Transform your attitude toward outreach

“Do the thing you think you cannot do.” -Eleanor Roosevelt

I can’t tell you how often I hear someone say, “I could never ask for money.” Fear of rejection is real. It’s easy to procrastinate difficult conversations, especially when our positivity-obsessed culture doesn’t give us many tools to work with anxiety. I’ve meditated, power-posed, and attempted to will myself out of fear.

But you know what? For all those years I sought to “fix” anxiety, I was on the road as a fundraiser at Yale, doing exactly those things that scared me! I was meeting with big donors, escorting our dean through busy days of visits, negotiating large asks. And I did them well. Not because I was free from fear. Because I took time to prepare, and I simply tried. The takeaway? You don’t need to feel great to “do the thing.” You just need to try!

What if your ostrich instinct is really throwing roadblocks? I spoke with my good friend Greg Rideout, MSW (see IntroView section below) who has raised seven-figure grants as a Chief Program Officer. Here are our top three reminders to beat rejection fear:

  • Rest assured that 1,700 millionaires are made every day. With economic growth strong, there are more donors than organizations can even reach. Even rejection isn’t the end of the world. Getting to an answer—even if that answer is no—frees you to work on other relationships. And you never know–you might get to yes!
  • Most outreach can be accomplished in small settings. Most foundation outreach—and much individual donor outreach as well—can be accomplished in emails, calls, zooms, and site visits. Some folks may thrive by working a room, but building personal relationships via intimate exchanges often reaps major rewards.
  • Tackle outreach when you’re in a good mood. As David Rock notes, people are more likely to do difficult things when already in good spirits. If you work best after your morning coffee, do your outreach then. You can’t change the date of the big gala, but you can schedule some zooms after your workout. If you experience PMS, you may find it easier to socialize more often during certain weeks of the month. Notice what circumstances create good vibes for you, and allow yourself to create the conditions for success. 

IntroView: Greg Rideout, MSW

After three years of direct practice in child welfare, Greg spent the last 20 plus years in successively larger nonprofit management roles. Today, he oversees community-based programs that support youth throughout the child welfare system in the state of California and is sharing his experience via program evaluation, fundraising, and financial management consulting services (

What’s been your fundraising experience? I’ve had the great fortune to be in the development space in each position I’ve had. In my most recent role, I worked side by side with our grant writer to submit more than $100 million in proposals to both government and private philanthropy. I also partnered with our membership organization to raise millions in private philanthropy and individual giving. As a result, the organization’s overall agency budget increased by $15M in just four years.  

As an introvert, what’s hard for you in fundraising, and what comes easy? As an introvert, I am overwhelmed by large spaces. I also think I am bothering foundation folks in a larger setting. I much prefer engaging folks in a smaller setting, established for the express purpose of the ask. That is where my rapport building skills, having often worked with resistant or at least skeptical clients, kick in.   

How can new fundraisers adopt positive mindsets?  As I always tell MSW students interested in leadership, take every clinical course you can to support that vision. Calls and site visits are all about rapport-building to move a funder from Point A to Point B, just as the therapist tries to do the same with their clients. Engage the funder in relationship-building conversation and then begin to infuse them with the same hope for program impact you have for your program. 

What excites you about consulting? In both large and small organizations, there’s always a service or program that can be sustained or enhanced for at least one year on just $5,000-25,000 grants. In larger organizations, program budgets are largely supported by government contracts, but need to be infused with smaller private philanthropy grants to support creativity and innovation. In small organizations, so many incredible leaders have incredible ideas to address a local need and just need small grants to pilot new ideas or bring proven concepts to scale. 

Just for fun: what’s the wackiest thing that happened to you in a funder meeting? The Executive Director had to step away in my first site visit ever. As it neared the end, the two foundation representatives indicated that they were willing to support with a $20,000 grant, despite our $50,000 ask. They asked me how that sounded. I very honestly told them that I would prefer $50,000. While the program ended up with $20,000, we became fast friends based on that transparent, organic exchange, which benefited the program immensely in the future.  

Final words of advice? I believe my success in the fundraising space grows from genuine conversations with potential funders, the intent to build rapport and create hope in the proposed program model, the ability to assure that program dollars will be spent carefully, and a focus on program evaluation so there are numbers to demonstrate need and a methodology to measure impact.