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The Gatekeepers

Meet the people standing between you and Jerry Jones, T. Boone Pickens, Gary Kelly, and other Dallas business leaders.
By Karen Nielsen |

Behind every successful top executive is someone responsible for making the big boss look good—helping them show up on time, preparing them for whatever gets thrown their way. Exactly how—and why—they do these things can vary. As the five stories in this feature show, the behind-the-scenes person is sometimes a vice president, an administrative assistant, or a public relations executive. In many cases, they have something in common with their bosses: generational experiences, perhaps, or similar professional backgrounds.

Other common denominators among these “right hands” are a fierce loyalty to the chief, and a passion for their industry—whether it’s professional football, advertising, energy, real estate, or transportation. And then there’s the ability, and the temperament, to serve as a jack-of-all-trades. 

Not every company is blessed with a longtime top executive like the ones included here. But, length of tenure aside, it’s clear that good communication, a healthy dose of respect, and a sense of purpose are important for sustaining these critical relationships. In the end, there’s no handbook or official training for being a gatekeeper. You just have to be flexible, talented, and hardworking. And the payoff is huge: There’s never—ever—a dull day.

Dallas Cowboys

Rich Dalrymple & Jerry Jones

Vice President Public Relations/Communications & Owner/President/GM

[inline_image id=”1″ align=”” crop=”full”]When Rich Dalrymple first landed his PR job with the Dallas Cowboys 25 years ago, his goal was to survive the first five years and qualify for a pension. Jerry Jones, who had just bought the NFL team, was not only intimidating, but he was also tightening his belt during those lean days. “Jerry was perceived as somebody who wasn’t afraid to fire someone—he let Tom Landry go,” Dalrymple recalls. “I was more scared of him than anything else.”

No matter that Dalrymple had come highly recommended by mutual friend and Cowboys head coach Jimmy Johnson, who hailed from the University of Miami, where Dalrymple had been working in public relations.

With his 400th regular-season game now under his belt, Dalrymple says that his “percentage of worry … has gone down tremendously. Even if I know he’s going to call and maybe start chewing on me a little bit, I know how to handle it,” he says.

It’s not so much that Jones is mellowing out. It’s more that Dalrymple—who has effectively become Jones’ right-hand man—has taken the role of sports PR to a new level. Says Jones: “They didn’t hand us out a bluebook on how to run the Cowboys or how to run a professional football team. I always thought the Cowboys had a unique place from other NFL teams. We wanted to incorporate many things that Tex Schramm did. We basically not only continued and tried to improve on the PR of the team, but we evolved it into marketing.”

The owner is talking about the kind of marketing that translates to dollars: branding. It was a move that set the Cowboys apart from any other NFL team. “There were a lot of things we did that were innovative, and Rich really digested all of that as we discovered it or started doing it,” Jones says. “He’s a unique individual relative to anything close to the definition of PR, and he’s a close confidant in our team management decisions.”

Dalrymple may hail from Pittsburgh, but he knows how to speak with an Arkansas accent. Only, sometimes, Jones goes off the script and there’s no place for the PR guy to hide. “When you have a colorful and dynamic personality like his and marry that to one of the most iconic teams in sports, it makes it interesting for me, but it also makes it exciting and challenging,” Dalrymple says.

Working for a team that generates year-round interest is a 24/7 job for Dalrymple, but Jones reciprocates by “always being receptive and on the clock as well,” Dalrymple says. He describes Jones as a good listener with a memory like an elephant, enthusiastic, and generous to Dalrymple’s family of six.

Jones, 72, wakes up at 5 a.m. to read the papers and work out on the elliptical machine—a full two hours before Dalrymple rises. Jones will often call him at 7:30 a.m. to discuss the news of the day.

“Sometimes I hear him on the radio when I’m in the shower or in the car,” Dalrymple says, referring to Jones’ twice-weekly radio show on 105.3 The Fan. “And I’m thinking, ‘What is going to come out of this interview that will change the rest of my afternoon or the rest of this week?’ ” 

When he’s not on the road with Jones—that means traveling in a private Gulfstream jet—Dalrymple checks in regularly in the locker room to remind players of upcoming interviews, attends four-times-a-week press conferences with head coach Jason Garrett during football season, escorts media to watch the first half hour of practices, oversees stadium publicity, and works closely with members of the high-profile Jones family.

