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IN THE FIELD

Objectives and Reflectives

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Kathleen Owings was 23 years old, fresh into her career and speaking on a phone with her husband — but there was so much she could not say.

She could not say that as a lieutenant in the U.S. Army Corps of Engineers, she was about to lead a group of her men to help Marines.

She could not guess how this disparate group would come together to do the tough jobs that needed to get done quickly. 

And she could not tell her husband that even though women were not yet allowed in combat, she was about to lead this group into Iraq, ahead of fighting forces on the first day of the 2003 Iraq war.

But she could see her way past all that to the most essential thing to say: “Hey, I love you. I’ll see you on the other side and if I don’t, it’s been great.”

No ornamentation. No hedging. No falsity. Just the things that need to be said.

That skill made Owings a leader all her life. It also made her into a financial advisor who tells clients what they need to hear, rather than what they want to hear.

If the potentially last communication with her husband seemed brusque, it was an appropriate tone for a fellow Army officer. Michael Owings was waiting to lead his own men into Iraq.

Devouring Goals

They met as cadets at West Point, the academy that she determined at age 13 she would someday attend. She pursued that goal with her usual tenacity. Straight from Point A to Point B but she will gladly wend through Points C and D to get there.

Owings decided to go to West Point even though women had been allowed to attend the academy only around the time she was born.
She became a congressional page, but the congressman she worked for did not nominate her for the academy. Competition was fierce for the limited slots available at West Point and no other congressional or Senate member from her state would nominate her.

Finally, she would be nominated by Vice President Al Gore, the same person who would later pin lieutenant bars to her uniform.

Her uniform would later also be decorated with a Bronze Star for leading that small group of men using heavy machinery through a war zone to rejoin their battalion at a loosely defined objective without losing anybody.

So, she must be tough stuff, right? Sure, but not with the bluster you might imagine from a military officer. Owings might be no-nonsense, but her method is to listen and ask questions.

Bob Ross saw Owings’ skill in action many times when he was the president of National Association of Insurance and Financial Advisors-Colorado. Ross nominated Owings for the Four Under Forty Award from NAIFA’s Advisor Today magazine.

Owings, who turned 40 this year, is a principal and financial advisor at Westbilt Financial Group, Colorado Springs.

She was 38 when she was nominated for the under-40 award. Owings also won the Women in Financial Services Circle of Excellence Award in 2016.

Ross, who has since retired from his insurance practice, said Owings had a way of asking just the right questions so that other people could reexamine their own reasoning.

For example, tension ratcheted up during a NAIFA state association meeting when a local president demanded that the state organization do something for the local. Owings asked a few questions about the issue.

“She asked, ‘If you were in our shoes, what resources would you use?’” Ross said. “He knew what we had available. Then she asked, ‘If we did that for you, wouldn’t we have to do that for all the associations?’ He knew we didn’t have the resources to do that.”

The local president realized his own organization was in the best position to handle the issue.

Bigger Than She Appears

Owings honed that leadership skill as an officer. If two soldiers were fighting, she would want to know what triggered the conflict. Was it a lack of resources? Was it tension from being in a war zone? Then she could solve the deeper problem.

Although she was a woman overseeing men doing heavy construction in a combat zone, she never felt disrespected. For one thing, she learned to rely on advice from fellow officers and her own noncommissioned officers to solve problems.

For another, there is that sense of presence.

“I’m like 5’4”,” Owings said. “I always saw myself bigger than probably how I actually appear.”

Her Myers-Briggs personality type, ENTJ, is known as The Commander. That indicates she’s an extrovert who values order and logic.

She brings all that to the table with her clients, many of whom are headstrong entrepreneurs. She starts by understanding, which also helps establish her authority.

“It’s asking questions and knowing what their challenges are, showing interest in their situation,” Owings said, adding that she withholds conclusions. “We might have a solution for them. But I really want to understand what’s going on for them. I don’t want to bring my own biases like, ‘Oh, I’ve worked with entrepreneurs before. I know exactly what your problems are.’”

Once she does that, she usually finds cooperation. But some hard-driving entrepreneurs are not great about taking direction.

“Some like to joke about it, especially men — ‘Oh, I don’t need life insurance,’” she said. “I’m like, ‘Oh really, so your wife who’s been staying at home raising the kids is going to get up one day, make a job and replace a six-figure income? Let’s talk to her and see what she thinks about that.’ I let them hear what they’ve said.”

Or she will pose another scenario with questions, such as, would the client like to move in with his parents? Most likely, the response would be an emphatic

“No.” Then she asks why the client thought his spouse would want to do that. And how do clients react to that?

“Well, usually I get them to buy life insurance,” Owings said.

