Why Do You Do What You Do? An Interview With Simon Sinek

By David Hassell

Simon Sinek is a best-selling author, speaker, and trusted advisor to 15Five who believes in the WHY behind our communication software.

{Watch the video on YouTube}

Over 90% of small businesses fail in the first 3 years.

But Simon Sinek beat those odds with his own company, only to discover that something was missing when he hit year 4. He realized that all of his energy was wrapped up in pretending that he had everything under control, and pretending he was happier and more successful than he actually was.

That is when Simon came to understand that every single business or career follows the same pattern:

– We need to know what we do.

– We need to know how we do it.

– We need to know WHY we do it.

This begs the all-important question, do you know WHY you do what you do

Simon discovered his own WHY and realized that it is truly the WHY that differentiates the simple do-ers from the fiery, passionate leaders that are disrupting industries and changing the world we live in.

Boba Fett?

Simon explains that leadership is the act of being a compass. Authorities think that they have all the answers and tell people what to do, but that is not leadership. Leaders must be in service to those who volunteer to help achieve the mission. They base their actions, thoughts and words off of the organization’s ‘WHY’. Leaders steer while others do the work to move things forward.

The words and symbols that leaders use to refer to their businesses are paramount. From the Boba Fett figurine on his desk reminding him of the importance of the rebel spirit, to his decision to refer to his business not as a ‘company’ but as ‘the movement’, Simon demonstrates the importance of a deliberate, consistent decision to keep our WHY at the center of all that we do as leaders.

It can be all too easy to lose sight of the impact that our daily words and actions have on our company while we are busy working on the bigger picture. But at the end of the day, it is those small actions and behaviors that define our leadership and shape our organizations.

WHY 2.0

Simon first shared his ‘Start With Why‘ philosophy with friends who immediately saw an improvement in their lives and businesses, and the movement spread like wildfire.

He has been instrumental to the development and continued growth of our organization and product, and has inspired every member of the team to consider their deepest life purpose.

In June, Simon surprised us with a visit to our San Francisco office. He asked the team several question and in less than an hour we had something.

Simon Sinek Igloo

Our WHY used to appear as follows:

15Five WHY version 1

We continue to help others achieve their potential through streamlined communication, but Simon worked with us to see that our WHY runs much deeper than that:

15Five Why Version 2

Our customers use our software in countless ways, and hopefully to help implement their own WHY’s. We support all of those initiatives, with our intention set on creating space for excellence within our organization and without.

Why Simon Doesn’t Answer Questions

We advocate asking great questions on a regular basis to get employees and managers talking about what is most important. Naturally, I asked Simon if he had any favorite questions that he liked to ask his team to ensure that they are staying aligned with the WHY. And in true Sinek style, he turned my question on it’s head.

Here are my two favorite take-aways from his response:

1. Questions Encourage Independence
Simon explained that whenever a team member comes to him with a question, he typically responds by throwing the question back to them. “The temptation to tell somebody what to do is so high” he explained, “but what happens is that people become very good at doing as they’re told, but they don’t get very good at thinking or solving problems”.

2. The Power Is In the Reason
In order to encourage his team to act with intention, all team members know that they need to be prepared at the drop of a hat to explain the reason behind their actions and decisions. This encourages intention and helps make sure that every action is taken with the goal of moving the WHY forward.

Personally, I have come to the conclusion that your WHY is your power. It is the drive, the fuel, the passion that propels you (and your business) forward. It can never be damaged, broken or taken away from you. But above all, it is your responsibility to nurture that WHY with every word you speak, every step you take and every decision you make. I encourage you to find your WHY – and become your greatest self.

What was your biggest takeaway from the interview? I’m looking forward to reading your answers in the comments below!


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