Why Asking “Why” Creates Better Employees

In his book (and TedTalk) Start with Why, Simon Sinek advocates for “purpose built” marketing. He makes the argument that powerful brands are built from an inspirational purpose and that people are naturally inclined to buy, and be passionate advocates for, something that they can identify with and believe in.

Purpose, or what some people call mission, is also essential for organizational success. Jim Collins, the Author of Good to Great, and many other articles and books on business and leadership advocates for developing a strong “core ideology” which includes a “reason for being.”

Unfortunately, we often see “Why” as a tool for putting together long-term strategies, not short-term tactics.

Why Asking "Why" Creates Better Employees - David DeWolf

I’m in the middle of an EA transition, and have decided to fill a six month gap with temporary employees. I was recently struck by the way my newest assistant came up to speed.

Having laid out quite a bit of background information about the objectives of her role, my expectations, and the peculiarities about me and my preferences, I expected that she would come back with a handful of clarifying questions. “I see that you prefer to avoid traveling on the weekends and flying your preferred airline. If I have to choose between the two, which one takes priority?” These are the types of questions I’ve received before.

Instead, my newest assistant asked “Why?” “I see that your ideal schedule is quite different on Tuesday and Wednesday than it is on the rest of the days of the week. I’m wondering why? Can you help me understand your intent?”

Wow! Powerful.

This person understands the importance of the reasons we do things. She understands that if she can get into my mind and understand my intent, that she can make better judgement calls – offloading even more from me.

Ask why, but also proactively communicate why, not only in the long term and strategic, but also in the short term and tactical. This is empowering to those who follow you. It provides context, motivation, and understanding — all of which will enable them to be more effective.


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