Author: Chris Clearfield

“As leaders, we need to get more comfortable with conflict and make space for disagreements. Messy is a valuable part of the process. Struggles, disagreement, and conflict in the mix creates authentic unity over time. Great work involves struggle.” – Emergent Strategy by Adrienne Maree Brown

 

I often work with leadership teams on problems that don’t have a fixed answer. Like heroes on a quest, we might know the direction of travel and have a sense of where we’re going, but we don’t know exactly how things will end up or what we will find along the way. Sometimes the destination is clear, but the route to get there is up for debate. Different team members see the value of one plan or the potential pitfalls in another, but no one can be certain that they know the best course of action.

 

One of the most valuable things leaders can do is hold space for ambiguity and disagreement. A leader’s job isn’t to come up with all the ideas on their own, it’s to create the conditions for ideas to flourish. Let people argue it out! Just make sure you focus the disagreement on the task and not on the personalities involved in the dispute.

 

Bring together a diverse group that doesn’t give ideas the benefit of the doubt. Diverse groups are better at questioning what they don’t understand.

 

As leaders, we’re rewarded for impatience and certainty. That can make holding space for disagreement, which is messy and time-consuming, challenging. But complex problems are characterized by ambiguity and disagreement. In fact, struggle is an indicator that you’re moving in the right direction. After all, if the problem were easy, it would already be solved.

 

To effectively hold space for disagreement, you need to manage your own uncertainty and anxieties. Anxiety can flare up as a problem gets messier. If you aren’t calm and open to the possibilities, your team won’t be either. People need to feel safe to put forward their ideas. And you, as their leader, need to trust that you and your team will eventually converge on the right path.

 

I support leaders as they co-create solutions to their most challenging problems. I coach people to lead transformational change. If you’re feeling daunted by a complex problem, send me an email or connect with me on LinkedIn.

 

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Some organizations I work with feel like perpetual startups.

 

They’re constantly moving in new directions, adding new technologies, and inventing new ways of working (I’ll admit that I feel like I’m like this sometimes, too).

 

It’s not that inventing things or exploring new ideas is bad. Of course not! Imagine a company that could never try or do something new. Over time, those companies go stale and, eventually, they all get a familiar label: bankrupt. However, companies that continually change their processes face the same threat. It’s easy to work really hard on the wrong things.

 

A software company I worked with became trapped in a cycle of reinvention, constantly changing its product and its offerings while ignoring issues that impacted functionality and utility. Leadership lacked an understanding of the product and its customers, handing down objectives that weren’t proven out in hopes that the company would be perceived as a cutting-edge industry disruptor. This caused a great deal of frustration, waste, and expensive employee and customer overturn.

 

You cannot be a startup forever. At some point, your company must stabilize, settle into itself, commit, and deliver. That isn’t to say you can’t or shouldn’t continue to innovate, but you should stop chasing every single shiny thing flashing in your periphery. If you can only ever originate new ideas and ways of working, you enter a separate area of challenge. Your leaders will be overtaxed, your teams will be pulled in a million different directions at once, and your people will suffer burnout.

 

If you are constantly switching up practices that work, you’re wasting a lot of energy.

 

A day of real-world trial-and-error teaches us more than we could learn with a month of theorizing. Buckle down and make something real, something with predictably favorable results. As you get confident that a new way of working is valuable, or a new approach to launching a product is successful, create a process that solidifies that practice and teaches others (including your future self!) how to duplicate it consistently.

 

Toyota is famous for doing this well. If a worker at a Toyota factory has an idea for a new tool that they think could make their job faster or easier, the company engineers work with the inventor and a small team to create and test a prototype. Based on the workers’ feedback, the engineers refine the tool and slowly distribute updated models, first within the factory where the tool was invented, and then to a widening group of workers who perform the same task at other Toyota factories.

 

This process of building a foundation from successful experiments is fundamental to shifting from growth to scale.

 

Growth is about adding things—people, practices, products. Scale is about consolidating—stopping what doesn’t work and improving what does. It’s about creating systems that help you leverage your talent base so people aren’t reinventing the wheel every time they come up against the same problem.

 

What are some ways you navigate between growth and scale? Email me at [email protected] and let me know.

 

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One of my friends and clients is the founder and CEO of a medium-sized, financially successful tech company. He’s kind and witty and down-to-earth, and I like and admire him a lot.

 

A while back, he was part of a conversation I facilitated about the nature of leadership, particularly when there is great uncertainty in your world.

