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My Adam’s apple tumbled into the back of my throat, and my intestines knotted themselves into a figure eight.

 

It reminded me of the awkward feeling of running into an ex-girlfriend.

 

Except I hadn’t bumped into someone I’d dated in a Walgreens, I’d read a story about the company I left about a decade ago, before starting my consulting work and writing Meltdown.

 

I was reading my daily email from Matt Levine, a Bloomberg columnist, when I saw the news.

 

My former company made gobs and gobs of money last year.

 

I mean gobs.

 

They’re a high-powered Wall Street trading firm, so making money wasn’t unexpected.

 

But they made a TON of it—a firm of a thousand people made around eight billion dollars.

 

I took a moment to fantasize about the bonus check I would’ve gotten had I still worked there. About the Egyptian cotton sheets I would’ve purchased, the vacation home I’d be off to.

 

And then I took a deep breath. I remembered how to swallow and un-tied my intestines. And I went about my day.

 

Because what motivates me in life isn’t money.

 

Don’t get me wrong—money is great! I use it to fund interesting things at work and do fun things at home. My hair tonic doesn’t pay for itself, after all 😉.

 

If money drove me, I would have stayed on Wall Street.

 

But I connect with my work because it meets my need to have an impact. To make a difference. To make things better.

 

That’s what motivates some of my favorite clients, too.

 

When I help leaders guide transformational change in their organizations, they’re doing it for so much more than the cost savings or growth they’re going to create for their company.

 

Money is great—it’s what creates a trigger for action. I loved helping a client revamp how his manufacturing group cooperated, netting them ten million dollars in savings a year.

 

But most of my clients are in it to do meaningful work that delights their bosses, energizes their colleagues, and tickles their customers. To make things better.

 

What about you? What motivates you to do your most ambitious work?

 

Comment and let me know.

 

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If you are a leader, you have a hard job.

 

Whether you’re in the C-suite or a recently promoted manager, you have a lot on your plate. Fighting fires. Balancing priorities. Working toward the ambitious goals of your company, organization, or team.

 

Plus, you’re often asked to solve problems where there’s no obvious answer, let alone a “right” one.

 

Like “return to work.”

 

Leaders all over the world are trying to figure this out. They come from organizations with different technological abilities, different kinds of work, and different norms. Some organizations are bureaucratic. Some are agile. Some are distributed and others are centralized. Some are rigid. Some are chaotic.

 

I’ll come out and say it right here: I don’t know how you should return to work.

 

But I do believe that teams should work in a way that supports their creativity and helps them advance their clearly defined objectives. I think this is more important than an arrangement built around face time.

 

But what this looks like depends on the culture and context of the organization.

 

To zoom out a bit: I think the return to work is an example of the continual change and need to adapt that leaders at all levels face.

 

It’s natural to think in terms of one monolithic solution with a “go live” date. But when I’ve talked with leaders about this, I’ve tried to encourage flexibility.

 

I think that the question deserves a process instead of a solution.

 

Here’s what some elements of a healthy process might look like:

 

• Engage. If you set aside the idea of a “right answer,” then you can get curious about the response to a change. “How would it affect you if we did XYZ?”

• Consider a combination of flexibility and constraints. Have different groups negotiate with each other around what they need and what they can provide.

• Be local. Let teams solve these problems in ways that work best for them—while helping to highlight the ways that cross-team and cross-business unit work can impose additional constraints.

• Support leaders in this journey. One of the toughest jobs of a leader is to help their teams resolve competing commitments; the transition to in-person work is but one example of this.

• Distribute innovation and centralize learning. Create a way for leaders to brainstorm and consult with each other, so that leaders can try things, get feedback, and share their wins (and misses).

 

You’ll notice that this process emphasizes engagement over top-down thinking. It seeks to help leaders influence and be influenced without getting stuck on the idea of the right answer.

 

By focusing on a combination of business outcomes and by understanding how others experience the problem, we can make tremendous progress in a short time.

 

It can even be fun!

 

P.S. A couple of weeks from now, I’ll send you some info about a course I’m launching on how to grow your influence at work by engaging with others in a different way.

 

Stay tuned—and if there’s someone you know who would find this interesting, send them this and let them know that they can subscribe here!

 

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I had a meeting with a leader and his team the other day where we reviewed the effectiveness of some of the experiments they had planned.

 

Regular readers will know that I emphasize experiments in place of rolling out organization-wide solutions. Experiments are flexible. We can often do them without much buy-in across the organization, and they get us info fast (whether or not the result is what we expected). Experiments aren’t “quick wins” of the old change literature; rather, they are ways for leaders, teams, and organizations to build their muscles around collaboration and their ability to sit with uncertainty.

 

A few weeks before our chat, one of the senior folks on the team suggested gathering together a small group of operational leaders from different sites for a focused conversation about the indicators that they found hardest to meet.

