“How do I get that job?” It’s a question frequently asked when anyone attempts to set on paper a career plan. But most often those plans don’t follow a planned trajectory and instead come from being in the right place, raising a hand at the right time and being flexible enough to go where needed. Aviation Week asked members of the Program Excellence Evaluation Team to diagram their career paths—and share the most important lesson learned. The stories are humbling, candid and carry a few tips for future leaders. And we found these paths to be anything but direct.

Jesse Stewart is considered the dean of program management for many in the defense industry. A retired naval officer, Stewart heads toward retirement as a program management professor at the Defense Acquisition University. Careers don't follow a straight line. Among the lessons he learned: “Any time you are having fun, get ready for payback big time with something that’s a lot less fun.” Stewart’s career began as a Navy fighter pilot, then flight test (“entirely too much fun”), before shifting to programs and a new aircraft being readied for flight testing. It was in this job that he learned the ins and outs of system design and the certification process. Stints in air-to-air missile development and then program management followed. “The only consistency to this career path was that I learned you get selected for a job or an old boss reaches out and puts his finger on you” to fill a slot. Stewart’s best lesson: There is no single way to fix anything, but rather it must be done through careful study and analysis of options.

Carol Armstrong started her 38-year career with Northrop Grumman’s legacy Westinghouse nuclear energy group. Along the winding trail of her career, she has worked in every function except a legal one. The green bubbles on her career path indicate major shifts away from engineering work. Smiley faces are children. The patterned box was a role in strategy, which allowed her to work in a virtual and flexible way long before these were common practices. The red star indicates her most valuable lesson. As the most junior person on a commercial nuclear design project located in Spain, she was found late one night to be the only team member with a current passport. “The customer took my passport and wouldn’t let me leave until the problem [with a piece of testing equipment] was solved,” she says. Armstrong’s lessons from that experience: Be flexible and have a valid passport. Second, establish credibility quickly—in this case by calling back to the home office and asking for help when it was needed, anything to keep things moving forward. Third, know what you don’t know. “When I didn’t know something, I told them so and when I’d be back with an answer.” Fourth, think of the overall system and the role you play in delivering value to the customer.

“No career path is very straight,” says Greg Heesacker, director of program management development and performance for Boeing Defense, Space & Security. “When I first started, I wanted to be the VP of manufacturing.” A labor strike put the young engineer out on the production line, where he learned valuable lessons before moving onto the C-17 program. “There was a dark cloud over our program, with a very adversarial relationship with our customer. Nothing was going well,” he recalls. At one point, all managers at the Long Beach facility were asked to meet in a paint hangar, told of a major restructuring and that they would have to reapply for jobs. “Candidly, it was a year of chaos,” Heesacker admits. “But during that time, I got my MBA. We reached an omnibus settlement on the [C-17] program in 1994. We agreed to a common vision, and if both counterparts [government and Boeing] weren’t on the same page, we were told, ‘There’s a room across the hall; when you get your act together, you can come back.’”

His top lesson: the importance of relationships and teaming. “If that doesn’t exist, along with frequent communications, the assumption is often that something is going wrong, resulting in distrust and erosion of credibility,” Heesacker says.

Kevin O’Brien’s career path is common, but it also resembles a snake more than a straight trajectory. An attack helicopter pilot at age 19, he left the military after 10 years to become an instructor pilot with McDonnell Douglas, specifically in instructional design and systems. “That was my first foray into the commercial world and cyclical businesses,” O’Brien says. “And the lesson was fast: You gotta be into self-improvement.” O’Brien earned his MBA and became interested in program management. He joined Honeywell, using his systems design and tools work in support of the air transport sector. He switched to a customer support role and then led a proposal effort for Tinker AFB. “It was ours to lose, and we were worrying about who to invite to the ribbon cutting,” he notes. But the deal included incentive clauses, and the money was viewed as too risky. Flight tests were added to the requirements. The business case fell apart, the schedule fell apart.

The lesson: “Certainties do not exist. No matter how confident you are, plan for [uncertainties and errors] to happen. I plan for natural disasters—what if a Tier 3 supplier were hit by hurricane? One of these times it will happen.”

Dave Rogers started his career in what some see as an enviable position: as a consultant. He notched up successes. He learned being a principal in that career means managing conflict. He became a partner in 1999 and in 2002 shifted to industry—a typical switch for consultants. With stints in strategy and mergers and acquisitions, Rogers took the big step in 2014 by starting his own business, a lesson in managing through chaos. “The greatest lesson learned I’m still learning: Don’t be difficult,” Rogers says. “In consulting, you are expected to create conflict. But at Honeywell that wasn’t my job, and I was carrying it as a core competency. In Southeast Asia with Dubai Aerospace, being difficult was a recipe for disaster. I needed to change. Hopefully, the people I work at Elbit see me as a person who isn’t difficult but as someone who gets through problems without causing organizational paralysis. Being right is irrelevant. Defending my position ends up in paralysis, and that doesn’t mean moving the business forward.”


Of these careers, that of Chris Seat most resembles a trajectory that might be expected. The senior vice president of programs at General Atomics Aeronautical Systems, Seat started in the Air Force — operational as a pilot for a number of years, then the move into military leadership roles, the F-22 program office, Pentagon and then F-22 testing. That lineup allowed Seat to retire and move into industry, first as a line program manager for two new programs, then in leadership of a portfolio of Air Force programs. Today he is responsible for program execution for General Atomics as well as identifying and developing new program managers. Seat’s No. 1 lesson: “Do the best job you can in the job you have now. Basically, don’t get so enamored with what you want to do next. Do your job, help your supervisor get his/her job done by doing your own. That’s how you will advance.”