 

There were about a dozen participants, and many shared their experiences. At one point, I turned to my friend and asked him if he, as the CEO and chairman of his company, felt like he was in charge.

 

He laughed, a bit chagrined, and said, “Of course not.”

 

Then he paused and got a bit quiet.

 

“You know,” he said, “this conversation is making me realize how afraid I am of being truly consultative. I’m worried that, if I really come to people without knowing the answer, they’ll think that I’m stupid.”

 

My friend is a powerful person. He runs a successful company. He has lots of resources at his disposal. But that does not make him feel safe. Those stark facts, facts that we could write in black ink on a fresh sheet of lined paper, do not make him feel safe. They don’t make him feel like he belongs. And they don’t create a sense of control.

 

Over and over, in myself and in the people, teams, and organizations that I work with, this fact becomes clear: success does not create a feeling of safety.

 

I think that this is a function of living in a world that measures and constantly compares everything, a world that pushes us toward scarcity. I’m a rich white American male and I’m always worried that there won’t be enough: food, space, housing, gas, power, water, etc.

 

What makes me feel safe is being in the moment. In the moment, there is always enough. When I notice the world that I’m actually standing in (rather than the world of my fears, projections, and what-ifs), it’s clear that I have enough in that moment.

 

What about you? Do you feel like you have enough? What makes you feel safe? Email me at [email protected] and let me know.

 

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One of my kiddos was doing a class project (a custom-made Valentine’s Day lunch box!) and got interested in making a solar system. (His friend, the recipient of the lunch box, is really interested in space.)

 

After considering the idea for a moment, he dismissed it, lamenting, “It would be too hard to make a good one.” His mom and I got curious. To us, this was a matter of spray painting some styrofoam balls and arranging them in a figurative solar system. What could be easier than that?

 

But, it turned out that he’d seen some examples of elaborate solar systems online and demurred; after all, he couldn’t make something like that!

 

And it’s true. No matter what the topic, if you look online, you can find an example of someone creating a “homemade” version of something with Hollywood-like production values.

 

Take this video of Jon Pumper’s Encanto spoof “We Don’t Talk About Pluto.”

 

Not only does the video have an amazing solar diorama, but it also has a highly produced, brilliantly shifted version of “We Don’t Talk about Bruno” from Disney’s Encanto. The quality of the video and the planetary models (which required no small investment of time and money) is phenomenal.

 

That got me thinking about how quickly so many things seem to be becoming incredibly slick and sophisticated these days. From YouTube channels to websites to everyday arts and crafts, it seems that advances in digital technology combined with the ability to share ideas over social media immediately are leading to an aesthetic of glossy perfection that feels necessary to uphold for fear of looking like an amateur.

 

It’s the double-edged sword of an information-rich, connected world. The ability to see what someone else can create means that we can access fantastic content and learn, but it also sets the bar (unrealistically) high.

 

Not that this is bad; after all, it wasn’t too long ago that the entire internet looked like this:

Image: https://websitesfromhell.net/

Nowadays, the tools to make a good product are more widely available than ever, and if you want to learn how to use one, there’s probably a YouTube channel dedicated to it. That doesn’t make the need to take a risk, put oneself out there, any easier. In fact, it can make it harder.

 

I don’t think my kids are the only ones who feel this way.

 

One of my team members likes to play guitar, and he shared with me that the fact that any song he’s trying to learn how to play is already on YouTube, in 4k, played by someone half his age (or even younger), with fancy video editing and high production value can be a discouraging feeling.

 

I feel the same. For years, I was unwilling to try things that might fail, whether that was content no one engaged with or my first online course that practically no one bought (subsequent offerings have landed better).

 

But I’ve learned to work with this. It’s not that I’ve gotten over my fear; it’s that I’ve gotten more comfortable with it. I’m willing to do more things even when I’m anxious. As a result, I’ve gotten better at this work — at writing things that people read and offering things that people want. That wouldn’t have happened without making things that just weren’t very good.

 

I believe learning new things and taking risks are important parts of being a fully expressed human.

 

I also believe that it’s one of the most essential skills for modern leaders. Without learning, without putting ourselves out there, we won’t be able to solve the problems we face. That’s because what’s worked for us for much of our careers — coming up with answers to problems — doesn’t serve as the world changes around us.

 

The most important problems don’t have answers. That doesn’t mean we can’t make progress with them; it means we have to learn to ask better questions, use our curiosity to reframe our challenges, and be willing to try new things.