 

Everyone thought it was a great idea—but, when we checked in, it hadn’t gone anywhere.

 

I got curious—and I asked if the group was willing to explore why they hadn’t moved this idea forward. My instincts told me that what we had on our hands was good, old-fashioned resistance.

 

The stated reasons that we don’t pursue a good idea are often tactical in nature. We don’t have the time. There’s no budget. We don’t have the right people. Folks are tied up with something else.

 

These are good reasons. But they’re often not the underlying reason. By definition, people make time for what they do (whether it’s something urgent or important). The same goes with budget and political capital.

 

This group of leaders was dealing with a competing commitment, an underlying desire to keep things as they were. Teams and organizations are really good at doing things in just the way they do them now. Changing that is hard.

 

And sustainable change can’t be done by pushing; it needs to be invited.

 

So, instead of thinking in terms of what wasn’t happening, we got curious about what happened instead.

 

The team saw that it was avoiding splitting the group of operational leaders into In and Out groups. They didn’t want to play politics, to exclude folks.

 

They didn’t want to make “enemies.”

 

Do you see how not wanting to offend folks by not including them is actually a really useful behavior?

 

It is useful, but, like all choices, it comes with a cost. Many of the operational leaders resisted the work this team was undertaking. They held fast to their opposition. By including them, the change process would stay stuck until those leaders loosened up.

 

The team reflected on this. They saw why they’d been reluctant to try this new approach—and they also more clearly saw the costs of sticking with the way they’d always done things.

 

In doing so, they were able to reflect and make their choice. They decided to move forward with the small group work, knowing that there might be backlash but also knowing that they were already dealing with a group of resistant leaders who felt excluded.

 

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Man, it’s hard to change your mind.

 

I think this is a universal truth. It’s certainly hard for me, and I see how it challenges a lot of the leaders that I work with, too.

 

Conviction and vision are great things. But, when we hold too tightly to them, there’s a cost. We pursue strategies for too long. We don’t see new information. And we don’t let ourselves be influenced by others.

 

I see one of the central challenges of business—whether we’re talking about my small-but-mighty consulting firm or one of my Fortune 100 clients—as dealing with uncertainty.

 

Some problems are execution problems. You know how to do something, you just need to do it. You may need to do it faster, cheaper, or differently, but these are differences in degree, not in kind.

 

But others, like culture change, entering a new market, or creating innovative practices, require the capacity to sit with uncertainty.

 

That’s because these are “impossible problems.” Problems where we have a vision (but don’t know the exact answer), where we don’t control the people we need to implement things, and where we don’t control the broader system—the technology, organizational structure, incentives, and regulations.

 

Bets and Doors

 

When you don’t know the answer, every decision is a bet. Everything is an experiment. There are lots of ways of thinking in bets, but I like how Jeff Bezos talks about bets in terms of one-way and two-way doors.

 

Going through a one-way door is a big deal. If you don’t like what’s on the other side of it, you can’t go back through. You’ve already made the big acquisition, launched the new product, or expanded into the new market. These kinds of bets require analysis, sensitivity to the effects of complexity, and a high-functioning, creative team.

 

In contrast, two-way doors are easy to go back through. There may be a cost, sure, but the cost is small relative to the upside that you’re trying to capture. Reversible decisions can (and should) be made in a nimble way and, if things don’t work out, we should change course and try the next thing.

 

It’s a great philosophy. But the biggest challenge is admitting that you want to turn around and go back. Amazon has carefully cultivated a culture of experimentation that celebrates failure. That approach is hard for people and rare in corporate cultures.

 

Going Back Through My Door

 

The newsletter list has been growing a lot lately, but long-time readers will know that, from time to time, I turn the lens around to myself and my own business. So, I’ll share my own recent struggle with a two-way door and how I eventually turned back.

 

At the end of 2020, I saw an opportunity in the market to work with lawyers at small law firms. I decided to move into that market—launching a side business, setting up infrastructure, a mailing list, and even creating a product to help attorneys set better goals.

 

It’s an important market and work that I deeply believe in. And I had some good success cultivating new clients. Attorneys at small firms often need help. They’re deep experts in the practice of law, but they don’t always get training in the business of law. They also have a lot of upside potential: by improving their businesses and systematizing their processes, they can often increase their revenue and profitability, allowing them to serve more clients better.

 

But, a few months later, I realized that even though it was a great business, it wasn’t the business I wanted to pursue. I still love working with those clients; it’s just not where I’m putting my efforts going forward.

 

My energy lies in guiding leaders to solve their impossible problems by helping them learn to influence at scale. Particularly at big organizations, a small change in a leader’s perspective and practices can positively affect tens of thousands of people.

