Simple Habits for Complex Times

Simple Habits for Complex Times Plot Summary

Introduction

We live in a world of unprecedented complexity, where traditional leadership approaches often fall short. The challenges we face today—from organizational transformation to global crises—require new ways of thinking and acting that embrace uncertainty rather than fight against it. When old solutions no longer work, we need fresh perspectives that help us see possibilities where others see only problems. This journey through complexity isn't about having all the answers—it's about developing practices that allow us to navigate uncertainty with confidence and creativity. The practices explored in these pages will help you expand your capacity to lead effectively when the path forward isn't clear. By learning to ask different questions, take multiple perspectives, see systems, and design thoughtful experiments, you'll discover that complexity, while challenging, also offers extraordinary opportunities for growth and innovation.

Chapter 1: Ask Different Questions to See New Possibilities

The questions we ask fundamentally shape what we can see and understand. In complex situations, our habitual questions often limit our perspective rather than expand it. Powerful leaders develop the ability to craft questions that open new possibilities rather than narrowing to premature solutions. Yolanda Murphy, director of a statewide Family and Children's Services Division, discovered this when facing a crisis. Multiple children under her agency's protection had been harmed, creating intense pressure to find quick answers. Her initial questions focused on blame: "Who is responsible?" and "Where in the system is the problem?" These questions, while natural, kept her trapped in a mindset of threat and narrowing to decide—looking for someone to blame rather than understanding the complex system at work. The breakthrough came when her colleague Doug suggested they needed entirely different questions. Instead of asking "Who failed?" Yolanda began asking "What if these terrible things were an opportunity to do something radically different?" and "What are the many different pieces that might be at play here?" This shift opened her thinking to patterns and possibilities she had previously missed, allowing her to see the situation with fresh eyes. To practice this habit yourself, start by noticing the questions you habitually ask when facing challenges. Group them according to the mindset they reflect—are they focused on threat or opportunity? Do they narrow to decisions or open to exploration? Then intentionally craft different questions that shift your perspective. If you typically ask "Who's at fault?" try "What patterns might be creating these outcomes?" If you usually ask "What's the fastest solution?" try "What if we approached this from an entirely different angle?" The power of asking different questions extends beyond immediate problem-solving. Each time you practice this habit, you're building neural pathways that make creative thinking more accessible in future challenges. You're training your mind to move fluidly between different ways of seeing, expanding your capacity to lead effectively in complexity. Remember that the goal isn't to abandon practical questions entirely, but to complement them with questions that invite deeper exploration. By developing this habit, you'll discover possibilities that remain invisible to those trapped in conventional thinking.

Chapter 2: Take Multiple Perspectives to Expand Understanding

In complex situations, no single perspective can capture the full reality. What looks like a straightforward problem from one angle reveals itself as multifaceted when viewed from multiple vantage points. Leaders who thrive in uncertainty cultivate the ability to see issues through diverse lenses, especially those that differ dramatically from their own. When Yolanda faced public criticism after another child protection failure, her deputy Doug reacted with anger toward a pastor who had criticized their agency. "I can't believe our partners in the community are coming down on us!" Doug exclaimed, ready to counterattack. But Yolanda recognized this as an opportunity to take a different perspective. Rather than seeing the pastor as an enemy, she wondered what might be motivating his concerns and what she might learn from his viewpoint. This shift from adversarial thinking to perspective-taking represents a crucial leadership habit. Yolanda realized that to make progress, she needed to understand the pastor's viewpoint—not to defeat it, but to learn from it. As she noted, "We don't need to defeat the enemy here, because the pastor isn't our enemy. We're on the same side. We just need to figure out why he might have said what he said." This approach opened the possibility of collaboration rather than conflict. To develop this habit in your own leadership, start by mapping the key players involved in a challenging situation. Identify those whose perspectives seem most foreign or frustrating to you. Then, for each person, ask: "If I had just done what that person did, and I thought my actions were perfectly reasonable, what story might I be telling myself?" Try to construct a narrative that makes their actions seem logical and even heroic from their viewpoint. This practice requires intellectual humility—recognizing that your perspective, while valid, is inherently limited. It also demands emotional discipline to temporarily set aside judgment. But the rewards are substantial: expanded understanding, greater empathy, and more creative problem-solving. When you regularly practice taking multiple perspectives, you'll find yourself becoming both more creative and more compassionate—two qualities essential for navigating complexity effectively. You'll make better decisions because they'll be informed by a richer understanding of the situation, and you'll build stronger relationships with those whose perspectives differ from your own.

