CFOs Unpack Toughest Leadership Challenges: Advocating for CEO Coaching and Decision Pushback

A recent gathering of Chief Financial Officers (CFOs), hosted by Shai Goldman, illuminated the complex and often "dysfunctional" dynamics within corporate leadership teams. The dinner, which took place "last night" according to Goldman's tweet on November 8, 2025, centered on the critical issues of "managing the founders, CEO and the board." Discussions highlighted the significant challenges CFOs face in their strategic roles.

The private dinner aligns with events like the Brex Supper Club, where Shai Goldman has previously hosted discussions for founders and CFOs on financial operations. Such forums provide a crucial space for finance leaders to candidly address sensitive topics. Goldman's tweet specifically noted that the "toughest part" of these roles involves navigating "how to push back on decisions the CEO wants to make & how to bring up that the CEO needs coaching/mentorship."

Industry experts emphasize the delicate balance CFOs must maintain between their fiduciary duties to the board and their operational tether to the CEO. Financial specialists indicate that while CFOs are increasingly strategic partners, challenging a CEO's decisions requires careful navigation of the corporate chain of command. This situation becomes particularly complex when strategic differences arise or when ethical concerns are at stake.

Raising the need for CEO coaching or mentorship presents another profound challenge for CFOs. According to financial industry specialists, CFOs must respect reporting lines while also cultivating an independent working relationship with the board. This allows for an objective perspective on leadership effectiveness, without directly undermining the CEO. The ability to articulate concerns and propose solutions, such as external coaching, is vital for long-term organizational health.

The evolving role of the CFO demands not only financial acumen but also strong interpersonal and communication skills to influence leadership effectively. These discussions among CFOs underscore a shared recognition of the pervasive nature of leadership challenges in today's corporate environment. Such candid exchanges are essential for developing strategies to foster healthier, more effective executive teams.