50: Navigating the Messy Middle of Organizational Transformation

How to Lead When the Old Way Is Gone and the New Way Isn’t Ready

“The messy middle isn’t a detour. It’s where real change becomes culture.”

The Power of the In-Between

Beyond the Process explored how design maturity isn’t just about better methods or more headcount—it’s a cultural transformation that emerges through resistance, reframing, and reinvention. But transformation doesn’t end with declaring new values or launching a design system. That’s when the real work begins.

After the friction of resistance and the clarity of a reset, organizations enter a fragile, uncertain space: the messy middle. This is the liminal phase—the old way is gone, but the new one isn’t yet solid. Strategy gives way to sensemaking, and change becomes a daily negotiation rather than a theory.

Most organizations treat transitions like speed bumps—temporary disruptions on the path to stability. But fundamental transformation doesn’t happen at the start or the finish. It occurs in the middle.

This liminal space isn’t a detour. It’s where culture is rewritten, trust is rebuilt, and new futures take root. It’s also the hardest place to lead. When the old way no longer works but the new one isn’t defined, discomfort runs high. Teams crave clarity, and leaders feel pressure to deliver. Yet rushing through this phase often undermines the change we seek.

The messy middle isn’t the enemy. It’s the work.

In stable environments, strategy is a map. In liminality, the map dissolves. As Karl Weick, the organizational theorist behind sensemaking research, says, leaders must “act their way into thinking” in volatile contexts rather than wait for clarity. Traditional planning assumes predictability, but sensemaking becomes the core leadership skill when the terrain shifts. Fixed roadmaps collapse under uncertainty, and clinging to past models blinds teams to emerging patterns.

Instead of forcing false clarity, leaders must shift from certainty to curiosity, spotting weak signals, reframing ambiguity as a creative space, and orchestrating rather than controlling. Visual mapping, decision pre-mortems, and structured listening rituals help externalize collective understanding. Most importantly, teams need spaces where they can voice uncertainty without fear.

Rebuilding Trust When Results Are Uncertain

Skepticism rises in times of transition. Edgar Schein, the father of organizational culture theory, observed that trust isn’t built through rhetoric but through consistent action. People don’t trust ideas—they trust behavior. When outcomes are unclear, psychological safety hinges on transparency and small wins. Leaders must “show their math,” making the invisible thought process visible, much like design thinker Tim Brown advocates in Change by Design.

Celebrating early signals—prototypes, micro-wins—becomes evidence of progress, reinforcing confidence. Narrative also plays a key role; as Harvard’s Marshall Ganz teaches, leaders must reweave a compelling story that connects actions to a larger transformation. “Design doesn’t need more evangelism. It needs evidence,” as the saying goes. Trust isn’t built through grand visions but through reliable, repeatable practices that demonstrate commitment.

Embedding New Norms Before They Harden

Culture isn’t declared—it’s shaped through repetition. Liminality offers a rare window to test, refine, and ritualize new working methods before solidifying into unconscious habit.

Organizational psychologist Edgar Schein noted that culture emerges from what is rewarded, repeated, and ritualized. In the uncertainty that follows a transformation effort, teams often look for new anchors—signals that reveal what is safe, valued, and expected. This is the moment when culture can be intentionally rewritten.

Instead of importing best practices, design leaders must tune into emergent norms that arise organically from the team’s lived experience and evolving challenges. Language matters here: calling something an “experiment” instead of a “pilot” signals permission to explore, not just execute. Small changes in vocabulary can lead to significant shifts in mindset.

Similarly, rituals become carriers of values. Redesigning critiques to focus on learning rather than judgment, reshaping standups to include intention-setting (not just status updates), and using outcome retrospectives to reflect on behavior, not just velocity, are all ways to embody new principles.

Even everyday meetings can become cultural mirrors. A simple “ritual audit” can reveal whether a team’s default behaviors reinforce the status quo or signal something new. In times of change, these moments matter more than formal declarations.

If done well, embedding new norms becomes less about rollout and more about resonance. In the liminal, culture is soft clay. What we shape now determines what holds later.

The Leader’s Inner Work

Holding ambiguity for an organization is exhausting. In times of transformation, leaders often become emotional shock absorbers—navigating uncertainty externally while managing doubt and decision fatigue internally.

Leadership scholar Herminia Ibarra writes that transitions aren’t just strategic but personal. When the old ways of leading no longer work, but the new ones aren’t fully formed, leaders must experiment with new identities before fully stepping into them. This liminal space isn’t just organizational—it’s deeply individual.

That’s why sustainability isn’t a side note; it’s the center of the work. Leaders must design conditions that support clarity, restoration, and reflection—not just for their teams but also for themselves. Peer learning circles counteract the isolation of change. Intentional feedback loops help distinguish between what energizes and what depletes. Revisiting one’s purpose becomes less of a luxury and more of a lifeline.

In this context, burnout isn’t a personal failure—it’s a signal that the system needs care. The work of sustaining others starts with how well we sustain ourselves.

Will You Rush Through—Or Lead from Within?

Organizations rarely fail because they lack ideas. They fail when they abandon the messy middle, retreating to familiar habits instead of staying with the discomfort of becoming something new.

This phase isn’t a pause. It’s a practice. It’s where fundamental transformation happens—not in the plan, but in the people, not in the outcome, but in the unfolding.

The question isn’t when clarity will arrive. It’s whether we can create the conditions for it to emerge.

Will you rush through the in-between? Or will you lead from within it?