Editor's Note: John Kessler (above) is answering your questions this week at IT Martini on LinkedIn. 

John Kessler: Win With Loyalty
By Terreece Clarke, February 22nd, 2012

The new CIO and Vice President of Motorists Insurance Group is not the new kid on the block. In fact, John Kessler started at Motorists 27 years ago as an entry-level programmer and worked his way up through the ranks. Kessler's tenure, while an exception the IT industry, is the norm at Motorists.

With a combined experience of nearly 100 years at Motorists between the outgoing CEO, John Bishop, the newly appointed CEO, David Kaufman, and Kessler, the pattern of loyalty is evident.

"What I do know is that there are advantages to loyalty. It can lead to a competitive advantage for your organization, and that certainly has been the case at Motorists," Kessler said.

Loyalty Defined

"We are led to believe that these days your best workers are likely to be more loyal to their careers than to their employers, but I'm not sure how that's any different than any other era. The best case scenario has always been if you can establish an alignment between an associate’s loyalty to their career and loyalty to the company,” Kessler said.

While there are definite benefits to loyalty and longevity in the workplace – like gaining a deep understanding of the company's needs and strengths – there are some challenges.

"I can be pretty candid about this stuff," Kessler said. "When you spend 27 years at the same company...you don't know what you don't know. I know a lot of people have worked at multiple companies and with that comes diverse backgrounds, diverse experiences and exposure to different things that make them more effective in their jobs. I haven't had that. I need to network with those people - and do everything I can to learn from them."

Loyalty does have its rewards. In December, Kessler became the chair of the Corporate Strategy Committees for all the major companies in The Motorists Insurance Group in addition to his CIO and vice president duties. In the position, he leads the strategic committees to review and approve initiatives.

"It's a tremendous opportunity for the CIO to not just be at the table, but to lead these committees responsible for establishing and executing the business strategies..." Kessler said.

In the Game

Growing up with the game of basketball as a point guard in high school, college, and then following in his father’s footsteps as a high school coach, Kessler admits he brings the competitive spirit and life lessons from basketball into his professional life.

"I love being in the position [where] I can make a difference everyday," Kessler said. "To use a sports analogy - I love having the ball, I love the opportunity to have the ball and being in this position you have the opportunity to have the ball everyday. That energizes me."

But it’s more than just a sports analogy. Kessler points to real life lessons that are available for the taking, “disguised by a pair of sneakers, a leather ball and a basket.”

"I always taught my sons and players during my coaching years that there is much more to learn from basketball than just the game itself...such as the desire to compete; the will to win; the work ethic it takes to be successful; how to deal with success; how to deal with failure; how to communicate laterally; how to communicate upward; how to effectively lead; how to effectively follow; how to work with others in a team atmosphere; and how to put other’s interests ahead of your own."

The $100 Million Dollar Challenge

As a company, Kessler said Motorist is challenged by the same thing every company in the industry faces - how to be profitable in a soft market and tough economic climate.

"The industry is in unprecedented times. It has shrunk four out of five years," he said. "In the Midwest, there have been more catastrophic weather event losses than any other area in the country in the last four to five years. The new norm is $100 million in catastrophic losses, when it used to be $25 million."

Dealing with the $100 million challenge has led to innovations in the way the company does business.

"Specific to the rise in the number of catastrophic losses in our industry, Motorists has been fortunate to have an innovative claims system that has provided us with a competitive service advantage," Kessler said. "It's a fully automated, paperless system that has allowed us to provide outstanding mobile service & support; while some of our competitors have struggled with keeping up with the high claims frequency demands that are typical with catastrophic weather events."

The award winning system is a big reason why The Motorists Insurance Group was named Professional Insurance Agents Company of the year in 2008, making it the only company to win the award twice. The first award was given in 2002.

IT Martini Rapid Fire

What book are you reading right now?

Switch. How to Change Things When Change is Hard

What books are part of your life philosophy?

The Four Agreements: A Practical Guide to Personal Freedom

[The book] says, if you can make four agreements with yourself and think about them each and everyday and stay true to them, then it's a guide to personal and professional freedom and success. The four agreements are: be positive with your words, don't take anything personal, don't make any assumptions and always do your best.

Name a leadership role model.

My father, someone who spent 50 years in the educational system, started as a high school coach for various sports, moved into administration and worked his way through from principal to superintendent. Everything he did involved leadership positions - he's always been an inspiration.