President of Fleming's Prime Steakhouse & Wine Bar, BLOOMIN' BRANDS INC
Well done: Life and leadership lessons from Bloomin’ Brands executive Sheilina Henry
Fleming's Prime Steakhouse and Wine Bar President Sheilina Henry wears her leadership style — authentically focused, ...
About Sheilina Henry
Sheilina Henry, president of Fleming's Prime Steakhouse & Wine Bar at Bloomin' Brands, discussed her career and leadership approach in a February 2025 podcast interview. Henry, who began her hospitality career as a server in high school, said she was drawn to Bloomin' Brands because it was "an international brand with really cool marketing" and an opportunity to try something new. She described looking for leaders who are "independent, accountable, creative, and resilient" to adapt to a constantly changing environment. Henry noted that personal setbacks have motivated her to view workplace challenges as "just another hurdle," and she said she draws inspiration from employees who rely on the company to support their families. Henry highlighted recent initiatives at Fleming's, including taking elements from the company's Tampa flagship restaurant—described as "the largest restaurant we've ever built"—and applying them across the country with localized activations. She cited examples such as introducing live music and a "mangrove room" in Sarasota, and a smaller wine bar activation in Maple Shade, New Jersey. Henry also discussed the company's employee assistance program, which provides gifts rather than loans during times of need, and noted that after setbacks such as the California wildfires, she was inspired by team members who continued to feed first responders and support their communities.
Transcript (26 segments)
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Narrator0:01
This episode is sponsored by Kirking, your trusted partner in tax, audit, and outsourced accounting services, serving Sarasota, Manatee, and the greater Tampa Bay area for over 50 years. KB helps clients achieve their personal and business goals. Visit kgp.com to learn more. Sheilina Henry has a compelling hospitality industry story, starting as a server at Chicago Pizza in high school and working her way up to running a major unit for restaurant giant Blooming Brands. It's an overused word, but I really love her authenticity. To read more about leaders like Sheilina, subscribe to the Business Observer at businessobserver.com.
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Mark Gordon0:47
Hello and welcome to the Business Observer From the Corner Office podcast. I'm Mark Gordon, managing editor of the Business Observer. Today's guest is Sheilina Henry, senior vice president at Bloom and Brands and president of Fleming's Prime Steakhouse and Wine Bar. Sheilina, thanks for being here. I'm excited to talk to you. You've done some really interesting things in hospitality, restaurant, and leadership. Before we get into some of those questions, tell us a little bit about your career in the restaurant business. I know it started maybe in high school, definitely in college. Tell us about growing up and how you came to be in the restaurant world.
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Sheilina Henry1:35
It definitely started in high school. I share this story with our new associates; yesterday I was in our new restaurant in Sarasota University Town Center and I shared it with a new associate who just started training as we prepared to open the restaurant on February 10th. I started in the restaurant industry in 1998, the same year that Fleming's Prime Steakhouse and Wine Bar was founded by Bill Allen and Paul F. So serendipitous! I started as a server on the south side of Chicago at Pizza Hut. I know I'm dating myself, but it was the Pizza Huts with the red roofs and the buffet line, lunch buffet, salad bar, the claw machine with toys, and a jukebox. That's how I started my career in the industry as a server. I've been very fortunate; Pizza Hut was part of Young Brands at that time, well renowned for developing people, training people, and having an energetic culture. That's what I fell in love with. I stayed with Young Brands for 12 years, off and on through college and post-college. It's been a joy. I intended to be a psychiatrist—I did not plan 20 years later to still be here in the industry—but I'm very grateful for that opening moment and becoming a server.
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Mark Gordon2:56
Yeah, and so you intended to be a psychiatrist. Wow. What did you learn and enjoy? For some, the restaurant business could be a grind, just a high school job. What grew your passion so that you stayed with it?
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Sheilina Henry3:15
One of the first things they taught us as a server, as an hourly employee on the front lines, is if you don't have a customer, you don't have anything. That was relevant when you're making $2.95 an hour plus tips. Making sure every guest felt special and unique, even if it was just pizza and a salad bar and breadsticks, to make them stand out so that a normal occasion for them becomes special—that motivated me. I learned hospitality in a way I had never experienced before: how to look at the situation and find what people needed in that moment and make them feel special.
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Mark Gordon4:09
Yeah, the thing you said about restaurant and waiting on tables and being a server—I was a server at Friendly's in New York growing up. There was nothing like getting the cash tips at the end of the shift. I'm probably a bit older, this was late '80s early '90s in high school. Nothing better than putting that cash in your apron, hands dirty, counting it out. As a young person, it's a great feeling. Now we're not waiting for the check to hit the bank account. Granted, it creates a different issue because you have cash in hand and you're out with your friends and it's gone in a second. You want to do it all over again. But relying on yourself... okay, so you grew into the restaurant business and got some leadership roles. What led you to the opportunity at Blooming Brands? What attracted you to that first role?