 

When I feel imperfect or like what I have to offer isn’t good enough, I try to pause, breathe deeply, and remind myself that it is.

 

Even if it’s not set to a highly-produced music video.

 

What about you? How do you support yourself as you try new things? Email me at [email protected] and let me know.

 

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In 2009, Harvard Business Review published an article by management scholar Rosabeth Moss Kanter called Management by Flying Around (MBFA). The article argued that even though email, text, and video calls (Skype!) were available for companies with offices in multiple cities, it was still important for upper-management leaders to get on a plane periodically and get an up-close look at operations. The “face time” provided by companies that used MBFA practices boosted team productivity.

 

MBFA is the knowledge-worker equivalent of the Toyota concept of “going to the genba” — going to the place where work gets done.

 

Times have changed, though. The pandemic suspended flights and office operations. We all learned through trial-and-error (ok, mostly error) how to successfully accomplish our work from the comfort of our homes. And, as lovely as Skype was (is?), technology has improved.

 

These days, MBFA is in flux because it’s no longer necessarily clear where work is done. But it’s done somewhere. Even though services like Slack, Zoom, and Microsoft Teams allow for easy and clear communication, there’s still something missing.

 

It’ll be interesting to see how this all develops over the next few years. At one of my clients’ workplaces, a decree was just passed down that employees would return to the office three days a week. To me, that’s the wrong approach. “Three days a week” is a strategy that is heavy on control and light on context.

 

It misses some important questions: Why do people need to come to work anyway? What’s the point of a workplace? And what is the magic that happens when people come together?

 

And there is some magic. This has become clear to me over the last few months as I’ve had the privilege of working, in person, with a developing leadership team. Our work in person is dramatically different than our work on a screen. This is both obvious and novel.

 

A better approach than “come back three days a week” might be to help people identify what kind of work benefits from being conducted in person (including things like casual meetings over lunch) and be clear about what can be done just as (or even more) effectively by working remotely.

 

Where is work done in your workplace? Do you see benefits from face-to-face interaction or is MBFA already an artifact of a bygone era? And what part of your work, if any, do you long to do in person again? Email me at [email protected] and let me know.

 

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I was watching a comedy special from James Acaster, one of my favorite comedians. His absurdist British humor is just the right mix of silly and thoughtful that I love to watch and relax to after a long day. Anyway, I was watching his Netflix special, James Acaster: Repertoire, and one of his jokes sparked a thought for me. To paraphrase the setup for the joke, Acaster says he was at a party where he was doing his best to start up a conversation:

 

“A lot of people tell you when you’re schmoozing to have a good icebreaker, but what they won’t tell you, yeah, is at the end of the conversation, unbreak the ice. You don’t want everyone else in, taking advantage of all the lovely little ice cubes that you created, so freeze it over again before you leave, so as you’re leaving just slide something under the fence like ‘death comes to us all’ or something like that.”

 

I love a little awkwardness as much as (more than, perhaps?) the next person. But what caught my attention is the deep truth in the line: “death comes to us all.”

 

Death isn’t something most of us like to think about. We all have so many hopes and dreams that we hope to realize one day, but whether we think about it or not, we’ve got a finite time on this planet to accomplish our goals. Someday we will look at our “To Do” list and have to accept that not everything will be crossed off in the end.

 

And it’s even starker than this as Oliver Burkeman writes in his delightful book, Four Thousand Weeks: Time Management for Mortals. Our to-do lists tend to push us to focus on the minutiae in our lives. Paying bills, sending emails, making reservations. We get a bit of a dopamine hit when we complete those. But, those tasks often generate more work for us. When I reply to an email, I’m more likely to get an email back that I — again — have to reply to. Being good at plowing through my to-do list paradoxically increases the length of my list.

 

This can either become a debilitating thought that stifles our creativity, or it can be a powerful motivator for change and growth.

 

In some Buddhist traditions, monks spend the first moments of their day meditating on the inevitability of change and death in order to understand the importance of living in the moment every day.

 

I don’t do that, but I do take some time to reflect each week on what my most important work is. That’s been a game-changer for me, not just because it helps me prioritize, but also because it helps me work through the fear that procrastination is often a cover for. After all, my most important tasks are, almost by definition, high stakes.

 

So I’ll go on with an inbox that’s a bit overgrown (sorry for not responding yet, Jack and James — I really appreciate both of you!) but rest in the knowledge that I’m doing hard, ambitious, and risky things, like the Leading Change group that just started today.

