AuthentiCityFM, Episode 42: Leap or Be Left Behind with Jerry Driessen and Brent Messer

Bayside, Wisconsin is a village of about 4,400 people on the shore of Lake Michigan. Andy Pederson has managed it for more than twenty years, and later this month he becomes president of ICMA. We sat down with him before the annual conference in Long Beach to talk about what a small place teaches about leading at a much larger scale. Much of the conversation lives where jurisdictional lines start to blur. Andy walks through the partnerships Bayside shares with its North Shore neighbors, from a consolidated dispatch center to a shared fire department and an IT team that now serves several communities. Each one had to improve the service, hold or lower the cost, and prove it could last. Trust sits underneath all of it, built slowly and kept with care. We also talk about staying. Long tenure is rare in this profession, and Andy describes what fit feels like when the community, the staff, and the board keep asking more of you. He also shares why he keeps raising his hand to serve, and how board service changed the way he sees his own elected officials. For anyone heading to a first national conference, there is a generous stretch of practical advice. Andy's counsel to his own assistant manager is to keep it small, say hi, and take the one open seat at the lunch table. We add a few favorite openers of our own. Andy offers an early look at the theme he will carry into his year as president, built around the word we. Then he turns the questions on us, asking what each of us believes now that we would have argued with a decade ago. The answers move through the weight of the chair, the cost of saying yes to everything, and the boundaries that protect public servants. There is plenty of Midwestern fun along the way, including Brewers legends, a Friday fish fry confession, and a long-promised trip to a cheese castle. 00:00 Welcome and a stop in Bayside 02:16 From law school to the village hall 05:24 Why a small community 11:31 Twenty-two years in one place 13:37 Why give back to the profession 17:30 Hallway conversations and an open invitation 19:39 Icebreakers for first-timers 28:15 What the ICMA president does 31:19 Reconnecting the membership 33:58 Showing up in every state 38:36 Wisconsin and Illinois, together 47:04 Up north, fish fry, and the cheese castle 53:06 Andy asks the hosts 1:00:54 Making local government cool 1:03:27 Looking two and three years ahead 1:08:35 Sit up front 1:10:16 Andy's final word Music licensed through Soundstripe. Code: JCDGU5WQKUPPX7XY

Ron Holifield has spent more than forty years in local government. He started in the city manager's office, then moved into the chair and went on to build the companies and networks that serve the profession, including SGR and Civic Marketplace. He no longer does city management, but he still calls himself a city manager. In this conversation, we talk about what that identity asks of people, and why the profession needs to remember where it came from. Ron traces his path from an internship in Lubbock to small-town Texas to Garland, where he wore a bulletproof vest for a year and was eventually fired. That experience taught him how isolating a forced exit can be, and how rarely the profession shows up for its own in those moments. It also gave him the belief he has carried ever since. It's not about me, it's not about now. From there the conversation widens. We talk about servant leadership as a working philosophy, the leadership pipeline the profession hollowed out after 2008, and why the best way to keep emerging leaders may be to prepare them to leave. Ron makes the case that the defining skill of a manager is the ability to engage, inspire, and lead people. We also explore why innovation needs room to fail, how councils elected by district can learn to serve as one body, and what it would take to equip elected officials for greatness. At the center of it all is a question the profession has been slow to answer. Who are today's Cookinghams? City management began as a reform movement, built by people who believed government could be truer, cleaner, and finer. Ron believes we have stopped telling those stories. He argues that the sewer plant operator keeping a city alive, and the council that protected public harbor access centuries ago, deserve the same telling. This is a conversation about camaraderie, courage, and the long view of public service. 00:00 Welcome Ron Holifield 01:09 From Lubbock to Sundown 03:03 Leaving the Chair, Keeping the Lens 09:01 Servant Leadership Out Loud 17:20 The Road to SGR 20:40 The Pipeline We Lost 32:30 Who Are Today's Cookinghams? 41:07 Connecting Beyond Communicating 47:31 Innovation and the Freedom to Fail 53:46 Equipping Elected Officials for Greatness 1:03:08 Ron Turns the Questions Around 1:17:53 The Last Word

