The Organize IT Habits: Always Ask Why And How

February 11th 2008

Ever met somebody who always had questions and continually looked to tweak and improve? These people aren’t negative and critical of everything, they are simply curious and inquisitive. Looking at why things are the way they are and how they can be improved is one of the strongest mindsets you can ever develop. Look at highly successful people and it’s a guarantee they will have thought about everything this way. In this second entry of my Organize IT Habits series, I will take a look at this mindset, encourage you to embrace your curiosity and to always ask why and how.

Here is a story from one of my previous jobs that stuck with me ever since. One month we failed to hit our targets for that period. Our manager, who was not one for motivating staff anyway, decided to lay down the law and made some idle threats about removing privileges, pay rises etc. She also decided to put up a big poster which detailed exactly what was expected of us and how we should hit out targets.

Three months later we failed to hit our targets again, by a bigger margin this time. What did she do? Made bigger threats, clamped down harder on any privileges we had left, and amusingly put up an even bigger poster. Lo and behold, yet another three months passed and our team performance and moral deteriorated even further. She ended up putting up a poster so big it covered an entire wall.

The point of this story? What really struck me from the whole experience was that at no point during that year did she look at herself or the situation in general and ask why things weren’t working. If she had she would have seen a clear correlation between her actions and our performance. In fact not once did she ask why the team failed to hit its targets in the first place. It could simply have been a blip or an issue with staff numbers. She wasn’t curious, she didn’t explore the issue, she just used her default response to any managerial problem. Needless to say, I left that job and am now much better off.

So many people end up on unhealthy paths or develop destructive mindsets simply because they don’t stop to ask why or how. Why are things the way they are? Why am I drinking so heavily every night? Why do I struggle to communicate with my boss? How can I find the motivation to go to the gym regularly? How can I improve my productivity system so it doesn’t keep falling apart? How can I save money on my groceries?

It’s the basic building block for improving anything, whether it be with turning around a struggling project or when focusing on your own personal development. Ask why something isn’t working and how it can be improved/fixed. Try doing it now. Open up your productivity system and look at one thing that isn’t functioning how you want it to. I’ve always tried to deal with cutting back the amount of times I would fall off the GTD wagon, and by asking “why” and “how” whenever it happened, I’ve slowly evolved my system to the point where having it fall apart is a rarity rather than the norm.

Another benefit of this habit is it plays into our natural curiosity. Curiosity is one of the strongest traits you can have, and it’s unfortunate that as people get older they tend to neglect and even suppress it. Just because curiosity killed the cat, it doesn’t mean you will suffer the same fate! Quite the opposite in fact, some of our greatest minds were extremely curious and inquisitive. It’s great for developing your brain to ask how something works the way it does or why things behave the way they do and you never know what sort of useful information you might discover.

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