The perks of working with America’s most loved and hated NFL team are enormous: guest spots on TV shows like “Entourage,” for example, or private helicopter tours around Manhattan. “Jerry’s always been able to inject levity and fun into the thing, and that makes you want to bust your butt for the guy even more,” Dalrymple says. “There’s really no other owner like him in sports in our country.”

The Richards Group

Jean Howe & Stan Richards

Coordinator for Stan Richards & Principal

[inline_image id=”2″ align=”” crop=”full”]Jean Howe remembers meeting Stan Richards 36 years ago to discuss a job opening. After he learned of her advertising and commercial photography agency experience, he told her, “This will be a piece of cake.” At 81, Howe laughs at that first encounter with her boss, who’s 82. “I will never forget that,” she says. “That was an incorrect statement. It was crazy.”

The help-wanted ad was seeking someone with 15 years of advertising experience, and Howe knew that “Disco Dollies,” as she puts it, need not apply. Her new boss was a serious businessman who was transitioning his creative resources company into an advertising agency. During her tenure, the firm has grown from 39 employees to 700, and created iconic campaigns for the likes of Chick-fil-A, Home Depot, Pier 1, Dodge, and Motel 6. 

The Richards Group isn’t big on titles, but Howe essentially serves as Richards’ executive assistant, managing his calendar and mail, scheduling meetings, working a bit with clients, and booking flights for the company plane. “We use it a lot,” she says of the Challenger 300. “Stan never wants to stay overnight at these meetings, so he can have a meeting in New York or L.A. in the morning and come back and be in his own bed by night.”

Howe is good at taking care of business, but it goes beyond that, Richards says. “For me it’s almost like having a family member sitting outside my office,” he says. “Jean’s a very, very nice person and she’s good at what she does and very effective in doing the things we pay her to do. But more than that, she’s a person that most people in the agency look up to and come to for advice and counsel.”

Howe describes her boss as someone who “has a lot of energy, is very athletic,” and is big into wellness. In the past, when employees hit their five-year anniversary, they were given a free membership to the Cooper Clinic—but they had to keep up their points or risk losing it. Howe was the one who called the slack employees to remind them to use their points. 

In January, the company moved into a new headquarters near the intersection of North Central Expressway and Lemmon Avenue, which has its own workout facility on the 18th floor. (Richards recently asked Motel 6 spokesman Tom Bodett to be the “voice of the elevator” that announces each floor in the company’s new building. On the ground floor Bodett says, “We’ll leave the light on for you.”)

Richards has a sense of humor, but he also runs a tight ship. Employees must clock in at 8:30 a.m., which he encourages so they can go home on time. And many things are decided by tenure, which saves a lot of arguing and problems. 

“That was another good rule,” Howe says. “Everyone knew what day they started at The Richards Group, and it’s still like that. It’s part of our culture.” A strong culture is good for retention, and 20 years of service is rewarded with a $10,000 travel award. 

Richards recognizes these milestones, holds company meetings, and introduces clients from the stairwell that winds through the middle of the office. “People stay at this agency for so long, which is rare,” says Howe, who enjoyed a Mediterranean cruise for her 20th anniversary. “He’s spending a lot of money.”

It has been decades since Howe and her husband moved from Chicago to Dallas as empty nesters ready to start a new adventure. She never expected a long career at one agency. 

“Before this job, five years was max for any job I had,” she says. “We grew so fast, and it was just fun all the way. It’s been quite a ride.” 

BP Capital

Jay Rosser, Sally Geymuller & T. Boone Pickens

Vice President of Public Affairs and Chief of Staff, Assistant to T.Boone Pickens & Founder and Chairman

[inline_image id=”3″ align=”” crop=”full”]Hanging in the BP Capital lobby, there’s an “I Want You for Pickens’ Army” poster with T. Boone Pickens dressed as Uncle Sam. It was an 81st birthday gift from his “foot soldiers,” Jay Rosser and Sally Geymüller, a telling description of the oil tycoon and philanthropist’s right and left hands.

