Finding Leverage in the Family Office: Chief of Staff or Not?

Executive Summary

The Chief of Staff title has become a catch-all in the family office world, and that ambiguity leads to expensive hiring mistakes. Many principals who believe they need a Chief of Staff would be better served by an exceptional Executive Assistant or Family Office Manager. Others genuinely need cross-organizational leverage but hire the wrong profile. The difference comes down to understanding where your friction actually lives—and what type of leverage would address it.

Three spheres determine the right hire:

Personal Sphere: Your calendar, communications, preparation, and travel. If friction lives here (overwhelm, poor preparation, constant context-switching between family and investment matters), the answer is an exceptional EA or Family Office Manager, regardless of the complexity of your holdings or family dynamics.

Organizational Sphere: Cross-functional coordination, execution across entities, strategic initiatives that span the family enterprise. If friction lives here (decisions stuck between investment and operating entities, family governance stalling, information not flowing between advisors), the answer is a Chief of Staff.

External Sphere: Investment managers, co-investors, service providers, philanthropic partners, and the broader family network. This sphere can fall to either role. The question is whether you need someone to support your external relationships or conduct them independently.

But identifying that you need a Chief of Staff is only half the diagnosis. The other half is understanding what kind of Chief of Staff. In the family office world, two distinct archetypes emerge: the Technical Chief of Staff, who creates leverage by interpreting complex information and translating specialist detail into decision-ready insight; and the Generalist Chief of Staff, who creates leverage by connecting dots across people, entities, and initiatives, maintaining momentum on cross-family priorities. Both are real Chiefs of Staff. Both create genuine leverage. But they do so differently—and both can fail spectacularly when hired into the wrong context.

The stakes are real. A principal with a $200 million single family office focused primarily on passive investments operates in a demanding environment, but the leverage gap is almost entirely personal. Hiring a Chief of Staff would be overkill and likely a poor fit. A multi-family office executive with solid administrative support but stalling strategic initiatives across client families has an organizational problem that no amount of EA excellence will solve. And a family office that hires a brilliant former consultant expecting strategic transformation when what they actually need is someone to integrate fragmented reporting across investment verticals will end up with a hire who feels "smart but ineffective."

This paper provides a framework for diagnosing your actual leverage gap, understanding what each type of hire can realistically deliver, distinguishing between Technical and Generalist Chief of Staff profiles, and avoiding the failure modes that derail these hires in the family office context.

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The Problem Worth Solving

Most family office principals and executives operate with a persistent sense that something isn't working. Not catastrophically. The investments are managed, the family's needs are met, decisions get made. But there's friction. A feeling that your attention is constantly being pulled toward work that doesn't require your judgment—coordinating between advisors, managing service providers, handling the administrative complexity that accumulates around significant wealth—while the work that does require it gets compressed into whatever margin remains.

This isn't a scheduling problem. It's a leverage problem.

The question of whether to hire a Chief of Staff is really a question about where your leverage is breaking down, and whether the solution requires someone who can reach across your family enterprise with autonomy and judgment, or someone who can bring exceptional order to your immediate orbit. These are fundamentally different capabilities, and conflating them is one of the most common mistakes family office principals make when seeking support.

But there's a second conflation that's equally costly: assuming that "Chief of Staff" means one thing. In the family office world, the role can take fundamentally different shapes depending on whether the leverage gap is technical or organizational in nature. Some family offices need someone who can synthesize complex investment information upstream, translating specialist detail into something the principal can act on. Others need someone who can connect dots across multiple people and initiatives, maintaining momentum on priorities that span the family enterprise. These require different capabilities, different backgrounds, and different ways of operating. Hiring a strategic thinker when you need an integrator—or vice versa—explains why so many Chief of Staff hires feel "smart but ineffective."

This paper is designed to help you think clearly about both distinctions. Not to sell you on the idea of a Chief of Staff (many principals don't need one), but to help you understand what's actually breaking, what kind of leverage would address it, and what the right hire looks like for your specific situation.

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Why This Matters Now

Governance is gaining new depth in family offices. UBS reports that 67% of family offices strengthened governance during 2025. Campden Wealth shows documented succession plans in 66% of surveyed families. EY estimates a multigenerational transition above six trillion dollars in the coming decade. Cerulli Associates offers broader context with a projection of more than 124 trillion dollars expected to transfer across generations by 2045.

Families are developing formal authority structures, written policies, and communication frameworks. What stands out most is how much of this comes back to disciplined information flow—governance, liquidity planning, clearer reporting, and structured decision systems.

In multi-generation, privately held wealth, the biggest risk isn't the investment strategy—it's the financial operating rhythm underneath it. When reporting, controls, and forecasting aren't tight, every other decision becomes harder. This is precisely where a strong Chief of Staff can make real impact: ensuring the infrastructure exists for good decisions to happen consistently.