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Sheilina Henry5:01
Young Brands was predominantly QSR, quick service. I moved from Pizza Hut to Bob Evans—different setting, breakfast, mornings aren't really my thing, but we opened at 5:15 a.m. That was a very different dynamic, but it taught me about standard operating procedures. Bob Evans was very objective, very black and white: exactly how you make this or that gravy. I expanded beyond QSR into family dining, and then to full service casual dining where liquor, beer, and wine play a more significant role. (Bob Evans didn't serve alcohol.) So that was a progression. I grew up in the Midwest and have been fortunate to stay in the Midwest for most of my roles, in the Chicago area. What excited me about Outback was that it's an international brand with cool marketing when we were growing up. It was an exciting opportunity to try something new. Also, while wrapping up my MBA, I chose to study abroad in Japan. The first stop I made in Japan, the hotel I stayed in had an Outback behind it. As soon as I got off the train, I saw the Outback while I was interviewing—I thought this might be destiny. Part of my MBA program in Japan studied women in the workplace and how they navigated without child care resources and the stigma. The first woman I interviewed had worked at Outback in Hawaii, so it was further confirmation that if they offered it to me, it would probably be the right time to take it.
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Mark Gordon7:23
Yeah, that's really interesting, how these signs pop up in life. You're where you need to be for things—that's really cool. Okay, so you've gotten there and had some other positions, now overseeing Fleming's, which you mentioned has a new flagship in Tampa. Thinking about your overall role there, is it in the mid-60s for restaurants?
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Sheilina Henry7:46
64? We're at 63 and growing. Sarasota University Town Center is opening February 10th, and the reason for my trip to New Jersey is our Maplewood, New Jersey restaurant opens March 3rd. We continue to grow and are looking for opportunities across the country.
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Mark Gordon8:03
So you have that number of restaurants, which also means a lot of leaders working alongside you. What do you look for in those leaders? What characteristics stand out to you as good leaders in hospitality?
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Sheilina Henry8:24
We have an operating partner and chef partner model. Each restaurant has its own operating partner and chef partner. I know you enjoyed some of Chef Brandon's creations at the Tampa flagship. I'm excited for you to try Chef Nat's featured menu—he brings a Florida flare because he grew up here. We allow them to introduce the community to their style of cooking while representing the brand. That model requires someone who is independent, accountable, and creative at the same time. Beyond the restaurant level, throughout the organization I look for leaders who are resilient. The environment is constantly changing; we have to be agile and adapt, yet still reach the same goal. Like New Year's resolutions—most people quit by day 21; I'm looking for the talents at 10, who will stick it out, set the plan, and even when it gets tough, they don't change the goal. They might navigate differently, use different tactics, but the goal is the goal, and we'll hit it together.
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Mark Gordon9:51
Yeah, it's process driven—set the process, work it, don't alter the goal, stick with it. That mental toughness... I also have a basketball coach at my house; my husband works at IMG Academy and he's played basketball his whole life. He constantly talks to the girls about being mentally tough because you're going to encounter an opponent you haven't seen, skills you haven't seen. We're going to encounter things in business we've never dealt with. So you'll activate new skills, learn new functional skills, but mental toughness is the will to make it through. Segueing a bit, I wanted to talk about another side of leadership. It sounds like you've dealt with this with your teenagers, but also in business: overcoming setbacks. In any business, there are things that just don't go your way—a bad month, a bad week, people calling out sick. How as a leader have you developed your skill set to overcome setbacks?
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Sheilina Henry10:55
Personally, I've had so many setbacks in my life that felt insurmountable and that I wouldn't get through, and I realized I did. That motivates me. When I encounter something at work, this is just another task, just another hurdle we can get through. There are setbacks—this year we saw the wildfires in California, the devastation in the LA area. One of the ways I get through is by listening to my people. I spoke to one of our chefs in Arcadia, and he shared stories about people who lost so much, but he did it in a way that said we are still positive, we're still showing up for our community, feeding first responders, taking care of our people who may be displaced temporarily. I get inspiration from that because this is an organization that always shows up for the community and takes care of its people. When I get skeptical about whether to continue down a path, I think about the people who work for us, who rely on us to feed their families and put their kids through college. That motivates and inspires me to keep going, to just keep swimming. I have five kids, so Nemo is in my vernacular—just keep swimming. I'm not doing it for me; I'm doing it for the people who work on our front line.
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Mark Gordon12:36
That just keep swimming is a great metaphor. You think about the devastation in LA; obviously there's the celebrity side of the news, but it's the people who work in the kitchen at Fleming's in Pasadena who really need help and community strength and resilience. It sounds like your colleagues are experiencing and utilizing that.
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Sheilina Henry13:01
Absolutely. Bloom Brands has a truck program that we participate in, and associates, employees, managers can donate. When there's a time of need for our people, it's not a loan, it's a gift. We do what we can to take care of people. That's been another shining point for me after joining Outback and really understanding the culture and seeing that it resonates at all our brands within Bloom Brands.
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Mark Gordon13:30
Why have you stayed at Bloom Brands for almost 13 years? In those years, tell us about some mentors you've had and what you learned from them about being a better leader.
