The power of a good mentor

A good mentor can help you navigate corporate politics, improve your skills, or teach you entirely new things. They can also help with more mundane activities like refining a PowerPoint presentation or reviewing a business model spreadsheet. Or they can change your life (and your career) entirely.

Here’s how one did exactly that for me.

Very early in my career — in fact, while I was still in college studying Computer Science — I ended up working at a startup company part time. Initially I worked in Operations, packing products for shipment and receiving returns for repair. I quickly moved into Technical Support, and from there ended up writing small software applications & installation scripts that shipped with a few of their products.

The startup was small, and in those days, the Product Management discipline wasn’t fully formed, and was treated more like the task of product/project management. The Executive team collaborated on the product offerings, Sales sold the products, and Engineering modified the products based on customer requests. Each time I got a request for a modification, I wanted to understand why the customer wanted this change. It wasn’t enough for me to understand the ask itself, I wanted — almost needed — to know why. So, I would ask. And ask. And ask. I became quite annoying.

At some point near the end of a work week, the CEO of the company pulled me aside and wanted to know what I was doing to make everyone frustrated with me. I explained myself as best I could, without any of the formal terminology or wording that would describe the profession today. The discussion ended with him wanting some time to think about it, and we’d re-group in a week.

The delay between those conversations felt like years. I was pretty sure I was going to get fired, but I kept on going to work and trying not to make things worse.

Eventually the meeting day arrived, and my (fuzzy) recollection of the conversation went something like this: “I talked to some people about your situation, and they think what you’re trying to do is Product Management, but you are terrible at it. I’m going to hire someone that knows what they are doing, and you’re going to work for them for a bit to learn and see if this can work out for you.” All I could think about at the time was, “Phew, I’m not getting fired.”

It turns out the product manager they hired was really good. Not just as product manager, but as a people manager, too. The way he approached the role and the way he approached me — who was handed to him as a problem to be dealt with — was exactly what I needed. I learned so much from him, both explicitly and implicitly, that my pivot to Product Management was all but guaranteed.

There is so much more I could say about that company, those people, and that time in my life, but it would take longer to write all of that than it is taking George R. R. Martin to finish writing the Song of Fire and Ice novels.

I still keep in (loose) touch with both that CEO and that Product Manager to this day. Not nearly as much as they both deserve, but after 30+ years in the working world, I still recall both of them fondly, and am indebted to them both for how they shaped my career at such an early stage. I often share this story with folks as an example of how a little kindness and investment in someone can have a massive, lifelong impact.

My key takeaway for you is to find a good mentor. The benefit can be immeasurable.