Mistakes. We all make them. Some are worse than other, but they all are suboptimal situations.

Photo by Brett Jordan on Unsplash

I have made many mistakes in my long career as a Product Manager. Some related to the role. Many not. Regardless, every one of them has left an imprint on me, my psyche, and my self image.

Ironically, they really haven’t impacted my career, even though at the time I thought I had made career limiting goofs.

Always know what screen is being shared

The first mistake came when we invited the front line support team to a sprint end demonstration, and retrospective. They were told that they were there to observe, and see how our team worked.

Alas, there was this one person who just couldn't keep his mouth shut. He asked about the process. He got in the face of the QA engineer who was demonstrating. He was compelled to ask over and over again every detail, every dialog box, every step in the demonstration.

It was painful to experience. So much so that I sent a snarky message to our scrum-master. Alas, she was sharing her screen, and while the message didn't pop up in real time, at the end it showed on the main screen for all to see.

Hoo boy, was that a bad scene. The person who was being tres annoying, and EVERYBODY else in the room saw it.

That opened a major rift between me and the support team.

I had to go hat in hand, multiple times, to apologize, to fall on my sword, to ask for forgiveness. I had conversations with my boss, my boss’s boss, and his boss.

Eventually, we got back to a formal working relationship, but there was never any trust.

Completely my own fault, and I took responsibility.

Deleting a file server

In the middle ‘aughts I worked at a medium sized company that was an amalgam of several acquisitions. The Business Unit I worked at was one of the smaller acquisitions, and we had remained somewhat autonomous. That meant that we were tied to the major IT systems of the corporate headquarters (email, ERP, finance) but had our own little universe of IT.

I was the only Mac user at the business unit. I knew the IT team, and they were totally cool with it, as long as I didn't need support.

A downside is that we had lousy WiFi support in our building. I think it was just because we used high end consumer grade AP’s and no real site survey or planning it just had a lot of holes in coverage, and performance was meh at best.

So, to get decent connectivity, one needed to plug into the ethernet cable.

My mistake came one afternoon. I was in a conference room, and I was plugged in there (it was 100BaseT, where my desk was 10BaseT) doing some arranging of files from my department (product marketing) on the main file server. After a couple hours of rebuilding a sane structure, I was ready to remove the old folder and rename the replacement that I had been working on.

I bet you can guess what is coming.

I was in the terminal, and I typed that one command that can totally ruin your day if you aren’t careful, ‘rm -rf *’.

I had thought I was inside the folder I wanted to empty, but alas, I was really at root (aka / ) and the system was dutifully recursing into every folder and erasing all the files.

Really really fast.

Once I realized what I had done, I grabbed the ethernet cable and removed it, but by that time I was well into the Finance team’s shares.

I was mortified.

I could have just pretended that it never happened. But alas, that really wasn’t an option. I sheepishly walked down to the IT team’s offices, and owned up to it. They were super cool about it, and pulled out the prior evening’s backup tapes, and got down to restoring. Really, we lost almost nothing, and this got them to be serious about adding access control lists and to structure access based on need versus being wide open.

Career Mistake

At first his one didn’t feel like a mistake, but in hindsight it was a huge mistake.

I had long been an instrumentation product manager, working in microscopy, line width metrology, industrial measurement and test and was deeply embedded in that domain. It was comfortable, and to be honest a bit mundane.

As we were closing out the ‘aughts I had a chance to jump to Enterprise Software product management, I took that opportunity. It was challenging, it was different (no hardware dependencies, YAY!), but a couple years in it became quite pedestrian. It was one dimensional, and to a degree boring.

I longed to get back to instrumentation, and when the opportunity came up, I jumped at it. It was a company I had been talking to for several years, but the opportunity was never ripe. Finally, they wanted to get serious, and I wanted a change.

The first 2 years were good, I was able to focus on the product and make a real contribution, but then big changes happened. The engineering and marketing team were moving back to Silicon Valley, and my boss decided to not make the move. I tried really hard to not take her job, as I knew that I was not happy as the manager or leader. I really prefer being an Individual Contributor.

But when no serious candidates came forward for the manager position, I got the dreaded call from our VP and the gentle pressure to take the role.

Fast forwarding, I was really unhappy in that role, and there were tons of red flags that I missed or overlooked (our products and technology were not a good match to the overall corporate mission, competition was remarkably fierce, and thus we were far out of our comfort zone)

I won’t belabor the point, but I became very self destructive, and the separation was not amicable.

The irony is that if I had stayed at the software company, I would probably be a VP by now, browsing yachts to buy.

Chasing Riches

The first time I bailed on a good gig to chase the dragon of wealth was in late 2000. I was working at a company that made capital equipment to support semiconductor manufacturing. It was a good gig, but it was a lot of work, and my product was very niche-y.

Several people I worked with had bolted for the web companies that were all the rage. I had an opportunity to take a cool job at Cisco, where a couple of my colleagues ended up, and they were talking about all the stock options they got, and how they were making tons of dollars (on paper).

The temptation was too great. I got a chance to join, and work with my brother in law. It was fun, exciting, and I was able to revel in doing high impact work.

And I got a LOT of stock options. I look back, and I am truly astounded at how many shares were granted, and how often they happened.

Alas, I was part of the last wave of big hiring classes (I think there were over 500 people who started that first week of 2001 with me), the volume of hiring was much less after that.

The reality is that I started at the very beginning of the dotcom bust, and I watched my stock grants go from $60+, to $50, to $45, to $42 per share options, thus they never were above water.

I left in 2003, to get back into instrumentation product management, moved to Arizona, and rebuilt my career.

One thing I did was keep a spreadsheet of the stock I had from the semiconductor company I worked at, and I tracked what the net value would have been had I stayed. I stopped tracking it when I would have cleared $250K from my meager option grants.



There are certainly more mistakes I have made over the years. There is the alcoholic coworker who I helped clean up the puke in his office after a boozy lunch who is now a managing director at a major company. But that gets depressing.

What I really wanted to get across is that it is impossible to never make a mistake, but what separates the great from the good is how you handle mistakes, how you recover, and not letting them drag you down.