The Power of the Messy Middle: Why Your Reorg is Failing
Dec 23, 2025
The "Messy Middle" that awkward liminal phase most companies try to skip
Hi, Hylke here!
I’m dropping into your space today with a pattern we are witnessing during a reorganization we've been asked to step in and help out. One that sits right at the intersection of Change Management and Emotional Intelligence. We created these insights because we love sharing the real-world markers that actually move the needle, and right now, the needle is stuck in what we call the "Messy Middle".
Reorganization's are often treated like a clinical, surgical move from Point A to Point B. You see it in the transformation roadmap: "Current State" leads to "Target Situation." It looks clean, organized, and entirely logical. But in our effort to drive results, we consistently try to skip the liminal phase, that awkward, uncertain "in-between" where the old rules no longer apply and the new ones haven’t been written yet.
The Anthropological Truth of the Messy Middle
In our work with Organizational Leadership, we often look through an anthropological lens. Tribal cultures didn't just tolerate this liminal phase; they embraced it as the essential time for learning and transformation. It was a sacred space of "betwixt and between".
Modern corporate tribes, however, usually try to rush through this chaos to find "clear" structures as fast as possible. We build, what Danielle Braun calls a new totem pole (a new org chart or a set of values) and expect everyone to worship it immediately. But ownership and involvement only happen when people feel safe enough to navigate the uncertainty together.
When we try to bypass the mess, we end up with "ideological cement": sticking to a plan because we want it to work, not because the reality of the company supports it.
Managing Uncertainty Like a Tribe leader
The magic happens when a leader stops trying to provide fake certainty and instead manages that uncertainty. Rather than offering surface-level fixes, the leader:
Recognizes the Internal Chaos: They see when the "parts" of the team, the Soloist, the Victim, or the Believer, start rushing the cockpit to take control out of fear.
Creates a "Campfire": They use stories and rituals to allow the team to process the chaos together, grounding the work in what is actually alive within the company, on a daily basis.
Practices Mental Liquidity: They possess the superpower of changing their mind when the reality of the market or the team changes.
Honestly, it is much better to admit you don't know the answer yet than to build a new totem pole that nobody actually believes in. That is the core of Regulated Leadership: staying at the wheel while the foundation feels like it’s shifting.
The Monthly Two's: Your Reflection Guide
To help you go deep where the fire starts, here are your reflection points for the week:
Two Questions:
Which "parts" of you are jumping into the cockpit right now? Is it the "Soloist" trying to carry the reorg alone to feel safe, or the "Believer" trying to bypass the pain of the mess?
Are you building a "totem pole" (a structure) that people actually believe in, or just one that looks good on the outside? And who's actually 'IN'
Two Actionable Insights:
Stop the "Bad Cop" Trap: Don't try to be the "bad cop" who forces the change while your managers stay "good cops". It annihilates their ability to work as leaders and kills honest communication.
Practice Professional Authenticity: Share your uncertainty, but regulate it. Tell the team: "I don't have the full map yet, but I am committed to walking through this messy middle with you".
One Anecdote from the Dojo Floor
I remember a training back when i was starting out. We had a carefully prepared script. Halfway through, it was clear the group wasn't "with" the playbook, the energy was falling, and there was a "pink elephant" of unaddressed resistance in the room.
Following the lead of my mentor, we flung the playbook aside and danced with what was alive in the room. It was scary, and the voices in my head asked, "What if I lose control?". But by ditching the script and trusting our intuition, the team came alive. We moved from ideological cement to mental liquidity in real-time.
Leadership transformation should be felt as much as it is seen. If you're ready to playfully unleash your team's potential instead of just managing, let's talk.
Welcome to the Tribe,
Hylke
———-—————————————————————————————--
If you’re currently navigating a transformation and feel the foundation crumbling despite "good" choices, let’s stop guessing. We don't do cookie-cutter playbooks; we do tailored assessments that define the markers that actually matter to your culture, from communication quality to true ownership, and yes, even the bottom line.
Let's sit down for a short call. We’ll look at the internal chaos together and define a regulating move to bring your team back to center.
Book your assessment session here
Or email us and tell me: "What is the biggest pink elephant in your process right now?''
The Highlights
The "A to B" Trap: We often treat reorganization like a clinical move from A to B, but we consistently try to skip the "liminal phase", the awkward period where old rules don't apply and new ones aren't written yet.
Tribe Leadership: Great leaders avoid giving fake certainty; instead, they manage uncertainty like a shaman, using stories and "campfires" to let the team process the internal chaos together.
Mental Liquidity vs. Ideological Cement: The ability to change your mind when reality changes is a leadership superpower that prevents "ideological cement" from quietly killing your culture.
Foundation of Trust: Every truly successful team works from the bottom up, building a foundation of trust to allow for failure and constructive conflict before chasing results.
Professional Authenticity: In a working environment, we don’t need unregulated authenticity; we need your professional, responsible self to keep a hand on the wheel when fear strikes.