 

Time is short, and none of our days are guaranteed, but that makes the time we have precious. Life is a limited-time offer, so act now!

 

How do you deal with impermanence? Does it depress you? Motivate you? Do you think about it at all? Email me at [email protected] and let me know.

 

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I’ve been watching Stranger Things for the first time. I am very late to everything pop culture-related, but the good news is that I’m all caught up and ready for season four.

 

The show got me thinking about team building.

 

“That’s weird, Chris,” you might be saying, “when I watch Stranger Things, I usually just think about how cool the 80s were,” but that’s just how my mind works.

 

Anyway, as I see it, Stranger Things is all about a team coming together to solve a set of complex problems. These problems involve interdimensional monsters, a missing friend, and a girl with telekinesis—essentially an allegory for the world of business.

 

Let’s take a look:

 

At the beginning of season one, the team (such as it is) is in disarray. Mike and his family don’t get along, and his friends can’t even agree on what to do in their Dungeons & Dragons game. Still, like many groups, they manage to function well enough despite their issues—until Will goes missing.

 

Right away, the small cracks in group cohesion grow and threaten to break apart the team, or as the Stranger Things kids call it, “the party” (in reference to their D&D party).

 

Suddenly beset by hard times, the party does their best to rally together and solve the problem, but their differences get in the way. No one can agree on the best course of action. Communication breaks down between Mike and his family and between Dustin and Lucas. With Will gone, the power dynamic of the friend group shifts, and then shifts again when they find Eleven and are forced to work with someone who has a different skill set and outlook on life.

 

The communication issues are so bad that they prevent Will and his sister Nancy from realizing that they are working on the same problem. Nancy’s friend Barbara was kidnapped by the same interdimensional horror that grabbed Will, but because they aren’t sharing information, and because Nancy belongs to a “company” that isn’t the right fit for her (Steve Harrington and his obnoxious friends), it takes a long time for them to realize they need to be working together.

 

Joyce and Jonathan Beyers are outsiders in their community, leading to misunderstandings and miscommunications that further complicate attempts at cooperation with Nancy, the kids, and Police Chief Hopper. Joyce and Hopper have to learn to trust each other, and Hopper needs to step up to his responsibilities as a leader as they look for Will.

 

I don’t want to spoil anything major, just in case you are also behind in all things pop culture-related and haven’t seen the show yet, but it’s not until the individuals and separate friend groups team up to form a coalition that the issue of monsters kidnapping townsfolk can be solved.

 

What are the obstacles to cooperation that keep your team from working together like the characters in Stranger Things eventually learn to do? How do you take your party from chaos to cohesion? Email me at [email protected] and let me know.

 

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I felt deeply uncomfortable with the person sitting next to me.

 

He didn’t have my back.

 

We depended on each other, and he’d made promises to me that he wasn’t keeping.

 

We were engaged in a risky activity: watching the Nutcracker.

 

The problem was that his mask wasn’t covering his nose.

 

I miss the before times. In 2019, I would have offered this man a pleasant holiday greeting, smiled at him, and maybe shook his hand.

 

Now, sitting next to his naked nose, I had to decide what to do. Do I say something, express my needs, and ask him to meet them? Do I ignore him?

 

Despite the fact that my job is essentially to have and facilitate conversations with people, I still find situations like this deeply challenging.

 

I think a lot of us do.

 

Mostly, we’re not trained to have conversations about our needs. Many of us are taught to swallow our desires, to bury them deep down. As kids, the adults around us are authority figures, most of whom have their own agendas that drive ours.

 

We’re told to be quiet.

 

To sit still.

 

To take a break.

 

So we learn to meet others’ needs; it’s an important life skill.

 

Later on, some of us learn to advocate for ourselves, to fight for what we want by being clever, negotiating, or ignoring others’ wants.

 

In consulting and coaching, we talk a lot about the skill of contracting. What can I offer you? What do I want from you? What do you want from me, and what can you offer?

 

Done well, the process reveals hidden assumptions and creates clarity. Implicit wants become explicit, and the whole system does better.

 

The last two years have demanded more contracting from us all.

 

I went for a walk with a friend recently (a retired consultant) and we contracted about how close we stood together.

 

During my son’s ski trip last week, I asked a fellow parent if I could take my mask off on the open-air ski lift.

 

And, with the man in the Nutcracker, I asked if he wouldn’t mind putting his mask over his nose.

 

(“It makes it hard for me to breathe.”)

