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3 Essential Questions to Assess Your Digital Transformation

By April 19, 2021

When I talk with nonprofit leaders about digital transformation, I get responses that range from excitement and optimism to skepticism and overwhelm. Even the leaders who are eager to reimagine the way their organizations work aren’t sure how to determine how far they’ve progressed on their path to transformation — and how much more lies ahead.

It can sound big and murky, but digital transformation simply means integrating technology into your organization in a way that enhances your ability to deliver on your mission.

Research shows that nonprofits that have worked through a digital transformation process are fast, agile, and resilient. They can work quickly to collect and learn from data. Their systems and processes help them pivot when an unexpected turn of events (a global pandemic or a tidal wave of social activism, for example) turns their operations upside-down. They’re flexible enough to pursue multiple paths to impact, which is critical given how quickly the world changes today.

While some organizations have sprinted ahead in their transformation journeys, others are in the early stages. If you’re curious about where your organization stands in its digital transformation, ask yourself three questions:

1. Do we make decisions based on data and evidence?

Do you have the information you need to guide your key strategic decisions? When there is a challenge to solve that involves multiple teams, is it easy to find and share data? While some nonprofits are highly evolved in this category, many organizations are struggling with the first step of identifying which metrics to collect. Where are you on the spectrum?

buildOn mobilizes young people to transform their communities and build schools in developing countries. The organization focused early in its transformation on unifying data about programming and volunteers. Data director Eric Dayton says their transformation work set them up to pivot strategically in 2020 when COVID-19 challenged every aspect of their model. Dayton also says their data-driven culture empowers staff. He tells his teammates, “I’m not going to tell you what to do, but here are the tools, here’s the data. I’d love to see what you can create.”

Screenshot of organizational dashboard

Bringing data together in one place helps organizations make strategic decisions and empower staff members.

2. Do we deliver personalized, meaningful engagement for both supporters and recipients of our programs and services?

Do we give each donor, volunteer, and partner a tailored experience based on their needs and preferences? Have we designed our programs and services around the specific needs of our participants? Every audience expects personalization and will be more loyal and supportive to organizations that deliver it.

For Big Brothers Big Sisters of America (BBBSA), personalization for each young person (a “Little”) and their adult mentor (a “Big”) is critical to its mission. The pandemic forced BBBSA to quickly transform deep, in-person connections into virtual relationships. The resulting digital community not only moved mentoring online in a vibrant, flexible way, but also showed BBBSA that it could use technology to learn more about its constituents, make better matches, and more effectively measure the progress of the connections between Littles and Bigs.

Woman and young adult sitting on steps laughing

BBBSA’s digital transformation enabled the organization to use technology to learn more about its constituents, make better matches, and more effectively measure the progress of the connections between Littles and Bigs.

3. Are we confident about what drives our fundraising results?

Can you accurately forecast income from your campaigns? Do you know which levers to pull to influence fundraising outcomes?

Surprising, out-of-this-world fundraising results are wonderful (think ALS Ice Bucket Challenge), but they’re as rare as a winning lottery ticket. For most organizations, the goal is to deeply understand how slight tweaks to timing, channels, content, and calls to action impact fundraising so that you can maximize each solicitation.

NAACP is on a journey from manual processes and siloed systems to data-powered marketing and fundraising. In 2020, NAACP moved 200,000 volunteers entirely online for phone banking and canvassing — and created a central place to capture all of the data generated from that outreach so that they can learn from it and optimize their fundraising efforts in the future.

Assessing Your Transformation

If you answered “no” or “not really” to these three questions, perhaps your organization is just beginning its transformation. The critical first step is to make sure your leaders are aligned about what you’re trying to achieve and why. Make sure you have a vision — a North Star for what digital transformation will make possible for your mission. Prioritize the elements of your vision and commit to making that first priority happen on a clear, agreed upon timeline.

If you answered “yes” to the questions above, congratulations on making the cultural and operational shifts that help you to be a digital-first, data-driven organization. Digital transformation is an ongoing process for all of us, so keep your momentum going and identify your next focus area as an organization.

Register now to join us at Nonprofit Summit on April 21 where you’ll hear from organizations like UNICEF, Teach for America, and the CDC Foundation about their digital transformation progress and how their work continues today.

About the Author

Greg Perlstein, Digital Transformation Lead for
Greg Perlstein is a digital transformation lead for, working with customers to chart their paths to greater social impact. Prior to joining three years ago, Greg was a senior director at, the world’s largest nonprofit for young people and social change. Greg holds an MBA from the University of Michigan and has over a decade of experience in the nonprofit sector.