 

So, here’s how I went back through this particular door:

 

1. I ignored the numbers and tuned into my feelings. This work with attorneys was a great business, both on the spreadsheet and in practice. But it didn’t capture my energy as I had hoped. When a task to draft a marketing email came to the top of my to-do list, I found myself dreading it instead of diving into it. That gave me pause and helped me realize that I needed to keep engaging with the decision to launch this side business.

2. I stayed with the ambiguity. As I struggled with the commitment to market to attorneys at small firms, I knew something was up. But I didn’t reverse course right away. I didn’t want to have a knee-jerk reaction.

    

   I also noticed what had my energy (helping leaders solve impossible problems, it turned out). All of this helped me deepen my sense of what wasn’t working and get to the point where I could commit to going back. 

3. I got a lot of input. I chatted about this decision with my team, guests on my podcast, my coach, and my mentors. One of my mentors, a master in his field, told me that our job as leaders is to “deliver ideas boldly—but hold them lightly.” We need to have a vision that drives us and be influenced by the feedback we’re getting from the world.

   I tuned in to both sides of the spectrum.

4. I made the big decision to stop pursuing this niche and used that to guide the many small decisions that followed. Even though I had invested time, money, and effort in setting up the business, I decided to pull the plug. And I used that decision to manage the work that had already been done.

   The question my team and I asked ourselves was this: “If we were new leaders put in charge today, would we make the decision to…”. That allowed us to “forget” about why we had invested in a new platform to host our website, for example, and cancel the service.

It sounds so simple on paper (or when Jeff Bezos says it), but, in practice, it’s hard to go back through any kind of door. But, now that I have, I’m excited to have turned back to focus on something that has my passion and attention.

 

Are you dealing with an impossible problem? I can help. It’s simple!

• Book a free 15-minute strategy call here: https://chrisclearfield.com/impossible-chat

• I’ll call you at the scheduled time

• You’ll go away with a plan for how you can move forward.

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A few weeks ago, I was chatting with an exec at a finance company, Susan. “My team just doesn’t engage,” she told me. “We like each other. We joke around. But we’re too… polite? I’m not sure of the right word.

 

“Whenever anything challenging comes up—like why a new product we rolled out isn’t getting as much traction as we thought—people seem to fade away. I think they don’t want to hurt each other’s feelings, but what happens is that no one contributes, and we don’t get anywhere.”

 

Contrast Susan’s team with John and his direct reports.

 

John is an engineering manager I worked with recently. “Our meetings are terrible. People show up and care about the work. But we often devolve into deeply technical conversations about machine learning. They’re important conversations but not when we’re trying to get everybody to think about the bigger picture of how to deliver new features to our [internal] customers.”

 

He went on, “I have two senior engineers—deeply skilled and technical guys—who dominate the conversation. They make our meetings feel more like academic seminars than work meetings. In one, they even spent about 10 minutes reading from dueling academic papers about which method was better.”

 

Susan and John were frustrated. But there was good news: they both wanted to improve and were open to exploring their own role in their respective team’s performance.

 

I started with the idea that each team’s behavior had value (otherwise they wouldn’t be doing it). Their dynamics were adaptive. They helped them do something better, though not necessarily the work that Susan and John wanted to get done.

 

In fact, we can see each team’s behavior at different ends of the same spectrum. We could see this spectrum through different lenses, like polite vs. argumentative, disengaged vs. engaged, or careful vs. pushy.

 

And we can see the benefit in each way of being. The goal, then, isn’t to stop being polite (or argumentative), it’s to grow the range of behaviors that each team can inhabit.

 

This is a learning that I’ve come to through my work and training in gestalt, a school of development rooted in the ability to see the whole system (and the value in what is happening right now). I draw on this perspective when I coach teams like Susan’s and John’s, when I coach individual leaders, and even when I work with larger organizational systems. I also use this approach to guide my own development—seeing the behaviors that come easily to me, the benefits of those, and the costs.

 

Inherent in gestalt is the belief that growth comes from awareness.

 

So, when I’m coaching a team, my role isn’t to weigh in on the technical details of a product rollout or the nuances of machine learning. It’s to help the team increase its awareness, see its own behaviors, and get curious about how things could be different. To expand its range rather than get rid of the way things are now.

 

Here’s the catch: it’s hard to see the behaviors of your own team. It’s like trying to read the label from inside the bottle. If you’re interested in exploring this kind of work with me, the best way would be to schedule a short strategy session. Click here to book a free 15-minute call with me. If it’s not the right time for that, the good news is that there are concrete things you can do now.

 

As a leader, you can use a set of simple behaviors to run better meetings. And, as a team member, you can notice how easily you do (or deviate from) these behaviors.

 

They’re not hard-and-fast rules, of course; rather, they’re a useful way to get a quick check of the health of your meetings:

• Scan the entire group at regular intervals, so that you’re aware of people’s individual experience. Are they engaged? Are they frustrated? Are they happy?

• In meetings, speak approximately 1/N times, where N = the number of people present.

