The 'Art' of the

Chief of Staff 

The prevalence of the Chief of Staff role in today's society is higher than ever before. What was initially a position confined to military and government circles has expanded to span all industries and sectors. The importance of this role was less recognized a decade ago than it is now.

Numerous articles are currently emerging that attempt to articulate and define the role of a Chief of Staff. However, deriving a uniform definition is challenging due to the role's varying nature and functions, which are similar to measuring its effectiveness. The Chief of Staff role entails six key functions designed to aid executives, teams, and organizations focus on strategic objectives. Chiefs of Staff are frequently called the ultimate guardians of executive time.

The Chief of Staff is the “Product Manager” of the CEO’s operating system, and strategic vision is directly responsible for ensuring the company works effectively toward the mission. This role requires someone who is a powerhouse multitasker and incredibly adaptable. The role is always to be able to advise the CEO on high-level strategic decisions and care about the lowest level of detail in materials for the Board of Directors. 

 They devise efficient and productive strategies to ensure that an executive’s time is optimally allocated towards key priorities and effectively managed with the assistance of administrative staff.

Considering this, one can see how a Chief of Staff might enhance executive efficiency.

The Evolving Role of the Chief of Staff: Key Archetypes in Modern Organizations

In the contemporary business landscape, the role of a Chief of Staff (CoS) is pivotal in steering the success of large, complex enterprises. The CoS is more than just an operational facilitator; they are a strategic partner who can significantly influence the organization's trajectory. As businesses evolve, the demands placed on a CoS have expanded, encompassing roles beyond ensuring operational efficiency.

The spectrum of Chief of Staff roles can be broadly categorized into three archetypes:

  • Director-Level, CoS (Chief of Staff): This role focuses on eliminating distractions, aligning senior leadership, and ensuring that the CEO remains concentrated on the organization's strategic priorities. This archetype is essential for maintaining focus and effectively driving the CEO's agenda.

  • Senior-Level, VP CoS (Senior Chief of Staff): In addition to performing the duties of a Director-Level CoS, this role also involves serving as a strategic advisor to the CEO. The Senior-Level VP CoS provides high-level counsel and supports the CEO in making critical decisions, often being the organization's sole mandate.

  • VP/Senior, VP CoS (Executive Chief of Staff): This archetype encompasses all the responsibilities of the previous levels but with the added dimension of acting as a proxy for the CEO. The VP/Senior VP CoS extends the CEO's internal and external influence, often combining this role with leading strategic or transformational initiatives.

These archetypes illustrate the increasing complexity and importance of the Chief of Staff role in modern organizations, where effectiveness, strategic alignment, and amplified leadership are key to driving success.

This framework reflects the necessity for CEOs to have a trusted partner who manages the day-to-day operations and plays a crucial role in shaping the company's future direction.

AI and the Philanthropic Chief of Staff: Balancing Efficiency with Empathy

In an era of accelerating technological change, artificial intelligence (AI) is reshaping industries and professions, including philanthropy. AI holds immense potential for the Chief of Staff (CoS), who serves as a strategic leader and steward of organizational effectiveness, but it also presents challenges that cannot be ignored. Whether assisting a foundation president, managing board relations, or overseeing complex projects, integrating AI can be both a powerful tool and a nuanced responsibility.

As we explore the role of AI in philanthropy, it is crucial to weigh both the benefits and the negatives. For every efficiency gained, there may be ethical considerations to account for. For every enhancement in impact measurement, there may be a risk of alienating the very communities we aim to serve. Below, we examine the core benefits and challenges of AI for a CoS in the philanthropic space:

The dual nature of AI in philanthropy requires thoughtful leadership and a strategic approach to maximize benefits while mitigating risks. For a CoS, the goal is not to fully replace human intuition and empathy with technology but rather to augment human capabilities through a well-balanced partnership with AI. The effective use of AI tools in philanthropy lies in discerning where automation ends and where the human element begins.

Balancing AI's Efficiency with Human Insight


The CoS is uniquely positioned to balance technological efficiency with human-centered leadership. One example of this is using AI to monitor grant compliance in real-time. AI-driven platforms can identify discrepancies in grant reporting, freeing up the CoS’s time to engage directly with grantees about their experiences and challenges. Here, the technology works in tandem with human empathy—AI handles data analytics, while the CoS dedicates their energy to building and nurturing relationships.

Consider another scenario: a philanthropic foundation aiming to expand its social impact in underrepresented regions. AI can swiftly analyze census data, social media trends, and public health statistics to recommend target areas and potential beneficiaries. However, it is the CoS who must take this data and contextualize it, considering cultural nuances, local leadership, and historical context to ensure that interventions align with community needs. Such a balanced approach ensures that AI-generated insights are not just actionable but also equitable and sustainable.

Additionally, the CoS plays a crucial role in governance—an area where AI can either be a significant asset or a point of concern. By deploying AI to track the success metrics of ongoing initiatives, boards can receive detailed reports that include both quantitative and qualitative analysis, ultimately leading to better decision-making. However, the CoS must oversee these analyses, ensuring that the data presented is transparent and devoid of the inherent biases that could sway board decisions away from an equitable outcome.

The Road Ahead: A Transformative Opportunity


The rise of AI in philanthropy presents a transformative opportunity that allows the sector to scale its impact more efficiently while pushing it to reconsider foundational values around equity, inclusivity, and human connection. For a CoS, integrating AI is not merely about adopting the latest technological tools; it is about shaping how these tools can be used to serve the greater mission.

AI offers significant opportunities to enhance operational efficiency, understand impact more sophisticatedly, and engage stakeholders more deeply. Yet, the philanthropic CoS must remain vigilant. The risks of data bias, ethical concerns, and an over-reliance on automation are real, and mitigating them requires a proactive, thoughtful strategy that values human oversight as much as technological advancement.

Ultimately, the philanthropic CoS must embrace AI as a tool—one that can amplify their effectiveness, deepen their strategic focus, and extend their reach—but never as a replacement for the human touch that underpins the ethos of philanthropy. AI should enhance, not replace, the foundational principles of empathy, connection, and cultural stewardship. By striking this balance, AI has the potential to transform philanthropy into a sector that is not only more effective but also more just, ensuring that technology and humanity work hand in hand to achieve the collective good.

Disclaimer: This work is entirely my own and not generated by artificial intelligence.