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What a Chief of Staff Actually Is

The title "Chief of Staff" has been stretched to cover everything from glorified executive assistants to de facto family office CEOs. This ambiguity isn't helpful. Let's be precise.

A Chief of Staff is someone who extends your reach across the family enterprise. They operate with meaningful autonomy, exercise judgment in situations where the right answer isn't obvious, and create leverage by handling complexity that would otherwise consume your attention. The defining characteristic isn't the tasks they perform. It's the scope of their authority and the independence with which they operate.

This distinguishes a Chief of Staff from an Executive Assistant or Family Office Manager, even an exceptional one. A great EA or FOM creates leverage by bringing order, anticipation, and flawless execution to your immediate environment. They manage your calendar with strategic intent, protect your attention, ensure you're prepared for what matters, and handle the operational texture of your day. They work within your orbit.

A Chief of Staff works across the family enterprise on your behalf. They attend meetings you can't, make decisions you've delegated, synthesize information from investment managers, attorneys, accountants, and family members into something actionable, and drive initiatives that span entities or generations. They need enough context to act with your interests in mind when you're not in the room.

Both create leverage. But the nature of that leverage is different, and so is the profile of the person who can deliver it.

What a Chief of Staff Is Not

Before going further, it's worth dispelling some common misconceptions. A Chief of Staff is not automatically a "strategy consultant" embedded in your family office. They're not a "mini-CEO" waiting in the wings. They're not necessarily the smartest person in the room or the one with the most impressive credentials.

The Chief of Staff role in a family office is fundamentally about creating leverage for the principal or executive—not about driving their own agenda or building their own empire. The best Chiefs of Staff are force multipliers who make the principal more effective. The worst are talented people in the wrong role, adding complexity without creating commensurate value.

Understanding this distinction is critical because it shapes how you define the role, who you hire, and how you measure success.

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Why This Paper Addresses Both Roles

You might wonder why a paper about Chiefs of Staff spends significant time on Executive Assistants and Family Office Managers. The answer is that both roles exist to solve the same fundamental problem: the principal's leverage is constrained, and the right hire can unlock it.

The question isn't "Do I need support?" Most principals at this level already know they do. The question is "What kind of support addresses my actual constraint?" And the answer depends entirely on where the work happens.

We find it useful to think about this in terms of three spheres:

The Personal Sphere. This is your immediate orbit: your calendar, your communications, your preparation, your travel, the operational texture of your day. Work in the personal sphere is oriented around you specifically: ensuring you're in the right place, talking to the right people, equipped with the right information, and protected from the noise that doesn't require your attention. An exceptional EA or Family Office Manager owns this sphere. They create leverage by bringing order, anticipation, and flawless execution to everything that touches you directly.

The Organizational Sphere. This is the broader family enterprise: cross-entity coordination, alignment between investment and operating businesses, information flows between advisors and family members, execution of strategic priorities that span multiple parts of the family's interests. Work in the organizational sphere isn't oriented around you personally; it's oriented around making the family enterprise function more effectively. A Chief of Staff owns this sphere. They create leverage by operating across the enterprise with autonomy, ensuring that what needs to connect actually connects.

The External Sphere. This includes investment managers, co-investors, service providers, philanthropic partners, and other stakeholders outside the immediate family. Work in the external sphere is about managing relationships and representing the principal beyond the walls of the family office. This sphere is particularly significant in the family office context, where relationships with wealth managers, deal sources, and philanthropic organizations often generate significant value.

The external sphere often overlaps with the personal sphere, and this is where exceptional EAs and Family Office Managers earn their premium in the family office world. A principal managing significant wealth needs someone who can manage the complexity of high-stakes relationships: coordinating across time zones with investment managers, preparing detailed briefing materials before meetings with potential co-investors, handling sensitive communications with discretion, and ensuring the principal shows up equipped to add value. The work is external in orientation but operates within the principal's orbit. It's about making the principal maximally effective in their external relationships, not acting independently on their behalf.

A Chief of Staff enters the external sphere differently. They might represent the principal at fund manager meetings, handle co-investment communications that require commercial judgment, or maintain stakeholder relationships where they can genuinely speak for the principal. The distinction is authority and independence: an EA supports the principal's external relationships; a Chief of Staff can conduct them.

The diagnostic question is straightforward: where is your leverage actually breaking down? If the friction is primarily in your personal sphere (you're overwhelmed, under-prepared, constantly context-switching between family matters and investment decisions), you likely need an exceptional EA or Family Office Manager, regardless of how significant your wealth or how complex your family dynamics. If the friction is in the organizational sphere (coordination is failing across entities, execution is inconsistent, information isn't flowing between advisors, family governance initiatives are stalling), you likely need a Chief of Staff.