• Ask at least one question of another person, using their name. Listen for an answer, and notice if you get one.

• Respond when a question is asked of you.

• In speaking, segue from what has been said just before you speak.

• “Pull out” of the energy of the group once or twice to take in the big picture.

• Be willing to influence and be influenced.

• Be aware of the available time and help summarize an ending.

 

Keeping these rules in mind helps us “bootstrap” our awareness, giving us something to connect to so that we can more easily see what’s present with our teams and see the direction we might want to move. And that awareness—that’s the first step to growth.

 

If you’re interested in digging deeper, these rules come from some pioneers in the field of team dynamics: Edwin C. Nevis, Joseph Melnick, and Sonia M. Nevis. Their paper “Organizational Change through Powerful Micro-Level Interventions” is a great overview of the form that this work can take (pdf). This approach has also guided some of my earlier writings on change.

 

If you lead a team and are interested in exploring how you might grow your team’s range, book a 15-minute call with me today.

 

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My client shook her head. “They just don’t get it.”

 

It’s something that I hear a lot from leaders (and something that I catch myself thinking, too).

 

“They just don’t get it.”

 

It’s a deeply human belief. We experience our own thought processes and believe our conclusions. So, when someone doesn’t agree with us, it’s easy to think that they’re wrong.

 

In fact, my client (an HR business partner) was dealing with the R-word: Resistance. And, like a lot of leaders, she saw it as something to be overcome.

 

She was struggling to convince a group of her peers to buy into a small piece of digital transformation.

 

“Our system for hiring contractors is a mess,” she lamented. “Different departments have different requirements around confidentiality and different contract structures. We don’t have a central place to store these contracts or even see how many contractors a given department has.

 

“I’ve spent a lot of time on how inefficient our system is. For example, every contract basically lives in email. So, when a leader transitions to a new role or leaves the company, we have to sift through years of email to figure out their outstanding contractor relationships. We’ve even had contractors take advantage of this gap by slyly renegotiating their terms with a leader’s successor. Obviously, we don’t work with those people anymore.

 

“We’re not even talking about the money; leaders hire contractors out of their own budgets. It’s just about getting some kind of rational system in place so that every department doesn’t have to reinvent the wheel.”

 

My client even had a technological solution in mind. It would be almost trivial to implement. And it wasn’t even that important of a problem. But it was emblematic of her struggle to contribute to the chief people officer’s push for digital transformation.

 

“This affects everybody’s departments. HR is on board. So are the CTO and people in other departments. It’s uncontroversial. But we can’t seem to get it done.

 

“If we can’t even take this small step, how can we expect to go after bigger things, like streamlining our hiring and promotion process?”

 

She assumed that people were resisting because they didn’t get it. So, she threw data at the problem: case studies. Examples of overspending and contracting chaos that could have easily been prevented. And a strong case for the return on investment.

 

But what my client missed—and what’s easy for a lot of leaders to miss—is that resistance comes in many flavors. What seems like people not “getting it” is often an expression of something deeper.

 

In my work, I draw on a model from Rick Maurer to help leaders work skillfully with resistance. This model divides resistance into three levels:

1. I don’t get it.

2. I don’t like it.

3. I don’t like (or trust) you!

 

It’s true: people may not get it. Most of us are very comfortable working at this level. We throw more data at others to try and convince them that we’re seeing the problem clearly. But that’s often not the whole story.

 

Repeated requests for more data can mask something else, a deeper type of resistance: people may not like your idea. It may require them to change or give up control. It may even threaten something deeper, like their professional identity. This came up recently with a team of lawyers I was working with. They were being asked to step away from their subject matter expertise to develop a system that could help them work better together.

 

Also, people may not trust you. Often this isn’t about you personally but about your role. One of my clients described this as “I’m from corporate, and I’m here to help.” A history of ill-handled changes, imposed from a central source, can engender (very justified) feelings of resistance.

 

Identifying these levels of resistance presents a whole new way of skillfully working with change. After talking it over with me, my client realized that people might not have liked what she was trying to do, even though it supported her boss’s and the CEO’s efforts.

 

So, she got curious. She started to engage with her peers by asking them a simple question: “What don’t you like about the system we’re thinking about setting up?”

 

What she heard was both obvious and insightful: senior leaders at her company liked the idea of a system to manage contractors better. But they were worried about imposing too much bureaucracy. As the head of manufacturing put it, “Sometimes I have an urgent technical problem. I have a consultant that I know can solve it. And I have the budget for it. I don’t want to be hamstrung by weeks of negotiation around unnecessary contract terms that are imposed by HR. That could cost me a fortune in inefficiency and downtime.”

 

Now that was something my client could engage with. As the importance of speed became clearer to the businesses she was supporting, my client made that the primary goal of the new approach to contracting. Working with legal, her team even created “one click” contracts: below a certain dollar value, managers could generate a contract by checking a set of boxes and the contractor, in one click, could sign it.

