Snapshot
A fast-moving organization brought me in to coach the CEO. As the engagement progressed it was expanded to first include the senior leadership team, then the managers, and finally key individual contributors. The result wasn’t a “coaching initiative” layered on top of a strained culture. It became a practical way to gain clarity, strengthen partnership across departments, modernize a few operating systems, and create communication habits that outlasted my involvement.
(Details are intentionally anonymized. The identifying specifics have been blended for confidentiality.)
The Context: A Capable CEO Under Pressure
When we began I quickly recognized that the CEO was smart, committed, and carrying too much. The business was growing, complexity was rapidly increasing, and the CEO’s leadership style was starting to show limits in this new environment.
In the early work, we oriented around three things:
- Leadership style: How the CEO naturally leads when calm vs. under pressure
- Leadership gaps: Where good intentions were colliding with blind spots
- Opportunities: Where small shifts could unlock disproportionate value
This phase often looks deceptively simple from the outside: weekly sessions, regular action items, and steady reflection. But it’s where clarity begins to form, and where operational trust between coach and client gets built.
And trust mattered, because the arc of this engagement was likely to expand beyond the CEO.
Phase 1: CEO-Only Coaching with objective to Stabilize, Clarify, and Create Options
Operational Goal: Help the CEO stop “white-knuckling” the top of the organization and start leading with more leverage.
We worked through the top-line problems first; addressing decision overload, recurring tensions, and patterns in communication that were creating drag. Over time, the CEO became able to name what was happening in the system without defensiveness, and willing to test new behaviors in real time.
This is also where the “safe place” function of coaching is pivotal: client was coached through venting and clearing frustration to metabolize complexity and take cleaner action. That combination of reflection plus movement creates momentum.
Phase 2: Added the Leadership Team with objective of Broader Lens, More Truth
Once the CEO had stabilized and worked through the highest-priority issues, we expanded to the senior leadership team.
They were receptive specifically because: they knew I had already been coaching the CEO, and that helped establish credibility.
But they were also hesitant—especially around one concern:
“Will what I say make its way back to the CEO?”
So we made confidentiality explicit and operational:
- What coaching is (and is not)
- How privacy works
- What themes might be shared upward (only with permission), vs. what stays private
- How each person retains autonomy in what they bring forward
As I coached the leadership team, I gained a wider and clearer view of the CEO’s leadership style. Not “good” or “bad”, but how his leadership impacted the team. Where it was helping. Where it was unintentionally costing the organization.
I also started seeing systemic patterns more clearly:
- communication habits that created misunderstanding
- meeting rhythms that sucked up time without decisions or action items
- tension points between departments that had become chronic
Phase 3: Managers and Individual Contributors — Where the System Shows Itself
As I moved down the org chart, something predictable happened:
I got more specific information.
Where leaders often speak in abstractions (“alignment,” “execution,” “accountability”), managers and individual contributors can point to the friction in lived experience:
- handoffs that fail
- standards that are implied rather than explicit
- processes that cause confusion
- meetings that feel mandatory but produce no ownership
- conflicts that are “managed” through avoidance until they calcify
This is also where dissatisfaction was most visible. Not because people were fragile, but because the organization was unintentionally creating conditions that made capable people feel powerless or unheard.
At this stage, coaching becomes more direct and actionable:
- helping individuals name concerns in clean, non-inflammatory language
- supporting them in how to bring issues to leaders and peers
- building the muscles of resolution rather than rumination
This is where psychological safety stops being a buzzword and becomes a performance requirement. When people believe it’s safe to take interpersonal risks—like raising concerns, admitting mistakes, or challenging assumptions—teams learn and adapt faster (Edmondson, 1999).
The Inflection Point: Meetings Became the Lever
As clarity, process, and accountability grew, meetings became the highest-leverage “system” to modernize.
We didn’t try to make meetings fun.
We made them meaningful, effective, and valuable.
Key changes included:
- Fewer meetings, by design (eliminate duplicates; collapse updates into written formats when possible, published status)
- Normalized structure (purpose → agenda → decisions/outputs → owners)
- Action items tracked and followed up with clear ownership and deadlines
- A cultural expectation of presence (less phone/laptop drift; prepared attendees, devices used mainly for relevant notes)
Research and evidence reviews on meetings consistently point to practical drivers of meeting quality: clear purpose, relevant attendance, strong facilitation, and reliable follow-through—and they tie meeting effectiveness to important outcomes like attendee attitudes, well-being, and behavior (Geimer et al., 2015; CIPD, 2023).
As meeting quality improved, two second-order effects showed up quickly:
- cross-department conflicts became easier to address because the forum worked
- people felt less drained, which increased follow-through and trust
Outcomes After Six Months
By the end of the engagement:
- Clarity improved across priorities, ownership, and escalation paths
- Communication improved vertically and laterally, especially across departments that previously felt misaligned
- Several longstanding “unsolvable” issues were resolved through coordinated inter-department effort
- Meetings reduced in frequency and increased in effectiveness—more decisions, cleaner action items, and better follow-up
- Leaders and team members reported more confidence in addressing issues directly, earlier, and with less heat
- The fast paced growth of the organization no longer felt overwhelming to team members, they were keeping up now
At the six-month mark, we moved to a maintenance model, because the organization had internalized the core practices. The goal wasn’t dependency—it was capability. People were more empowered to resolve issues without outside support, and the CEO was no longer the single point of emotional or operational pressure.
Why This Worked
Three elements created durable change:
- Sequencing (top-down, then outward)Starting with the CEO created coherence. Expanding later created scale.
- Confidentiality as a real operating principleNot just a promise—an explicit design choice that made truth-telling possible (especially further down the org chart).
- Coaching as “safe space + skill building”A place to speak honestly and learn how to bring issues into the light with leaders and peers—so the organization builds partnership and momentum rather than recycling frustration.
A line the CEO came back to more than once:
“The greatest danger in times of turbulence is not the turbulence; it is to act with yesterday’s logic.” — Peter Drucker
Looking to build lasting change in your organization?
Let’s connect and discuss how executive coaching can help your leadership team gain clarity, improve collaboration, and create momentum that lasts.
