High-end steakhouse president leads by taking others with her

In a 25-year restaurant career, Sheilina Henry has spent considerable time helping others rise to new positions and promotions — a source of pride. 

“When you meet people in the role they're in, they may or may not be in their sweet spot,” Henry says. “And helping someone realize this is what I love. This is what gives me energy. This is what makes me want to jump out of bed in the morning.”

Henry has risen in her career as well, to now holding a key leadership spot in one of the region’s largest companies: Henry is president of Fleming’s Prime Steakhouse & Wine Bar, a unit of Tampa-based Bloomin’ Brands. Henry was named to lead the brand in summer 2023 after a decade of other Bloomin’ leadership posts, starting in 2012 as a joint venture partner overseeing Outback Steakhouse locations in her native Chicago and Wisconsin. Her role right before Fleming’s was Bloomin’ senior vice president of diversity, equity and inclusion and off-premise dining, which she held from 2021-2023. (Brands under publicly-traded Bloomin’ include Outback, Bonefish Grill, Carrabba’s Italian Grill and Aussie Grill. The company posted $4.67 billion in revenue in 2023.) 

In both her own career and in guiding and mentoring others to their just-right position, a consistent theme for Henry can be distilled down to two words: just ask. 

That’s how she got her first management position in restaurants, in 2003. She was in her early 20s and working at a Chicago Pizza Hut — the old-school ones with the sloped roofs and salad bars — while going to college. She planned to be a psychiatrist. But she also loved the hustle, and money-in-the-pocket, of the restaurant industry, where she worked during summer and winter breaks. 

“There came a point in my life where I didn't want to go to school anymore,” Henry says. “And I went back to my manager and asked him, can I become a manager rather than just waiting tables? I needed something that could sustain me on my own. I went back to my parents house, but I knew I didn't want to live in my parents house. I needed a real job. And I'll never forget, he said yes. And I said, ‘but I don't want to be a shift supervisor. I know I really need a salary. And he made me a salaried manager.”

That gig — it paid $26,000 a year — launched her restaurant leadership career. She never became a psychiatrist, though she did go back to college: she earned a degree in psychology from The Ohio State University and an MBA from DePaul University’s Kellstadt Graduate School of Business. 

Career path

Some two decades after the Pizza Hut ‘just-ask’ Henry found herself in another similar situation. It was in 2023, and she was on maternity leave with what’s now her fifth child — all daughters. Prior to her leave, she had been having meetings twice a year with Bloomin’ CEO David Deno, focusing on her career trajectory. Her roles in DEI, off-premises dining and training and operations exposed her to the executive team, and Henry knew she “wanted a pathway to be a brand president.” She followed a checklist from Deno, taking an MBA finance class, leading company initiatives and doing other work. 

Yet on maternity leave Henry initially balked at going for the Fleming’s president job when it opened up.

Courtesy image

“I looked at my husband and asked, ‘what should I do?’ He’s like ‘it's what you've been talking about for years. Why would you just let this opportunity pass on?’”

“Because I'm on leave,” Henry responded. 

“But I picked up the phone and called David and said ‘I just don't want to be out of sight, out of mind. To make sure you know I'm still interested in the role of president. I love the Fleming's brand, I’m a big fan of the experience. (I told David) this was a unique opportunity, and I wasn't going to miss out.”

Henry got the position and a year later she’s guiding Flemings into a new chapter. That starts with a new flagship location being built on Boy Scout Boulevard in Tampa, across from International Plaza and near Tampa International Airport. The new Fleming’s — next to an old Fleming’s, which will be turned into a Bonefish — is some 13,000 square feet and seats up to 350 people inside. New features include a glass wine vault that holds 2,500 bottles of chilled wine and an open floor plan that goes light and airy where some older Fleming’s focused on darker and a more mahogany beam vibe. 

Good eats

The flagship Tampa location is expected to open in September 2024. During a recent media day tour Henry chatted with the Business Observer about her career and lessons learned in leadership. Edited excerpts: 

Lots of winning

Henry was motivated early on by a competitive spirit, which guided her as a leader. At Pizza Hut parent Yum! Brands Henry rose quickly, from overseeing one store to becoming regional manager. “I loved running the restaurant…I loved the business aspect of it, to see my profit and loss statement and know that I was doing good but also to see the 16 year olds I could hire into this business and give them a means to pay for prom, and some of them went on to become managers in the business.”

Point made

A key to Henry’s management style, beyond the ask, is her ability to be adaptable — something, she says, she learned on the job. That includes going from restaurant operations to the corporate office. At the former, Henry says there's a no-nonsense approach to it, where, “if you're a guest in my restaurant, and you tell me you need water, there's no debate, we just go get the water and bring it to you.” 

Photo by Mark Wemple

Yet in a corporate office setting, while results, of course, matter, the way there is not nearly as direct, Henry learned. “I have a tendency to just get straight to the point,” she says. “And people still say today I'm a straight shooter, pretty transparent. I have no issues telling my story. But I'm also not afraid of conflict.” 

That conflict, at first, was internal. Henry says she had to balance her past experience and instincts with “meeting people where they are and understanding the environment that we're operating in to still get to that outcome.” 

Do big things

Mind set

More adaptability comes from a mentor, longtime Bloomin’ executive Gregg Scarlett, who was president of Outback and Bonefish Grill during his nearly 30 years with the company. “I learned a growth mindset from him,” says Henry, “that everyone is capable of change, because when I met him in 2012 he was very tactical and very much about black and white and the numbers, get this result, get this outcome. And the more he grew as a leader, the more balanced he became in his approach, and I do believe everyone has that capability.” (Scarlett, in talking about Henry in 2020 when she was named to Restaurant Business Power magazine’s top 20 list of the industry’s rising stars, calls Henry a “beacon of light.”)

Not a straight line

A common link in Henry and Deno’s career is they both worked at Yum! Brands, which founder David Novak built into a fast-food conglomerate with brands like Pizza Hut, Taco Bell and KFC. Novak also wrote the book “Taking People With You: The Only Way to Achieve Big Things.” The book, says Henry, is “about achieving results through people. Not running over people to get the results, but really bringing people along for the journey (and) telling them the story, explaining the why.”

Deno, says Henry, would sometimes remind her of the book’s lessons when they had one-on-ones. Henry read the book twice, but also realized one day she wasn’t following some of the principles, thinking about the transition from field operations to corporate office. “Clearly,” she thought, “I need a reinforcement.” Henry listened to the book again — she’s an audiobook fan — and even used it as a teaching moment for one of her young daughters.

“I don't think any journey is ever linear,” she says. “I think there's going to be times where you touch on something and you have to reinforce it. You have to refresh yourself. It's no different than playing sports. I was talking to my five-year-old last night and she's a dancer but she wanted to know, ‘how do people get so good at singing? And I said, ‘well, they practice, they have a trainer. And they practice the same way you practice dance.’” 

“And leadership is the same way. You can learn something mentally and be able to quote it back verbatim. But it's the practice that takes time and reinforcement. And you'll stub your toe, and say ‘I knew better,’ right? And then we try again next time.”