Jerry* was a sharp, systems-minded Chief of Staff with a big challenge: the executive team at his company was pulling in different directions, and his CEO was tired of playing referee.
Jerry had what many Chiefs of Staff dream of—direct access to the CEO, the authority to drive change, and a genuine mandate to “fix it.” He assumed the problem was structural: no shared goals, unclear decision rights, no regular touchpoints to keep the team aligned.
So Jerry did what Jerry was great at: he built a plan.
But even the cleanest frameworks fell flat. When he introduced prioritization rubrics and ownership maps, leaders nodded—and then went right back to advocating for their own teams. The most resistant voice came from Rahul*, the company’s brilliant but bristly VP of Engineering, who openly pushed for Engineering’s needs to take priority over everything else.
That’s when Jerry reached out for coaching.
Spoiler: Clarity Wasn’t the Answer—Trust Was
In our early conversations, it became clear that Jerry’s strength—bringing clarity and structure to complexity—had become a bit of a crutch. He believed that if he could just get the right spreadsheet, framework, or cadence in place, the team would snap into alignment.
But as we worked together, Jerry started to realize something deeper. Clarity isn’t enough.
In one of our sessions, Jerry said something that stopped us both in our tracks:
I’ve been trying to engineer alignment like it’s a product launch. But it’s not. It’s trust. And trust doesn’t follow a Gantt chart.
That insight changed everything.
He Didn’t Abandon Structure—He Led With Empathy
Instead of pushing through his original plan, Jerry reworked his entire approach—this time, with empathy and emotional safety at the center.
Jerry and I designed a two-day executive offsite that wasn’t just about setting priorities—it was about rebuilding relationships. He pre-interviewed every exec, ensuring that quiet voices and contrarian views (including Rahul’s) would be represented. He facilitated conversations not just around “what are our top goals?” but also “what’s getting in our way of working as a team?”
The result? The group aligned on four enterprise-wide priorities, each co-owned by leaders from different departments. But just as importantly, they re-established a baseline of mutual respect and shared accountability.
Same Tools, New Mindset
Jerry rolled out some structure—but with a new tone:
- Monthly Executive Prioritization Check-Ins weren’t just status updates. They were collaborative conversations where leaders surfaced tradeoffs, asked for help, and discussed how shifting priorities impacted each other’s teams.
- Quarterly Reprioritization Sessions weren’t rigid reset meetings. They were designed as open forums to reflect on what was working, what wasn’t, and where the team needed to flex.
- A shared Decision Log helped track major cross-functional choices—not just to capture rationale, but to create transparency and reduce defensiveness.
These were the same tools Jerry would have introduced six months earlier—but implemented with humility, curiosity, and care.
Rahul didn’t become a different person. But he began to show up a bit differently—especially once he saw that his perspective wasn’t being overruled or ignored, but integrated into company-wide decisions.
And Jerry? He didn’t stop being a systems thinker. He just learned that the best systems are built to serve relationships—not replace them.
* All names have been changed to protect confidentiality.
