Chris Wayne is not the typical tech-giant executive. Before taking the chief technology officer (CTO) reins of Yahoo Small Business, he started his adult life in 1996 as a combat engineer with the U.S. Army's 82nd Airborne Division.
When he left the military as a sergeant, his path wasn't as clear as it might have been today. When troops leave the military for civilian life these days, they have mandatory transition classes, nonprofits that are ready to impart new skills upon them and an improved GI Bill to help take care of that transition.
In August 2000, there wasn't any of that for soldiers like Wayne. His first job outside of the military was a basic data entry-type gig that he did while going to school at San Jose State -- all with a baby on the way.
"I would just describe it as 'uninformed,'" he said. "There's positive intent, but the wisdom to success isn't quite there yet. There were some programs that existed; I was just eager to get on with the next chapter of my life."
He worked hard and eventually found himself a job at Yahoo as a contractor. He worked his way up from customer support to managing customer support. Next, he worked his way into engineering and, eventually, the C-suite of Yahoo Small Business. By 2015, he was the chief information officer, and three years later, he became the CTO.
1. It's OK to Start Over at Entry Level
Whether you served four years in the military or 10, chances are good you're going to be starting over to some degree. And that's OK, Wayne said. Just remember to keep your eyes open for opportunities to advance.
"It's going to be scary, but it's also only temporary. And you're going to get opportunities to lead," he said. "You just have to know when those opportunities exist and take advantage of them. Whether it's a project or a team, those opportunities exist."
2. Delegate Authority, Not Responsibility
When you do get into a leadership position, you don't have the luxury of passing the blame onto one of your subordinates. That would be delegating the responsibility of leadership. If you accept the responsibility for group failures when your leadership tasks you to do something, it can be an everyday game-changer for the people who work for you.
"You have to be able to say, 'I did that. I dropped the ball. It's my failure,'" Wayne said. "That's something that your employees really respond to, and they know that you have their backs. The underlying mantra is, 'Wins are yours; losses are mine.'"
3. Never Hide from Failure
"If you mess up, you've got to say that you messed up," Wayne stressed. "If you try to hide it or blame someone else, everyone is going to find out, and it's really gonna hurt you in the long run."
In Wayne's experience, the people who do the best in their post-military careers are those who fail the most and own it. That's where they learn from their mistakes. The more you fail, he tells people, the more you learn.
"Some of the best people I know continue to fail all the time," he said. "But then they extract those learnings on a regular basis, and it's just phenomenal."
4. Form Connections with Those Around You
Whether those around you are veterans or not, you need to network and form close, supportive relationships with those who are closest to you.
"You want people to like to work with you," Wayne said. "You want people to listen to you because they trust you, because they're loyal and because they believe in you."
This is also important because the civilian world has hierarchies, just like the military. Civilian hierarchies are harder to suss out because no one walks around wearing rank on their sleeves. Motivating workers and partners isn't just about rank, and it takes more finesse in the civilian world.
5. Trust and Respect Those Around You
You aren't going to make any friends by throwing others under a bus to try to make yourself look good. If you do things as a co-worker, leader or even as a friend that are purely self-serving, especially if they're to the detriment of others, everyone will soon know about it.
"You can earn a lot of trust and respect just by inspiring employees to do their best," Wayne said. "You earn respect and trust along the way. You can get a lot out of your employees by not forcing them to do work and trusting them to meet goals."
-- Blake Stilwell can be reached at blake.stilwell@military.com. He can also be found on Twitter @blakestilwell or on Facebook.
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