Longboat town manager shares insights, challenges ahead of second season

The mid-year review. It's a workplace occurrence that some dread, but Town Manager Howard Tipton passed his with flying colors. 

At the Oct. 2 Town Commission meeting, commissioners were asked to review a form and give their feedback on Tipton’s performance thus far. Tipton is nearly nine months into his first contract year as Longboat Key’s town manager.  

After the commissioners’ public reviews, which were positive across the board, Commissioner-at-Large BJ Bishop suggested the idea of a raise.

Without much deliberation aside from ensuring it was already in the budget, the mayor and commission approved a 3% raise for Tipton starting with his second contract year on Jan. 30, 2024. 

The Observer sat down with Tipton after the review to discuss his thoughts about the job so far and what the near future may hold. 

Nine months into the job, how are you feeling about things so far?

I think living on the island has really helped because I’m here on the weekends, I’m here after hours, and I think that allows me to get to know some of the issues a little bit better and maybe a little bit faster. … I think the transition has been relatively smooth from my perspective. I’ve gotten to know the team and the issues well, and what they need.

I’ve also come from a large organization to a smaller organization, and I think that helps. If you were doing the opposite, it’s harder.

Photo by Lori Sax

What has been the most challenging obstacle you’ve faced and how did you see it through?

Aside from pickleball…I think it was the salary issues originally. We couldn’t hire people and we were losing people, and just being able to get our arms around that pretty quickly. And then being able to implement a solution mid-year. I give the commission all the credit in the world for stepping up and supporting that recommendation. That was really critical for us. 

As the season approaches, what’s the thing you’re most looking forward to?

Cooler weather.

I think it’s fun when the town is full, you know other than the traffic. It’s just nice to see everybody out and more people are biking and walking. So there’s just so much more social interaction and energy on the island..The island just kind of comes to life.

I’m cautiously optimistic about the traffic. (Last year) we still had the roundabouts in downtown Sarasota that were under construction. And so I’m cautiously optimistic that it will be slightly better. 

What’s something specific that you have learned about Longboat that you hadn’t really thought about before?

Being as close as I am to the citizens.

In larger organizations, you have layers of people between you and everybody. So when you do interact, it's certainly not every day. Coming here, you’re it, so people just walk in. That’s been kind of fun actually. 

I guess I expected it but I didn’t know what it would be like. Residents here are engaged, they’re thoughtful, and they give very reasoned ideas and opinions which is helpful. 

So far, what has been the thing that you are the most proud of?

The thing I’m the most proud about is the team was able to transition from (Tom Harmer), who was a highly respected manager and leader. (The team) was able to turn around and start working with me immediately. We really didn’t miss a beat. 

I give all the credit to them for their flexibility, because we all have different styles and approaches and ways that we communicate, and I’m still a work in progress on my communications. But I never felt like we were missing something. It really is a strong team for a small team. Pound for pound, we’re as strong as any organization I’ve ever worked for. 

Their ability to shift and pivot and work with me without blinking has just been amazing. I’m very grateful for that.