 

In learning what was important—and in honoring what she learned—my client converted one of her project’s biggest detractors into an early adopter who is even advocating to his peers.

 

So, what’s next? As you work on an important problem, instead of trying to overcome resistance, get curious. Download this handy diagram, and pencil in resistance on the diagram where it fits best. This can help guide you to engage more effectively on the parts of your problem that matter to others.

 

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“I am so done with Zoom.” –Everyone in 2021

 

Man, aren’t we all? Kids, parents, teachers.

 

Zoom calls can be really fun. They can be energizing and creative.

 

But they can also be terrible. Meetings full of participants where only a few people talk the whole time. Meetings where you feel like you would rather be doing anything else. (And meetings when you turn your video off and actually DO something else!)

 

Zoom fatigue—the brain ache that comes after a day of virtual meetings—is real (article, theory paper from Stanford researchers). There are a bunch of different reasons for this.

 

In virtual meetings, we lack nonverbal cues. People can’t make eye contact, so you don’t know when they’re focusing on you (and vice versa).

 

Video limits body language. And social cues—like a small hand gesture that warns of an interruption—are lost.

 

All of this increases cognitive load. We need to use our thinking brain, instead of our intuitive, social brain, to make sense of what’s going on.

 

Yes, we still need to receive updates from our colleagues. We need to ask questions and share our work. And we need to uncover creative solutions to hard problems—all challenges exacerbated by the COVID-19 pandemic.

 

But even as we absorb the impact of coronavirus, the way we work has changed forever.

 

Video calls are here to stay.

 

So, how can you stay connected while minimizing Zoom fatigue? How can you prevent endless video chats from dominating the calendar? And how can you create space for the creative problem-solving that is at the heart of your work?

 

Here are some practices I’ve developed through managing my team, working one-on-one with coaching clients, and helping large, distributed groups define and solve their most challenging problems.

 

Have fewer Zoom calls

 

What can you do instead of clicking that “New Meeting” button?

Inform without Zoom

If you need to tell people about an upcoming event, deadline, or project, draft a short and informal document that your team can engage with asynchronously. Have your team edit the doc and use comments to provide feedback and ask questions.

Do this even if you know that you’ll need to have a discussion with your team. Circulate your document as a pre-read or—as is the practice at Amazon—begin your meeting by reading it. (Pro tip: have everyone turn their video off.)

Even though it may take you longer to write something, you will reclaim energy for you and your team. It’s not just about time, it’s also about fatigue. Shaving off 15 minutes of video chat may not seem like much, but it adds up, particularly when everyone on your team gets that time back.

Update without Zoom

Instead of endless update meetings, experiment with structured questions.

Every Friday, for example, we ask my team

• What are you going to work on next week?
• What obstacles do you anticipate and what input or support do you need to make progress?
• Do you have quarterly goals that you are going to be moving forward?

Or if it’s something that’s hard to write about—something where tone and sensitivity matters—consider circulating a short video message with your team.

 

Create without Zoom

 

I’m a person who loves to create in partnerships. But in a Zoom meeting, even with just a handful of people, it’s too easy for creative conversations to become stilted. It’s hard to interrupt, and many participants remain silent.

 

Instead of bringing together a group on Zoom, create a mini-podcast. Host a podcast with a peer and record the conversation. You can share the resulting file with your team (often with transcription through a service like Otter.ai) to share your thoughts.

 

Communicate without Zoom

 

Finally, recognize that sometimes you just don’t need video calls. Sometimes I use video conferencing with my coaching clients, sometimes I just ring them up on the good, old-fashioned cellular telephone.

 

Video is great. But so is the phone. I often find that I’m more focused, less distracted, and less fatigued when I can move around instead of staring at my screen.

 

Have better Zoom calls

 

Zoom can be a wonderful tool that helps people feel engaged and creative. And there is still some work that really requires real-time collaboration. So, how can you best collaborate while managing fatigue?

 

Create space to bond

 

With fewer video calls on your calendar, you can afford to spend some time strengthening connections within your team. Rather than run a “Zoom happy hour,” create space for your team to share what’s going on in their lives. Or start with a warm-up, something as simple as having participants cover and uncover their cameras in response to questions: “Leave your camera on if you’re a coffee drinker… a tea drinker… ate meat last night.” It’s a simple exercise, but it helps mobilize energy.

 

Create space to think

Not everybody thinks at the same speed. When you ask a question of your team, set aside a minute for everyone to think about it before the discussion starts. Then put pairs in breakout rooms (yes, even in small teams) to seed the discussion before rejoining the larger group. Not only will this generate better ideas, but it will also reduce fatigue since there are fewer people to divide attention between in breakout rooms.

