Leading with Clarity in the Messiness of Change

Introduction

I was sitting in my driveway in 2017, car packed for a road trip with my son, when the call came. It was our key funder, and I knew from the tone of voice before they even delivered the news: our funding would be cut by 60%. Not reduced. Not delayed. Cut.

As I sat there listening to explanations about shifted priorities and budget constraints, I watched my son sitting next to me, excited about our upcoming adventure, completely unaware that everything had just changed. The organization I had built over seven years was heavily dependent on this funding—not just for programs, but for the staff salaries that kept talented people working in our neighborhood.

In that moment, I had a stark choice: quit or adapt.

The months that followed became some of the most challenging of my life, requiring me to reduce our workforce by nearly 60% and completely reimagine our operating model. But they also taught me something crucial about leadership that I hadn't fully grasped in my previous twenty years of community work. The organizations that create lasting transformation aren't the ones that execute perfect plans in ideal conditions. They're the ones that build capacity to respond effectively to whatever conditions actually emerge.

This is the daily reality of adaptive leadership in community work. Unlike technical problems—where we know what needs to happen and just need resources to implement solutions—most of the challenges that keep neighborhoods from thriving are adaptive challenges that require new learning, behavior change, and innovative approaches. The leader who can navigate this distinction, who can build teams that combine visionary capacity with implementation expertise, and who can read the waves of change to position their community for emerging opportunities, is the leader who creates lasting impact.

The Visionary-Integrator Dynamic in Complex Environments

In the months following that devastating funding cut, our organization identified an unexpected opportunity: the federal government was dramatically increasing funding for Community Development Financial Institutions, and our three-year plan to develop local lending capacity could potentially be accelerated.

But having a clear vision and actually operationalizing a CDFI are entirely different challenges. The visionary in me could see how community-controlled lending could transform economic opportunity. I could imagine the restaurant owner finally getting equipment financing, the family achieving homeownership, the daycare provider expanding.

The execution challenge, however, required completely different thinking. Someone needed to research CDFI certification requirements, develop lending policies, create underwriting criteria, and establish operational systems. The visionary capacity that could see the potential had to work in partnership with integrator capacity that could make it real.

This dynamic—between seeing what's possible and building what's practical—becomes especially critical when leading through complexity. Gino Wickman's work in "Rocket Fuel" identifies this as the fundamental partnership between visionary and integrator roles that drives organizational success. When conditions are shifting rapidly and opportunities appear and disappear quickly, you need both perspectives working in productive tension.

Visionary capacity sees patterns and possibilities that others might miss. But without integrator thinking, it creates what I call "beautiful impossibilities"—inspiring ideas that never quite translate into actionable plans. The integrator capacity provides the counterbalance: breaking down big ideas into manageable steps, identifying resource requirements, building the systems that sustain progress.

In our CDFI development, this meant the difference between having community meetings about accessible capital and actually having a functioning loan fund eighteen months later. The vision attracted initial support and kept everyone oriented toward purpose. The integration work created the legal structure, operational procedures, and staff capacity that made community lending a reality.

What makes this dynamic particularly important in community work is that adaptive challenges require both perspectives simultaneously. You can't solve gentrification pressure or educational inequity with purely technical solutions. These challenges require innovation that comes from visionary capacity, but only becomes sustainable change through integrator capacity that builds new systems.

The most effective community development leaders understand this dynamic and structure their teams accordingly. It's about creating productive tension between "what should be" and "what's possible now" that drives continuous learning and adaptation.

Distinguishing Technical Problems from Adaptive Challenges

By 2019, two years after rebuilding from that devastating funding cut, I faced what felt like a puzzle wrapped in politeness. Our leaner team was full of genuinely caring people who believed deeply in our mission, yet projects were consistently falling behind and important deliverables were slipping through cracks. Staff meetings felt warm and collaborative, but when it came time to address missed deadlines, conversations would drift toward relationship-building or get postponed for "better timing."

The pattern became clear: we had team members who were exceptionally gifted at building rapport with community members and colleagues. They could facilitate beautiful conversations and bring warmth to every interaction. But when it came to less glamorous work—writing grant reports, following up on commitments, or having direct conversations about performance expectations—they consistently found ways to avoid or defer these responsibilities.

