Beyond the Title is a series of Q&As with alumni of Madison365’s Most Influential lists.
Ryan Crain (Wisconsin’s Most Influential Native American Leaders, 2025) is executive director of education for the Ho Chunk Nation, where he oversees a variety of early childhood, cultural and language education, and academic support programs. He too that role on in 2023 after several years as a project director and interim treasurer for the nation. He earned a degree in business administration at UW-La Crosse and a master’s degree in servant leadership at Viterbo.
What does presence before performance mean to you – and how do you stay grounded when the pressure to perform is high?
Presence is about consistently bringing positive energy that inspires confidence from the very start, even before any work begins. In those high-pressure moments, I find my anchor by reflecting on my “why.” It’s a powerful reminder of my purpose and passion, helping me stay focused and composed when the stakes are high.
What’s the best advice you’ve received from a mentor?
Only one person can be the greatest at something, so don’t aim to be the best in the world; instead, strive to be the best version of yourself.
Tell us about a time you had to lead before there was consensus – when you were the only one who saw it, believed it or were willing to act. What gave you the courage to move anyway?
I believed we needed to enhance literacy outcomes and provide our students with the chance to become passionate readers through stories that reflect their experiences. I brought on a talented individual who was more than capable of conquering this task, and with the proper support, they will undoubtedly succeed. Simply, it was the right thing to do.
What’s one question every new leader should ask during their first 100 days and why?
Can I perform this work without compromising my integrity? To determine whether you’re the right fit for this job, it’s essential to remain authentic and avoid getting involved in situations that exceed your capabilities.
Who’s in your “corner” – that voice of wisdom you trust when things get tough? How do you build and protect that circle?
My wife, Cassidee, is my biggest supporter. She believed in me from day one and has always given me that extra motivation to get the job done. My best friend, Mark, is also someone who, no matter how impossible a situation seems, always knows the right words to say to make me believe that everything will work out.
Leadership can be exhausting. What practices or boundaries help you avoid burnout and stay aligned with your purpose?
Leadership has a considerable impact on the body, mind, and spirit. This is why I make it a priority to position myself for success every day. I start with early morning workouts and take time for reflection before my family wakes up. I enjoy a good espresso and have meaningful conversations before entering any decision-making situations.
Clout fades. Calling lasts. How do you stay anchored in impact over recognition?
Too many people are counting on me, so I don’t have the luxury of worrying about being recognized for doing what is needed.
What’s a leadership value you refuse to compromise even when its inconvenient?
Extending grace to others may sometimes feel inconvenient, yet it’s essential to remember that every human being deserves to maintain their dignity. Compassion can go a long way in uplifting those around us. A leader’s words tend to carry additional weight, so I want to choose mine wisely.
What book, quote, lyric or even scripture captures how you lead or how you live?
Aye aye aye! I’m on vacation every single day because I love my occupation
When life gets heavy or leadership feels overwhelming, what’s something you turn to: music, travel or cultural connection that helps you feel like yourself again?
Activities with my boys, such as visiting the children’s museums or parks.
Who is your favorite sports team?
Go Pack Go!
What is your favorite holiday and why?
Indigenous Peoples Day. We get to celebrate our culture with the communities that care for and appreciate us.
