Author: Chris Clearfield

How is your relationship with uncertainty? If you’re like many of the senior leaders I work with, you’ll benefit from strengthening your uncertainty muscles.

If you can strengthen your uncertainty muscles, you’ll be able to develop a solid strategy to tackle your organization’s biggest challenges.

You’ll work with more ease because you’ll let go of the anxiety to know the answer and you won’t feel like you need to be right all the time. As a result, you’ll be able to tackle more meaningful problems.

Why is growing our ability to work with uncertainty important? Well, so much of leadership these days is about moving toward the unknown.

That’s because the world has gotten so complex and so interdependent. So many stakeholders, so much to track. Zoom, hybrid work, generational shifts, AI — the list goes on.

We’re at a point where answers aren’t knowable, they are discoverable.

Discovery requires exploration. And exploration is, by definition, moving toward the unknown.

This is distinct from taking risks. Risk is a left-brained phenomenon. Risks are calculable. Uncertainty is right brained — it’s about not knowing the outcomes.

The poet Keats, in a letter to his brother about Shakespeare’s genius, coined the term Negative Capability — “capable of being in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason.”

As leaders we all need to be a little more Shakespearean — to rest in uncertainty without moving too quickly toward solutions.

Here’s three strategies that can help:

Create “Safe Emergencies”

A “safe emergency,” a term borrowed from Gestalt, is a situation that helps us expand our way of being while simultaneously holding us in a safe container.

A safe emergency is a situation that has enough anxiety to prompt us to try something different but has enough safety to make failure feel possible without being devastating.

As a coach and consultant, I’m doing this all the time in my work — challenging my clients in coaching sessions and supporting them as they try something new. 

Leaders can do this, too. Right now I’m working with a skilled CEO who has managed to create a safe emergency in her organization. Her leadership team structure, inherited over successive generations of her predecessors, just isn’t fit for the business’ current challenges, requiring a re-organization. That’s the emergency.

The safe part comes from how she talks about this. “This may not work,” she says openly, again and again. “We think this is the right direction, but we’re not sure.”

Use Experiments to Convert Uncertainty Into Risk

As leaders, we are often so “uncertainty-averse” that we often don’t want to know what’s beyond the metaphorical campfire. We’d rather stick with the tactical and day-to-day than explore the unknown.

How can we make the unknown less daunting?

When we think in terms of experiments — tests with measurable outcomes — we exchange uncertainty for risk. When we’re clear about what we’re trying, when we’re measuring outcomes and changing as a result, we’ve started operating in a different framework.

This is important because, in today’s world, so much is uncertain. The campfire is small and the light fades quickly.

Yes, there is still uncertainty. But bundling that uncertainty into a framework of experimentation changes the nature of it. This is, in a sense, a specific kind of a “safe emergency.”

Join a Community of Learners

Awareness is always our starting point because it’s critical to recognize when uncertainty prevents us from moving forward.

Yet awareness alone doesn’t necessarily solve the problem. Uncertainty aversion is scary and deep, especially as we grow into more senior positions.

Senior leaders — with bigger mandates and greater responsibility for strategy — need to feel more comfortable with uncertainty. There is no magic pill to help them. They need to build these muscles.

A community of learners can help. Your fellow leader-learners can support you, not by providing expert advice on your problems, but rather by supporting you in your own journey. They’re experiencing these issues alongside you — sometimes in different industries or disciplines.

Before I created The C.L.E.A.R. Path to Executive Leadership, my signature 12-week-long journey designed specifically for busy leaders, I interviewed leaders from dozens of organizations.

So many of them told me they wanted to be part of a community of leader-learners that I made this a centerpiece for my program. We just launched our first cohort this week and I couldn’t be more thrilled. Not only are we hosting a community membership platform, leaders will support each other through group coaching and other interactive experiences.

Curious? Book a complimentary 30-minute call. We’ll chat about your challenges and see whether this program might be a fit for you.

Book here: https://calendly.com/chris-clearfield/30-minutes-with-chris?month=2023-10

A few years ago, I was speaking with a senior leader in a conference room at Starbucks (like, Starbucks headquarters, not the coffee shop). We talked about his team and some of the struggles he faced around unleashing their creativity.

About halfway through the meeting, I noticed a plaque on the wall behind him, inscribed with the current version of Starbucks’ values. There was one (I’ll paraphrase it here) that read:

       Have the courage to speak up.

“Huh,” I said, pointing to the plaque. “I think that’s wrong.”

“What do you mean?”

“Well, it’s actually not about having the courage to speak up. It’s about leaders having the courage to listen up.”

Amy Edmondson, a pioneering researcher and scholar I feel lucky to count as a friend, once told me that she wished she’d named her groundbreaking research around “psychological safety” differently.

Psychological safety is all about creating a culture of creativity, sharing, and speaking up. Teams with a high degree of psychological safety learn faster and perform better.

So what did she wish she called her research?

       A felt sense of candor.

That framing resonates with me so much.

In the modern world, the leaders I work with are awash in complex challenges, competing commitments, deadlines, and back-to-back meetings.

Even the best of them are daunted.

This is exactly why they need a cohesive and empowered team around them.

The strongest leaders know that seniority does not guarantee correctness. They try to cultivate a culture of challenge, especially toward them, in their teams.

The strongest leaders learn that their job isn’t to know the answer, it’s to create the conditions for answers to emerge and be acted on.

They know that knowledge and skills are distributed and everyone has unique value to add.

