The Investigative Mindset

Knowing where to look for answers is more important than memorizing a set of requirements or rules.

I have a confession: I often have no idea what I’m doing.

I remember clearly what it felt like my first day at my job: I was new, overwhelmed, and maybe even scared. But the work was exciting, mind-filling, and fun. Now, several years into the role, I still feel this push-and-pull. I’ve learned to juggle these opposing feelings and be both productive and successful at my job.

The key to this—and I believe one of the most important traits for my success—is an investigative mindset. Knowing where to look for answers is more important than memorizing a set of requirements or rules.

Why? Rules and requirements change, and the context I work in is constantly changing. I’m more productive in my work by making good, informed decisions—not by the book. I can work smarter, gaining a new awareness of how everything works.

How? To develop this mindset, I exercise the following:

1. Take initiative on my own first: do the legwork to find the answer. Be tenacious and know where to look.
2. Ask questions, know when to stop looking and ask for help. Not being afraid to be ignorant or wrong.
3. Share my ideas for the better solution.
4. Look to my teammates as a critical force—we learn together.

Often, the investigation takes me out of bounds—out of my “area”—that’s OK, and natural. I talk to other people outside my team, and I learn a bit more about how it all works together. I fill in the gaps in my knowledge. I’ve raised my awareness.

It wasn’t always this clear for me … after only 3 or 4 months into being at Automattic I had a revelation that changed my mindset—put it into words. One day, I ran into a quote one of our internal P2 sites, expressed as a formula or pseudocode.

( intuition + investigation ) > memorization

I said “Yes, Yes, YES!” I was in the privacy of my home office, so no one heard me, of course. It really made sense, though. And it alleviated part of the struggle I was having to completely internalize all the things I was supposed to know and do. All the stats and bots and checklists and dos and donts.

This was later echoed by something UX guru Jared Spool said at An Event Apart:

The mindset of investigation is about informed decisions, not going “by the book.” Dogmatic, rule-based methodologies exist only to enforce things; they avoid critical thinking and good decision making.

I realized if I made good, informed decisions I could solve problems in both normal and edge cases. Instead of a one-time answer, I could build a framework to answer any question. A mentality. The outcome of finding the answer, solving the problem, sharing the solution—rewards this mindset. A loop. Doing it over and over.

This feedback loop is hugely powerful. It gives me confidence to continue to strive for an investigative mind.

Notes:

1. A video my colleague Justin Shreve posted echoes this investigative mindset, specifically as it applies to software development: Being a developer is being a problem solver.

2. Thinking about investigation reminded me of my time in the Future Problem Solving (FPS) club in high school. We found creative solutions to mock issues like world hunger or renewable energy. It was fun and challenging, but the best part was the process itself. Investigate, organize, present, debate. Learn. (Random trivia: according to Wikipedia a later team from my school won a state FPS competition. Rock!)

3. One more quote: “Never memorize what you can look up in books.” —Einstein (unsourced)