to model the change we wish to see in the world. By doing so, we ensure that our efforts remain relevant and impactful, and that we are truly addressing the complex, entrenched issues that our communities face.

To hear the full webinar, check out the on-demand recording of Leading with Courage: What the Future Holds for Philanthropy.

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