 

You can also create space by inviting fewer people to your meetings. It will result in better meetings that create less fatigue. And the people who don’t join? You just eliminated a source of fatigue from their lives.

 

As long as people trust that you’ll inform and engage with them when the time comes, not everyone needs to be part of every discussion.

 

Create space to collaborate

 

Zoom limits throughput. There are delays. We can’t interrupt, we can’t have simultaneous conversations. We can’t build off each other’s ideas.

 

In short, it’s harder to collaborate.

 

So, take advantage of the format. Create a parallel workspace with shared visibility—in Google Docs, OneNote, chat, live Q&A software, or an online whiteboard. Having your co-creators type in ideas in a Google Doc is a remarkable way to multiply the impact of your collaboration.

 

Create space to plan

 

Spend as much energy planning your Zoom meeting as you spend engaging with the problem you’re actually trying to solve.

 

Planning how you engaged was important (and often undervalued) before the COVID-19 pandemic, but the cost of Zoom fatigue—and the limitations of video—makes it critical now.

 

For every meeting, choose one content goal and one process goal ahead of time and encourage your team to do the same. Write them down. And consider sharing them.

 

What does that look like? Here’s an example.

• Content goal: I want to get three ideas for how we can message our new product to customers.
• Process goal: I want to make sure everyone shares at least two ideas.

 

Create space to experiment

 

We’re in a brave new world—one that’s here to stay. Be open with your team about your efforts to reduce their fatigue.

 

To that end, create space for ideas and suggestions. Consider using the approaches above to talk with your team about how you will reduce video conference fatigue. (Meta, I know.)

 

Remember, there is no right answer, there are just things we can learn. Be open. Be curious. Run better meetings. That will go a long way to reducing fatigue and, ultimately, empower your team to do great work.

 

And don’t stop experimenting with Zoom! For more on the power of experimentation (and why we need it now more than ever), check out my essay on The Transformational Power of Curiosity.

 

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I recently spoke with a client—let’s call him John—who asked me a very dangerous question.

 

A question that could have wasted hours of his time and tens of thousands of dollars of his budget, as well as created conflict and confusion within his team.

 

John had a challenging mandate. A technology leader in a high-profile role at a major manufacturer, he needed to improve the way three separate teams worked together in order to delight their customers with a new generation of connected devices.

 

It was an exciting opportunity for John and his company. But different operating philosophies had created simmering tension that made it hard for the teams to collaborate—which they had to do to succeed. He also needed to overcome the historical culture of blame, so that issues didn’t linger as they had with his predecessor.

 

After describing his situation, John asked me, “What do you think we should do?”

 

Now, I like to be helpful. My instinct was to ask clarifying questions and respond with thoughtful suggestions.

 

But I stopped myself. His question was well-meaning. And it seemed like a good question. Most of us have asked a variation of it at some point in our lives. But it threatened to lead us down a treacherous path.

 

Because to solve a thorny problem, you have to start with the right question. If you don’t, you’re in danger of spinning your wheels, wasting time and resources, and making the problem worse.

 

The “What do you think I should do?” question, in particular, carries a lot of baggage. It creates two new problems that can further stymie teams. Luckily, there is one small yet powerful tweak to the question that will supercharge your effectiveness.

 

First, let’s dig into why it’s wise to avoid the “Should do” question.

 

The “Should do” question focuses on the wrong thing. 

 

It puts us on a quest for certainty that is at odds with the challenge of solving hard problems.

 

I get the desire for certainty. I feel it—like all of us. It’s nice to imagine a future state where things… just work. Where you’ve arrived, as if the solution is your favorite meal waiting for you at the end of a long day. You can look back, satisfied, at a job well done.

 

But that’s not how complex problems work. After all, if there were a “Should do” just hanging around, waiting to be scooped up, you and your team would have figured things out already!

 

As you push toward certainty, you’ll stop being curious. You’ll fixate on an early solution, discarding other ideas (and contradictory data) that come in later.

 

You’ll charge forward like an angry bull running through the streets of Pamplona. Only to find yourself trapped in the bullfighting ring.

 

The “Should do” question creates resistance.

 

You—your team, your division, your organization, your industry—have all arrived, together, at this particular moment in time. You’ve gotten here with some luck and by developing a set of skills that help you solve your problems very effectively.

 

Consider a team of sophisticated engineers I recently worked with in a high-risk industry. They, along with their company, had spent decades honing their skills to keep things from falling apart. Maintenance. Safety. Planning and executing complex work.

 

To support this, they were incredibly good at creating long, intricate procedures.

 

But, over time, operations grew more complex. Line employees became frustrated at the bloated requirements. “Corporate just doesn’t get it.”

 

The leader I worked with understood this problem, but both he and his team struggled to influence the rest of the company.

 

At this point, it was tempting to play with a “What should we do?” question. There were some pretty interesting answers: we should trim our procedures. We should let people apply for waivers. We should create a process to reassess the risks of all our procedures.

