I recently finished reading every book Malcolm Gladwell ever wrote. I started with The Tipping Point, then read Blink. Next I covered Outliers,  David and Goliath, and finally, What the Dog Saw. None of these books are explicitly about leadership or technology, but there was something about Gladwell’s writing that compelled me to consume more of it. About the time that I was finishing up What the Dog Saw, it dawned on me: Gladwell has a stark and unique ability to look at the world around him and think critically.

Here’s why that overarching theme wasn’t initially obvious to me: Gladwell doesn’t teach his readers how to think critically, he simply demonstrates it, over and over again, until you eventually get it. In The Tipping Point, I learned how trends move from nothing to world-wide phenomena. In Blink, I learned that sometimes my subconscious makes me brilliant, and sometimes it holds me back. In Outliers, I learned what appears to be overnight success actually takes a lot of focus, practice, and good circumstances. In David and Goliath, I learned that what looks like an underdog upset really wasn’t. Upon closer analysis, Goliath didn’t have a chance against David. In What the Dog Saw, I learned that Enron employed top talent, embodied innovative leadership best-practices, empowered their self-directed teams, and it all drove them into oblivion.

Critical Thinking for Building a Tree House

About three years ago, my family convinced me to build a tree house in the woods in the back yard. I do not consider myself a handy individual, by any means. I don’t do my own remodeling, and I rarely fix my own car. I was quite intimidated by the task. I bought the book: Tree Houses You Can Actually Build. I needed to do this because for once, the internet was pretty much useless. Stuff online was either too elaborate to replicate, or so simple, it wasn’t very inspiring.

The book helped a lot, but it didn’t do all of the work for me. The thing about building a tree house is that what you do all depends on the tree on-which you build it upon. The book gave me confidence to tackle to task. I knew what structural principles to apply so the tree house would be safe and durable. I remember spending a lot of time just thinking. I really mean it: A lot of time thinking. My wife and boys would often see me sawing or pounding, but also, they’d see me staring at a sheet of paper or off into the distance. They’d ask me what I’m doing, and I’d answer: “I’m building a tree house. That requires a lot of thinking and only some pounding and sawing.”

The reason I needed to do so much thinking was because I didn’t have an exact plan, only principles to guide me. I spent time thinking because I wanted to avoid wasting materials, or doing any building that I’d later need to tear down and redo. I met that goal, and it’s still standing today.

Critical Thinking for Enterprise Technology

Enterprise technology is my specialty, while carpentry is not. I need to take the lessons from tree house building, and the lessons from Malcolm Gladwell books, and make sure I apply them to my daily work. We’re all really busy. We mostly already know the answers to the questions we will face in a given day. That leaves little time and little motivation to do what is needed most: stop and think.

We depend on experience, knowledge, best practices, frameworks, and methodologies. Based on that we make decisions, analyze problems, build road maps, and develop strategies. We need to pose questions like, why do we believe that? What if what we know is right is actually wrong? What if our efforts don’t actually produce the results we think they should? Is there a different way to look at this? What if yesterday’s solutions solve yesterday’s problems, but don’t work for what we are facing today or tomorrow? What hard work can we do now to be tomorrow’s overnight success?

Experience simultaneously helps us and hurts us. Intuition can be genius or blinding. Best practices may be the path toward stability, but they won’t change the world. What we consider a strength may in-fact be a weakness. What makes us vulnerable, may in-fact make us triumphant. We must never stop questioning and never let someone else do the thinking for us. Context matters. What worked elsewhere might not work here. If something deep inside our subconscious speaks, we should listen.

Technology leaders have plenty going on and very little time and space to do the critical thinking that our organizations are counting on us to do. Read my blog article on Time Management and put some “think time” on your calendar this week. Read Malcolm Gladwell’s books and get blown away by how critical thinking changes the world. Get outside your area of expertise and exercise your thinking skills to get through the challenge.

Thoughts on thinking? Please share them in the comments below. Like my blog? Please share it with your colleagues. Thanks for reading.