Leading While Lost

Can we lead when we're lost?

This is an unsettling question. Because knowing where to go and how to get there — being the one who can guide the others — is a big part of what many people imagine leadership to be about: a leader-follower model.

This is also an urgent question. Because so much of the leader’s role today involves being stuck. Stuck, for example, between opposing objectives. You can’t seem to get closer to one without getting further from the other. Short-term versus long-term. Profit versus sustainability. Work versus family. Shareholders versus society. Time for others versus time for me.

Or stuck in a different way: by the awful recognition of giant problems that need to be solved but can’t be solved. Like climate change. Or the death of truth in public discourse. Or the deepening of inequality. Or the spread of addictions — chemical and digital. Or social fragmentation.

What is leadership when there is no way forward?

For the last 15 months or so, I’ve been working out a response to this question — in part in-tellectually, but mostly in-collaboration with hundreds of people who have courageously joined me in some social experiments to “lead while lost.”

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In-tellectually

My personal conviction has become that the most impactful forms of leadership today requirenot knowing the way forward. Maybe I’d go so far as to say that leadership today is when people who should know where we need to go and how to get there instead have the courage to stand up and say: “I’m lost.”

For two reasons. First, because that admission is True. When people who should know instead admit that they are lost, it helps begin to restore society’s broken relationship with Truth. It helps restore Truth as something complex. As something bigger than any leader can possess or understand. (And if you’ve seen my TED Talk, you know that I’m much more worried about society’s addiction to simple truths than I am about the lies we spread.)

Second, having the courage to stand up and “not-know” invites others to do the same. The world is changing fast. And so at least some of the maps we navigate the world by — the maps that tell us where to go and how to get there — don’t reliably do either of those two things. We need to make new maps. That much is obvious from the outset. But what is wrong with which of our maps? That only becomes obvious after some brave stumbling into the unknown.

To stand up and say “I’m lost” invites the people around us to explore that unknown together. To journey.

Here’s an overview of what that journey might look like. (If you want the details, you know how to reach me.)

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In collaboration - basecamp:London

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A few weeks ago, 100 improbable people came together for basecamp:London, to experiment with how to take the first steps on this journey.

Basecamp:London was the second such experiment. The first was basecamp:Toronto, last November. The Toronto experiment validated the idea that whenever the way forward is not clear, coming together can be a powerful, meaningful response that reveals unexpected pathways to action.

Basecamp:London sought to repeat that meaningful act of coming together, and to test what happens when we collectively invest more resources into the gathering. Toronto was one day, London was a full day-and-a-half, with a night in between to eat together, play together and “consult with our pillows.” Toronto was in a tight downtown room; London was in a sprawling castle. In Toronto, we navigated an improbable diversity of backgrounds and perspectives on our own. In London, we had help from a half-dozen professional facilitators.

Some things stayed the same. London, like Toronto, was an entirely volunteer-organized, non-profit gathering. Despite the heavy financial risk to the organizers (!!), invitees were not obliged to pay any fee to take part. Instead, everyone was invited to “contribute what you can.” Most of the 100 participants opted to accept that invitation and contributed in amounts ranging from $10 to $10,000.

Basecamp:London taught a lot of lessons. It clarified several “tensions” — from the interpersonal to the theoretical — that efforts like this raise. It showed the magical possibilities and awkward challenges of the “contribute what you can” model. It made clear that the journey from “unsettling question” to “bold expedition” is longer than a single meetup.

For me, basecamp:London was personal proof that the same circumstances that make us feel stuck can also liberate us. Not knowing the solution, not knowing the way forward, is not an obstacle to hope. It is the wellspring of hope. It is what compels us to come together in new ways, to surround ourselves with the “mix that is missing” from our daily lives. All in a spirit of discovery, and healthy self-doubt. Not knowing the way forward is what entitles us to explore fresh directions for human flourishing.

I’m grateful for this shift. I want everyone to experience it.

Right now, the organizing team and I are collating the output scrapbook from basecamp:London. We’re also finalizing a journey proposal for 2020 and beyond. If you were at basecamp, you’ll be the first to receive an invitation to access both. (Our intent is before year-end).

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From Question to Conversation

For now, let me share one concrete take-away from these basecamp experiments, which is an emerging method for reliably turning “unsettling questions” into “unusual conversations.”

“Leading while lost” begins with an unsettling question, along the lines of “I don’t think we can stay here anymore. But where else could we go?”

(For example, at basecamp:London one group re-examined society’s whole relationship between people and computers. They realized that the present relationship must change, because our present ways of thinking about and using computing technologies are dehumanizing. But how is a humanizing use of technology possible?)

The next step is to broaden that question into a conversation. The conversation has to be unusual. Otherwise, it will simply reinforce our usual ways of seeing the problem.

So, diversity matters. But what kind of diversity should we aspire for? In the weeks since basecamp:London, I’ve had to answer this question several times, to several different audiences. And (with the help of others) I’ve begun to draw this picture to explain what I think we’ve learned so far. I’ve begun to call it our “conversation canvas.”

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The canvas is made up of five questions:

1. Who’s going to bring us back to where we began? It’s hard to fully appreciate how far our own thinking on a question has evolved, without a reference point—someone who can tell us how much our thinking has changed since embarking on these conversations.
2. Who can connect us to what came before? Who can we speak to who can help us connect to values, to principles, to beginnings, to history…?
3. Who can we reach out to? Who is usually at the margins of this question? Whose views aren’t normally taken seriously, but that we will commit to hearing?
4. Who can we bring together? What is the mixing that rarely happens on this question, that we have the opportunity to convene?
5. And finally (5), What is the conversation I need to have with myself? Have these conversations led to a new awareness of our own assumptions, biases or blindspots, so that we can now see them and reflect upon them?

“What is leadership when there is no way forward?”

This canvas is one meaningful, tested response. The outcome of completing the conversation canvas, I’ve learned, is not the answer to the question. Instead, it’s a deeper insight into the problem. Into “what’s wrong with which maps.” The outcome is also a strongly committed group of diverse people from diverse viewpoints. All of whom feel heard. All of whom want to explore new pathways together.

I shared an early draft of this canvas publicly for the first time a couple weeks ago, in a workshop with a global group of 24 senior executives on Oxford University’s Strategic Leadership Program. They found it to be a useful frame for shifting from feeling “I’m stuck” to feeling “I’m at the beginning of a journey, whose destination is uncertain but probably significant.”

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Possible next step

Apply the “canvas” to convene an unusual conversation around an unsettling question that’s got you stuck — then tell me your story. This is an emerging method, not a refined tool. Please help it evolve. (Find me on Twitter @ChrisKutarna.)