Service Runs In The Family

She credits her military experience for shaping her approach. But even before she attended West Point, there was something pushing her to lead and serve.

“I feel like I’ve had it my whole life,” she said. “It really does come up from a place of service whether it be my soldiers, other officers or my clients. I want them to walk away from the experience having felt it was meaningful and that they were heard.”

She comes from a long line of people who serve. Her father, Robert Quinlan, was a captain in the Army, stationed in Korea during the Vietnam era. Her grandmother served as an Army captain and nurse in Europe during World War II. Her grandfather was an Army veteran serving in Europe.

Her father and mother are also life and health insurance agents in upstate New York, where Owings is from. But her parents did not guide Owings into insurance and financial services.

“Never in a million years did I think I would end up in this business,” Owings said. “I remember as a kid hearing about commission checks in the mail and life insurance. I remember hearing these conversations that I now have as well.”

When she left the Army, she tried a civilian version of her military job. She was a civil engineer overseeing construction workers, but after a year she believed it was clearly not her calling.

Then she tried being an executive recruiter. Although that was not ringing any bells for her either, it did lead to her eventual profession.

A colleague of hers put the pieces together. She was a friend, fellow West Point grad and a sharp executive recruiter.

“She said, ‘Hey, you like math and you like problems and you like pushing yourself,’” Owings said. “She pieced all these parts together for me and said, ‘Why don’t you call the managing director at New England Financial here in Colorado Springs?’” 

Owings did and things just clicked. She eventually ended up partnering with him at Westbilt Financial.

She liked the constant learning and not feeling static. Owings is now licensed in life and health insurance and maintains Series 6, 7, 63 and 65 securities registrations.

The profession calls on almost every aspect of her personality type. She is high up the extrovert scale and loves to intuit her way through a problem to establish order and develop a plan.

“I like the problem-solving part of it,” she said. “The parts that people are turned off by. Many times, people don’t do something because it seems like such a monumental task to figure out a plan, their investment, their insurance and all these parts. I’m like, the messier the better. I like that aspect where you piece it all together and make it work. And I like the fact that it can change as well.”

She enjoys turning the dials, asking the what-ifs and thinking several steps ahead. Owings employs what she and her husband call “flexecuting,” following a plan but improvising along the way. Much like someone would do to build infrastructure in a combat zone.

Learning To Turn Around

Owings was in a reflective mood recently after returning from her husband’s 20-year reunion at West Point. He was in the class of 1998; she graduated in 2000.

Both of those classes were in peacetime with not a hint of war on the horizon — certainly not the endless war in Afghanistan and against terrorism. Owings and her classmates were joining as a career. For them, wars were brief conflicts like Desert Storm in 1990.

Part of their visit was to the graveyard where they saw the final resting places of far more of their classmates than they might have imagined when they graduated from the academy. She had come to terms with her mortality before — over the phone with her husband, the day before she charged into Iraq.

“So at a very young age, I had to come to grips with my own mortality in a weird way knowing that I could have easily died there,” she said.

But this latest revelation was different. Her life had always been about pushing ahead to her next goal. Even when she runs, she’s training for the next race and climbing the next Colorado mountain.

“I always felt that I wanted to do more, be more,” Owings said. “And it wasn’t even to be the best. I wasn’t the top of my class at West Point. It’s never been that drive for the recognition to be the best. But it’s to be the best version of myself. I’m very much inspired by hard work and driving to be better and better. It’s a double-edged sword, though.”

And what’s that other edge?

“It’s never settling to be where you are,” she said. “So, I have to work on being happy when I achieve those goals. You can’t blow through goals and say that’s not enough — I want more. I have learned to be better at reflecting.”

That has meant taking the time to appreciate the moments with her husband and their 13-year-old daughter. She still competes and conquers mountains, but she is turning around afterward.

“My husband and I run and we do races,” she said. “And I can look back and say, ‘I just climbed that better. I just ran up that hill.’ I can stop and say, ‘Wow, look what I did,’ and be cool with that.”

Another experience back in New York reminded Owings that she still has a mission in front of her. She and her parents were admiring a restaurant where they were having dinner when they learned it would be shuttering soon. They were surprised because they had enjoyed the food and service.

The server said the owner died and Owings recognized the typical, sad story of a small business dying with its proprietor. That owner needed an advisor who would have set the business up with a key man plan funded by insurance.

Owings saw through the sad story to her own simple, essential truth: “People like me help people like that.”

Steven A. Morelli is editor-in-chief for InsuranceNewsNet. He has more than 25 years of experience as a reporter and editor for newspapers, magazines and insurance periodicals. Steve may be reached at [email protected] Follow him on Twitter @INNSteveM. [email protected].


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