My initial instinct was to treat this as a technical problem. Better tracking systems, more explicit deadlines, project management software. The solutions felt straightforward: better systems would create better accountability.

But something felt insufficient. We actually had decent systems. The challenge was that certain team members were skilled at maintaining positive relationships while consistently avoiding aspects of work that might create tension.

Technical problems are challenges where the solution is known, even if difficult to implement. You can address them through improved processes, additional training, or clearer structures.

Adaptive challenges are fundamentally different. Ronald Heifetz's work in "The Practice of Adaptive Leadership" defines these as situations where the solution isn't known and can't be implemented by authority alone. They require new learning, often involve changing deeply held beliefs or behaviors, and typically demand that multiple people take ownership of creating solutions.

I realized we were facing an adaptive challenge that couldn't be solved through better project management alone. Our organizational culture had developed a pattern where avoiding conflict was valued more highly than achieving results. The team members who struggled with follow-through had learned that maintaining harmony was safer than risking the discomfort that comes with direct accountability.

This showed up in ways that implicated everyone, including me. High-performing staff would quietly pick up slack rather than address missed deadlines directly. I found myself hesitating to have direct conversations about unmet expectations because these team members were so genuinely likeable.

Recognizing this as an adaptive challenge changed my approach entirely. Yes, I still needed better tracking systems—that technical work was necessary. But I also needed to engage the entire team in examining how we had collectively created a culture where avoiding difficult conversations was prioritized over achieving community impact.

We explored questions like: How do we balance relationship maintenance with results that serve our community? When does avoiding conflict actually harm the relationships we're trying to protect? What does genuine support look like when colleagues are struggling to meet expectations?

The technical solutions were still necessary, but the adaptive work was what enabled those systems to actually function. We built team capacity to have honest conversations about performance because we understood that avoiding those conversations ultimately served no one.

Reading and Riding the Waves of Change

By late 2019, our organization had developed a solid three-year plan for launching our CDFI. We had conducted market research, identified potential board members, and begun conversations with a bank partner. The timeline felt reasonable: two years for planning, followed by launch in 2022.

Then March 2020 arrived, and everything changed overnight.

Within weeks, it became clear that COVID-19 wasn't just disrupting our timeline—it was creating an entirely different environment for our work. Small businesses were suddenly facing closure. Families who had never needed emergency assistance were applying for rental relief. The federal government was pouring unprecedented resources into community development, including massive increases in funding for CDFIs.

I remember the phone call from our bank partner in April 2020. "The landscape has completely shifted," she said. "CDFI funding that used to take two years to secure is now available in six months. But the window won't stay open indefinitely, and community need is exploding right now."

This was my introduction to reading and riding the waves of change—learning to recognize when external conditions create opportunities that weren't in your original plan, and developing organizational agility to respond effectively without losing strategic direction.

The visionary in me could immediately see the possibilities. Instead of waiting until 2022, we could potentially launch our CDFI in 2021 and serve families and businesses during their moment of greatest need. The timing wasn't what we had planned, but it was precisely aligned with our mission.

But recognizing an opportunity and capitalizing on it are very different challenges. Accelerating our CDFI timeline by eighteen months meant front-loading work we had planned to do gradually while managing existing programs during a pandemic. The wave of opportunity was real, but we had to develop the capacity to ride it effectively.

This required environmental scanning—developing practices for detecting early signals of change that might create new possibilities for your work. But scanning isn't just about gathering information—it's about developing analytical capacity to distinguish between changes that align with your strategic direction and changes that might distract from your core mission.

The CDFI acceleration opportunity was different because it aligned perfectly with our existing strategy while taking advantage of external conditions we couldn't control. We had been planning to develop lending capacity anyway—the pandemic simply created conditions that made faster implementation both possible and necessary.

What made this decision strategic rather than reactive was maintaining clarity about our underlying theory of change while adapting our tactics to emerging conditions. The direction remained constant while the path shifted based on external conditions.

