Five Lessons from the Oracle of Cincinnatus

Update: Terry Crilley passed away November 9, 2014. He will be missed by his friends, his family and the thousands of co-workers and clients he impacted during his career. I wrote this on the occasion of his retirement in April 2012.

Last week I traveled from Seattle to Cincinnati to celebrate the retirement of my colleague, friend and mentor Terry Crilley after 31 years of service. I once dubbed Terry the “Oracle of Cincinnatus” because I declared him to be the font from which all wealth management knowledge flowed.


It’s not that much of an exaggeration, and no one who knows him has disagreed yet. Terry was the primary driving force that began the transformation of an indistinguishable regional bank trust department with stocks, bonds and a few of its own mutual funds into a full open architecture platform of best-in-class investment managers.

No less than two American Banker “Banker of the Year” award winning CEOs (Richard Davis, 2010 and Jerry Grundhofer, 1999) took to the microphone to celebrate Terry’s contributions to the company, his clients, his employees, his community and his family.

I won’t even try to capture his 31 years of positive impact, but I will attempt to offer a few of the best lessons he has passed down over the years.

Ask great questions

Terry never tried to display his considerable intelligence by asking long and complex questions, but often his deceptively simple ones were far more unsettling. “Let me make sure I understand… we’re trying to encourage our clients to use this service right?” He would say. “Then why are we making it so hard for them?” When working with Terry on a project, I often thought of Hubert Humphrey’s famous quote “Never answer a question from a farmer.”

Grow leaders, not followers

Terry was never a farmer, as far as I know, but he sure knew how to grow leaders. He was explicit about that. One of his direct reports told me a story about how he asked Terry for his input on deciding between two difficult business choices, one of which contravened Terry’s direct request. Terry listened quietly as the employee explained the seemingly no-win set of conflicting choices, then replied simply: “I expect to grow leaders, and this is your decision to make. Just let me know what you decide.” Not what the employee wanted to hear at the time, but ultimately a response that did help him become a better leader.

“This stuff doesn’t just happen”

Even though Terry preferred not to micro-manage, he knew that sometimes he had to be more prescriptive in his leadership style. He was often quoted as saying “This stuff doesn’t just happen”, which was his way of saying “We have done a lot of work on this. This is the right thing to do, and I expect you to ensure it gets carried out.” He delegated well, freely and often; but he knew that merely delegating would be an abdication of his responsibilities as a leader.

“Learn to dribble with your left hand”

Terry is a lifelong learner, and he expected the same from those around him. While he was adept at helping people figure out their unique strengths and how to play to them, he also expected people to learn new skills and to practice them. He was a patient but insistent teacher, and he often encouraged others to “learn how to dribble with their left hand” so they could be more effective in more situations.

Disagree without being disagreeable

Terry and I agreed on many things, but when we disagreed he always listened and debated respectfully. He never made it personal, and he never took things personally. He was interested in getting to the right answer, and sometimes we ended up agreeing to disagree. But we always ended the conversation as friends, usually talking about our families.

Thank you, oh wise Oracle, for your dedicated service and your many lessons. I look forward to seeing how your future chapters unfold.

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