For all the methodologies, crappy business books, and numerous project management/product management/brain storming/planning software out there, most of it fails at deep thinking on how a product should work.

My number one tool remains a notepad and a pen. When we had an office, it was a white board and as many markers I could find that still work.

This isn’t in praise of the blank slate of analog tools. This isn’t a comment on the tactile nature of physical things. What I actually want to do is highlight a process I go through.

The most important “tool” in product management is writing things down over and over and over again until they feel right. Write down a flow chart, vocabulary words, diagrams, paragraphs, or whatever it takes to describe a problem and one possible solution and then stop. Think about how it feels. A few days later, don’t review what you wrote– do it again.

Do it again.

Do it again.

Every time I write it down, I either become more convinced that the rough edges are not so rough or I find my way to a slightly different perspective on a problem that leads me closer to the answer. The end result may look exactly like the first thing I wrote down. Maybe the language is a bit different and there are fewer squiggles as I got to my end state more assuredly. But the thought process that took me from my “guess” to my “solution” is a powerful one.

Through repeating my thought process, I become powerful at objection handling. I see the false paths I have already traveled. I become confident in the trade offs I am making along the way. I don’t know the answer to every question about what we’re about to build, but I come to believe that there are answers and that the problems which remain are relatively small. I have avoided the essential pitfalls that lead to us being stuck with no way out but to scrap all our work.

At this point, I have something damn near a “rule of three”– if I haven’t tried to work a problem from a blank page three times, I haven’t thought about it enough.

A vertical notebook with writing about a product problem I was facing, including some small diagrams and many arrows.