What executives regret most about their transitions – and how to avoid the same mistakes.

When an executive reflects on the first months of a new leadership role, the regrets rarely center on financials or technical expertise. More often, they speak of missed cues, misjudged timing, and overlooked relationships.

 In over 30 years of working alongside senior leaders during pivotal transitions, I’ve found that the same themes surface again and again—quiet, recurring regrets that are often shared only in hindsight. These are not signs of failure, but rather the lessons that shape seasoned leadership.

 If you’re stepping into a new executive role—or guiding someone who is—these reflections may help you avoid the most common pitfalls and position your transition for lasting success.

 1. “I Wish I Had Listened More”

The urgency to perform often overrides the patience to listen. New leaders, eager to prove value, may begin solving problems before fully understanding them. In retrospect, many wish they had asked better questions and waited longer before forming conclusions.

Listening early is not passive—it’s strategic reconnaissance.

 2. “I Applied the Wrong Playbook”

Confidence in a proven approach is valuable—but context is everything. Leaders who import strategies wholesale from previous roles often find them misaligned with the new culture, capabilities, or pace.

Assume your past success earned you the seat—not the solution.

3. “I Misjudged the Clock”

Transitions demand timing. Some move too fast and disrupt trust. Others move too slowly and miss key windows of opportunity. The art lies in knowing when to observe, when to act, and how to sequence change.

Every transition comes with an expiration date on grace—and a window for momentum.

4. “I Didn’t Map the Real Power Grid”

Organizational charts are tidy. Influence is not. Leaders often regret failing to identify who actually shapes opinion, maintains continuity, or holds the team together behind the scenes.

The informal network usually carries more weight than the org chart.

5. “I Neglected My Own Integration”

Relocation, family disruption, and new role demands often collide. Executives who focus solely on professional ramp-up at the expense of personal grounding frequently experience burnout or isolation.

Sustainable leadership begins with full-life integration.

6. “I Thought I Had to Go It Alone”

Many leaders delay asking for help—whether from a coach, peer network, or board chair—believing they need to earn credibility first. By the time they ask, pressure has compounded and course correction is harder.

Strength in transition comes not from solo mastery, but trusted guidance.

7. “I Assumed We Were Aligned”

Misalignment with the board or CEO can fester silently until it erupts. Executives often wish they had more proactively clarified expectations, communication rhythms, and success metrics from day one.

Silence is not alignment—clarity is your currency.

8. “I Let Legacy Culture Drift”

Without deliberate intervention, cultural norms will default to the status quo. Executives regret waiting too long to model new behaviors, reinforce desired values, or reset expectations.

Culture won’t change just because you showed up.

9. “I Didn’t Stage Early Wins”

Every team watches closely during the first 90 days. Leaders who miss the chance to create small but meaningful wins often struggle to build momentum.

Trust is built through visible progress, not vision statements.

10. “I Missed the Story I Was Living”

Few leaders document or reflect on their early transition. Later, they realize they could have captured insights to share with their teams, boards, or even successors.

Your transition is not just a task list—it’s a leadership narrative.

The Case for Structured Onboarding

These regrets point to a simple truth: successful transitions don’t happen by chance. They are designed.

A structured onboarding and integration plan—tailored to the organization’s priorities and the leader’s unique context—serves as both compass and accelerant. It ensures time is spent where it matters most: building trust, aligning expectations, capturing input, and creating early wins that compound.

At Tartan Group, we work with boards, CEOs, and new leaders to develop custom onboarding strategies that go beyond the orientation checklist. Our approach is intentional, relational, and results-focused—because a strong start isn’t just about learning the ropes. It’s about building the foundation for long-term leadership impact.

Moving Forward with Foresight

Transitions are defining moments—not just for the executive, but for the organization they serve. By naming these common regrets, we give language to what often remains unspoken—and offer future leaders a map drawn from the hard-earned lessons of those who came before them.

The most effective transitions don’t avoid tension. They anticipate it—and navigate it with humility, clarity, and connection.

Visit us @ TartanGroupLLC.comTartan Group, LLC