E6. Thriving in the Messy Middle

Boi Carpenter

Welcome to the Inquisitive Leader podcast! My name is Boi Carpenter. I am a visionary, advisor, strategist, and executive coach, bringing over twenty-nine years of professional experience as an individual contributor, manager, and leader of large-scale teams. I'm also the creative architect of this podcast.

Boi Carpenter

It is such a pleasure to welcome you into the Inquisitive Leader community. Today's episode is about thriving in the messy middle.

Boi Carpenter

Well, the messy middle. It's uncomfortable, isn’t it? That space where things are uncertain, where answers seem frustratingly out of reach. But what if I told you that this liminal space—this in-between—might just be the most fertile ground for growth? A place where breakthroughs, both personal and organizational, can take root.

Boi Carpenter

In anthropology, liminality refers to transitional phases, those "neither here nor there" moments. And while uncertainty might make us uneasy, neuroscience has shown us something remarkable. When we face the unknown, parts of our brain associated with curiosity and learning light up. It's as though our minds, despite the discomfort, are wired to explore, to question, and to grow.

Boi Carpenter

And that’s the paradox, isn’t it? By resisting the urge to grasp for immediate answers and instead leaning into the ambiguity, we unlock a powerful mindset: what I like to call "productive uncertainty." This mindset encourages us to ask better questions—not just, "How do I fix this?"—but also, "What can I learn here?" or "What’s this discomfort revealing?"

Boi Carpenter

For leaders, this approach is transformative. When we model curiosity and embrace the messy middle ourselves, we inspire our teams to do the same. It invites innovation because, instead of clinging to old stories or processes, we begin to see what could be. And let me tell you, resilience thrives in this space—it’s where adaptability is born.

Boi Carpenter

So, when we think about navigating uncertainty—not just for ourselves, but with a team—what’s the cornerstone? It's psychological safety. That’s the foundation for innovation, for creativity. Without it, teams are hesitant; people hold back their thoughts, their questions, their discoveries. And truly, without that environment of safety, collective inquiry simply... falters.

Boi Carpenter

Now, collective inquiry—it’s not about coming to the table with all the answers. In fact, it's quite the opposite. It's about saying, "What don’t we know? What haven’t we considered yet? Where are the blind spots?" And creating space for everyone, every voice, to contribute to those questions. It’s humbling, isn’t it? To acknowledge that we as leaders might not see the full picture, but that together—with curiosity—we can find clarity.

Boi Carpenter

We’ve explored the messy middle and the power of collective inquiry. But now, let’s bring it closer to home—to the practical actions that we, as leaders and individuals, can take to thrive amid uncertainty.

Boi Carpenter

First—reflection. It might sound simple, but taking the time to observe your own reactions during uncertainty is profound. Notice what happens in those moments when answers seem elusive. Do you rush to over-plan? Do you avoid decisions altogether? This practice of self-inquiry, of noticing patterns without judgment, is the groundwork for building resilience. And resilience, you know, isn’t about simply enduring. It’s about adapting, iterating, and growing stronger with every challenge.

Boi Carpenter

Now, think about iterative planning. When you’re navigating uncertainty, don’t lock yourself into rigid strategies. Instead, hold plans lightly—almost as micro-experiments. For example, let’s say you’re leading through organizational change, and a clear pathway isn’t obvious. Start small. Test ideas, learn from the outcomes, and refine as you go. Each tiny step gives you data—information that allows you to adapt as new insights arise.

Boi Carpenter

Here are some questions to explore further: “What don’t we know yet?” “Where might we need to pause and listen more deeply?” “What can we do differently to meet this moment?” “What new possibilities does this uncertainty open up for our organization?" "How might this period of change allow us to innovate in ways we haven't before?" and "In what ways could this change make us more resilient and adaptable in the long run?"

Boi Carpenter

I once worked with a coaching client who was facing what seemed like insurmountable volatility in their market. Every day brought fresh challenges. Instead of trying to control the uncontrollable, they shifted their focus to what was within reach. They ran small experiments—adapting workflows, testing new systems—and stayed open to their team’s feedback. Over time, they not only weathered the storm but uncovered opportunities that reshaped their entire strategy. Shifting from rigidity to adaptability doesn't just solve problems; it helps you find hidden opportunities you didn’t know existed.

Boi Carpenter

And let’s not forget the heart of it all: embracing the mess. You see, there’s a tendency to resist discomfort, to tidy things up too quickly. But I’d like to invite you to think differently. Think of the mess as fertile ground. It may be foggy, unclear, but it reveals patterns beneath the surface—the hidden fears, the assumptions we need to unlearn, the pathways we’ve yet to discover. Growth, real, transformative growth, begins right there.

Boi Carpenter

So, as we close today's conversation, I encourage you to lean into this practice of productive uncertainty. Self-reflection, micro-experiments, and open questions—they’re all tools to help you navigate this in-between space with intention. And more than that, they’re an invitation to deepen trust—in yourself, in your team, and in the process.

Boi Carpenter

And that’s all for today. Thank you for joining me in this exploration of the messy middle. Let’s continue to hold space for the unknown, knowing that some of our greatest discoveries begin in uncertainty. Until next time, take good care of yourselves—and each other.