Chapter 3: See Systems, Not Just Parts

Complex challenges rarely have simple, linear causes. Instead, they emerge from the interactions of many elements within a system. Leaders who navigate complexity successfully develop the ability to see patterns, connections, and the way entire systems function rather than focusing on isolated events or individuals. When Yolanda and Doug were investigating the child protection failures, they initially looked for simple causes—perhaps a particular caseworker or office was the problem. But as they examined the data, they realized something more complex was happening. The incidents involved five different local bureaus, seven different caseworkers, and various types of situations. Doug suggested it might just be "a run of bad luck," but Yolanda sensed a deeper pattern: "Every system is perfectly designed to get the results it gets." This shift from linear thinking to systems thinking transformed their approach. Rather than looking for who to blame, Yolanda began examining how the entire child protection system was functioning—its procedures, relationships, incentives, and feedback loops. She recognized that none of the policies or people directly caused the violence to vulnerable children—the violence emerged from a complex system of policies, people, relationships, experiences, and histories. To develop this systems-seeing habit, start by resisting the urge to find simple cause-effect relationships. Instead, look for patterns and connections. Map out the key elements in your situation and how they influence each other. Pay attention to non-linear relationships where small changes might produce large effects (or vice versa). Look for feedback loops where effects become causes in an ongoing cycle. A particularly powerful approach is to identify what complexity theorists call "emergence"—when the nature of something emerges from the interaction of many parts. For example, teamwork emerges from the interactions of team members; it isn't caused by any single factor. By understanding emergence, you can focus on creating conditions that allow positive outcomes to emerge rather than trying to force specific results. Seeing systems doesn't mean abandoning responsibility or action. Rather, it allows you to influence complex situations more effectively by working with the system's natural tendencies rather than against them. This habit helps you move beyond the frustration of trying to control the uncontrollable and toward the wisdom of shaping conditions that make desired outcomes more likely.

Chapter 4: Design Safe-to-Fail Experiments

In predictable environments, we can plan carefully, implement thoroughly, and expect consistent results. But in complex situations, even the best-laid plans often produce unexpected outcomes. Leaders who thrive in uncertainty embrace experimentation as a primary strategy for learning and progress. At Actualeyes, a software company transitioning to include more service offerings, CEO Squint and his leadership team faced a challenging strategic shift. Their initial approach of simply declaring "We are a software and services company now" had moved the needle only slightly after a year. During a strategy retreat, they realized they needed a different approach—one based on experimentation rather than declaration. Hannah, one of the founders, helped the team understand that in complexity, they couldn't predict exactly what would work. Instead, they needed to create multiple small experiments that could safely fail while generating valuable learning. The team developed ideas like connecting engineers directly with customers weekly, creating spaces where marketing and engineering staff could interact informally, and allowing engineers time to build whatever excited them most. To create effective safe-to-fail experiments in your organization, follow these key principles. First, ensure experiments are truly safe to fail—if they don't work, no catastrophic consequences should result. Second, run multiple experiments simultaneously rather than betting everything on one approach. Third, design some experiments that contradict each other, testing different hypotheses. Fourth, keep experiments small, pragmatic, and inexpensive in the initial phase. The power of this approach lies in its combination of direction and freedom. Leaders set clear boundaries and direction (like "more service orientation") while enabling diverse, creative experiments within those boundaries. This creates conditions for innovation while managing risk. Remember that the primary goal isn't immediate success but accelerated learning. When experiments fail safely, they provide invaluable information about what doesn't work and why. When they succeed, they can be amplified. Either way, the organization becomes more adaptive and resilient—crucial qualities in an uncertain world.

Chapter 5: Communicate Certainty About Uncertainty

In times of change and complexity, people naturally look to leaders for clarity and direction. Traditional leadership advice emphasizes being clear, consistent, and confident in your messaging. But what happens when the future genuinely is uncertain? How do you communicate effectively without pretending to know more than you do? When Yolanda gathered a diverse group to discuss the challenges at Family and Children's Services, she faced this exact dilemma. "I've been more confused by this situation and about what to do with it than I can ever remember being," she admitted. Rather than hiding this uncertainty, she embraced it as a starting point for a different kind of leadership conversation. Ramona, one of her bureau chiefs, pushed back: "We can't just tell people that! People need real direction so that they can feel good about getting on with their jobs." This tension—between acknowledging uncertainty and providing direction—is at the heart of leadership communication in complex times. The solution isn't choosing between clarity and honesty about uncertainty, but rather being clear about what you do know while acknowledging what you don't. Effective leaders in complexity communicate with certainty about their direction and boundaries while being honest about the unpredictability of specific outcomes. To communicate effectively in uncertainty, start by clearly articulating your overall direction and the boundaries within which people can experiment and learn. Use stories and metaphors that engage both emotions and logic. Connect new approaches to successful experiments or experiences from the past to make them feel less foreign. Most importantly, model the mindset you want others to adopt—one that values learning, adaptation, and thoughtful experimentation. Remember that in complexity, your communication needs to evolve as you learn. This isn't inconsistency—it's appropriate adaptation. The key is to be transparent about why your message is changing: "We've learned X, which means we now need to focus more on Y." This builds trust while reinforcing the learning orientation your organization needs. By communicating your certainty about uncertainty, you create psychological safety for your team to acknowledge what they don't know and to learn together—the foundation for thriving in complex times.

