How repairing one relationship unlocked clarity, speed, and impact across the whole organization.
The Situation
At a fast-growing, late-stage company on the path to IPO, the CEO faced a critical challenge: their two most senior executives, responsible for the largest organizations in the company, were in open conflict. The tension was visible to everyone, leaving their teams caught in the middle. Angry emails, passive-aggressive Slack messages, and finger-pointing had eroded trust. Instead of collaborating, the executives were avoiding each other. The result: stalled decision-making, unclear product and market strategy, and customer commitments at risk. The CEO knew something had to change — that the leaders needed to grow and mature so the company could, too. That’s when we were brought in.
Coaching Goals
We set out to help the executives:
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Repair and rebuild their relationship into a trusting, collaborative, and productive partnership
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Elevate their individual leadership to operate as mature, strategic executives
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Align their teams to reduce friction and deliver consistent, high-quality results
Our Approach
We began with 1:1 coaching to uncover each leader’s frustrations, perceptions, and blind spots. Using relationship assessments and progress maps, each executive articulated their perspective on the most painful aspects of their dynamic and where they were willing to change.
From there, we brought them together for joint coaching sessions. They shared their perspectives openly, sat in each other’s shoes, and began to see intention where they had initially assumed malice. Together, they co-created rules of engagement, some of which included:
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Commit to regular one-on-ones
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Give the benefit of the doubt before jumping to conclusions
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Address issues directly, not through their teams
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Use blameless retrospectives to learn from mistakes
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Express appreciation and acknowledge different working styles
In parallel, we built individualized development plans to help the executives grow their leadership—stepping out of firefighting, thinking more strategically, communicating more openly, and leading with greater empathy across the organization.
Behavioral Shifts
Over time, each leader evolved—both in how they showed up individually, and in how they worked together.
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Regular one-on-ones fostered alignment and trust, making communication more transparent and consistent—no more mixed signals to teams or customers.
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General well-being increased and stress levels dropped as conflict gave way to calm, constructive dialogue.
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Both leaders took more ownership, leaning into proactive behaviors instead of avoidance.
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Decision-making sped up, with issues resolved together instead of being escalated.
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Problem-solving became joint and balanced, holding each other accountable while showing empathy.
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The two executives began actively supporting each other and each other’s teams, strengthening teamwork across the organization.
Key Outcomes
For the CEO:
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Reported “faster decisions, fewer escalations” as their top two executives began resolving problems together before they reached them.
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Saw a shift from bickering to collaboration, including joint support of budgets and unified recommendations.
For the Team:
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Felt a visible drop in tension as open conflict between these leaders disappeared.
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Experienced clearer communication and more accurate and reliable roadmaps, reducing confusion and misalignment.
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Noticed executives modeling healthy conflict resolution and appreciation for one another’s functions, creating a more collaborative environment.
For the Company:
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Gained greater reliability in customer commitments and external communications, building trust with key stakeholders.
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Strengthened company culture through executive collaboration and trust, which modeled healthy behaviors across the organization.
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Enabled the company to move forward with greater velocity and stability during a volatile period.