 

We both reshuffled seats to be a bit farther apart and I tried not to think about it.

 

But it was uncomfortable.

 

It felt like a big deal to go to a big, public event as Omicron started to break in Seattle, and how, even though I knew going to any event involved a degree of risk, I wished he were following the rules.

 

I will keep trying to grow my awareness of how I feel and speak up from a place of truth and empathy.

 

In this case, I wish I had been able to tell him how afraid I felt.

 

Because, deep down, I’d like to believe that we all want to take care of each other.

 

I believe that, if we had a bit more skill, we’d be able to see others more clearly and allow ourselves to be seen.

 

So I will continue to practice.

 

What about you? How have you found yourself contracting with others? Email me at [email protected] and let me know.

 

I can’t wait to hear from you.

 

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The rocket streaked across the battlefield, aimed directly at a soldier.

 

Despite the danger, the soldier didn’t flinch. Instead, he lined up his shot and brought down his target.

 

As the wounded combatant fell, his helmet tumbled down, knocking out another soldier, whose rocket misfired, bringing down an orbiting enemy ship.

 

Since I study how complexity creates failure, you’d be forgiven for thinking that this might be a scene from a military disaster I studied.

 

In fact, it’s from something that my son T drew.

 

It’s pretty fun to see what he (and his brothers) create. They’re prolific.

 

The work is a mix of juvenile and elaborate. A recent comic, for example, featured a drawing of a poop emoji with tiny flies circling it.

 

Their scenes are also action-packed.

 

On Sunday night, we relaxed together, T drawing on his sketch pad while I read a book. When I looked over, I saw T deep into a battle scene.

 

His drawings are never really done. When I asked him to describe a scene, he explains by drawing more and narrating. Here it was: “This rocket is going to blow up this guy [draws rocket streaking across the page], but he’s shooting back, which hits this guy [draws death process] whose helmet falls off and knocks out this guy [draws a helmet falling]…”

 

(BTW, they’re all guys that he draws. But that’s an essay for another day).

 

“These guys are battling here, and this guy throws a bomb [draws a bomb] which explodes here [draws explosion]. And these guys over here….”

 

I mentioned that I have mostly seen him drawing battle scenes recently and wondered what it would be like if he drew a different kind of scene.

 

He nodded thoughtfully and turned to a fresh sheet in his notebook. He drew two people standing next to each other.

 

He considered them for about ten seconds.

 

Then, he drew a sword and had one of the guys stab the other.

 

The battle raged.

 

It was a sweet moment to be a parent—just being with my kiddo, witnessing him, and hanging out.

 

But it also reminded me of my work.

 

Drawing battle scenes comes easily for T.

 

When I pointed that out to him, he got curious about drawing other kinds of things, and he gave it a shot. But—left to his own devices—he quickly returned to his well-trodden, mayhem-filled path.

 

I think this is pretty universal. We all like doing what we’re good at. It’s comfortable, and it often serves us very well, bringing us success, promotion, and accolades.

 

But when we can only be one way—when we can only draw battle scenes, or when we can only ask questions, or when we only attend to the content of our work (and not the relationships), or we focus almost exclusively on planning without ever moving things forward—we can get stuck.

 

That’s true even though that way of being is valuable. For example, a team of engineers I worked with was very good at data-driven decision-making. That served them very well until they were trying to map out a strategy for leading change where there was very little data available.

 

Or consider the leader of a functional team I worked with who was very good at saying yes to her colleagues and enabling their work. This tendency to say yes was critical to her success, but it came at a cost: her team started to burn out because they were overworked and constantly cycling between priorities.

 

And as my experience with T suggests, even if we get curious about being a different way, we often go back to drawing battle scenes, back to that which comes easily to us. To shift, we need support.

 

When I’m coaching a client or a team, we start by exploring what they are good at—whether that’s attending to the content of their work, getting the task in front of them done, or building relationships.

 

Then we’ll get curious about whether they want to try something different.

 

Sometimes the answer is no. And that’s OK!

 

But when the answer is yes, we’re exploring these ideas together. I’m supporting them as they play with the process of their work or ask their teammates questions (instead of constantly responding with statements). By helping them explore a different way of being, they grow into a different part of their range.

 

And that can be delightful.

 

Are you looking to grow your range (or that of your team)? If so, let’s connect and talk about that. Email me at [email protected] and tell me how you feel about your potential and progress. In what ways do you get stuck and retreat to your comfort zone? What about your team?

 

I can’t wait to hear from you.

 

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