Believe in Yourself

During Kimberly Stewart’s childhood, her parents believed she and her siblings could accomplish anything they put their mind to. Anytime she or her siblings approached their father and mother with an idea, no matter how farfetched, they supported them. “They always believed in us and gave us the freedom to pursue it,” she recounts today. “We would come up with a concept and they’d say, okay, what’s your plan? Then it was up to us to figure out how to accomplish it. If we tried one way and failed, they encouraged us to find another way. It taught me how to believe in myself and figure out how to accomplish whatever I set my mind to do.”

Years later, while working for American Management Systems, Kim was the Deputy Program Manager for a major Information Technology (IT) project. Over the next few months, as they neared the Go Live Day, it became apparent the system was not ready for end-to-end production. The Project Manager (PM) took a leave of absence, and the Go Live was a failure.

Thanks to the strong foundation of resiliency and industriousness set in her by her parents, Kim set to work strategizing solutions and forging a path forward. “In the immediate aftermath, we assembled a team and worked round the clock to rebuild the system,” she recounts. “Once we got it up and running, we worked to improve it. It was not a position I wanted to have, but I resolved to get through it by taking each problem and laying it out on the table, giving my recommendation and then acting on the client’s direction.”

Little by little, things started to improve, and in the end, the strategy worked. “I still have great working relationships with the senior leadership from that client because they know they can trust me to tell it like it is, and to do everything in my power to get the job done,” she says. “It was one of the most trying challenges I’ve ever gone through, but also the best learning experience I’ve ever had, and it absolutely defines how I work with clients today.” Now the Founder and President of Stepping Stone Consulting, an IT Program Management firm that partners with the federal government to implement IT services and infrastructure solutions, Kim has built her career through the power of possibility—the kind of power unleashed when you’re given the tools to succeed and then let loose to go figure it out.

Kim launched Stepping Stone in June of 2010 as a “stepping stone” to program management success in the federal IT space. “We support the government’s IT program management offices,” she clarifies. “We work directly with the program offices of these agencies, helping the government acquire, implement, and manage the products, services, and software.” Now a small team of two employees that brings on contractors as needed, the company was focused entirely on the Department of Defense until it recently won a Department of Transportation contract, and plans to continue to grow.

This core business of Stepping Stone allows Kim to continue her lifelong dedication to the success of others through her focus on the growth and prosperity of her clients and employees. This aligns with a budding branch of the company, a coaching service for PMs in small and mid-sized businesses. “Smaller companies often don’t have a senior PM that can act as a mentor, so they bring me on to provide that expertise and guidance,” she says. “Whether I’m advising on an issue, guiding on certain deliverables, providing templates, or supporting staff during a meeting, I’m a safety net for executives because they know I’ll always come to them before it’s too late. I have a confidential relationship with the PMs I coach, but if there ever comes a point that the company or project is at risk, I’m the executives’ backstop and get the appropriate people involved to avoid catastrophe.”

Kim’s love of mentoring and coaching junior PMs is a reflection of her broader focus on promoting the success of others—a passion she first connected with as a five-year-old girl while vacationing in Cape Cod. That summer, the kids in the area decided to clean up an abandoned boathouse on the water so they could use it to host a surprise dinner party for their parents. “Some of the parents helped with little chores, like getting the electricity working again,” she says. “But we swept it, decorated it, and brought in all the food. I’ll never forget how proud I was when our parents came for that meal, and I fell in love with the feeling of doing things for other people.”

Born in the Columbia Hospital for Women in Washington, DC, Kim grew up in Chevy Chase, Maryland, as the third of four children, in the home where her parents still live. The back of the house juts up against the Kenwood Golf and Country Club, and Kim remembers cherry blossom seasons when she joined her older brother and sister in collecting tennis balls hit over the fence and abandoned in the woods. They sold them, three balls for a dollar, at a lemonade and cookie stand they set up for tourists—a lucrative venture undertaken mostly on their own. “Our mother would buy the first packet of lemonade mix and tell us we were responsible for everything else.”