They seek to work flat to unleash the creativity to solve their challenges, seeking ideas and input regardless of where in the hierarchy they come from.

For all these reasons, wise leaders establish a norm of speaking up in their teams.

A norm of speaking up is about people sharing their views. That’s psychological safety — the felt sense of candor your team shares enables them to contribute authentically, without fear of humiliation or harm.

It’s easy to place this burden on others, as Starbucks did — to imagine that our team members or peers need to find the inner courage to speak up.

That’s a mistake because it focuses on a behavior. The thing that we need to focus on is the underlying emotional need: the felt sense of candor.

And that starts with us as leaders.

The intention to listen is what creates the space for others to speak at all.

As leaders, creating psychological safety is about creating a culture where people are willing to listen deeply to others’ wisdom.

We need a “listen up,” rather than a “speak up” culture.

Listening more is a simple prescription, but not an easy one.

That’s why I created The C.L.E.A.R. Path to Executive

Leadership, a program crafted after in-depth research and work with hundreds of leaders at global organizations.

(Spoiler alert: the “L” in C.L.E.A.R. is listening!)

The C.L.E.A.R. Path to Executive Leadership is a 12-week-long journey designed specifically for busy leaders and emphasizes reflection, practice, and tools.

After this program, you will listen better, lead more confidently, empower others (while holding them accountable), and create cohesive and empowered teams with a unified vision so you can drive results.

I’m opening the program up to the first cohort right now.

Curious? Book a complimentary 30-minute call. We’ll spend the first part of the call reflecting on your approach to leadership and wrap up by seeing whether this program might be a good fit for you.

Book here: https://calendly.com/chris-clearfield/30-minutes-with-chris?month=2023-10

I’ve been interested in sharing more of my internal process with you. Why? Well, I talk a lot about staying with the problem instead of immediately jumping to solutions, and embracing the process instead of racing for results. The process of coming to a solution can be messy, non-linear, and dynamic. In my experience, the process of arriving at a solution is often just as important as the solution itself. Solutions may solve one problem, but the right process can solve many. This week, instead of talking about process as a concept, I wanted to give you a behind-the-scenes peek at what mine recently looked like.

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Adrian Lee, an editor at The Globe and Mail, reached out to me a couple of months ago and asked if I would be interested in writing an 800-word opinion piece about the current challenges in Canadian civil service.

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My first response was, “No.”

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A shift I’ve made that has been significant as a regular over-committer is to evaluate potential opportunities and commitments through the lens of “the full body yes.” It’s a concept I picked up from Scott Schute’s book, The Full Body Yes, which I wholeheartedly recommend. I didn’t think there was anything there for me to say. I was reluctant to be seen as a U.S. citizen critiquing Canada from the south, especially when American institutions are fraught with their own challenges and deficiencies. Adrian told me to think it over. You see, I’d written an article for The Globe and Mail around the time that Meltdown came out, and he believed there were connections to be made.

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So, I went away and thought about it, jotted some ideas down, did a little bit of outlining, and started forming a conversation. Once I got started, the ideas kept piling up! I got to a place where I thought, “Okay, I have something to say here, but I think I’ll need more than 800 words.”

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Zooming Out

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As I zoomed out, I began to think about the examples we wrote about in Meltdown. I realized that a lot of them really are public sector challenges. We wrote about the Washington State Department of Corrections releasing prisoners early, for example.

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The last couple of years have seen no shortage of public sector institutional challenges—delays in the U.S. State Department, disruptions in Britain’s National Health Service, backlogs in the Canadian passport system, the global handling of COVID (and how successful different countries were with that).

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As my thinking broadened, it became clear that my resistance was needless. Really, this is a global question: “How can leaders who are responsible for essential systems implement the changes they need without breaking the metaphorical plane mid-flight?”

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While Meltdown is about systems and organizations, my work since then has been to support leaders to build cohesive and empowered teams. So, the question put forth by The Globe and Mail was not so different from my own day-to-day work with organizations and the leaders who run them. The complexity and challenges faced by modern organizations are not limited to commercial enterprises. Public sector organizations are likewise affected by rising complexity.

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It became clear to me that the tactic to employ here is similar to one I use with the leaders I work with: Rather than come at the challenge through the lens of systems and complexity, we need to approach it through the lens of leadership.

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Writing the Article

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The process of writing the article itself was an exercise in working across multiple teams, collaborating on a goal that was broadly defined at the outset but desperately needed focus. The initial goal of an 800-word opinion piece about Canadian bureaucratic issues ballooned into a 2500-word treatise on the challenge of being a leader charged with combating the global decay of civic institutions. It’s a deep, heady topic — big, and easy to get lost in.

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I paused for reflection often, allowing ample opportunity to collaborate with The Globe and Mail’s team and to receive feedback on what was working, what wasn’t, and what we wanted to try next time. Fortunately, this process of using open curiosity and co-creation is one that I teach leaders to employ in their own organizations and with their own teams. I found the synchronicity of that to be gratifying.

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You can see how my thinking shifted throughout the process, slowly morphing from a “No” (or at least not quite a “full-body yes”) to a “Yes,” but with iteration — namely the expansion from an 800-word essay to a 2500-word article. By slowing down versus rushing to an answer, and by focusing on the process instead of the end result, I was able to turn an opportunity I nearly declined into something I’m really proud of.

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So, how did the article turn out? I’d be so grateful if you gave it a read. Feel free to leave a comment to let me know what you think. After all, feedback is an integral part of the process.