We are back. The return came wrapped in a run of eighties movie references, because of course it did, and underneath the fun was something real. After a few weeks of stepping away to enjoy the end of summer, we sat back down to do the thing leaders rarely allow themselves to do, which is stop long enough to notice what the pause was teaching us. This episode is part homecoming and part preview, a conversation about rituals, return, and the quiet renewal that comes from slowing down. We start with what the last five weeks actually held. A shadow from the past that resurfaced without warning. A week among 1,500 strangers at a conference far outside local government, where being a complete beginner turned out to be its own kind of gift. Two and a half days of full immersion with the newest members of the ICMA board, and the surprising speed with which shared purpose turns strangers into friends. Different experiences, one throughline about belonging and the value of seeing familiar work through unfamiliar eyes. From there we circle back to the ideas that stayed with us from our end of summer episodes. History rhymes. What feels like unprecedented instability has arrived before in different clothes, and the profession has always found its footing. Judgment, we keep returning to, is a form of civic infrastructure worth protecting. Then we turn toward what is coming. The ICMA conference in Long Beach and how to make a room of thousands feel human again. The questions we cannot keep deferring about how communities will pay for what they have promised. And a line one of us wrote while working through it all, that nostalgia is not a business plan. This is a return episode and a road map for the season ahead, made for anyone who has felt the pull to slow down and wondered what waits on the other side of the pause.

Coherence was the note the summer kept building toward, the thread that holds when everything else is pulling apart. This is the conversation about what that thread is actually for. We close the season with Bob O'Neill, former executive director of ICMA and one of the most respected thinkers this profession has produced, for an hour that keeps returning to a single idea, that the power that matters most in local government is the power to convene. Bob makes the case that local government is the last fully functioning level of government we have, which means the work of rebuilding civic life is going to bubble up from communities rather than arrive from anywhere else. That puts the manager in an unfamiliar seat. Writing a check used to solve most problems, and it rarely does anymore. What the moment asks for instead is someone who can bring a room together, hold a hard conversation inside a set of shared values, and keep it grounded when the forces nobody controls start to pull. Along the way we get into the traits that carry a leader through disruptive change, from anchoring an organization around mission and values to becoming what Bob calls the chief meaning officer, the person who keeps reminding everyone why the work matters at all. We talk about working across the lines on the map, the boundaries drawn long ago for taxation that no longer match how communities actually live. We talk about reverse mentorship and the handoff already underway, because the next generation is watching how we carry the work far more closely than they are reading any job description. There is a night at the White House and a conga line, because Bob tells a story as well as anyone in the business. And underneath all of it runs a steady, hard-won optimism, the belief that this profession has met moments like this before and found its way back toward the middle. Chapters 00:00 Closing the summer and what coherence is for 01:40 Welcoming Bob O'Neill 07:35 The last fully functioning level of government 09:19 When facts get treated as partisan 18:03 We have been through disruptive change before 20:38 The chief meaning officer 27:22 The social network that keeps you steady 35:50 The biggest power is the power to convene 41:15 The four traits that matter most 45:30 Putting meaning back into the work 47:59 Three reasons for optimism 53:10 Reverse mentorship and blending the generations 56:24 A night at the White House 1:03:14 ICMA, and why the network is the whole point 1:10:18 What better looks like for the profession 1:21:31 Welcoming people in and generational work 1:29:44 Closing thoughts GUEST Bob O’Neill LinkedIn: https://www.linkedin.com/in/bob-o-neill-5206a010/ HOSTS Phil Kiraly, Village Manager, Glencoe, Illinois LinkedIn: https://www.linkedin.com/in/philkiraly/ Mike Sable, City Manager, Maplewood, Minnesota LinkedIn: https://www.linkedin.com/in/michael-sable-b7994a14/ Corri Spiegel, President & CEO, Arete Strategic Website: www.aretestrategic.com LinkedIn: https://www.linkedin.com/in/corrispiegel/ Music licensed through Soundstripe. Code: S9H34SYCGYLJ18VL Follow AuthentiCity FM for more conversations with the people doing the work of local government: https://www.linkedin.com/company/authenticityfm

Some conversations wander. This one converges. After a summer spent working through truth and trust and the discipline of holding more than one version of what's real, we follow those threads to where they lead, which is coherence, and the clarity and curiosity that keep it alive. Coherence is the thread that holds when the forces you do not control try to pull everything apart. Clarity is what it brings, the center of gravity that lets you keep moving on ground that will not sit still. Curiosity is what keeps both sharp, because the moment we decide we have all the answers is the moment we stop asking the questions. None of this stays abstract for long. It lives in the hard conversation a supervisor keeps postponing, in respect offered freely and the harder truth that respect is not infinite, in what the 140-character world has quietly trained out of us. And it lives in the small acts of presence that cut through the noise. Ten days without devices. A cooler of ice cream carried through a public works garage after the storm. The conversations that only arrive when you finally slow down and sit with someone.