My Biggest Product Management Failure

Jason Alba
Dec 20, 2017 · 4 min read

I’ve had a few PM failures in my 18ish years working with software products. Okay, maybe more than a few. My most embarrassing one had been spending $2,000 of my own money on a software project that failed. Pulling the plug on that hurt, not because I was personally out $2,000, but because it was my first real false start where I had invested too much time and out of pocket money on something that would completely and utterly die.

The bruise on my track record and ego was nothing compared to my biggest product management failure. It was years in the making and the repercussions where shamefully wide-reaching.

To set the stage you must know that I started a CRM for job seekers in 2006. My site, JibberJobber, was a pioneer in this space. I found evidence of two other startups like mine, but both had been started by software developers and, well, they were in high demand. So they started, got a real job, and then left their projects half-done.

I wasn’t a developer (anymore) and so my job search didn’t go like theirs. I was unemployed long enough to keep working on JibberJobber, to the point of launching, marketing, getting customers, etc. My failure in my job search enabled my success in my entrepreneurship.

And, I was hooked. I loved getting positive response from the job search world, especially after months and months of no, or negative, response from my own job search.

One thing led to another and I found myself an author (three times), and flown across the country (and to Istanbul and Belgium!) to speak. Sometimes I was treated like a mini-celebrity… it was probably addicting.

Eventually I was invited to do a course for Pluralsight, which at the time was the best, most amazing company delivering training to programmers and technologists. They promised the moon as far as earning potential, so, even though I had to sign over some IP for my presentations, I decided to do my first course with them.

It didn’t go as planned. The moon was pretty dim, as far as my first royalty check. About nine months later my contact reached out and said “everyone loves your course! Can you update it?” My response was “according to my royalty checks, hardly anyone loves my course…”

Long story short, we talked, figured some stuff out, and I went all-in on their vision. To the point where I spent probably an average of 30 hours a week making courses for Pluralsight. By the time I finished I had spent four years to make 30 courses. That was an enormous undertaking. It was fun, but it was mentally exhausting.

And therein lies my biggest product management failure.

What did I do with JibberJobber during those four years? Not much. Mind you, I had developers, editors, QA, and other people I worked with to “do things.”

But “do things” was not “do the right things.”

My focus was on pushing out the next Pluralsight course while JibberJobber moved forward. The problem was that I had assumed that my team would have picked “the right things” and moved the product in the right direction.

I love my team. I’ve had them for years, and I feel a strong loyalty towards them. I respect them a lot. But at the end of the day, I am the CEO, owner, and product manager, and they are not.

I have been treating them like associate product managers, even to the point of training them to think about product the way I do. But there is a difference in the way a developer things and the way a PM thinks about products and priorities. Don’t get me wrong… I’ve worked with developers who think more like a PM than PMs do. And I love that. But while I was gone for four years I gave very weak product leadership direction, assuming that the individuals on my team would choose to do the right things.

While they did good things, I can’t say they did the right things. I take full responsibility for this, of course. That’s why I say it was my greatest PM failure.

Over the last two years, since I stepped away from my job as a Pluralsight author and back into my role as JibberJobber Product Manager, I have had various emotions. At first it was surprise (at where we weren’t… I thought we had made more progress over those four years). Then it was anger (at where we were… seemingly backwards). And as I worked through the anger, it became hope (for new opportunities and another chance to refocus).

These four years taught me a very expensive lesson: Product management is intention, purposeful, and strategic.

No matter how good your team is at what they do, unless you have an active, focused, and skilled product manager doing what they do, then they will do what they think is best.

They might not be wrong, but their right and your right are probably not going to be the same.

Over the years, developers I’ve worked with have chosen projects for various reason. Maybe it’s the underlying code that is an embarrassing mess and they want to clean it up (that provides little-to-no value to the user). Maybe it’s a pet project they are proud of and want to see through to completion. Maybe it’s a project they think is really, really important, even though it’s not even on the top fifty things customers and prospects ask for.

As a product manager you think about developing products that will increase revenue, increase user interaction, increase branding, increase market share, and position for more increases in all of these. You think about competition, and how you’ll be positioned. You think about sustainability, and the future of the market. You think about partnerships and where technology is headed.

As I think about my future, and the future of JibberJobber, I think of many of these things. But no matter how much time I have… a few hours a week or 80 hours a week, I’ll never step away from my role as product manager again, assuming that anyone else (unless it is another product manager) will give the team the direction they need.

Jason Alba

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CEO of Organize and manage your job search and networking.