Chapter 6: Embrace Human Irrationality as a Resource

Traditional leadership models often assume humans are primarily rational beings who make logical decisions based on clear information. But decades of research in psychology and behavioral economics reveal this isn't how we actually operate. Effective leaders in complexity understand and work with human irrationality rather than fighting against it. When Ramona took over the Proucheford bureau office, she approached her role with a purely logical mindset: "In a job like this, you just have to use cool logic or else you'll get swept away." She implemented standardized procedures, clear metrics, and strict professional boundaries. While these changes brought some improvements, they also created unexpected problems—staff gaming the metrics system and a collapse in the previously strong workplace culture. During her visit to the office, Yolanda discovered that Ramona's logical approach had overlooked crucial emotional and social dimensions of the workplace. The previous "family feel" of the office, with celebrations and personal connections, had supported staff through the emotional challenges of child protection work. By removing these elements in the name of professionalism, Ramona had inadvertently undermined the system's effectiveness. To embrace human irrationality as a resource, start by recognizing common cognitive biases that affect all of us. We tend to notice information that confirms what we already believe. We give more weight to vivid or recent events than to statistical likelihoods. We attribute others' actions to their personality rather than circumstances, while doing the opposite for ourselves. Acknowledging these tendencies in yourself and others isn't a weakness—it's wisdom. Next, design systems and processes that work with human nature rather than against it. Consider how social relationships differ from market relationships in your workplace. Recognize that emotions aren't separate from decision-making—they're integral to it. Create environments that support psychological safety, meaningful connection, and intrinsic motivation. The goal isn't to eliminate irrationality but to harness it productively. Our emotional responses, intuitions, and social connections can be powerful resources when understood and channeled effectively. By embracing the full spectrum of human experience, leaders can create organizations that are not just more humane but also more effective in navigating complexity.

Chapter 7: Foster Learning Through Feedback

In volatile, uncertain environments, an organization's ability to learn quickly becomes its greatest competitive advantage. At the heart of this learning capacity is effective feedback—the lifeblood of adaptation and growth. Yet most leaders struggle to create the conditions for honest, productive feedback exchanges. Jarred, a newly promoted manager at Actualeyes, experienced this challenge firsthand. After receiving harsh criticism from his boss Murray, Jarred was determined to handle his own feedback session with team member Michelle differently. But his attempt to be gentle led to a confusing conversation where neither person learned anything useful. "I told her the truth, only in a gentle way," Jarred explained to his mother later. "I told her how she was disruptive in meetings and that needed to stop." This approach—focusing solely on delivering his message without creating space for genuine exchange—represents the common mistake most leaders make. True feedback isn't a one-way delivery of information but a learning conversation where both parties gain new insights. To foster learning through feedback, start by examining your mindset. Rather than seeing the other person as a problem to solve, approach them as a sense-maker with valuable perspectives. Ask yourself: "What might this person know that could change my understanding?" This shift from judgment to curiosity creates the foundation for genuine learning. Next, separate your observations into three components: data (what actually happened), feelings (your emotional response), and impact (the consequences of the behavior). Instead of saying "You're argumentative and disruptive," try "In our last three meetings, you interrupted colleagues several times. This left me frustrated because I noticed others stopped sharing their ideas afterward." Most importantly, make listening central to your feedback approach. After sharing your perspective, ask questions that invite the other person's view: "How do you see this situation?" Then listen—really listen—to understand rather than to respond. This often reveals crucial information that changes your own understanding. When Jarred finally tried this approach with Michelle, he discovered that what he perceived as disruptiveness stemmed from her deep concern about the company's strategic direction. This insight not only improved their relationship but also highlighted important issues the leadership team needed to address. By fostering these learning conversations throughout your organization, you create the conditions for continuous adaptation—the key to thriving in complexity.

Summary

Navigating complexity requires us to fundamentally reimagine leadership. The traditional image of the all-knowing leader who predicts the future and controls outcomes simply doesn't match the reality of our interconnected, rapidly changing world. Instead, adaptive leadership means creating conditions where people can collectively sense, respond to, and learn from emerging challenges. As Yolanda reflected near the end of her transformation journey: "I think we could all stand to give some of it up. Take these two approaches to organizational change we've seen recently... Organization 2 has a wide variety of much smaller bets out, and some resources are going to the creation of even more bets. In a world where people orient to the possible rather than the probable, Organization 2 is clearly in better shape for an uncertain future." Start today by identifying one area where you've been seeking certainty and control, and experiment instead with creating conditions for learning and adaptation. The complex world will not get more simple to make us more comfortable—now is our chance to grow as big as the world requires us to be.

About Author

Loading...

Jennifer Garvey Berger

Read more