12 Questions We Would Ask the Candidates for City Manager

In Brief

• Five City Manager candidates are being interviewed Saturday, March 14th at 8:30 AM at City Hall.

• Each interview is one hour. Citizens are welcome. No Zoom/You Tube.

• The people in that room carry the community’s eyes and ears.

• Below are 12 questions for the City Manager candidates.

Time for the First Interviews

Most of us who have hired someone for an important job have done it wrong at least once. You move fast, go with your gut, and hire the person who interviewed best. In a small city, a mismatch in the City Manager’s office doesn’t affect one department, it touches everything.

When this search began, WLHS asked the City Council to gather structured community input before moving forward. The core idea: you can’t hire the right person without a shared picture of what this town actually needs.

Do we want someone who can run a utility and DPW? Reform economic development? Run a tight budget? Win grants?

These aren’t rhetorical questions. They have real answers and a recent example shows what happens when we skip them.

For 15+ years, Harbor Springs has known a major electric substation upgrade was coming. It was predictable and plannable. It was deferred repeatedly. Now we’re borrowing $8 million to cover it. A City Manager with utility experience would have seen this coming, built reserves through incremental rate increases, and moved when quotes were lower. When we hired the last City Manager, utility experience wasn’t weighted in the process. Not the candidates fault, it was ours. We didn’t know what we needed, so we didn’t ask for it.

Three things you can do right now:

• Know a strong candidate? Call the City.

• Have a view on what skills matter most? Send a note to Council.

• Can you make Saturday morning? Show up. 8:30 AM, City Hall. No Zoom means your presence matters more, not less.

These are not the final candidates; they are the candidates we have. We need to decide…..

Should we pick from the candidates we have, or hire only if we find someone that fits the job?

Why should we settle for anything less? Especially if a mistake might cost $8M.

A Field Guide of Possible Questions for the Candidates

This is a field guide for anyone attending, observing, or simply asking a council member afterward: “So how did it go?”

For each question area, we’ve described what should be asked, what a strong answer sounds like, and what gives pause. You don’t need a scorecard. You need to know the difference between an answer that proves something and one that sounds good while proving nothing.

The signal to listen for, every time:

• Did they name a real place?

• Did they describe what they specifically did?

• Did they give you a number or outcome you could verify?

• Did they acknowledge what went wrong?

Answers that check all four boxes are worth trusting. Answers that don’t — regardless of how confident or warm the candidate seems — should be noted.

The Questions

1. Community Communication

What should be asked: Provide five examples of citizen-facing communications you’ve written in prior roles. Walk us through one that didn’t land and what you changed. - They should provide the examples before the interview for use during the interview.

Strong answer sounds like: A candidate who pulls up real examples: a newsletter, a public notice, a town hall recap. Who can walk through the thinking behind them. The failure story is just as important as the wins. Someone who has never misjudged their audience hasn’t communicated enough or paid enough attention.

Give pause if: The candidate speaks in generalities (”I believe in clear communication,” “I always make myself available”). Anyone can say that. The question is whether they’ve actually produced the work. No examples = no evidence.

2. The Hardest Problem They’ve Solved

What should be asked: Not the most visible win but the hardest operational problem. What was broken? What exactly did you do? And what’s the measurable proof it worked?

Strong answer sounds like: Specific. Uncomfortable, even. A candidate who says “our water billing system was losing $200,000 a year, I found it in the third month, here’s how I fixed it” is telling you something real. The best answers name the problem clearly, own their role without overclaiming, and cite an outcome you could look up. The detail in he answer means they really led the effort.

Give pause if: The answer is about a team accomplishment described entirely in “we.” City managers lead teams, but in an interview, “we” without “here’s what I specifically did” is a flag. Also, watch for answers where the problem is vague, and the resolution is even vaguer.

3. Financial Discipline: The Courage to Say No

What should be asked: Harbor Springs capital needs consistently outpace revenue. Describe a time you told a council, a mayor, or the public “no” on something they wanted. What was the financial case, and how did the relationship survive it?

