Jay Coughlan – successful former Chairman and CEO of XRS Corporation, President and CEO of Lawson Software, convicted felon, husband, father, board member, speaker, coach, and now the CEO and Managing Director of TruBalanced – and I reconnected after several years for this bold leader conversation.

Wait! Back up! What was that “convicted felon” part there in the middle of all those other descriptors?

True. Jay has an amazing story. A life on a “roller coaster” as he describes it. Today he asks other executives he now works with, “What roller coaster are you on?”jay coughlan

Jay’s story is worth a visit to the TruBalanced site where, in his own words, he describes hitting a train going 60 miles an hour while driving drunk, in an accident that killed his father, left Jay physically and emotionally damaged, and landed him in jail. Then he tells about his long, tumultuous journey back, turning his personal life and career around, and how he found the will to lead others through tremendous times of change while also coming to grips with who he is as a leader. No matter what your worst days are at work or how big the challenge, you have to admire a guy with this much tenacity, understanding of self, grit, and courage to speak the truth.

As we leapt into the bold leader conversation – aside, I had forgotten how fast paced and intense conversations with Jay can be! – he credits the foundation for who he is to the hard work and early life lessons he got as a kid helping his dad, a beer hauler, deliver in some of the roughest neighborhoods of Philadelphia. He learned early to not be afraid, know what you want, and work hard to accomplish it.

Those lessons were present at both XRS and Lawson, where as Jay says, “There was no plan B. This had to work. It is easy to talk about being bold when you have options. Not so easy when there is no other viable option.” Like so many of the bold leaders we’ve interviewed, Jay reiterates that you have to have a vision. You have to sell it, and to sell it, you have to believe it. “You have to keep reminding people (board members, investors, and employees) of the original vision and keep reinforcing progress – to ‘keep the rats from jumping ship!’”

Another aside – Jay is also a very direct and colorful guy which is why hearing him speak is so fun and refreshing!

Jay goes on to say, “The optics in the short term can look bad. Terrible. You have to keep the long view. Even when the product is taking too long in development. Even when others are questioning your judgement. Every day you have to be ‘on message!’ You can’t blink! Everyone is watching and you set the pace and tone.”

About people, Jay says, “You want everyone to make it through a change, but in reality, not everyone does. That doesn’t make them bad people. Or bad employees. They just don’t or can’t fit the circumstances. Socially, this is very hard when some don’t make it.” But you have to deal with it or it can destroy a team. And bold leaders need the smartest, best people around them to help get through uncertain times.

“Use data.” That was Jay’s answer to my question about how he works through his own doubts or what he does when he hits a wall. According to Jay, you need to have confidence that you made the right decision in the first place. Stay the course and use data, and keep confirming and getting new data. He says, “If the data changes, make a new decision. Get smart people in a room – who aren’t panicking – and confront the data – honestly. Then as the leader you make a call and move on.”

Regarding mistakes and arrogance, Jay says, “Look, I’ve made more mistakes than most people! I’ve had to learn my way through them and get to the other side.” This is the roller coaster ride Jay is talking about. We all have them. “I guess I’ve always had the confidence that I’d find my way through. Early in my life I was maybe over-confident, even arrogant. What I’ve learned through life, and from those I admire, is that humility gets you farther than arrogance, or even confidence.”

“When you’re down or in a bad place, you’ve made a terrible mistake, self-talk can destroy you.” Humility can save you. “When you’re on the top of the world and people are telling you how great you are, it’s easy to become self-important, arrogant.” Humility is equally or more important then.

As we ended, Jay went back to a theme that ran throughout the conversation, “What is the truth?” If you know that, you can solve anything.

So what brutal truth are you confronting? What roller coaster are you on? What lessons through life have shaped you? Important questions for all of us. If you’re willing to share or ask your own questions, I’d love to hear them. I know Jay would, too.