The Hidden Challenge of Leading Transformations

For seasoned leaders, the most surprising professional challenge often doesn’t arrive at the start of a career but after years of achievement. It comes in the form of a new mandate: a complex transformation, a high-stakes organizational bet, or an ambiguous problem that refuses easy answers. Sometimes this assignment is linked to a promotion, but often it is handed to an incumbent leader who already holds significant authority. In either case, what once felt effortless—the ability to chart direction, resolve conflicts, and inspire momentum—can suddenly feel shaky.

Why Experienced Leaders Feel Unsteady

The disorientation is rarely about raw capability. It is about contextual stretch. As William Bridges (2009) noted, transitions create turbulence not only because of external change but because of the “psychological reorientation” required. Leaders accustomed to reliable playbooks and established authority find themselves facing situations where the rules seem rewritten.

In these moments:

• Trusted strategies don’t land as reliably.
• Small wins are harder to secure, and mistakes feel amplified.
• Even the most confident executives can slip into extended self-doubt, questioning whether they are keeping up or falling behind.

Herminia Ibarra (2015) explains this as a clash between competence and identity. The behaviours and instincts that once fit neatly no longer deliver the same results. Meanwhile, Ronald Heifetz (1994) draws the distinction between technical problems, which can be solved with expertise, and adaptive challenges, which require experimentation and learning in real time. Transformational mandates are, almost by definition, adaptive. That is why seasoned leaders can feel suddenly unsteady—not because they are unqualified, but because the work is different in kind, not just in scale.

The Unique Strain of Transformational Assignments

Transformational initiatives are not routine projects. They involve shifting organizational culture, upending entrenched processes, or delivering new capabilities under political or public scrutiny. For Canadian federal executives, this may mean implementing a digital-first service strategy, restructuring a department in line with government priorities, or tackling systemic challenges such as climate policy. For private-sector leaders, it may be a merger integration, market disruption, or pivot to new technologies.

These assignments share three traits that put extraordinary strain on leadership confidence:

1. Novelty and Ambiguity
   Transformations often have no precedent. Kahneman (2011) reminds us that ambiguity pushes the brain out of intuitive, quick “System 1” thinking into slower, effortful “System 2” mode. Leaders feel less fluid because they are genuinely required to think harder and more deliberately.
2. Visibility and Stakes
   High-stakes initiatives rarely stay in the background. Federal executives contend with oversight from central agencies and ministers; private-sector leaders face shareholders, regulators, or media. Under such scrutiny, even small missteps feel magnified.
3. Erosion of Familiar Facility
   Leaders accustomed to fluency find themselves clumsy. As Edgar Schein (2013) suggests, effective leaders in complex environments must embrace “humble inquiry”—asking more than telling. That shift can feel, at first, like loss rather than growth.

The Psychology of Self-Doubt in Transformation

Self-doubt is a predictable response to these pressures. Zenger and Folkman (2019), writing in Harvard Business Review, found that confidence dips are common among leaders during transitions and new mandates. The danger lies not in doubt itself but in how it is handled.

Unchecked, self-doubt can paralyze decision-making or drive defensive arrogance. But harnessed, it can sharpen judgment. Brené Brown (2018) argues in Dare to Lead that vulnerability—the willingness to admit uncertainty—is the foundation of courageous leadership. Real confidence, then, is not blind certainty but grounded resilience: the conviction that you can face the unknown, adapt, and continue forward.

Why Support Matters

During a transformation, no leader can rely solely on internal structures for support. Organizations are rarely equipped to provide candid, non-political feedback to those leading the charge. As Robert Kegan and Lisa Lahey (2009) argue, growth depends on surfacing hidden assumptions and testing them against reality. Without a trusted partner, leaders risk falling into insularity, overconfidence, or paralysis.

A confidential ally—whether an executive coach, mentor, or advisor—offers:

• Clarity amid noise by helping sort urgent issues from distractions.
• Challenge to assumptions that might otherwise go untested.
• A safe testbed for ideas before they are exposed to institutional or political risk.
• Acceleration of learning so the leader regains confidence faster.

This is not therapy or handholding. It is disciplined partnership, designed to maximize a leader’s effectiveness under pressure. Douglas Riddle of the Center for Creative Leadership describes coaching as “a disciplined way of helping leaders face reality, see possibilities, and take action that accelerates their effectiveness” (Conference Board, 2016). That definition captures the value of support precisely in transformational contexts.

Thriving Beyond the Mandate

The turbulence of transformational leadership cannot be avoided. What can be managed is the leader’s trajectory through it. With the right support, executives not only survive the disorientation but emerge stronger—more resilient, more adaptive, and more confident in navigating ambiguity.

In practice, this means reframing shaky ground as evidence of growth, not failure. It means treating self-doubt as a catalyst for better questions, not as a threat to authority. And it means embracing the fact that in high-stakes transformations, the leader’s presence and steadiness are not ancillary—they are central.

The Institute X Coaching Option

If you’ve been tasked with leading a transformational initiative and find yourself feeling less steady than expected, take that as a signal of growth, not weakness. Now is the time to bring in a trusted partner who can help you restore clarity, harness self-doubt as fuel, and accelerate your path back to confident, effective leadership.

Institute X is a transformation leadership consultancy and transformation/change leader coaching firm. One of its online presences is The Change Playbook. Be sure to check out the abundance of practical and pragmatic guidance. Subscribe to be notified of new, fresh content.

References

Bridges, W. (2009). Managing transitions: Making the most of change (3rd ed.). Da Capo Press.

Brown, B. (2018). Dare to lead: Brave work. Tough conversations. Whole hearts. Random House.

Heifetz, R. A. (1994). Leadership without easy answers. Harvard University Press.

Ibarra, H. (2015). Act like a leader, think like a leader. Harvard Business Review Press.

Kahneman, D. (2011). Thinking, fast and slow. Farrar, Straus and Giroux.

Kegan, R., & Lahey, L. L. (2009). Immunity to change: How to overcome it and unlock the potential in yourself and your organization. Harvard Business Press.

Riddle, D. (2016). Quoted in The Conference Board. Coaching: A global study of successful practices. The Conference Board.

Schein, E. H. (2013). Humble inquiry: The gentle art of asking instead of telling. Berrett-Koehler Publishers.

Zenger, J., & Folkman, J. (2019). The trickiest part of a promotion is the first few months. Harvard Business Review.