The Messy Middle: Leading Between Decisions and Destinations
KEY INSIGHTS
Most leadership is tested not in the bold decision or the crisis response, but in the long, uncertain stretch that follows — between what was decided and where it ultimately leads. When leaders across industries were asked how much of their work involves navigating decisions they didn't make, nearly two-thirds said often or almost always — and named the gap between what's expected and what's possible as their most frequent and draining tension. The messy middle isn't a detour from real leadership; it is real leadership — and navigating it well requires less focus on finding the right answer and more on developing the people, trust, and culture that make progress possible when the path isn't clear.
Why Most Leaders Aren't Prepared for the Messy Middle - We Were Trained for the Wrong Weather
Most leadership development is built for one of two conditions. The first is clear skies: stable, predictable environments where you can plan carefully, execute with discipline, and optimize for efficiency. The second is stormy weather: crisis and chaos, where decisive action is what the moment demands.
Both conditions are real. But as Pete Behrens, founder of Agile Leadership Journey and author of
Into the Fog, observes, most of leadership doesn't happen in either of those places.
"I describe most of leadership somewhere in between these two states — in the fog. This murky, uncertain space where change is happening beneath our feet. And we're not really trained for this."
Geopolitical upheaval. AI reshaping entire industries. Reorganizations, mergers, layoffs, and shifting strategies landing on teams who didn't ask for any of it. If it all feels foggy right now, that's not a personal failure of clarity. It's the landscape most leaders are actually living in, whether they have language for it or not.
This is the messy middle.
The Decision Is Just the Beginning
To open a discussion with a gathering of global alumni leaders, Pete read from the Resilience section of Into the Fog — a passage grounded in his own experience leading a team through an across-the-board layoff he had fought against, lost, and eventually resigned himself to. By the time the decision was implemented, he had processed it. He was ready to move on.
His team was not.
"After the layoff, I was ready to move on. But my team? Those who remained after the layoff? Their journey had just begun. They were only just entering the fog, hiking the trail, watching to see if I was too."
His cost: being emotionally spent precisely when his team needed him most. The end of his journey was the start of theirs — and he had nothing left to give.
This is the hidden toll of the messy middle. Not just the difficulty of navigating it, but the way it depletes the very resources leaders need to show up for others. When participants were asked what it costs them to support a decision they didn't agree with, the answers came quickly: cognitive dissonance, lost trust, credibility, a sense of worth and integrity, internal peace.
Five Types of Messy Middle Leaders Experience Most
One of the most clarifying things a leader can do in the fog is name specifically what kind of messy middle they're in. Pete shared five recurring forms that show up across industries, organizations, and levels of leadership:
- Between senior leadership and your team — being the shock absorber between those who make decisions and those who must live with them
- Between a decision and the destination — the long hike after the adrenaline of a major choice fades
- Between competing needs or priorities — holding the tension when legitimate demands point in different directions
- Between what's expected and what's possible — managing the gap between what stakeholders want and what is actually achievable
- Between your own commitment and delivering on it — the stretch between having said yes and figuring out how
When participants ranked which they experience most, the top result was the gap between what's expected and what's possible — the chronic pressure of being held to a standard that available resources, time, or conditions may not support. Close behind: competing needs or priorities, and sitting between senior leadership and their teams.
Richard Dolman, an ALJ Guide and leadership coach who works with leaders and organizations navigating complexity, named his own most pressing middle: right now it's between his own commitment and delivering on it. But what he finds frustrating professionally is something different — a pattern he observes repeatedly in the leaders he works with.
"Leaders understand the challenge in front of them when making decisions, but they often choose a shortsighted or less disciplined decision rather than seeing the long-term effects."
The decision gets made. The leader moves on. The people living with the consequences navigate a transition that was never fully considered. It's a reminder that the middle you're personally in and the middle you're creating for others aren't always the same — and awareness of both matters.
The pattern worth noting: the messiest middles aren't the dramatic ones. They're the structural ones — chronic tensions built into what it means to lead in complex organizations. Not crises to resolve but conditions to navigate, repeatedly, often without resolution.
What the Messy Middle Actually Costs Leaders
Leaders rarely talk openly about what the messy middle costs them. The professional expectation is to absorb it, adapt, and keep moving. But beneath that surface, the toll is real — and it shows up in ways that matter for the people depending on those leaders to show up.
Some leaders describe the experience of being so consumed by a change that was out of their control — trying to hold things together, backtrack where needed, protect the people around them — that they lose sight of their own limits. "I was inundated. I was drowning. When you're drowning, you don't realize it sometimes because you're just trying to keep everybody else from sinking." The self-blame that follows — "Why didn't I stop this? I could have stopped this" — often misses the reality that when you're submerged, stopping isn't always a visible option.
Others find themselves navigating decisions made far above them, watching the consequences ripple through their organizations in ways the decision-makers never anticipated. The frustration of seeing the same patterns repeat — of being close enough to see what's going wrong but not positioned to change it — accumulates over time into something heavier than any single incident. Pete observed that the bigger the organization, the more likely a leader is to spend significant energy defending decisions they didn't make, while the people who made those decisions have already moved on to the next thing.
Leaders who try to fix what's broken and find their efforts ignored or dismissed face a particular kind of middle: the gap between knowing what's needed and having no path to implement it. One participant connected her experience to something John Maxwell calls the leadership lid — the principle that an organization can only rise to the level of its leadership. She had found the concept clarifying after going through Maxwell's certification program: when the leader at the top is operating with a limited view, that lid is felt most acutely by everyone working beneath it. "In order to be a leader, you need to have followers. And no one was following him."
Rashmi Fernandes, an ALJ Guide and leadership coach, named an insidious cost that compounds quietly over time. When leaders are repeatedly exposed to these dynamics, she observed, something begins to shift internally.
