Do You Know Your WHY? You Can’t Lead Without It

by / ⠀Career Advice Entrepreneurship / December 31, 2013

I find it very strange how often we’re asked, “So what do you want to do with your life?” or better still, the post-education version, “So what do you do for a living?”

Oh the joys of small talk.

The reason why most people hate this mindless (sometimes awkward) chit-chat is because it’s all about the “what” and never about the why. When did it become more important to have a job description but not necessarily a purpose?

To me, no one wins when we don’t push each other or ourselves to bring meaning to what we do. As leaders, we cannot skate by on an idea, no matter how great, without knowing the reasons driving us forward. We must demand this of ourselves and the people we work with.

Your North Star

Purpose is what stokes our passion and guides our decisions. I am constantly inspired by Simon Sinek’s philosophy on becoming obsessed with your “why” and have folded it into my company’s culture

Why did we create 15Five?

Why should people use 15Five?

Why would we change x or fix y?

Most of the time we’re all too busy focusing on the how and the what, but with so many tools and experts out there to help us build, fix, change and grow our businesses, those aspects just take some time and effort. Understanding your motivations, however, is an inside job and requires frequent reflection. 

I have heard from other entrepreneurs of times they’ve headed in a direction, usually the path of least resistance, just because they could or as a knee-jerk reaction. Whether it was building out a million features, going on a hiring spree or seeking investment, they did so out of reactive momentum not because it contributed to their fundamental goals or why they started their business in the first place.

They did not stop to ask themselves why they were doing it, but became content with the sense of “accomplishment” that came from getting stuff done. Before they knew it, the company was running them and not the other way around.

Choose whatever metaphor you like: a barometer, a guiding light, a compass, a map, however you describe your WHY, it will always serve as a measure to only do what needs to be done and actualize your true intentions.

Stop The Clock

As the saying goes, do what you love and you’ll never work a day in your life. Of course, this is the ultimate goal right? To lose the extraneous feeling that comes with tedious, meaningless work and only do the things that make you happy and fired up.

When you become obsessed with your why you will lead your team with passion. You request their commitment to the cause and not their time tied to a desk. When you create this purpose-driven culture, you don’t have to be slave to the clock. Enthusiasm and energy to reach goals means you’ll be better at prioritizing your projects and honing your focus on only the things that matter.

If you feel yourself anxious to leave work, counting down to your next vacation or just feeling listless and low energy, it might be time to revisit your original desires and see if they are a) still the same and b) reflected in the work you are doing. When the answer is “no” for either, you owe it to yourself to take some time to really think things through and perhaps, make some changes.

The impact of bringing in a lackadaisical attitude into work can ripple through your team and destroy even the best company cultures.

Simple Ways to Uncover or Rediscover Your Why

The rush of running a business can mean juggling a million thoughts at once. Sometimes, without knowing, your goals can get buried with the piles of to-dos or your passion flickering from exhaustion. Here are just a few tips to help you keep in touch with your intentions and motivations:

1. Press Pause

It can be difficult for leaders to turn themselves off or distance themselves from work without the fear of control slipping away. Great leaders allow themselves time to pause by empowering their teams to steer the ship without fear of falling off course. Even if you’re not 100% comfortable with taking a break to unplug and reflect, you still should. Really. You win by giving yourself time to explore how you feel about the current state of your business and your team wins by learning how to run things without you.

Another way to look at pause is to allow 10 percent of your time at work to be spent tackling something you’re passionate about. Brad Smith, CEO of Intuit is considered a thought leader when it comes to providing unstructured time, for yourself and your team. He believes allowing for freedoms to pursue ideas, even those unrelated to work, is how to generate new and innovative ideas. The proof is in the pudding:

“Last year we counted $100M in new revenue from product offerings that didn’t exist three years ago, and much of that was the fruit of unstructured time.”

How can you argue with that?

2. Conversation is Currency

Feeling lost? Open up.

Many people feel vulnerable when they feel like they’ve lost their sense of purpose. Some might even feel as if they have failed if they can’t remember what their pursuit has all been for. I know I have days where I’m not sure what to do next or why what I’m doing even matters. Going inward is always important, but that doesn’t mean help can’t be found on the outside of your head.

Talking to a good friend, a colleague, family or a mentor can help you offload the clutter. They can steer the ship so you can navigate your way back to the core of your intentions. Or you can ask of your team what their understanding is of the company’s mission and direction. It can be an incredibly illuminating litmus test to hear their interpretation of the high-level direction and purpose of your organization.

3.  The “At the end of the day” exercise

I do this a lot, and not just with work-related matters. If I find myself with scattered thoughts and tangents running wild, I stop whatever I’m doing or thinking about and say “At the end of the day, I just want to build a product that helps people.” Or “At the end of the day, I just want to be a good father and husband.” This sentence helps you boil everything down to what truly matters to you. Knowing you want to “help people” does away with building features that are cool but useless or adding services that are nice-to-haves but add zero value to your clients. The above are general examples, but the point is to translate your WHY into a specific mantra. Use this exercise to re-center yourself and clear your head.

Leading without a why is like the blind leading the blind and eventually the inmates will run the asylum. You’re more susceptible to taking bad advice and you end up getting stuck in a reactionary rut, derailing your desire to truly be innovative and unique. Only when you find your purpose and demand the same introspection of your team, can you truly achieve success — and sustain it.

David Hassell is a serial entrepreneur and current founder & CEO of 15Five, a SaaS company that enables organizations to streamline communication and feedback. Follow him on Twitter @dhassell.

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About The Author

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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