The Monthly Leap - May 2026

Hi there!

May marks a time of transition and brings a different kind of energy than the first four months of the year. Two of our team members are wrapping up their semesters. We’re planning for summer gardens and vacations. The weather is getting warmer and the days are longer, but we know that we’ll still get some grey, rainy, spring days before we’re officially in summer. It’s easy to get caught up in the frantic rhythm many of us experience at this time of year. But May can also be an opportunity to slow down, even briefly, and consider how we want to show up in the work ahead. 

So for this month keep reading to find out:  

• What's on Rikki’s mind: How I’m thinking about questions these days 

• Tip of the month: Ask for a specific example! 

• What's coming up 

I hope this post is a little spot of joy in your month! 

Rikki 

What's on Rikki’s mind?

As many of you know, alongside my role at LEAP, I’m also working toward my doctorate through Viterbo University. And right now? What’s on my mind is very simple: I made it through finals week. 🎉 

This semester stretched me in so many ways. Running a business, taking both a statistics and a philosophy course (which use very different parts of my brain!), and building out my dissertation proposal all at the same time is no joke.  

But what surprised me most in this process wasn’t actually the workload. It was the questions. Specifically, how hard it was to write good ones. 

I’ll be honest, this caught me off guard. Asking thoughtful, intentional questions is core to my work. It’s what I’ve done throughout my career to understand donor motivations. It’s what I do now while coaching clients every day. It’s what shapes campaign testing conversations and strengthens relationships. I literally teach people how to ask good questions! 

And yet… sitting down to write research interview questions felt entirely different. I realized the shift wasn’t about skill. It was about intention. 

In donor conversations, we’re often working toward something specific. There’s a direction, a purpose, something we’re hoping to uncover or move forward. Of course, I have central research questions I’m exploring in my dissertation. But in qualitative research, the questions I’ll ask interview participants require something else entirely. 

Openness. Flexibility. A willingness to let the conversation lead. 

That tension has been sitting with me. And it’s bringing new ideas into our work. 

While I still firmly believe in preparing questions ahead of time (it’s what allows you to truly listen instead of planning your next response), I’m wondering if sometimes we hold those questions a little too tightly… Especially in early donor conversations. 

What might shift if we lead with a bit more curiosity and a little less directing?

I’m still exploring that in my research, but one thing is already clear. When we loosen our grip on getting the “right” answer, we create space for something more honest, more human, and ultimately more useful. And that’s a mindset I’m excited to keep bringing into our work. 

Tip of the month

When you’re preparing for a donor conversation, it’s easy to default to broad questions: 

Why do you care about this work? 

What inspires your giving?

Those aren’t bad questions at all! But if you really want to understand someone, try inviting them into a specific moment instead. 

Ask: 

“Can you tell me about a time when you felt especially connected to this mission?”

or 

“What’s an experience that really shaped your passion for this?”

Something shifts when people move from general ideas to lived experiences. Stories create clarity both for you and the person telling them. They reveal emotion. They give you insight you simply can’t get from surface-level answers. 

As you’re preparing your questions before a meeting, look for opportunities to turn one or two of them into an invitation for a story. You might be surprised by what you learn.  

What's coming up?

• We’re excited to relaunch the Executive Director Group Coaching program through UWGB this summer! The cohort won’t officially kick off until June, but we’re hosting an informational session on Thursday, May 7 for people who are interested in learning more. Please help us spread the word! 

• Rikki will be holding two board training sessions in partnership with the Marshfield Area United Way and Mid-State Technical College in mid-May. We love gathering board members and nonprofit leaders together to help them understand their role, build connections among organizations, and give everyone new strategies for how to recruit and retain board members. 

• We have had so much fun talking about how to secure donor meetings and what to say during those meetings over the last few months! During our office hours on May 28, we’ll keep the discussion going. Join us to think out loud about how to ask good questions in donor meetings, how to lead with curiosity, and how to feel confident and grounded in conversations with stakeholders. 

We’re also still in the process of hiring our next team member! If you know someone in Central Wisconsin who is looking for a part-time, flexible position and has a passion for mission-driven work, please send them our way. Learn more about the role we’re hiring for on our website.