"You stop feeling what used to affect you. You become numb. It thickens your skin but it also makes you emotionally unavailable for your people — because you've lost trust. Your words don't feel as valuable for yourself anymore."
When a leader stops trusting their own voice, they become less able to offer the support, clarity, or direction their teams need. That erosion of self-trust doesn't announce itself. It accumulates — until the leader who was once most present for others finds they have less and less to give.
How to Navigate Leadership Transitions: The Language That Helps
Having words for what you're in doesn't make it easier to bear, but it does make it easier to navigate.
A clarifying distinction is one William Bridges draws in his work on managing transitions — and one Pete returns to throughout
Into the Fog: the difference between change and transition. Change is organizational — the decision, the reorg, the acquisition. It happens at a point in time and is relatively clean. Transition is personal — the internal, psychological process each individual goes through as they let go of what was, move through the uncertainty, and gradually arrive at what's next. It's slow and it's messy. And it doesn't happen on the same timeline for everyone.
"Change is organizational. Transitions are personal."
A leader who spent weeks processing a difficult decision before it was announced has already traveled a significant distance by the time their team receives the news. Expecting others to be where you are is one of the most common ways leaders fail the people they lead. The decision may feel finished. For everyone else, it may be just beginning.
"Change only kicks off the journey, quick and clean. Transition is everything that follows, slow and messy."
Several other concepts are worth keeping close. Bridges calls the in-between the Neutral Zone — the wilderness where what was no longer exists and what will be hasn't yet arrived. Kegan and Lahey's Immunity to Change names the inner resistance that keeps people from becoming who the situation requires. Tim Arnold's Power of Healthy Tension reframes the polarities leaders navigate — assertive and accommodative, strategic and tactical, hands-on and hands-off — not as problems to solve but as tensions to manage. Michael Fullan's Implementation Dip names the performance drop that is a predictable feature of any genuine transition: you get worse before you get better, and that's not a sign something is wrong. It's a sign you're in the middle of something.
These concepts share a common thread: most leadership challenges aren't problems with a solution. They're terrains that require navigation. That distinction matters because how you frame the challenge shapes how you show up for it.
How to Start Navigating the Messy Middle
If you are currently somewhere in a messy middle, the most important work isn't finding a quick solution — it's developing the catalyst leadership orientation required to navigate the terrain. That means making fundamental shifts from relying on your own expertise or driving results through personal authority toward building the people, trust, and culture that make results possible when the path isn't clear.
As Pete Behrens writes in Into the Fog, a catalyst leader fosters change first in themselves, then in the organizations around them. The internal shift comes first and it begins with how you show up right now, in whatever middle you're in.
Here are seven ways to begin that shift while holding space for others:
1. Name the messy middle you're in.
The first and most underused act of leadership in the fog is simply acknowledging that the fog exists. Vague overwhelm is harder to navigate than a clearly identified tension. Not passing the fog forward means being honest about uncertainty while still holding steadiness for the people around you. When leaders pretend the middle isn't happening, people feel the gap between what they're being told and what they're experiencing — and they fill it with their own conclusions. Naming the specific kind of middle you're in, and inviting others to do the same, gives people something real to orient around.
2. Distinguish the change from the transition.
The decision may feel finished. For everyone else, it may be just beginning. Change is organizational — it happens at a point in time. Transition is personal — it unfolds inside people, on timelines no one controls. Where are you in this transition? Where is your team? The gap between those two answers is often where the most important leadership work lives.
3. Communicate through it all — especially when things are going well.
The instinct to communicate more in crisis and less in calm is understandable but costly. Trust is built in the quiet periods — through check-ins that didn't need to happen, updates that weren't urgent, conversations that happened before anything went wrong. When disruption arrives, people who already feel seen and heard can process it faster and show up more fully. As Lupe P. put it, drawing on years of experience working with families through difficult transitions: "You don't stop checking on your kids when things are going well."
4. Create space for the human experience.
People cannot engage with what comes next until they feel their current reality has been acknowledged. This means creating room for frustration, grief, confusion, and uncertainty — not as a distraction from the work, but as part of it. Pete describes a leader who, ahead of a round of layoffs, gave his team an hour to vent about everything they were hearing and feeling — against company policy. "I know you're talking about this. I know it's bothering you. Take an hour, vent with your team, hash it out." What followed was genuine engagement rather than performed professionalism. Permission to be frustrated is permission to be human, and it can be a precondition for genuine engagement.
5. Notice the wallflower.
People navigating personal difficulty rarely announce it. They show up differently — quieter, less engaged, off their usual rhythm. The leader who notices and acts on that noticing creates a different kind of safety than any policy can. Valynn W. carried a lesson from her Marine Corps days on this: "Be aware of the wallflower. They might be an introvert, but they might have something going on." Ask how people are doing and mean it. Be aware of who has gone quiet.
6. Celebrate endings.
Every transition requires letting go of something, and letting go deserves acknowledgment — not just as grief, but as recognition of what was built, accomplished, or learned. When endings go unmarked, people move on without closure. When they are celebrated, people carry the accomplishment or the closure forward. Recognize what is ending before rushing to what comes next. Honor the work, the culture, or the chapter that got you here. Small rituals of celebration and closure matter more than most organizations acknowledge.
7. Take care of yourself first.
Resilience isn't infinite, and it erodes fastest under sustained pressure. The capacity to pause, to notice, to respond rather than react — these are the foundation of effective leadership in the fog, not a peripheral concern. That means different things for different people: a consistent mindfulness or meditation practice, regular exercise, adequate rest, honest conversations with trusted peers, or simply protecting time to think and recover. What you don't replenish, you eventually can't give.
