David Whyte : How do you hold courageous conversations to lead in times of magnified uncertainty?

In today’s complex organisational world, and in these times of exponential change, we face a growing number of wicked problems and systemic challenges beyond the reach of existing institutions and structures. It is therefore crucial to equip ourselves as leaders with the tools to navigate the volatile, uncertain, complex and ambiguous (VUCA) world we live in and deepen our engagement with our real work.


As we stand at quite a powerful threshold in history, I share with most of you an unquenchable thirst to understand who we need to be and how we need to lead, and that very quest informs the work I’m developing with MACRO Leaders.


 I am well aware that the world as we know it is disappearing at an accelerated rate and that, collectively, we don’t seem to have found ways to navigate the one that is emerging, so I became part of several communities of pioneers that are courageously exploring the edges of this new territory.


 We could easily make the words of Antonio Machado our motto : 
"Traveller, there is no path,
The path is made by walking,
By walking you make the path"

That’s how I got to host systems thinking U-labs in Sydney, assist the production team for Creative Innovation conferences, discover Snowden’s Cynefin framework for leading in complexity through the Leadership Lab, convene the Sydney Facilitators Network, lead sustainability organisations, serve the board of directors for the Welcome Dinner Project, meet monthly with Women in Leadership, support the work of the Hunger Project, teach mindfulness to homeless people at the Ozanam Learning Centre, promote the work of Adam Kahane in Sydney, hold space for the Anthropocene dialogue group, teach resilience at a Networking In Nature event, take part in Mentor Walks, support the work of Wake Up Project, and Humanity in Business, contribute to the Conscious Capital Summit, attend Mindful Leadership Forums and Google Search Inside Yourself Seminars, deepen my understanding of Meg Wheatley’s and Sacred Leadership through assisting the TalkPoint team, etc.


One of the common threads between all the extraordinary people I’ve met through these eclectic communities is their deep love and reverence for the legendary work of David Whyte and their profound appreciation for his unique fusion of poetry and philosophy with the practicalities of leadership and management.


So it was an absolute delight to see so many familiar faces attend the TalkingSticks conference he hosted with Gayle Karen Young Whyte at Sydney State Library on the theme of leading in times of magnified uncertainty. Not only I reconnected with my different tribes as if we were one but I also had the incommensurable pleasure to add some newfound gems to my growing family of misfits and boundary walkers.


The great task, according to David, is to find out what we care about and to risk ourselves on behalf of that. Therefore, to manage the transition ahead, we need, as leaders to take increasing responsibility, and with this increasing responsibility comes increasing visibility and exposure. This is what creates an urgent necessity for conversational leadership : Not only do we need to uncover our blindspots quickly because we are running out of time, but the complexity of the problems we face require many hands, eyes and ears, working collaboratively towards holistic solutions and this requires an unprecedented level of transparency in our communication.

If, to solve the problem, we refer to the strategic and analytical mind, and use mechanistic language, we’ll only access the edge of the pattern. In the field of organisational development, says David Whyte, we need to cultivate the ability to step back in order to get to the center of the pattern and affect the whole system in a huge way.

What does it take to step in the center of the pattern ? It is about settling into our own physical bodies that we have abstracted ourselves from to create a corporate identity. That very body that allows us to sense and represents who we are in the world. The issue is that we are used to associate the body with trauma, heartbreak, and vulnerability. If we think that it is a weakness that we need to hide, we tend to dissociate and numb ourselves in order not to feel our own pain.


However, vulnerability is our key to the world, a way to understand what is about to happen. a way a human being can make a heartfelt invitation to have a conversation.
At its core, vulnerability is derived from the Latin noun vulnus ("wound") and it’s only through that wound, that opening, that we can fully welcome the world in, according to David Whyte or as Leonard Cohen says : « There is a crack in everything, that’s how the light gets in ».


 To be authentic leaders, we need to bring a real physical sense of presence and voice the places where we don’t have competency. We need to invite people to work with us in ways we are not good at. Leading is holding a position with nowhere to hide. Instead of asking : « What is it I have to do ? », we need to ask « What is the courageous conversation I’m not having ? » and let the conversation do the work.


More than ever before, we need to foster collective leadership and a spirit of authenticity and true collaboration to manage the massive transition ahead.
Furthermore, as leaders, we need to be deeply aware of tour own flaws and foibles, and not hesitate to ask the people who depend on us to point at our blindspots. The usual conversations will prevent us from knowing what it is we are not good at unless we dare to ask others : « What are my biggest weaknesses ? »
There is no conversation without vulnerability in the workplace, says David Whyte. At its core, it is about admitting that not only we don’t have all the answers but that we are not meant to have all the answers. If we stop trying to be a paragon of perfection, we’ll find ourselves in a proper and realistic relationship to reality, because then we have to ask for help, then we have to create a conversation, then we have to get the right people in the room with the right talents. And some of our team members might outshine us, so it’s a test of our character and humility to be able to follow a conversation through to harvest.


If you don’t know how to have a courageous conversation, the first step you can take as a leader, says David Whyte, is to stop having the conversation you are currently having, giving up the conversation that is taking your energy and the energy of your team, holding you in the prison of the past.
 As a leader, he declares, you need to bring forth a real possibility for imagination, and hold a space that is big enough to encompass others in a vision of thriving. You need to be willing to be visible even in your wounds, to include even the ones you don’t want to, to have the conversations you are scared to have, to be a face that people are willing to turn towards, to be someone that people can speak truth to.
 As leaders we have to be boundary walkers, and create something we’ll never be completely part of. As Gayle Karen Young Whyte says, we have to be able to be passionate about something and have enough distance to transform it. To see the beauty, and be able to tweak it. We need to cultivate a good relationship to the unknown, to start a meaningful relationship to what cannot be as yet spoken, realise we’re walking into new territory. We can no longer pretend that the change is not happening.
 To cleave, adds David Whyte, means both to bring together and to split apart. As leaders, we don’t get to choose between the two, otherwise we might lose compassion for other people’s troubles and we won’t be able to make a genuine invitation to them, an invitation where we see their places of exile and invite them to belong.
We have to become that conversation and that invitation. That invitation not only makes us human but also fully attentive to other human beings.
 “... to be human
is to become visible
while carrying
what is hidden
as a gift to others...” 
- David Whyte If you are in a position of responsibility, I invite you to reflect on David’s beautiful questions and if you are willing, to share your answers in the comments section : What is the conversation you need to stop having right now ? What’s the real conversation you can start and keep alive? What is your relationship to the unknown ?
And if you care about leadership and having conversations that matter, I invite you to join me either for a one-on-one mindful coffee or at any of the really exciting events I'm taking part of next:
Creative Innovation 2019 is the premiere conference for anyone who cares about creativity, innovation, leadership, change, transformation and the future. The event brings together up to 1000 leaders from business, government, academia, community, not-for-profits and media, who will hear from a world-class line-up of over 40 visionary innovators, futurists and leaders.
As a partner for this event, I am proud to offer you an exclusive discount of 10% off Platinum, Gold and Silver conference packages. To activate your discount, enter the password ‘collective’ when purchasing tickets on the website.