Four seats are up for grabs on the Islamorada dais in this year’s election, with current council members either running for other offices, terming out or choosing not to seek re-election. As a result, new faces will be seen come November. 

Each week, the Upper Keys Weekly will pose a question to each candidate in the race on a village issue. Candidates have the opportunity to respond to the question in 100 words or less. 

For this week, the question surrounds the village manager position, which Finance Director Maria Bassett is currently serving on an acting basis. In August, Seth Lawless announced his resignation verbally to the village due to health reasons. Lawless had been on medical leave since July 6, and since then, Bassett has taken control of day-to-day village operations. 

The current village council decided not to choose the next village manager, with a new council set to convene after the Nov. 3 election. 

QUESTION: If elected, what qualities and qualifications will you be looking for in determining who the next Islamorada Village Manager will be? (Answers are as submitted.)



In looking for the village manager, we need someone who manages a town similar to Islamorada, a shoreline community with hurricanes and flood elevation criteria. They must have experience with a comprehensive land-use plan with LDRs. The applicant must be a current city manager with several years of experience. Critical as well, they must communicate with the public from the property owners to company owners to retirees. The applicant will also have to be able to hire and fire staff members as the situation requires. We are looking for a well-rounded city manager to manage our village.


The first step in hiring the best manager possible has already taken place – the old council decided to leave it to the new council we elect in November. Now all that the community needs to do is elect Frank Lavin, Cheryl Meads, Joseph “Buddy” Pinder and Dave Webb.





The ideal candidate must have a knowledge of the principles and practices of local government administration, including organizational forms and structures, budgets, contracts and operating methods and procedures; excellent communication, managerial, verbal and financial skills; be an enthusiastic team builder; possess the ability to confer with local, county and government officials and other key individuals to resolve problems. Good understanding and familiarity with ordinances, zoning and planning issues.


For me the manager should have several years of experience in a smaller coastal, tourist oriented community with hurricane preparation and recovery as part of that experience. A good manager is a good communicator and must be able to earn the trust and respect of the village council, the staff, and especially the members of our community. A successful manager executes the direction of the council into action and positive results by using knowledge, insight, people skills, and resources. I would carefully evaluate an applicant’s references, track record of accomplishments and past performance in other communities.



I would like a committee of citizens to lead the search for a new village manager. Qualifications would include experience in a coastal community where tourism is the main driver of the economy. The candidates should be diverse, have a record of performance excellence, and a desire to be here for the long term.




Seth left such big shoes to fill. He demonstrated to our community what a great manager looks like. He had ideal qualifications and so many of the qualities that make an ideal manager. Applicants can be found with the experience we need. Finding one with the qualities we want will be most important: action and solution oriented; can identify the complex problems we face and evaluate options and make the best recommendations. We need a manager who is a leader… who inspires people to work harder and get our community moving forward with a direction that makes Islamorada the best it can be.



The Islamorada Village Manager should be a customer service-oriented individual ready to build a solid community relationship serving the residents of Islamorada. The position presents unique challenges — preparing for hurricanes, maintaining our small-town character, and handling the needs of the visitors to our islands. The manager should have excellent leadership and managerial skills to follow direction from the council while leading the village and staff into 2021 and beyond. Finally, Islamorada will thrive under the direction of an individual with a demonstrated managerial history and experience with a coastal community set in a fragile environment.


The village manager implements and oversees the decisions of the council. Our unique community requires several uncommon skills. Administrative expertise, team building acumen, integrity and character are fundamental but just minimal for consideration. I would be looking for experience in preparation for and recovery from major disasters, an understanding of the history of Islamorada, a recognition that both the council and staff work for all citizens of our community and the ability to make the council aware of any unintended consequences of the decisions that are before them. I believe both internal and external candidates should be considered.

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