Harness the Unknown: Transforming Uncertainty into Strategy

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

3 Mistakes most leaders make with change

And how to avoid them!

download the free guide

* When you subscribe, you’ll also receive The Breakdown newsletter: tools and reflections on the practice of solving impossible problems. We respect your privacy. Unsubscribe at any time.