Panels & Panelists - 365 Leadership Summit 2026
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Built to Last · October 19, 2026

Panels & Panelists

Everything on this page is subject to change.

Select a name to read their bio.

7:30–10:00 AMRegistration with continental breakfast
9:15 AMWelcome
2025 Summit panelists and audience 2025 Summit panelists and audience 2025 Summit panelists and audience 2025 Summit panelists and audience 2025 Summit panelists and audience 2025 Summit panelists and audience

From the 2025 Summit · Hedi LaMarr Photography

Block 1 · 10:00–11:00 AM

AI and the Long Game: Positioning to Benefit

AI is already changing how organizations hire, work, and decide, and the leaders who benefit most will be the ones who think past the next tool release. This conversation brings together leaders from technology, higher education, and the regional business community to talk honestly about what adoption actually looks like, where jobs and workflows are really changing, how to bring a team along, and how to make sure the benefits reach the communities too often left out of technology gains.

Generational Wealth in Wisconsin: Building What Outlasts You

Wealth is what turns a good income into something a family can build on for generations, yet the path to it looks very different depending on who you are and where you started. This conversation brings together leaders in real estate development, housing and community economic development, wealth management, higher education, and community-based work to talk plainly about what generational wealth actually is, the historical and current barriers that keep it out of reach, and the real steps, from ownership to equity to estate planning, that help families build something that outlasts them.

Who Gets the Keys? When Leadership Changes Hands

Every leader eventually hands something over, and most organizations are less ready for that moment than they think. This conversation brings together leaders from athletics, banking, education, and youth programs to talk honestly about succession: how to prepare the next leader, how to share power before it has to be given up, what makes a transition go well or badly, and what it means to build something that does not depend on one person.

What the Body Carries

Leadership takes a physical toll that rarely gets named alongside the strategic and emotional weight everyone talks about. This session looks at what actually sustains a body through years of high-pressure work: what gets worn down, what gets ignored until it can't be anymore, and what it takes to build health into the work itself rather than squeezing it in around the edges. It's a conversation about the physical foundation underneath everything else this summit covers, and what it would mean to actually last, not just push through.

Block 2 · 11:15 AM–12:15 PM

The Trust Deficit: Can We Still Build Anything Together?

Institutions are only as durable as the trust underneath them, and trust in government, media, business, philanthropy, and even one another is strained. This conversation brings together leaders from different sectors and perspectives to examine how trust gets lost, what actually earns it back, and how leaders work across disagreement without pretending the disagreement does not exist. In an increasingly fractured environment, the ability to build relationships across differences may be one of the most important leadership skills we have.

The Weight Leaders Carry

Leadership carries a weight that rarely makes it into the job description: the decisions that follow you home, the pressure to appear steady when you're not, the cost of holding things together for everyone else. This conversation invites leaders to speak honestly about what that weight actually feels like, what they've done with it, and what they wish someone had told them sooner.

Built Without Permission: The Entrepreneurs Creating Their Own Doors

Some of the most durable institutions begin because somebody stopped waiting to be invited. This session brings together entrepreneurs and founders who built businesses without the traditional advantages of capital, networks, pedigree, or an obvious path in. They'll talk candidly about getting the first customer, surviving the years nobody celebrates, accessing capital, making payroll, building a team, and turning an idea into an institution that can exist beyond its founder.

Block 3 · 1:30–2:30 PM

Supporting the Support System

What it actually costs, financially and personally, to keep a community organization running, and what a genuine partnership between funders and grassroots groups looks like versus a transactional one.

Brother Deficit

A space for men to do what they are rarely given room to do: care for themselves, heal, and grieve. Leadership and life pile up losses: of people, of former versions of ourselves, of paths not taken. Men are too often taught to carry all of it silently. This facilitated conversation names that deficit honestly and treats brotherhood, vulnerability, and rest as forms of strength. Less a panel than a room built for honesty.

Built to Educate: The Future of Wisconsin's Public Schools

Wisconsin's schools, colleges, and universities face growing questions about whether the way we fund education is sustainable. This conversation looks past any single budget or referendum to the long-term future of public education in Wisconsin, from K-12 through higher ed. What does equitable funding require when districts and campuses increasingly lean on referendums, tuition, and fees to cover essential services, and who bears the cost when resources fall short? Bringing together K-12 and higher education leaders, parents, and policymakers, this panel asks what Wisconsin must build today for public education to endure.

Masterclass

The Future Isn't AI, It's Leaders Who Know How to Use It

A practical look at what leaders need to know now to put AI to work without losing sight of the people it's meant to serve.

Block 4 · 2:45–3:45 PM

Authentic Leadership Across Cultures

Leading across cultures means being asked, again and again, how much of yourself to bring into the room. This conversation brings together leaders from health care, higher education, banking, community-based leadership, and Ho-Chunk storytelling and elder wisdom to talk honestly about code-switching, communication, and building trust across cultural difference, and about where the line sits between adapting to a room and losing yourself in it.

Sister, Rest

A space for women who are used to holding everyone else. The strong friend is the one people lean on, the one who always shows up, the one who never seems to need anything and quietly runs on empty. This session turns that care back toward the women themselves: rest without guilt, being held rather than only holding, healing, and permission to set the weight down. The title says the whole invitation in two words.

Built to Stay: Housing, Homeownership, and the Future of Wisconsin

A community built to last has to be a place its people can afford to stay. This conversation brings together leaders from city government, state housing finance, real estate, and community organizations to talk plainly about affordability, renting, homeownership, and development: who is being priced out, what actually expands access, and what Wisconsin must build and protect so the families who make a community can remain in it.

Masterclass

Marketing Must Do’s for Small Businesses and Nonprofits

A panel of experts from KennedyC, a woman-owned, full-service advertising agency, sharing practical insights and must-do marketing strategies for social media, web search and customer reviews. As AI reshapes the digital marketing landscape, learn what small businesses and nonprofits should prioritize first to strengthen visibility, reputation and impact.

Block 5 · Closing · 4:00–5:00 PM

Protecting the Work for the Long Haul

Leaders whose work touches equity and opportunity are operating under sharper scrutiny than they were two years ago. This is a practical clinic in agency rather than defense: how to protect programs and the people who run them, how to speak about the work with confidence without abandoning its substance, and how to keep a team steady when the ground feels unstable. Drawing on leaders from youth mentoring, utilities, community organizing and small business, and DEI strategy, this conversation is built for leaders who fully intend to still be doing this work in ten years.

Behind the Campaign: What It Takes to Run and Stay Grounded

Running for office asks for more than a platform. It asks candidates to knock on doors, make the fundraising calls nobody wants to make, put their record up for public judgment, and keep something of themselves intact through all of it. This conversation brings together leaders who have run at different levels, from city council to statewide office, to talk honestly about what a campaign actually costs, what it takes to stay grounded through it, and what changes once the race is over and the job begins.

Holy Imagination: Faith, Race, and Radical Grace

A session on the faith and spiritual grounding that has long sustained leaders through injustice and exhaustion. Holy Imagination explores how belief, race, and radical grace meet in the work of leading: the imagination to envision a more just future, the honesty to name what race costs, and the grace, extended to others and to oneself, that keeps a leader whole. Part reflection and part conversation, it makes room for the spiritual dimension of endurance that most leadership gatherings leave out.

Everything on this page is subject to change.