Geymüller is the keeper of the oversized relic Rolodex, which she frequently refers to in order to satisfy her 86-year-old boss’ “insatiable thirst for knowledge” and interest in keeping up with former high school and college friends, employees, and colleagues.

“Invariably, he will ask me when so-and-so died. I’ll flip open the Rolodex and it’s in there,” says Geymüller. She became Pickens’ assistant 28 years ago, back when he was running Mesa Petroleum in Amarillo, but has worked with his companies a total of 36 years.

She answers Pickens’ phone and manages his schedule, letters (he answers them all), personal business, and foundation matters. Rosser is in charge of public affairs, political “stuff,” and the media. Pickens relishes his media roles, which keeps Rosser hopping.

“He’s very good because he understands how important the media is to communicate his message, and he has an uncanny ability to articulate well, with a clear, folksy, and commanding grasp of the numbers,” Rosser says. “The guy has a passion for energy.”

The legendary entrepreneur’s favorite media activity is appearing on the set of CNBC’s morning “Squawk Box” show, where he comments on energy issues and often promotes his Pickens Plan. It advocates ending America’s dependence on OPEC oil by conserving energy, moving to renewables, and increasing the use of natural gas.

Rosser, a former deputy press secretary for Texas Gov. Bill Clements who has worked with Pickens for 16 years, says his boss also has a penchant for social media. One of Pickens’ tweets, reacting to a comment by the rapper Drake about how hard it is to make the first million, was among the most popular tweets of 2012. “I thought that was really cool,” Rosser says of Pickens’ tweet, which read: “The first billion is a helluva lot harder.” 

Pickens should know. After appearing on the Forbes billionaire list every year since 2005, his net worth dipped last year to a still-respectable $950 million. He has already donated more than $1 billion to charity, and the hit to his Dallas-based, energy-focused investment firm doesn’t rile him. Rosser remembers a particularly bad day when, after the company had lost tens of millions of dollars, Pickens said to his investment team: “Fellas, your faces are so long it would take two barbers to shave them.”

Pickens’ enthusiasm hasn’t waned, but his travel has dropped considerably from the 600 hours he and Rosser logged on the private Gulfstream jet in 2008 when they launched the Pickens Plan. The octogenarian is notoriously early for everything. He starts his day with a 6:30 a.m. workout and hits the office by 8. “It’s never a dull moment and never a boring day—ever,” Geymüller says, rattling off a full schedule of activities and interviews on a recent day.

Pickens says Rosser and Geymüller keep him organized, active, and productive. “I do my best to grind them down,” he says. “We’ve been in a lot of battles together and we have fun in all of them. We’re all in a race. It will be interesting to see who checks out of this partnership first. If they’re planning on it being me, they may well end up scratching a loser’s ass.”

The Ebby Halliday Cos.

Betty Misko & Mary Frances Burleson

Executive Vice President and Director of Sales Offices & President and CEO

[inline_image id=”4″ align=”” crop=”full”]There aren’t enough hours in the day for Mary Frances Burleson to personally manage the flurry of activity at the residential real estate empire of the Ebby Halliday Cos. With 2014 sales volume exceeding $6.6 billion, the president and CEO relies on Betty Misko, her friend, confidant, and vice president and director of sales offices. “Between the both of us we have 100 years in this business,” says Misko (at left in photo). “There’s a lot of experience we can draw on.”

The two think alike, often dress alike, are high-touch managers, and as pre-baby boomers share not only a generation but by-the-book values. “I trust her implicitly,” says Burleson, who has been in her position since 1989. “That’s important.”

While Burleson is out front managing the business, attending board meetings, and actively serving in the community, Misko is in the background overseeing the company’s 1,700 agents and 32 sales offices. 

The two met in the early 1980s, when both were working as branch managers in competing offices. Misko jokes that Burleson was “constantly recruiting her,” sending her cards over the holidays and keeping in touch. She reciprocated, and remembers feeling impressed when she read in the newspaper that Burleson had earned a degree from Southern Methodist University, wondering where she found the time.