Through her childhood, Kim’s mother stayed home with the children and worked parttime for the Campaign Committee of Texas Congressman Jack Brooks. Her father was a partner at his own law firm in D.C. The children were never allowed to miss school, so when the exception was made for her father arguing before the Supreme Court she was very excited. “We were excited to finally miss a day of school, only to realize it was the Easter Monday, a school holiday,” Kim laughs. “Education was our job, and a big priority for my parents.”

During her early academic years, Kim worked with a speech therapist and recalls anxiety about reading aloud or speaking up in class. For her fourth-grade year, she transferred to Maret School, where her older sister attended. There, she began to flourish in math and gradually became more comfortable academically. The summer after her sixth-grade year, however, she noticed that the community around her identified her as “Angie’s little sister.” She was upset at first, but fortunately, things began to change when her sister invited her to come be part of the backstage crew for the school’s middle and high school plays. “No other seventh graders got to do that,” Kim recounts. “I loved the work and meeting the upper classmen, and I started standing out on my own.”

A year later, the drama teachers created a new student drama position for her as a student producer of the middle school play. The following summer, she started working as a counselor at Maret’s summer camp. Empowered by the sense of creating her own identity, she found she was drawn to leadership and decided to run for president of her ninth-grade class. “I intuitively knew the groups to reach out to and the support I needed to win,” she reflects. “It was another step in defining who I was and finding that I was much more comfortable leading than following. I was always one to take initiative, never sitting back and just waiting for things to happen.”

Through high school, Kim was often at school from 8:00 AM to 9:00 or even 10:00 at night, her time joyfully dedicated to class, sports, and drama rehearsals. She became president of the drama group, directing and producing plays. She played JV and Varsity softball and soccer, and also fell in love with Physics. Well-rounded and a master of time management, she stood on her own with her own identity.

“I was probably the third or fourth person in Maret’s history to receive their diploma from a parent. For me, it symbolized that my parents had given me the foundation and guidance to be successful, and now I was on my way. I treasure that memory very much.”

When it came time to consider colleges, her mother encouraged her to apply to attend Wellesley College, the women’s college in Wellesley, Massachusetts, where her mother grew up. “When I went in to interview, we had a great conversation,” Kim recalls. “The interviewer said that every school was going to want me, given my grades, athletics, and community engagement. She asked if I would come if I was accepted. Without skipping a beat, I answered honestly, ‘No.’ When the interviewer asked me why, I said that if I was going to compete with men in the real world, I wanted to compete with them in the classroom.”

Kim effectively threw the interview and was waitlisted at Wellesley, ultimately accepting a place at Hamilton College in Clinton, New York. She remembers her high school graduation day with tremendous love and gratitude, particularly for her father, who handed her her diploma. “He was President of the Board of Trustees at the time, so he handed out all of the diplomas, including mine,” Kim recounts. “I was probably the third or fourth person in Maret’s history to receive their diploma from a parent. For me, it symbolized that my parents had given me the foundation and guidance to be successful, and now I was on my way. I treasure that memory very much.”

At Hamilton, Kim planned to major in Physics but was discouraged when she kept failing tests in Physics 101. Her professor confirmed that her conceptual understanding made her one of the better students in the class, but her answers weren’t the exact answer as his, and he didn’t give partial credit. Frustrated, she switched to a government major with a minor in economics. “Leadership was what I was really interested in, and I felt that leading a country was the ultimate test of leadership,” she explains.

Upon graduating Hamilton in 1992, Kim spent several months working on various political campaigns and then interviewed at the University of Maryland University College for the role of Assistant Director of Annual Giving, during the interview, she was asked why she wanted to wake up each morning and take money away from people. Without missing a beat, she spoke from the heart. “I told them I didn’t want to do that,” she recounts. “I said, I want to give people the opportunity to support a cause they’re passionate about. If they don’t want to support it, I don’t want their money. Looking back, that’s what’s driven me through my entire career—that desire to provide opportunity and to make individuals or organizations successful. It’s the same goal I work toward now through the framework of program management.”

