Asking the Right Questions: Lessons From the Best Mentor I Ever Had

We all have those people we work with early in our careers whose influence we don’t fully appreciate until years later.

We move on to different companies, roles, and challenges, but we still find ourselves using the disciplines they taught us. We ask the same questions or approach problems the same way. And then we realize that some of how we lead came from someone who taught us decades earlier.

For me, that person was Peter W. Shoemaker.

Peter was President and CEO of A-Copy when I joined the company in the early 1990s. A finance and operations leader hired by legendary entrepreneur Herb Chambers, Peter was instrumental in A-Copy’s success.

He was also, without question, the best mentor I ever had.

Peter brought something to the organization that stayed with me long after my time there: an unwavering emphasis on process, discipline, and accountability. If you worked with him, you learned quickly that those weren’t just management buzzwords.

Details mattered. Meeting agendas and notes mattered. Follow-up mattered. Metrics and operational reviews mattered. When we had a difficult problem to solve, we used Critical Action Documents (CADs) to define the issue, establish ownership, and make sure it actually got solved.

Peter was famous for asking the third, fourth, and fifth questions. You might walk into a review convinced you knew why something happened. Then, Peter would ask a question and another. By the fifth question, you often discovered that the answer you walked in with wasn’t really the answer at all.

Did we sometimes dread those reviews? Absolutely. But we almost always walked away better. Peter taught us not to accept the easy explanation and not to assume a problem was solved simply because everyone agreed on what needed to happen.

What also made Peter such an important mentor to me was that his thinking wasn’t confined to his own area of expertise.

His background was finance and operations, yet he taught me as much as anyone about sales—territory reviews, forecasting, sales coverage models, and compensation strategies.

The lesson stayed with me: good process doesn’t belong to one function. It’s a foundation for consistent performance and good leadership.

I carried Peter’s process-driven mentality into every leadership role that followed. I’ve often found myself asking one more question, pushing for a clearer answer, or insisting on ownership and follow-up. I know exactly where those instincts came from.

I’ve also tried to pass those lessons along.

That may be the real “bottom line” of mentorship. What someone teaches you becomes part of how you lead, and eventually, part of what you teach someone else.

In business, we measure success in all kinds of ways. But perhaps there is another measure of a leader’s impact that never appears on a financial statement:

How much of what you taught continues to live in the people you led?

By that measure, Peter W. Shoemaker’s contribution is still paying dividends.

I’m grateful to have learned from him and to still be carrying those lessons forward.

Thank you, Pete.