The result was launching our CDFI in October 2021, fifteen months ahead of schedule and precisely when community need was highest. By the end of our first year, we had originated over $500,000 in loans to local businesses and families, focusing on immigrant entrepreneurs and first-time homebuyers who had been excluded from traditional lending.

The deeper learning was about building organizational agility to respond to change without losing strategic focus. This required developing "strategic scaffolding"—core principles and relationships that remain stable while specific tactics and timelines adapt to changing conditions.

What made this approach sustainable was understanding that riding waves of change isn't about chasing every new opportunity. It's about developing the clarity and agility to recognize when external changes create possibilities for advancing work you were already committed to doing.

Holding Steady in the Whirlwind

The months following our CDFI launch taught me something unexpected: the external capacity to navigate change depends entirely on internal practices that sustain you through uncertainty. Without conscious practices for staying grounded, I realized I was at risk of becoming reactive rather than responsive—managing crisis rather than leading transformation.

For me, this meant developing "anchor practices"—regular activities that connect me back to my core purpose and provide space for reflection amid constant action. Monthly conversations with longtime community leaders became essential for maintaining perspective. Quarterly reviews of our theory of change helped distinguish between tactical adaptations and mission drift. Weekly time for reading and thinking provided the mental space necessary for strategic leadership.

But personal practices alone weren't sufficient. Leading through complexity requires building organizational capacity for learning and adaptation, not just individual resilience. Our monthly staff learning sessions became essential infrastructure for reflecting on what we were learning about community development in rapidly changing conditions.

Each new opportunity required what I learned to think of as "strategic experimenting"—trying new approaches while maintaining clear criteria for evaluating success and failure. This meant being willing to invest time and resources in initiatives that might not work, while building organizational capacity to learn from whatever outcomes emerged.

The most important insight was understanding that sustainable leadership through complexity requires balancing individual grounding practices with collective learning systems. Personal resilience provides the foundation for clear thinking and strategic vision. Organizational learning capacity ensures that insights get captured and integrated rather than lost in constant activity.

Conclusion

That driveway moment in 2017 feels like a lifetime ago. The organization that emerged from that 60% funding cut became more resilient, more strategically focused, and ultimately more effective at creating community impact. The staff members who stayed became deeply invested in building sustainable systems rather than just delivering programs.

Perhaps the most unexpected outcome is that my son—the same one who sat excitedly in that car, unaware that everything was about to change—is now my business partner, helping lead community transformation organizations through their own complex challenges. The adaptive leadership skills that carried us through that crisis didn't just save an organization; they modeled approaches to navigating uncertainty that now shape how the next generation thinks about community development work.

Their transformation—and ours—illustrates something fundamental about leading through complexity. The goal isn't to eliminate uncertainty or control change, but to build individual and collective capacity to navigate whatever conditions actually emerge. This requires integrating visionary capacity that sees possibilities with integrator skills that make those possibilities real. It demands distinguishing between technical problems that can be solved with existing knowledge and adaptive challenges that require new learning and behavior change.

Effective leadership through complexity requires building teams that combine different strengths, creating organizational cultures that can experiment and learn, developing practices for detecting and responding to external changes, and maintaining personal and collective practices that sustain clarity and purpose amid constant motion.

The communities that thrive during periods of rapid change aren't the ones that predict the future most accurately. They're the ones that develop resilience, agility, and learning capacity to respond effectively to whatever future actually emerges. They understand that clarity in complex environments comes not from having all the answers but from maintaining clear values and adaptive capacity while experimenting with innovative approaches.

As you reflect on your own leadership challenges, I invite you to consider: Are you treating your biggest challenges as technical problems requiring better implementation, or adaptive challenges requiring new learning and behavior change? Do you have both visionary and integrator capacity within your leadership team? What practices help you stay grounded while riding the waves of change that characterize our field?

The future of community development belongs to leaders who can hold both vision and pragmatism, who can build organizations that learn and adapt, and who understand that sustainable transformation requires navigating complexity rather than avoiding it. The messiness isn't a problem to solve—it's the environment where the most important work happens.

What adaptive challenge is your organization currently facing, and how might approaching it differently unlock new possibilities for community impact?