Kim landed the job, setting the tone of her professional career with the mission-focused mindset of the nonprofit world. There, she raised money and served as the campus representative on a University-wide committee to evaluate a new alumni and development software system. That experience marked her initial foray into the IT world—a path furthered when she left in 1995 to accept a similar position at the Chesapeake Bay Foundation. She implemented and ran their new development software system as well, and grew even more intrigued by the power of data and IT to manage and transfer information quickly and efficiently. “I worked with consultants that were implementing software and teaching people to incorporate it into their processes to do their jobs better,” she says. “That experience helped clarify for me why I wanted my MBA.”

Kim knew she wanted to one day have her own consulting business, and when she applied to business school, she decided to write her business plan for the admissions essay. She married her husband, Gary, obtained a position at American Management Systems (AMS), and completed her degree in 1999.

AMS, known for producing high-caliber consultants that share an iron bond of strong values and unyielding work ethic, was a hugely transformative experience for Kim. She started her tenure working on Army projects, but when she returned to work after giving birth to her son, Patrick, she found herself thrown into the fray of the a severely challenging system implementation for the Federal Agency—a critical learning experience that taught her how to navigate a crisis from a place of strength. “It really drove home the reality that bad news doesn’t get better over time, so it’s most important to be upfront and honest,” she recalls. “If there’s a problem, don’t hold onto it—get other people involved and figure out together how to come up with the solution. It was the best lesson I could have learned so early in my career—one I return to all the time. It has never failed me.”

In 2004, while preparing for the birth of her daughter, Ashley, AMS was bought by CACI and CGI. She took a position with Preferred Systems Solutions (PSS), a small business focused on professional and technical services contracts, where she quickly rose to the rank of VP and wore many hats. “I fine-tuned my business acumen, developing my experience in proposal work, budget management, and building business,” she says. “It was perfect training ground for preparing to start my own company.”

By 2007, Kim felt ready to take her entrepreneurial leap, but as she prepared PSS plans and budgets for the following year, she realized she was responsible for a significant portion of the company’s revenue. “I knew I had to tell the CEO my plans to resign in February.” Prepared to leave two months ahead of schedule if requested, she ended up being able to stay on until her ideal departure date in February. When the leadership then had to let go of another VP a couple of weeks before her last day, she was asked to stay longer, so she negotiated an ownership stake in the company. Finally, in 2010, she stepped out, stepped up, and started Stepping Stone Consulting.

Today, Kim focuses primarily on supporting her team members in their pursuit of success. Sometimes this requires guidance and mentoring, which might warrant a chat over her highlighted and heavily-notated copy of Stephen Covey’s The 7 Habits of Highly Effective People. Other times it requires doing nothing, which can be the hardest challenge of all for Kim. “If something’s not getting done, my tendency is to jump in and do it,” she says. “But I’ve learned that sometimes I need to just sit back and give others the space to step up on their own terms.” She also measures her success through the success she helps create for others, like a longstanding Army client who was recognized as a Top 100 CIO by CIO.com Magazine. “I helped set up a program management office in his shop, which really moved the needle for him.”

None of this would have been possible without the love and support of her husband, Gary. A defense consultant as well, he has maintained a stable career that has given Kim the leeway to take bigger risks. “Gary goes into work early because he knows I often have to work late,” Kim says. “I get the kids to school, and he makes sure he’s there by the time they get home. He’s always believed in my vision for my career path, and been the core that has helped me do everything I want to do. I’m very grateful for what we’ve built together.” Now, as they raise their two children, Kim strives to provide Patrick and Ashley with the same boundless sense of possibility and capability that her parents gave her. To them, and to young people entering the working world, she underscores the importance of authenticity and honesty. “Be true to yourself,” she stresses. “If it doesn’t feel right, take the time to think about what you’re doing and why you’re doing it. Look deep inside and make sure it resonates with your values, passion, and identity.”

Beyond that, Kim invokes the positivity of her parents as a foundational key to success, shaping the character and vision that brought her here today. “Thanks to them, I’m always looking at the positive side,” she affirms. “Things happen for a reason. You might not know what it is right now, but you will eventually. So, if tough times come, just focus on how you’ll come out stronger. Set out your goals, figure out how to get there, and believe in yourself, because you are the only real limit you have.”

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