Why “Good Enough” Leadership Is Breaking Earlier in This Cycle
September 4, 2025
For much of the last decade, organizations were able to stretch leadership teams through periods of growth, integration, and change. Strong markets, abundant capital, and forgiving timelines allowed capable leaders to learn on the job.
That tolerance is disappearing.
Across both private equity and corporate environments, leadership gaps that once took years to surface are now breaking far earlier in the cycle. The issue is not competence, but rather the ability to survive and thrive in the higher levels of complexity every company now finds itself in.
What has changed about the operating environment
Three dynamics are converging.
First, execution windows are tighter. With fewer initiatives competing for capital and attention, leadership misalignment is exposed more quickly.
Second, complexity has increased faster than headcount. Add-ons, system changes, geographic expansion, and shifting customer expectations are piling onto leadership teams already operating at full capacity.
Third, expectations are clearer. Boards and investors are more explicit about what success looks like and less patient when teams struggle to deliver against it.
In this environment, leaders who were previously “good enough” are finding themselves outpaced.
Where “good enough” leadership shows stress
The breakdown tends to follow a familiar pattern.
Decision-making slows.
Leaders hesitate as complexity increases. Decisions that once felt straightforward now require more analysis, more consensus, and more time.
Operating rhythm erodes.
Meetings multiply, priorities shift, and accountability becomes less clear. Teams stay busy but lose momentum.
Cross-functional alignment weakens.
Functional leaders retreat into their lanes when integration and coordination become harder, creating friction that leadership must constantly resolve.
Confidence declines quietly.
Boards and executive teams sense something is off long before results fully reflect it. By the time performance metrics confirm the issue, the organization is already behind.
None of this indicates failure. It indicates mismatch.
Why early leadership upgrades matter
The most effective organizations treat leadership capability as a dynamic requirement, not a fixed asset.
Rather than asking, “Is this leader performing?” they ask, “Is this leader equipped for what comes next?”
When leadership upgrades happen early:
Expectations reset clearly
Operating cadence stabilizes
Teams regain confidence
Execution accelerates
When upgrades are delayed, organizations often end up layering support around leaders instead of addressing the root issue directly.
What boards and executives should watch for
A few signals consistently precede early leadership breakdowns:
Leaders spending more time explaining complexity than resolving it
Decisions escalating that previously sat comfortably at lower levels
Repeated rework after initiatives launch
Growing reliance on external advisors for internal clarity
These are not red flags. They are indicators that the role has outgrown the person, not the person failing the role.
Looking ahead
As markets remain selective and execution expectations stay high, leadership mismatches will surface faster. Organizations that address them early protect value and preserve momentum.
In this cycle, “good enough” is rarely enough for long.
About the Author
Ken Wilcox
Senior Client Partner
Ken Wilcox is a Senior Client Partner at Morgan Samuels, where he partners with clients to deliver executive search outcomes with a high standard of rigor, judgment, and care. His work is grounded in a balance of strategic insight and emotional intelligence, shaped by a career spent leading and advising complex organizations.
Prior to executive search, Ken spent three decades as a senior executive within some of the world’s most recognized global brands, leading organizations across sales, marketing, operations, and customer experience. Having operated inside the roles he now helps place, Ken brings a rare dual perspective—speaking the language of both clients and candidates as they navigate critical leadership decisions.
This perspective reflects patterns observed across leadership engagements where execution, alignment, and credibility at the senior level matter most.