 

Many of these are good ideas. But they all required a change from business as usual and would have created resistance—not just within the team of engineers I worked with but across the organization.

 

“Should do” questions emerge when something isn’t going quite right—when you need to move in a different direction. But the question itself encourages rigid, definitive answers that create resistance.

 

People don’t like being made to change, but they’re often excited to be invited to take part in a change. But that’s just not possible with a “Should do” question.

 

Ask this question instead.

 

At this point, you might be feeling frustrated. If you can’t ask people what they think, how can you move forward when you’re stuck?

 

It turns out there’s a simple tweak that makes all the difference. Instead of asking a “Should do” question, ask “What can we try next?”

 

This question embraces uncertainty by acknowledging that the solutions to your thorniest problems aren’t out there in neat packages to be found.

 

The solutions emerge from a series of small steps that you discover over time. Asking a “What can we try?” question gets us moving. And the word “next” means that it doesn’t matter if we’re moving in the right or the wrong direction, because we’ve chosen a small enough step to experiment with.

 

“What can we try next?” also avoids the wrong kind of resistance. By working through a series of experiments, you get people engaged in defining the problem and testing solutions as you go. You transform resistance into creativity. And where you do get resistance, it’s a good indication that you’re probably moving too fast, that you’re missing something.

 

In the SimplerTimes™, asking the right question would not have mattered so much. There were lots of problems that could be solved with hard work and by implementing basic approaches like procedures or checklists. The answers were out there, we just needed to figure out what we should do.

 

But that’s not the world we live in anymore.

 

So, we need a new question.

 

As John and I talked, we came up with his very own “Try next” strategy. Instead of picking a direction and moving toward it, his first step was to meet individually with the leaders of his three teams, describe what he was seeing, and ask them what they thought they could try next.

 

So, dear reader, what problem will you try this approach on next? Comment below and let me know.

 

P.S. If you’re interested in how the modern world creates thorny problems, listen to my podcast with my friend and Harvard Business School professor Amy Edmondson for an in-depth discussion of these issues.

 

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I’ve got a bit of a different newsletter for you today.

 

I’ve got something that’s on the tip of my tongue that I’m trying to articulate. A thought that’s in the process of crystallizing—and I could use your input to solidify it.

 

Recently, I’ve been thinking a lot about the way that work has changed over the last 20 to 30 years. I think that that’s the time frame in which the world really shifted from being complicated (lots of things to keep track of) to being complex (driven by systems and interactions).

 

In a complicated world, we can improve things with better procedures. We can consider what needs to be done and, if we make sure we do the right things at the right time, we’ll mostly be OK. (Think Atul Gawande’s Checklist Manifesto).

 

But, in a complex world, we improve by learning from the system itself. We gather data about what works and what doesn’t. We need people to speak up. Managers to listen. And feedback loops that capture both positive lessons and cautionary tales and distribute them throughout an organization or company.

 

As many of you know, my book Meltdown was all about the way that things go wrong in complex systems. Complexity can push systems toward catastrophic outcomes where the system behaves in ways that designers and operators never foresaw.

 

That brings us to the theory I’m developing now.

 

In addition to the ways that complexity creates opportunities for failure, I think it makes day-to-day work harder.

 

We have to process more information and manage more connections than ever before. Complexity obscures the solutions to problems. And even when we come up with solutions, we have to implement them within a system where we may only be able to influence a slice of things.

 

I’m hoping to gather some data on people’s experiences. Whether you’ve been in the workforce for decades or just started your career, I suspect each and every one of you have insights on this.

 

So, please tag me on social media (handles below) and let me know:

• How has your industry or discipline gotten more complex over time?

• How has that affected your day-to-day work?

 

Thanks. It’s a big help.

 

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Maybe you’re not in a position to lose $900,000,000 for your company.

 

But, if you’re like most leaders, you don’t know all the ways in which the things you’re responsible for can go drastically wrong.

 

Even if you’re very good at your job.

 

Even if you’ve been at your company for a long time.

 

Even if you know the technical ins and outs of the business.

 

Good leaders know the limitations of their knowledge. They have what I like to call “objective curiosity” about their work and their systems. They’re asking about what might go wrong, sure. But they’re also asking about how things work. They’re continually refining their mental models of the work that they’re responsible for.

 

It’s dangerous not to.

 

If you need convincing, take this story from Citibank as a cautionary tale.

 

In 2016, an operations group at Citi in charge of managing payments for loans—the bread and butter of finance—accidentally wired some money outside of the bank.

 

And by “some money,” I mean $900,000,000.

 

The story is almost comical in its complexity (my favorite finance writer, Matt Levine, dissects some of the high points).

 

The transaction itself was complex, involving the refinancing of a large commercial loan. Some lenders were participating in the new loan, some were not.