Strong answer sounds like: A story that includes an actual dollar amount, a real political cost, and a relationship that either held or broke, and why. Bonus points for a candidate who acknowledges the emotional difficulty of that moment. Financial discipline without political skill is useless in a council-manager system.

Give pause if: The candidate can’t recall a time they pushed back. Or if the “no” story conveniently had no downside. Real fiscal courage has real friction. If the story is too clean, it probably didn’t happen the way they’re describing it.

4. Infrastructure: Electric Substation and Beyond

What should be asked: Harbor Springs is completing a new electric substation while balancing the sustainability of the rate structure. Walk us through a major infrastructure project you managed. What were the cost overruns, the political pressure points, and how did you communicate progress to residents?

Strong answer sounds like: Someone who understands that infrastructure projects are as much about communication and trust as they are about engineering. Strong candidates know the numbers: budget, timeline, variance. They can explain them to a non-technical audience. They’ve had hard conversations with ratepayers and didn’t hide from them.

Give pause if: The candidate describes infrastructure management as purely technical. In a small city, every rate increase and every project delay hits residents directly. A City Manager who doesn’t lead the public communication on these projects is missing half the job.

5. Grant Funding: Bring the Money

What should be asked: Name two grants you personally secured for water, sewer, street, or utility infrastructure. Who did you engage in Lansing or Washington, and what did the funding actually build?

Strong answer sounds like: Grant names, funding agencies, dollar amounts, and completed projects. Ideally, the candidate has existing relationships with MEDC, USDA Rural Development, EGLE, or federal infrastructure programs. The best answers include the near-misses too. Grants they pursued and didn’t get, and what they learned.

Give pause if: The candidate describes grant activity vaguely or credits a grants consultant for the win. Consultants help, but the City Manager has to drive the relationships and the strategy. Vague credit-claiming here often means limited direct experience.

6. Succession Planning: Did It Survive After They Left?

What should be asked: Several city hall roles will turn over in the next 2–4 years. What succession planning did you build, not recommend, in a prior role? Name the positions and whether those transitions held after you left.

Strong answer sounds like: Real names (or real titles), real timelines, and honest reflection on what held and what didn’t. The “after you left” framing is intentional. Systems that only work while their architect is in the building aren’t systems; they’re personality cults.

Give pause if: The candidate conflates succession planning with hiring well. Those aren’t the same thing. Succession planning is structural: documented, cross-trained, institutionalized. If the answer is “I always tried to hire good people,” that’s a different skill than what was asked.

7. Regional Relationships: Still Standing

What should be asked: Describe a regional partnership you built or repaired with a township, school district, or neighboring municipality. What was the sticking point, and what’s still in place because of your work?

Strong answer sounds like: a named partnership, a named counterpart, and a clear description of the obstacle and how it was resolved. Harbor Springs’ relationship with adjacent townships and the school district matters operationally and financially. A candidate who has navigated similar terrain will have a specific story.

Give pause if: The answer is about “building relationships” without any friction. Real partnerships, especially ones that were repaired, involved a conflict. If there was no conflict in their story, either the relationship wasn’t that important or the candidate isn’t being fully candid.

8. Conflict De-escalation: When the Room Goes Sideways

What should be asked: Describe a public meeting that went badly: angry residents, a divided council, a staff crisis. You were responsible for the outcome. What did you do in the moment?

Strong answer sounds like: Calm and specific. The best city managers have stories like this and tell them without drama, because they’ve processed them. Look for someone who de-escalated without capitulating, who heard the anger without being destabilized by it, and who followed up afterward to rebuild trust.

Give pause if: The candidate has no such story, or tells one where they were entirely right and the room was entirely wrong. Every manager who’s been in the job long enough has gotten it wrong in a charged moment. The absence of that self-awareness is a real signal.

9. Balancing Development With Harbor Springs’ Character

What should be asked: This community is actively navigating the tension between preserving its historic character and meeting growth and housing demands. Name a community where you managed that same tension. What decisions were made, who opposed them, and what would you do differently?

Strong answer sounds like: Nuanced. Someone who understands that “smart growth” is not a slogan, it requires zoning discipline, community engagement, and the ability to hold a long-term vision against short-term pressure. The “what would you do differently” question is the most important part. Intellectual honesty here signals a lot.

