Jack was my boss when I worked in the Commercial Home Office of Allstate. He had held virtually every other important job at Allstate prior to being asked to run our business. I had known him casually over the years, but quickly got to know him well in his new assignment.
This was in the 1990’s and things were different then…and Jack looked like he was the poster boy for CEO…tall, distinguished, male (in those days…most were male…some might say the same today), experienced, smart, personable and very well connected. His wife, Lucy, was the perfect corporate CEO wife…beautiful, smart, friendly…with one additional descriptor…really really successful in her own right as a clothing store owner.
Jack took over an organization and changed it in unimaginable ways. He did it by empowering people to do the right thing. He did it by educating all of us. He did it by careful attention to the numbers. And…something we were not use to at all…he did it by staying very well connected politically with the rest of the Allstate organization.
Jack brought women to the top of our organization and then helped them make their way into the bigger Allstate organization. One of them became the overall head of Human Resources for the entire company. Another took on major responsibilities within the overall Claim organization. Another within the IT area. Another helped transform the culture of the entire company. Minorities got opportunities and made the best of them. And the rest of us…we had opportunities, as well. Jack always said…he could not guarantee any of us long term jobs…but he could guarantee we would get the education, mindset and skill set to be long term employable anywhere. That really turned out right for me. I eventually left the Allstate organization, but ended up as Chief Underwriting Officer for another company and CEO/President of a sizable middle market and program business commercial insurance company.
Here is what I enjoyed the most about working for Jack…I was his speech writer. If he said something on video or in a presentation or wrote something for publication…I probably actually wrote it. To be fair, he had other people in Corporate and at Commercial who also wrote things for him…but I got the lions share. Bragging….no, and you will see why in a moment.
I took dictation in high school…dictation. I was the only guy in the all girl class. Why?….well, think about it. Best move I ever made…met a lot of ladies that way. And I got good at dictation…that turned out to be an asset throughout my career. We had a Zone VP once who took me under his wing and said to me “Son…always be the one who writes the minutes of the meeting. If you control the minutes, you control the outcome of the meeting.” So…I volunteered often to take the notes and write the minutes.
Now to get to the point about why I am not really bragging about my writing for Jack…and I will tell a quick story that tells the tale…
Jack was asked to give the commencement speech for the University of Illinois Circle Campus Business College…a large class of graduates at a university that we had connected with on several projects. I don’t think Jack ever figured out where the invitation to be the commencement speaker ever came from…but I know. My daughter, Stephanie, was the assistant to the Dean of the Business School…and she loved Jack Callahan. I think she pointed the Dean toward Jack. Jack accepted and asked the Dean to visit him to discuss the speech. He asked me to sit in on the meeting. I did…never said a word as the two discussed potential topics and what he might say. At the end, the two of them went to lunch. My dictation pad and I went to my office. When their lunch was done, I gave them both a draft of the possible speech. Their jaws dropped. Jack read it. He looked at the Dean and said “Don…this is brilliant…you are a genius.” Not a word was changed and that was the speech he gave.
Genius huh…every single word of that speech was EXACTLY as Jack had said it in his “off the top of my head” green lighting of potential thoughts and phrases…exactly. I added nothing. I don’t even recall having to put them in good order…just transferred them from my dictation pad to my computer, hit spell check and then printed it out. It was a brilliant speech…but I had absolutely nothing to do with it. That was Jack.
And one other thing about Jack…he was human. By that I mean, he lived with a painful injury from a fall. He had a major disappointment in his career. He had a divorce that was painful as heck. At the end of his life, he ran into the things that aging can do to all of us. He was a person…just like all of us. But…if you ask me…he was not just like all of us. Jack was one of a kind…and kind…and I am thankful til the day I die for the opportunity to learn from him and to be his friend. My best to Lucy and his family and to all of us who loved him. Aloha Jack.