Fleming’s Prime Steakhouse and Wine Bar President Sheilina Henry wears her leadership style — authentically focused, mission-driven and people-centric — on her sleeve. And with a sense of humility. (The first entry on her LinkedIn profile says Girl Mom.) On this episode Sheilina talks about her restaurant career start (old-school Pizza Hut in Chicago) and how she found her way and climbed the career ladder at Tampa-based restaurant giant Bloomin’ Brands. She also talks about her mentors, what motivates her to lead people and overcoming mistakes and setbacks.

3 Takeaways:

1. (03:10) Without a customer, you have nothing, treat them well
2. (09:35) I am looking for leaders who make it through adversity
3. (17:30) Keep fighting

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(01:15) Introducing Sheilina Henry, president Fleming’s Prime Steakhouse and Wine Bar

(03:10) What grew your passion in the restaurant industry?

(05:10) What led you to Bloomin Brands?

(07:45) What do you look for in leaders?

(10:35) Overcoming setbacks

(13:45) Mentors

(17:45) Developing relationships within Bloomin Brands

(20:50) Fleming’s in 2025

This week, we speak with Megan Rose, president and CEO of Better Together. Better Together, based in Fort Myers, has served more than 10,000 children across Florida, keeping families intact and out of the state system. And it’s helped nearly 40,000 people, many in ‘second-chance’ life situations, find employment across 24 states. On the episode, Better Together CEO Megan Rose talks about the importance of failing fast and failing forward, while not losing your innovative edge in nonprofit work. Megan also talks about her childhood, and how others in her community helped her family overcome some difficult circumstances.

3 Takeaways:

(14:40) There is no fear of failure, but you must learn from it

(15:05) Focus on 3 things at a time

(20:00) Self-discipline is a must-have

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(01:00) Introducing Megan Rose and rapid fire questions

(02:35) Tell us about Better Together

(05:10) How Better Together helps people find employment

(08:40) What led you to this career path?

(13:40) Leadership advice

(17:20) What do you look for in leaders?

(21:25) Examples of failure you learned from

(27:15) What can we look forward to in 2025?

Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more.

Visit businessobserverfl.com for more.

Freddy Williams was named CEO of the Boys & Girls Clubs of Lake and Sumter County in 2012, when he was 28-years-old. Four years later he was CEO of the youth-focused nonprofit in Pinellas County. And now he’s at the helm of a Boys & Girls Club operation that stretches through Pinellas, Pasco and Hillsborough counties. On this episode Freddie chats with Business Observer Managing Editor Mark Gordon about his first summer at a Boys & Girls Club — it wasn’t necessarily voluntary; his five pillars of intentional leadership; and why Denzel Washington is the one person, dead or alive, he’d love to have dinner with.

3 Takeaways:

(14:45) A strong moral compass and a spirit of continuous improvement are key leadership characteristics

(16:50) A board is powerful if you can tap into their expertise

(17:30) Never ask someone to do something you aren’t willing to do yourself

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(00:25) Introducing Freddy Williams, CEO of Boy & Girls Clubs of The Suncoast and Tampa Bay

(01:30) Rapid Fire Questions

(05:05) How did you discover the Boys & Girls Clubs?

(07:40) Kids hold on to your every word

(08:40) Freddy’s leadership style

(10:05) What does Boys & Girls Clubs do?

(11:20) Strategic Merger

(14:45) What do you look for in leaders?

(16:10) Becoming a CEO at 27

(17:20) Leadership advice

(19:25) How do you manage leading as a CEO and being involved in the programs

(21:25) What is coming up in 2025?

Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more.

Visit businessobserverfl.com for more.