Can Old Dogs Learn New Tricks?

When I started Doescher Advisors, I knew I would miss the Plante Moran help desk. Little did I realize how much.

That was a very different season of my professional life, and like many new chapters, it came with a learning curve.

Almost daily, I seemed to have a technology-related hiccup. For example, I was unaware of the ongoing war between Apple and Microsoft and how that might, at some point, have an impact on my own business.

For several years, I had excitedly anticipated the purchase of my first Apple computer. I was simply waiting for the perfect time. Finally, that time arrived.

Much to my dismay, however, I discovered that Apple’s iCalendar was not compatible with Outlook, and most of my clients and business colleagues used Outlook. I had no choice but to purchase Outlook for Apple. That, of course, created other issues.

In the long run, it also made me more proficient with that particular technology.

That is one of the things I have learned in business. Sometimes frustration is the teacher. We do not always learn new systems, tools, or habits because we feel inspired. Sometimes we learn because we have to.

My latest discovery at the time was that although I thought I understood how my blog and e-newsletter sign-ups worked, I was wrong.

Thanks to some directions that were not completely on the mark, I realized that many readers who were receiving the e-newsletter were signed up for that, but not for the blog.

There is probably a leadership lesson in there somewhere.

As business owners and executives, we often assume we understand how something works because we were told how it works, or because it worked once before. But systems change. Technology changes. Communication channels change. And occasionally, we have to stop, ask questions, and admit we may not understand the process as well as we thought.

That is not always fun, but it is necessary.

So, yes, old dogs can learn new tricks. Sometimes we just need a little help from someone who understands the trick better than we do.

If your team is spending too much time fighting systems instead of serving customers, it may be time to step back and rethink the process.

Tom Doescher

Tom Doescher, founder of Doescher Advisors, previously built and led Plante Moran’s largest industry group, the manufacturing and distribution practice, advising middle-market manufacturers and distributors worldwide. A Harvard-trained leader known for his integrity and strategic vision, Tom helped establish multiple firm practices, mentored future partners, and continues to serve on industry and community boards. In 2011, after many years as a senior partner with Plante Moran, one of the nation’s largest and most well-respected accounting and business advisory firms, Tom launched Doescher Advisors. In 2025, Doescher Advisors joined Doescher Group, where Tom continues to advise privately owned business owners & executives.

This post was written by Tom, a real person at Doescher Group. We use AI tools in our work, but this article came from human experience, thoughtful analysis, and the kind of perspective you only get from working with real business owners.

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