Give pause if: The candidate picks a side cleanly, either pure preservationist or pure growth advocate. Harbor Springs’ future depends on holding both. A candidate who hasn’t wrestled with that tension hasn’t managed a community like this one.

10. Full-Time vs. Seasonal: Holding Both Communities

What should be asked: Harbor Springs serves two distinct communities: year-round residents who depend on the city for daily services, workforce housing, and schools. Seasonal residents and visitors generate much of our tax base and commercial activity. These interests don’t always align. How have you managed that structural tension elsewhere, and how do you think about it when they genuinely conflict?

Strong answer sounds like: Honest acknowledgment that both communities are essential and that the tension is real not something to be managed with better PR. Strong candidates understand that year-round residents bear the governance burden (they vote, they show up, they pay year-round) while seasonal residents and visitors provide the economic engine. Neither group works without the other. Look for someone who has run genuine engagement with both. Not just town halls, but structured input that shows up in actual decisions.

Give pause if: The candidate defaults entirely to “everyone’s a stakeholder” language without acknowledging the real asymmetries. Seasonal residents don’t vote in city elections. Full-time residents can’t afford to live here without the economic activity the seasonal community generates. A City Manager who hasn’t thought through those dynamics carefully hasn’t thought through Harbor Springs carefully.

11. Attainable Housing: What Mechanism, What Units?

What should be asked: Housing affordability is a priority for some in the community, but not others. Have you implemented a housing initiative in a resort or high-cost community? What was the specific mechanism? Zoning change, density bonus, public-private partnership? What units resulted?

Strong answer sounds like: A mechanism and an outcome. Not a philosophy. “We created a density bonus overlay in the R-2 district that incentivized three workforce projects and produced 24 units over five years” is an answer. “I believe housing is a core community need” is not.

Give pause if: The candidate has only worked on housing in conventional markets. Resort-community housing is structurally different. Land costs are higher, local opposition is more intense, and the workforce the housing serves is often seasonal itself. Generic housing experience transfers imperfectly. Push for resort-specific examples. Look for novel solutions to the workforce that avoid the construction debate.

12. Ethics and Transparency: When It Cost Them Something

What should be asked: Tell us about a time being transparent with the public or a council cost you something: politically, professionally, or personally. What did you disclose, what was the fallout, and would you do it the same way again?

Strong answer sounds like: A story with a real cost. A budget number that was uncomfortable to release. A performance issue that needed to be public. A council decision the manager disagreed with and said so on the record. The “would you do it the same way again” question forces a values statement grounded in lived experience, not aspiration. Transparency that has never been tested isn’t really a value, it’s just a preference for easy situations.

Give pause if: The candidate describes transparency purely as a communication style. In municipal government, transparency is structural. It’s about how decisions get made, documented, and shared before residents have to ask. A candidate who frames it as “I have an open door policy” has misunderstood the question.

After the Interview: What to Ask Your Council Member

If you weren’t in the room, these are the right questions to ask someone who was:

• Did any candidate give you a specific number when they talked about a past challenge?

• Did any candidate describe a time they were wrong and say what they’d do differently?

• Did the candidate seem to understand that Harbor Springs has two communities, not one?

• When asked about transparency, did they describe a structure — or just a personality?

• Did anyone give you an answer that surprised you?

The last one matters most. Surprise means something real got said.

Why This Matters

The City Manager is not an elected official. They don’t campaign and they don’t stand for reelection. Once hired, they run the day-to-day operations of this city: staff, budget, infrastructure, zoning administration, vendor contracts, and more.

That’s a lot of power for a position most residents have little visibility into.

The interview process is one of the few public-facing moments in this hire. The questions asked, and the answers given, shape Harbor Springs for years. Our job as a community isn’t to interfere with that process. It’s about paying attention, sharing what we hear, and holding the outcome accountable to the standards our Council itself published.

We’ll be watching. We hope you will too.

We Love Harbor Springs is a 501(c)(4) organization focused on government transparency, civic education, and community engagement. We take no position on specific candidates. We do take a position on informed community participation.

Attend. Listen. Share what you heard.