Advising Case Study: Strengthening the CEO–GC Partnership During a Financing Event

Client Context

A privately held company preparing for a potential sale or financing event was experiencing elevated legal costs and increasing board scrutiny. The CEO began to question the General Counsel’s judgment on risk assessment and litigation strategy, putting additional pressure on the partnership at a critical time.

Challenges:

• The CEO had started to question the GC’s ability to evaluate risk and manage litigation strategy.
• Legal expenses were escalating when the company needed to demonstrate fiscal discipline to prospective investors or buyers.
• Board questions over legal costs intensified pressure on the CEO–GC relationship.
• Limited in-person interactions with the CEO made it difficult for the GC to understand leadership style and decision-making context.

Advisory Approach

The General Counsel engaged a BarkerGilmore Strategic Advisor and Executive Coach — an experienced former Fortune 500 GC — to assess and strengthen the CEO/GC dynamic. The engagement included:

• A structured review of the CEO/GC relationship — its history, values, and behavioral patterns — to identify underlying sources of tension.
• Evaluation of the GC’s approach to the priority docket, including litigation strategy, risk assessment practices, and use of outside counsel.
• Guidance for the GC to assume greater ownership of analysis and narrative, ensuring clearer and more strategic communication with the CEO.
• Development of cost-forecasting models to enhance fiscal transparency, avoid unanticipated expenses, and restore CEO/board confidence.

Results

Within four to five months, the engagement delivered measurable improvements:

• The CEO–GC relationship stabilized, and mutual trust was reestablished.
• The GC gained confidence, strengthened executive presence, and reduced concerns about role security.
• More proactive ownership of litigation and risk assessment narratives enhanced credibility with both the CEO and the board.
• Improved forecasting practices mitigated friction at the leadership level.

Key Insights for Legal Leaders

This engagement illustrates how lonely the GC role can be and highlights the unique value of confidential guidance from a seasoned former GC. An objective, external perspective provides a safe environment to refine strategies and communication approaches. The most significant shift often comes not from altering legal decisions but from reframing how those decisions are conveyed to senior leadership.

Early intervention of this kind can:

• Prevent attrition of key legal executives.
• Strengthen leadership and communication skills.
• Enhance stability during pivotal corporate events.
• Reinforce GC confidence and influence.

Conclusion

Through BarkerGilmore’s executive coaching, the General Counsel evolved from a leader under pressure to a more trusted and effective partner. By combining enhanced communication, stronger cost discipline, and advisor-led support, the company achieved a more collaborative and transparent approach to legal strategy, positioning itself for success during the upcoming financing event.