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At the Heart of It All

“Regardless of the myths we are telling ourselves, what kind of company or organization are we truly building? At the end of our days, are we becoming the person we’d like to be?”

– Jerry Colonna, from Reboot: Leadership and the Art of Growing Up

As COO I sit in the tension between strategy and structure when it comes to building our company with my fellow amazing partners. Part of my job is to plan the work and work the plan– to operate and execute towards where we say we’re heading. I (partially) joke that part of sitting in that tension means I make a lot of to-do lists and then get frustrated when we’re not crossing things off fast enough. The things I keep in the back of my mind that guide the to-do lists are qualitative questions: Are we executing according to our vision and mission? Are we in integrity? Are we clear about what we’re creating, what needs to be done, and who’s doing what?

The big question we hang right near decision making and visioning is: Are we building the company we want to work for? This has become our guiding principle in many decisions. How do we define our benefits and company policies? How do we want to interface with potential clients? How do we keep fiscal responsibility and sustainability in mind at every juncture? How do we hire? How do we fire? How do we grow? The Big Question is like a moral imperative that keeps us honest. It keeps us on the course we say we want when faced with all the questions that come with building and running a company at inflection points and fast growth, and even when we lift our head up from the daily grind.

We often couple this big question with another litmus test: As Jerry often asks, How would we feel if our kids worked at our company? Would we be proud of what they would experience? As he’ll challenge, would we feel good knowing that they are safe, well-treated, and being given the opportunity to grow into their fullest, most adult selves?

Are we, at Reboot, building the company we challenge our clients to build? And, if not, why not?

What surfaces from these inquiries then reverberates into the lists of things to be done, to the hearts showing up with us each day, to how we execute growth. It carries with it our ethos and the experience of the container we set up (that being the company), and for all the good work we’re delivering.

The bigger the decisions we face, the more we sit with such questions. For, as anyone who’s been coached by one of our amazing coaches knows, there’s a power in grappling with such questions. Such questions are, after all, at the core of Reboot’s encouragement to radically inquire within.

As Jerry points out in his forthcoming book, well-asked questions are not only core to good coaching but essential to great leadership. They are, in fact, the means to a well-lived life.

In some ways, we let these questions speak and rattle around in us a bit. These are questions that keep us clear on not only what we want, but what’s important. They help us to hold fast to those anchors so we do not get lost in the friendly noise, suggestions, thoughts that sound like “You know, what you should do….” from the outside-world-slash-peanut-gallery.

A couples therapist I know often says that no one knows what’s happening in your relationship more than you and your partner. I think the same goes for the questions and issues arising at the heart of our businesses and companies. While the questions or issues may feel hard, rushing through them doesn’t make it easier or more graceful. Advice from the external world doesn’t always fit, either, because the proverbial ‘they’ aren’t living with your specific edge-case-to-any-playbook situation. Lao Tzu’s oft-uttered lines tell us:

“At the center of your being you have the answer; you know who you are and you know what you want.”

In this podcast conversation with the Wistia Co-founders, they talk about how they circled around the question “What kind of company do I want to build?” and decided to take back their company from their investors. Sitting with that question and then acting on their decision aligned them with what they really wanted in what some would call a bold move.

So often we heed the questions we face and the decisions we need to make with a frenetic sensibility towards answering them. We move fast and fail often to sit with our own thoughts and feelings. In our Operation team call this week, a colleague reminded me of the lines from John O’Donohue’s poem For One Who Is Exhausted

“You have traveled too fast over false ground;
Now your soul has come to take you back.”

The false ground is where we find ourselves when we rush through life and the questions we’re presented with. How do you create space to be intentional in your decisions, to sit with all of the questions at the helm? How can you slow down and sense what’s emerging from the questions or chaos or new growth?

It’s a different way of being with things. Sometimes we have to look awry versus straight on at something. Slowing down allows us to move at a pace different from rapid-fire thoughts and rationalizations. We sense with the largeness of our body, with the fullness of our hearts to pick up on emergent themes. Our soul comes to take us back.

What kind of company do you want to work for?

Whether you answer that question consciously, intentionally or not, you’re creating that company every day. Each day we show up at work we’re committing to that. Without a pause to question and get clear about what we’re showing up for, as the days go by, we could find ourselves muttering “Well… How did I get here?” As you sit with the big questions yourself, I’ll offer you a poem as a companion penned by our very own Jim Marsden, which has become the official Reboot poem:

The Question

an homage to David Whyte’s ‘Self Portrait’

It doesn’t matter to me how much you’re worth on paper,
or who you know or hang out with.
I want to know what your heart values
and what courage – perhaps dormant –
inside of you
to dare to pursue that for which your heart truly longs.

It doesn’t matter to me how close you are to an IPO,
or if there are whispers of “unicorn” stirring among investors.
I want to know why this business matters to you
and if there’s any chance of cultivating
culture, relationships, and business that
brings people – including you –
into their own wholeness and vitality.

And what stops you.

It doesn’t matter if your bank account has one zero or many,
I want to know if you’re willing to melt
into the fire of why it is you are you in the first place.

I’m not interested in the litany
of sacrifices and trade-offs
you’ve made to get here.

What is it that you carry
that cannot and
will not be sacrificed,
no matter what the opportunity
or the promise of salvation?

I’m curious if you know or sense the amazing
power and vitality that comes from
for this being the day to be alive.

And to know that prosperity is to be found in how we live our lives,
not in the spreadsheets and stories
we tell our investors, our colleagues or ourselves.

I have come to see that those who speak
and step into
the paradox and tension of not knowing
guided by haunting questions of
“where do I go from here?”
“but how can I? and, how can I not?”
“who or where am I now?”
cross a threshold of not knowing

toward a place where you become aware of things
your body can not remain unaware of any longer,

where vitality, success and
the joy of simply being human


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