Many leaderships teams staring down the barrel of organizational transformation face a similar dilemma: How do you take a leap into the unknown when there are no clear data, no well-trodden path to follow, and no assurance of success? What if the change you’re considering is uncharted territory, but waiting for certainty means standing still?

Over the years, we’ve seen countless organizations struggle with these questions, whether they’re trying to flatten hierarchies, implement new processes, or change how decisions are made. Through our five-year study of a company we’ll call by the pseudonym Pharma Global (PG), we uncovered key insights into how executive teams can deftly navigate a high-stakes and uncertain transformation and move forward with conviction.

Trap 1: Overthinking the leap

Like its competitors, PG had long relied on a few blockbuster drugs. But by the 2010s, as a major acquisition expanded its R&D pipeline, its commercial team was managing an increasingly complex and expansive portfolio.

Unfortunately, PG’s long-standing top-down culture and bureaucratic rules were an obstacle to the agility the company now required. So its executive team hired two top consulting firms to build the case for transformation. Both said the company needed a significant reorganization to become more agile. Yet, two years later, the executive team was still asking for more data, benchmarking, and risk assessments.

The executive team overlooked a crucial factor—the nature of the problem they were trying to solve. Traditional organizational changes are technical problems with clear, well-defined solutions. But PG’s transformation was an adaptive problem.

Although the direction was clear, specific solutions had to come from within the organization. Instead of a single structural fix, multiple interconnected decisions had to be made by different teams. Additionally, there were no direct industry benchmarks or large-scale models to follow. PG would be the first to implement this approach at its scale.

Leadership shift: Assume change, justify inaction

No amount of analysis could provide the certainty to which the executive team was accustomed. So, “Gerrick,” the head of PG, and “Giorgio,” who led seven affiliates, reframed the situation by posing this question: Why shouldn’t we change? The resulting shift in thinking was subtle yet powerful. Rather than seeking comfort in more data, the executive team recognized that the real risk lay in maintaining the status quo.

They embraced a new ambition: PG would become the very first large pharmaceutical firm to flatten its organizational design. The risk was worth taking because it would send a strong message to employees that leadership was serious about purpose-driven and empowered ways of working. PG could also scale the learning curve and shape the playbook for a new kind of organization—one that could become a competitive advantage in itself.

If your organization is overthinking the leap, ask these questions:
• Are we trying to solve a technical problem or an adaptive challenge?
• Are we reducing risks or avoiding uncertainty? What are the risks of not changing?
• What are the benefits and costs of being the first to experiment with the transformation? What are the consequences of competitors successfully developing a proof of concept first?

Trap 2: Waiting for a full road map

The next challenge to overcome was the desire for a perfect plan. In traditional organizational change, a detailed step-by-step road map is typically seen as essential. However, given the adaptive nature of the problem and inherent ambiguity in the transformation process, only the initial stages could be mapped out. Subsequent stages would have to evolve based on early actions and results.

Leadership shift: Visualize the destination

To move forward, PG’s executive team made a second important shift: letting go of the need for a perfect plan, which simply didn’t exist, and acknowledging that a period of instability was inevitable.

Rather than fixating on the structure, they visualized their ideal outcome: an organization where people are empowered to make decisions with minimal approval, guided by a shared understanding of strategic priorities, decision-making criteria, and operational boundaries.

Focusing on the envisioned outcome not only made the executive team feel less anxious, it also energized them to move forward. They outlined critical success factors, including clarity when it came to roles and responsibilities, direction, and communication. This created a collective confidence that the transformation could succeed even without a predefined plan.

To build confidence amid uncertainty, consider the following questions:
• What should the future organization look like? How should it function?
• If chaos is inevitable, how can we make it productive by reducing disruptions, staying agile, and supporting each other when unexpected challenges arise?
• What key values, behaviors, and commitments will help us navigate uncertainty, maintain momentum, and ensure the organization adapts effectively throughout the change?

Trap 3: The control reflex

The next challenge: What did it mean to “lead” a transformation aimed at decentralizing decision-making? Given the vast scope of the transformation, the executive team couldn’t possibly deal with every challenge at once. Such a top-down approach would also contradict the very purpose of the change, which was to empower PG’s employees to design an organization that truly worked for them.

The answer was clear and unnerving at the same time—ownership of the transformation had to belong to employees.

Leadership shift: Build the trust muscle

The executive team wasn’t giving up all control. It was responsible for the objectives, directions, and process of the transformation, and remained accountable for its success or failure. However, self-organizing teams—called “circles”—would own the analysis, recommendations, decisions, and implementation.

The executive team understood that their role wasn’t to dictate solutions but to support the process. They created an internal communication platform for employees to form circles, suggest projects, and share progress updates. The system also supported the early detection of signs of failure, allowing for timely course corrections and careful interventions when necessary.

Within weeks, energy surged throughout the company. Employees began to view the transformation as their own. As the executive team empowered the circles, trust deepened on both sides. With this came a greater willingness of the executive team to shoulder accountability while letting go of control.

To prevent the control reflex and build the trust muscle, think through these questions:
• Can ownership of the tasks be separated from ownership of the process? Who should own each aspect?
• What would make you comfortable relinquishing control? How can you remain accountable for outcomes without directly executing the transformation?
• What systems will help you ensure strong information-sharing, monitor progress, detect weak signals of failure, and make timely interventions without taking back control?

Trap 4: One foot in, one foot out

The executive team was still in an uncertain position: responsible for the transformation’s success, yet lacking the traditional levers of authority. This discomfort could lead to the instinct to hedge—to keep one foot in, one foot out.

Anticipating this risk, the executive team members saw that for the transformation to succeed, they had to redefine their role. They identified two key responsibilities: safeguarding decision-making processes and ensuring teams had the resources to execute effectively, and facilitating coordination across circles and representing PG within the wider organization.

Leadership shift: Codify the shift

The executive team made a public commitment, beginning with a name change: It would now be known as the network empowering team (NET). It established a team charter that outlined its new responsibilities to the organization and to each other. This sent a message that leadership was no longer about command and control but about enabling the system to function.

Soon, the NET faced its first real test. The finance circle decided to replace the traditional months-long budgeting cycle with AI-driven forecasting. Although this approach was innovative, Giorgio, who had to sign off on the numbers for the board, hesitated.

Rather than override the circle, the NET collectively reviewed the process, asked clarifying questions, and ensured rigor without undermining the team’s ownership. By following their formalized charter, the NET reinforced the transformation’s principles and set a precedent, changing its role from negotiating financial targets to providing resources to support execution.

To ensure your leadership team fully embodies a new vision, ponder these questions:
• Have we clearly defined, formalized, and communicated our new role in a way that differentiates it from the past?
• Are we consistently role-modeling and communicating behaviors that reinforce our new organizational design? How do we show our commitment to enabling vs. directing?
• How are we holding ourselves accountable to our new leadership approach?

Successful change amid uncertainty

PG’s transformation wasn’t driven by a detailed road map, perfect plan, or guarantee of success. Rather, it was spurred by a series of deliberate leadership shifts that empowered the executive team to move from hesitation to action.

The experience provides a striking lesson for any executive team confronted with a similar challenge: Waiting for certainty is a trap, and moving forward requires leaders who can recognize and overcome the common stumbling blocks that stall transformation.

When leaders take the leap, they enable a system where employees aren’t just adapting to change—they’re driving it.

This is an adaptation of an article published in Harvard Business Review. Published May 6, 2026, by INSEAD.