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Sheilina Henry13:47
One of my mentors worked in human resources, but she was a unique HR individual. Her name is Ania Smith. She would visit my restaurant and do it in a way an operator would: ask if my dough was fresh, if I answered the phone properly—very tactically tough. I started hearing rumblings that she was really tough, had a high bar and high standards. That motivated me to meet and exceed that standard. She pushed me in ways others wouldn't, she was honest and transparent. People need feedback; it's a gift. We don't need someone on the sideline saying 'her dough wasn't fresh'—you need someone to just tell you. Once you give me that piece of feedback, that gift, I'm like a dog with a bone—I'll hold on to it, address it, and never want you to see that again. When I joined Bloom Brands, Dave Dino had also joined the same year. I only knew him from his signature as CFO of Young Brands. As a general manager and area coach, he sent an annual letter and I knew his signature from earnings calls. I moved to Tampa in 2014 and got to know him personally. There's no bigger competitor—I thought I was competitive, but he competes in every way. We have a rivalry: I am a Buckeye (congratulations to the 2024 national champions) and he's a Michigan Wolverine. In business, we want to win. I've learned from him to believe in your people, set high goals, make it a high target so your team aspires for greatness. That's been a gift.
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Mark Gordon15:57
That's really important. A bit off topic, but I have to ask because of the competition part: is it better as a Buckeye to have won the national championship or to have beaten Michigan? I'm not in that rivalry, but there are people who think it would be better to beat Michigan. Where do you come down?
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Sheilina Henry16:40
There are varying opinions. I heard a different opinion yesterday. Historically, I was like 'beat Michigan, I don't care'—but at the end of the day, we got the national championship. You can lose the battle and win the war. So I'm happy with the outcome. In the restaurant business, you want Fleming's to be number one in its class, not just beat the competition one time. You want them to be number one in whatever your metrics are all the time. What excited me most is how the team closed out the year. They could have been discouraged by the Ohio State loss, given how seriously Columbus takes their football and the negativity, but instead of letting that defeat them, they came back stronger and played their best football against playoff teams. I was super proud of how they showed resilience—personally, one thing I learned from Ohio State is how to keep fighting: fall down seven times, get up eight. It's a Japanese proverb I really believe in.
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Mark Gordon17:26
Resiliency for sure. I want to go back to David, one of your mentors at Bloom Brands. In a Business Observer story you told, you had meetings with him maybe every year or every six months. Tell me about how that relationship developed and how it led to the position you have currently.
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Sheilina Henry18:02
Yes. I had been with Bloom Brands since 2012 in Chicago. I moved to Tampa in 2014 as a member of a new department that had never been created before, part of what we were standing up to drive efficiency enterprise wide. Over time, that department became part of Dave Dino's organization, the CFO. I would get little notes from him—Post-it notes asking 'Hey, what are you working on?' We gradually developed a relationship because I was activating an enabler for the system. Then in 2020, he shared his personal story about his impact during the pandemic in Minnesota, where he's from, and how he gave back personally. As we worked remotely, he started sharing more about his family and the women in his life. That connected with me because I am very pro-female as a five-time girl mom. He gave me the opportunity to lead the diversity and inclusion function at Bloom Brands in 2020, and in 2021 he asked me to take on off-premise dining as well. I reported directly to him. Over the next two years we worked together on D&I and the off-premise business, which was huge during the pandemic. We had midyear reviews, annual reviews, monthly one-on-ones. He challenged me to get better financially—as a CFO, that's obvious. I asked him where I should go to improve, and he suggested the University of Chicago. I found a program, he said 'absolutely go do it.' His openness and giving his time—the most valuable thing—had a huge impact on my career.
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Mark Gordon20:45
Yeah, sounds like that had a big impact. As we're winding down here—we're recording in late January, you mentioned February 10th for Sarasota and others coming up. Tell us about the next six months for Fleming's as a brand. What can we expect in the first half of 2025?
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Sheilina Henry21:09
The Tampa flagship that you've been to is the largest restaurant we've ever built. I'm incredibly proud of how my team came together to make it unique and different while staying true to our traditions and our founding roots. What we're doing is taking the elements you find at the flagship and applying them across the country with different activations. In Sarasota, you'll find live music unlike what we've had on the Sun Coast side, new menu items, our chefs stepping up and showing off their features. We introduced a new version of the champagne room we call the Mango Room, because we're in Sarasota—we localized our approach. When we get to Maplewood, New Jersey and the surrounding area, you'll see a smaller activation of our rooted wine bar. We're taking slices of the Tampa flagship experience and activating them across the country to learn what has scalability and what would be applicable to all 63 or 65 restaurants going forward.
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Mark Gordon22:18
Different, excellent. Well, big things happening at Fleming's. Sheilina Henry, president of Fleming's Prime Steakhouse and Wine Bar, thank you for joining us on From the Corner Office podcast.
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Sheilina Henry22:28
Thank you, Mark. It's always good to talk to you. So comfortable.
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Mark Gordon22:31
Thank you. Thank you for listening to the Business Observer From the Corner Office podcast. I'm your host, Mark Gordon. This podcast was produced by Reed Corley of the Corley Company in Sarasota. To hear more episodes, go to businessobserver.com.