As a result, Citi didn’t actually need to wire any money [1]—but, because of the way their systems were set up, they couldn’t facilitate their client’s loan transaction without at least pretending to wire a bunch of money.

 

So, there was a work-around. The operations group handling the transaction could create an override by wiring the funds to an internal Citi account, instead. All they had to do was check a box and put in the number of the internal account (called a wash account because the transaction washes out). The operations person who created the transaction did that. He got two others to look at it (a “six-eye review process”). It looked good to everybody, so they put the transaction through.

 

The next day, operators realized that they had incorrectly wired out nearly a billion dollars.

 

As it turns out, they understood the transaction, but they misunderstood their systems. They had put in an override. They checked the override in the “PRINCIPAL” box and put in the number of the wash account.

 

But, as Levine reported, they needed to check three boxes:

 

[The manual] explains that, in order to suppress payment of a principal amount, “ALL of the below field[s] must be set to the wash account: FRONT[;] FUND[; and] PRINCIPAL”—meaning that the employee had to check all three of those boxes and input the wash account number into the relevant fields.

 

Whoops.

 

It’s tempting to blame the operations folks, isn’t it? But we’re not going to do that. The operators were doing their best in the system they were in. To really learn from something like this… you have to believe that you might have made the same mistake in their shoes.

 

This example from Citi highlights three specific lessons that can help you in any complex project or work setting. You need to be sensitive to the strengths and limitations of your people, develop awareness of how your processes really work, and seek out the unvarnished truth so you don’t ignore important issues:

Trust humans—but expect them to make mistakes.

 

We cannot expect humans to be perfect. We all make mistakes. And we will miss the mistakes others make.

 

So, you can’t just add more checks. You can’t just add more instructions.

 

Instead… add transparency to the system. 

 

Generate a big, screaming graphic that shows that $900,000,000 will be wired out of your bank.

 

Use a Sharpie to put a big “X” on the side of the patient where you will operate.

 

Create a system that says “Pull up, pull up, pull up” when you are about to fly into the ground.

 

Make blindingly obvious what is happening—so it’s easy to see and correct.

Pay attention to work-arounds.

 

Safety experts talk a lot about the gaps between “work as imagined,” “work as prescribed,” and “work as done.”

 

Work as imagined: Managers get together in a conference room for hours of discussion about how something should work.

 

Work as prescribed: Managers then write a procedure (or maybe external consultants do) to tell operators how the work should actually be done.

 

Work as done: That procedure is given to a new group of people. These folks aren’t in a conference room. They don’t always have the right tools, the right resources, the right information, or the right amount of time. But they’re expected to do the work! And, mostly, they do.

 

But there are gaps—gaps that require operators to skillfully “work around” the constraints of the system and the work as it has been designed.

 

These gaps are an inevitable part of operating in a complex system.

 

Good leaders realize this. They create feedback loops to understand what’s actually being done. They listen to operators. They learn and adapt, closing those gaps over time.

 

But what happened at Citi was a bit different. The procedure itself was a work-around for a fundamentally flawed system. It was far too complex. It wasn’t logical. And there were few checks for when things went wrong.

 

Instead of accepting work-arounds… pay attention to the places where you’ve made them a part of your system. They point to places where complexity can cause failure.

 

Ignore them at your peril.

Seek out what’s not working.

 

I’m willing to bet that Citi’s system was not a topic of conversation among its senior leadership.

 

Why not? Obviously, it could cost them hundreds of millions of dollars.

 

Many organizations deal with (and ignore) systems like this all the time.

 

That’s dangerous. Beyond being a source of risk, I’m willing to bet that Citi’s system was an impediment to agility, innovation, and competitiveness.

 

I don’t know for sure. But I’m guessing that even leaders who had operational experience and deep knowledge of the business accepted the terrible system as just part of “how we do things.”

 

Instead… good leaders seek out the unvarnished truth about their systems. They need to know what works and what doesn’t. And they have two sources of information they rely on to know what needs to be fixed:

 

1. Their teams: By creating a psychologically safe environment—one where people feel encouraged to share their true thoughts and feelings—leaders can learn about underlying problems and start to work on them.

2. Outsiders: Part of the challenge of running a complex system is normalization of deviance, or comfort with increasingly risky setups. Outsiders can point out blind spots in your operations (“Wait, what? How does your system work… that’s kind of nuts!”).

 

Outsiders can also help you see the idiosyncrasies of how you operate as a team—the assumptions you make. The way you talk to each other. The presence or absence of hierarchy. A skilled outsider can help you see your strengths and your opportunities for growth.

 

Are you a leader who works in a complex system? Book a free 15-minute call with me if you’d like to talk with an interested outsider.

 

[1]This isn’t quite true—they needed to wire around $7 million for some accrued interest. But not the $900 million of outstanding principal that they had to “trick” their system with.

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