Finally, in 2001, Burleson hired Misko for the newly created position of director of sales offices, which covered about 1,200 agents. A few years later, Misko became broker of record when Ebby Halliday’s younger brother, Paul Hanson, retired. The broker of record is responsible for all actions, including complaints and mediation, of the salespeople or agents.

“One of the critical things that’s helpful to Mary Frances is when we have a retiring manager or sometimes have to dismiss people, I’m very involved in the process,” Misko says. “I interview people first and pre-select for her. If the office is vacant, then I serve as the interim manager so she doesn’t have to worry.”

Misko takes the time to learn each office’s unique culture, which gives her better insights to hire the proper replacement, ensuring staff continuity, and assuring the staff knows that corporate “is there to care about them, so they can continue doing business uninterrupted,” Burleson says. Says Misko: “That’s very unusual. I don’t know of another company that has that kind of procedure.”

Over the years, Misko has managed nearly all of the three dozen offices, which allows her to be on a first-name basis with many of the agents. Both women value a personalized approach and understand the importance of being accessible and visible. 

“No two days in a week are ever alike,” Burleson says. “When you’re dealing with agents, staff, the marketplace, and clients, you have to be very flexible, resilient, and hardworking.”

Burleson, who began working with founder Ebby Halliday when the business had just three offices and 35 agents, says she learned from the best. Misko feels the same way about Burleson.

“Ebby has put out the footprint for all us, and set the pace, and we take that to heart,” Burleson says of Halliday, who turned 104 in March.


Southwest Airlines

Nan Barry & Gary Kelly

Managing Director of The Executive Office & Chairman, President and CEO

[inline_image id=”5″ align=”” crop=”full”]Southwest Airlines is a fun-loving company that always celebrates Halloween in a big way. But to this day, Nan Barry still jokes with CEO Gary Kelly about his “Dorothy” costume from 2009. 

As his chief of staff, Barry works closely with the small team that helps brainstorm Kelly’s annual costume. Instead of taking one of their suggestions that year, Kelly had his own idea. “Could I be Dorothy?” he asked Barry.

“The year he was Dorothy was not the direction we were headed, but it was the 50th anniversary of The Wizard of Oz,” she says. “On Halloween, it’s an exhausting, but really fun day. He spends all day with the employees and he really loves it. He’s all in for the fun stuff.”

“Fun days” aren’t infrequent at Southwest Airlines. Kelly and Barry are veterans of the super-successful Dallas-based airline, dating back 29 and 27 years, respectively. Before that they both worked as certified public accountants at Arthur Young & Co., but didn’t know each other at the time. Southwest was a big Arthur Young client and, in the late 1980s, many were attracted to the low-cost carrier’s culture, Barry recalls.

Before taking her current position, Barry held several leadership positions in Southwest’s finance department, where Kelly also worked as controller and CFO before taking over as chief executive 10 years ago. Barry oversees administration of the board of directors and Kelly’s office, manages the company’s executive committees, and leads the internal “customer care” team. That group assists employees who are injured, experience a death in the family, or when an employee dies. 

“I feel like I play connect the dots,” she says. “I spend a lot of time looking at the schedule to maximize Gary’s time. There are a lot of audiences he’s trying to satisfy—media, investors, employees—and I try to make sure that stays balanced. I’m thinking through when he travels. Making the best use [of his time] means saying no to things, or trying to play with a chess board and move another piece.”

Kelly is a what-you-see-is-what-you-get kind of guy, Barry says. “He cares deeply about our employees and is extremely passionate about our company,” she says, calling her boss a visionary for leading the company through a transformational period in the airline’s history.

Their bond may be sealed by the fact that they’re both meticulous, detail-oriented, and good with numbers. Says Kelly: “Nan is a trusted colleague, a passionate Southwest leader, and a personal friend. I view her role like a point guard on a basketball team. She keeps things moving smoothly and efficiently, distributing the ball where it needs to be. The airline industry is the ultimate team sport, and I count my blessings every day that Nan is on our team.”  

Through the years, Barry’s husband has jokingly reminded her that Kelly is the CEO. “It’s a very personal relationship and comfortable,” she says. “I can talk to [Kelly] about anything, and I have the utmost respect for him. Over the last 10 years it’s been very great to have a seat at the table.”