Leadership Insights

Final Chapter: The Work That Could Have Been Done First

The most important leadership work is rarely the most urgent. This piece explores why senior executives consistently defer the foundational work that would have prevented their biggest problems.

In short: The most common pattern in leadership transitions is that outgoing executives spend their final months on structural, cultural, and team work that should have been done in year one. Foundational work gets deferred because it lacks a deadline, carries political cost, and doesn't produce near-term visible results. The incoming leader inherits a foundation just poured — and the cycle repeats.

  • Foundational work — team realignment, operating model redesign, cultural issues — gets deferred because it has no hard deadline, is politically expensive, and doesn't show up in the next earnings call.
  • The cost of deferral compounds: a team misalignment resolvable in year one becomes a cultural fixture by year three.
  • Incoming leaders who treat the first ninety days as a diagnostic sprint — not a listening tour — break the cycle by sequencing foundational work deliberately from day one.
Final Chapter: The Work That Could Have Been Done First

The most common pattern in leadership transitions is that outgoing executives spend their final months on structural, cultural, and team work that should have been done in year one. Foundational work gets deferred because it lacks a deadline, carries political cost, and doesn't produce near-term visible results. The incoming leader then inherits a foundation just poured — and the cycle repeats.

There is a pattern we observe in nearly every leadership transition we've been close to. The outgoing executive's final months — sometimes their final year — are consumed by work that should have been done in their first year. The structural decisions get made. The team realignments happen. The cultural issues that everyone knew about finally get addressed. And then the leader leaves, and the incoming executive inherits a foundation that was just laid.

It's not that these leaders were negligent. Most of them were working hard on the right things — the urgent things, the visible things, the things that produced results in the near term. The foundational work kept getting deferred because it was uncomfortable, politically costly, or simply less pressing than whatever was in front of them that week.

Why Foundational Work Gets Deferred

The deferral pattern has a few consistent causes. First, foundational work rarely has a clear deadline. Restructuring a team, redesigning an operating model, or addressing a cultural dysfunction can always wait until next quarter. And next quarter becomes next year, and next year becomes the final chapter.

Second, foundational work is often politically expensive. Changing how decisions get made, realigning accountabilities, or removing a long-tenured leader who is no longer the right fit — these actions create friction. Early in a tenure, leaders are often reluctant to spend the political capital required. By the time they're willing to spend it, they're running out of time.

Third, foundational work doesn't produce visible results quickly. Boards and stakeholders reward near-term performance. The structural investments that would have compounded over a decade don't show up in the next earnings call.

The Compounding Cost

The cost of deferral is not linear — it compounds. A team misalignment that could have been resolved in year one becomes a cultural fixture by year three. A structural ambiguity that could have been clarified early becomes the source of years of organizational friction. The leader who finally addresses these issues in their final chapter often does so under time pressure, without the runway to see the changes take hold.

The incoming executive then inherits a foundation that was just poured. They can build on it, but they didn't get to design it. And the cycle often repeats.

What Incoming Leaders Should Do Differently

The leaders who break this pattern share a common characteristic: they treat the first ninety days not as a listening tour but as a diagnostic sprint. They're asking hard questions about organizational design, decision rights, and team composition from day one — not because they're going to act immediately, but because they want to understand what foundational work needs to happen and sequence it deliberately.

They also develop a clear view of what they're willing to spend political capital on and when. Foundational work requires political investment. The leaders who do it well are the ones who budget for it explicitly, rather than treating it as something they'll get to when conditions are right. Conditions are never right. The work has to be chosen.

If you're preparing for a leadership transition — as an incoming or outgoing executive — we're glad to think through the sequencing with you. The organizations that get this right build durable advantages. The ones that don't spend years managing the consequences.

Share:

Last updated:

leadershipstrategyorganizational design

Frequently Asked Questions

Why do senior executives consistently defer foundational organizational work?

Three reasons: it has no hard deadline, it is politically expensive early in a tenure, and it doesn't produce results that show up in the next earnings call. The urgency of near-term performance consistently crowds it out.

What should an incoming executive do in the first ninety days to avoid repeating this pattern?

Treat the first ninety days as a diagnostic sprint, not a listening tour. Ask hard questions about organizational design, decision rights, and team composition from day one — not to act immediately, but to sequence the foundational work deliberately.

How should a leader budget for politically costly organizational changes?

Explicitly. Foundational work requires political capital. Leaders who do it well decide in advance what they are willing to spend that capital on and when — rather than waiting for conditions that are never quite right.

By Chuck Doherty, President & Founder — Doherty Search Partners. Subscribe to DSP Insights for leadership and talent intelligence in banking and private credit.

Working on a leadership challenge in financial services?

Doherty Search Partners works exclusively with banks, private credit firms, and financial services organizations on executive search and strategic team builds.