Chief Executives Workshop
The Chief Executives Workshop is built for municipal chief executives across Wisconsin who want real conversation with peers who understand the job.
It's a small-format program that makes room for candid discussion, strategic thinking, and peer connection among leaders who share similar responsibilities, pressures, and opportunities.
Fewer topics, deeper conversations, and the chance to dig into tough issues with people who get it.
Unlike larger conferences, this workshop is designed for smaller group discussion. You'll have time to ask the tough questions and work through complex challenges alongside trusted peers.
The Value of Stepping Away
Leadership in local government is demanding, and often isolating. The Chief Executives Workshop is a chance to step back from the day-to-day, reflect on your role, and spend time with peers who understand the weight of the work.
2026 Chief Executives Workshop
August 20–21, 2026 · Lake Lawn Resort, Delavan
Register Today!
Register Now| Room Rate | Check-In | Check-Out |
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| $165 / night | 4:00 PM | 11:00 AM |
Wednesday, August 19
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5:30 PM – 7:30 PM
Networking
Informal Networking Meet-Up
Lookout Bar · Lake Lawn Resort
Join attendees and League staff for an unstructured, no-agenda gathering for early arrivals — drop in anytime between 5:30 and 7:30 PM to meet new peers and reconnect with familiar faces before the program kicks off Thursday morning. |
Thursday, August 20
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7:00 AM – 11:00 AM
Optional Add-on
Golf at Majestic Oaks
Majestic Oaks Golf Course · Lake Lawn Resort
Start the day on the course. Majestic Oaks at Lake Lawn Resort offers a championship layout set along the lakeshore, with over 250 tree-lined acres and two miles of shoreline as your backdrop. Sign up independently — tee times can be booked online or by calling the Pro Shop directly at 262.725.9200.
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11:00 AM – 12:00 PM
Check-In
Registration
Upper Pre-Function Area
Check in, pick up your name badge and materials, and get oriented before the opening session. Staff will be on hand to answer questions and help you get settled. |
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12:00 PM – 1:00 PM
Lunch & General Session
Opening General Session: Building Trust in Public Leadership
Geneva Club
Facilitated by Jerry Deschane, Executive Director, League of Wisconsin Municipalities
Kick off the meeting with a shared lunch and an opening conversation centered on the enduring foundations of effective local leadership: building trust in institutions, maintaining civility in a fractured landscape, and the case for servant leadership at every level of municipal government. |
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1:15 PM – 2:00 PM
Session
Emerging Economic Development Tools
Geneva 2
This panel conversation explores the range of economic development mechanisms including Neighborhood Improvement Districts (NIDs), Tax Increment Districts (TIDs), Opportunity Zones (OZs), and more. Hear directly from practitioners — municipal leader and developer representative — on how these tools work in the real world, what it takes to get them off the ground, and where communities are finding success. |
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2:00 PM – 2:15 PM
Break · Upper Pre-Function Area
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2:15 PM – 3:00 PM
Session
Innovation Grants in Action: Meet Milwaukee Metro Fire
Geneva 2
Innovation Grants exist to help municipalities take smart risks and try new things — but how do you actually make one happen? This session features Wauwatosa mayor Dennis McBride, the chairman of the board of Milwaukee Metro Fire Rescue - the new Wauwatosa-West Allis fire department - sharing his city's innovation grant experience: how the cities and their staffs built the case internally, got their councils on board, and have begun the merger process. The goal is a candid, behind-the-scenes conversation that gives other communities the confidence and practical knowhow to pursue grant opportunities of their own. |
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3:00 PM – 4:15 PM
Concurrent Roundtables
Peer Roundtables
Break into a roundtable sized for your community context and dig into the challenges that are most relevant to you. These facilitated peer discussions are designed to surface practical ideas, surface shared frustrations, and generate real takeaways. As a general guide for this event, the League defines small communities as those under 10,000 in population and large communities as those with 10,000 or more. Attendees are encouraged to choose the roundtable that best fits their community’s context.
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6:00 PM – 8:00 PM
Social Event
Farewell Reception Honoring Outgoing Executive Director Jerry Deschane
Enchanted Shores (Outdoors) · Rain Location: Geneva Club
Join us for an evening reception celebrating the remarkable career and contributions of outgoing Executive Director Jerry Deschane. Set against the scenic backdrop of Enchanted Shores on the lakefront, the event features good food, a great atmosphere and plenty of time to connect with colleagues in a relaxed setting. Come ready to raise a glass, share a story, and send Jerry off right. |
Friday, August 21
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8:15 AM – 9:15 AM
Breakfast & General Session
The Wisconsin Voter Playbook: Inside Wisconsin's Political Crystal Ball
Geneva 2
As Wisconsin once again takes center stage in American politics, understanding the forces driving voters, elections, and public opinion has never been more important. Join nationally recognized pollster Charles Franklin, director of the renowned Marquette Law School Poll, for an in-depth look at Wisconsin's rapidly evolving political landscape and what it means for local governments. From the highly anticipated race for Governor and other pivotal statewide contests to the issues shaping public opinion, Franklin will unpack the latest polling data and long-term trends influencing voters across the state. Attendees will gain valuable insights into how Wisconsinites view issues affecting cities and villages—including property taxes, local government funding, and other key policy challenges. Widely regarded as one of the nation's premier state polling operations, the Marquette Law School Poll has earned a national reputation for exceptional accuracy, unmatched transparency, and rigorous methodology. Join us in this informative session as Franklin’s data-driven analysis goes beyond election forecasts to explain why voters think the way they do and how public opinion is evolving on the issues that matter most. |
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9:15 AM – 10:00 AM
Session
By the Numbers; using data to build housing
Geneva 2
Your community needs housing. But what kind, how much, and what strategies will attract builders and investment? The answers start with data. In this session, Prof. Kurt Paulsen, one of Wisconsin’s foremost housing market researchers, will provide a data-driven overview of the forces shaping housing markets and affordability across the state. Drawing on statewide and regional data, he will break down trends in housing prices, construction, income, demand, and affordability, and explain how Wisconsin’s housing challenges vary from one region to another. The session will also highlight innovative land use, zoning, financing, and development strategies that communities are using to encourage housing production and attract private-sector development. |
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10:00 AM – 10:15 AM
Break · Upper Pre-Function Area
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10:15 AM – 12:00 PM
Peer Discussion
Case Consultancies
Geneva 2
In the League's first Case Consultancy we'll leverage the collective knowledge and experience of attendees to dig into current, real issues facing municipalities. Using a facilitated format built around thoughtful questions and shared experience. The goal is to foster deep thinking, practical clarity and potential solutions you can carry back to your community. |
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12:00 PM – 1:00 PM
Lunch & Closing Session
Closing General Session: If I Knew Then What I Know Now
Geneva 2
Close out the meeting with a candid, cross-generational conversation over lunch. A panel of seasoned veterans and newer local officials reflect on what they wish they'd known earlier — about leadership, navigating politics, building relationships, and showing up for their communities. Hear how perspectives have shifted, what's stayed constant, and what the next generation of leaders brings to the work. A fitting close to two days of peer-driven learning. |
Why Attend
+ Real Conversations with People Who Get It
Connect with fellow mayors, administrators, and chief executives who understand the realities of leading a municipality. This is a space for honest dialogue, shared experiences, and practical insight.
+ Focused, Relevant Content
Sessions are intentionally curated to reflect the most pressing issues facing municipal leadership—from governance and community dynamics to strategic decision-making and organizational leadership.
+ Actionable Takeaways
Leave with ideas you can put into practice right away—whether it's a new approach to navigating conflict, strengthening your team, or advancing key priorities in your community.
+ Built-In Peer Network
The relationships formed here extend beyond the meeting itself. Participants gain a trusted network of colleagues to call on throughout the year.
What Makes This Different
The Chief Executives Meeting is intentionally designed to be:
+ Small & Interactive
Allowing for meaningful participation and discussion among peers who face similar challenges and opportunities.
+ Peer-Driven
Grounded in the real experiences of municipal leaders—not theory, but practice.
+ Strategic in Focus
Centered on leadership, governance, and long-term impact rather than day-to-day operations.
+ Confidential & Candid
Creating a space where leaders can speak openly about challenges, successes, and lessons learned.
Who Should Attend
This meeting is designed for municipal chief executives, including:
Other senior municipal leaders serving in a chief executive capacity are also welcome.
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