The mistake is assuming that wealth complexity or multi-generational dynamics automatically means you need a Chief of Staff. A principal with a $300 million portfolio concentrated in public equities and real estate operates in a demanding environment, but the leverage gap is almost entirely in the personal sphere. They need someone who understands their world deeply, manages the complexity around them flawlessly, and operates with the discretion their family and financial matters require. That's EA or Family Office Manager work, even if the sophistication and compensation exceed what most people associate with those titles.

Conversely, a multi-family office executive might have a perfectly functional personal sphere (good calendar management, solid administrative support) but find that strategic initiatives keep stalling, information isn't flowing between client families, and decisions made at the top aren't translating into action across the organization. That's an organizational sphere problem, and no amount of EA excellence will solve it.

The framework also explains hybrid situations. A principal with a moderately complex family office—say, a mix of managed investments and some real estate—might have leverage gaps in both the personal and external spheres. They need someone who can support the movements of the principal and family leaders, connect dots and "shake trees" to support decision-making, and coordinate high-stakes external engagements with advisors and managers. This is sophisticated EA or Family Office Manager work, requiring discretion, anticipation, and the ability to operate across personal and professional contexts.

But add family governance responsibilities (a family council, oversight of next-generation education, or involvement in family-wide strategic planning), technical support on investment decisions, and the need to maintain key relationships on behalf of the family office, and suddenly the organizational sphere expands significantly. Now they need someone who can synthesize investment information upstream, represent the family's interests in external meetings, drive follow-through on initiatives that span multiple entities, and navigate the interpersonal complexity of multi-generational wealth. That's Chief of Staff territory. They might genuinely need both an exceptional EA (for the personal sphere) and a Chief of Staff (for the organizational and external spheres), or a single hire who can bridge all three—which is rare and commands a premium.

Understanding which sphere (or spheres) your friction lives in is the first step to making the right hire.

One final note on this framework: within each sphere, the work exists on a spectrum from coordination to judgment. Even within the personal sphere, there's a difference between an EA who manages logistics reliably and one who operates as a true "quarterback"—anticipating needs, catching nuance in family dynamics, and making judgment calls within your orbit. The same applies to Chiefs of Staff: some are primarily coordinators across the enterprise; others operate with genuine strategic authority.

The mistake many principals make is assuming they need the highest point on the spectrum when their actual friction is in the middle. If your primary frustration is that you're overwhelmed by volume and struggling to stay prepared for the decisions that matter, an exceptional EA or Family Office Manager might solve 80% of your problem at a fraction of the complexity. Match the solution to the actual constraint, not to your sense of what someone with significant wealth "should" have.

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The Two Types of Chief of Staff

Once you've determined that your leverage gap genuinely requires a Chief of Staff—someone who can operate across the family enterprise with autonomy and judgment—there's a second diagnostic question that's equally important: what type of Chief of Staff?

In the family office world, two distinct archetypes emerge. Both are legitimate Chiefs of Staff. Both create real leverage. But they do so in fundamentally different ways, and hiring the wrong type for your situation is one of the most common reasons Chief of Staff hires fail.

The Technical Chief of Staff

The Technical Chief of Staff creates leverage by interpreting complex information and translating specialist detail into decision-ready insight. They act as a filter between specialists, advisors, and the principal—synthesizing information upstream so the principal can make better, faster decisions without drowning in technical detail.

This profile typically emerges from investment backgrounds. They might be a former investment professional who has stepped into an operating role, a management consultant with financial services experience, or an operations specialist who has worked across multiple asset classes. What distinguishes them is domain expertise: they understand the substance of what the family office does, not just how it's organized.

The Technical Chief of Staff is most valuable when:

• The family office has significant direct investment activity or complex alternative exposure
• Reporting is fragmented across multiple investment verticals
• The principal or MFO CEO is struggling to synthesize information from specialists
• There's heavy deal flow that requires evaluation and prioritization
• Investment professionals and advisors speak different "languages" that need translation

In a multi-family office or investment-heavy single family office, the Technical Chief of Staff becomes the integrator of intelligence. They don't just coordinate—they interpret. They take the quarterly reports from the private equity manager, the tax implications from the accountant, the estate planning considerations from the attorney, and the market outlook from the wealth advisor, and they synthesize these into a coherent picture the principal can act on. They're not the doer; they're the one who makes sure the principal has what they need to decide.

The risk with the Technical Chief of Staff is hiring someone with impressive analytical credentials who lacks the interpersonal skills to operate in a family context, or someone who wants to be a principal investor rather than a force multiplier for the actual principal.

The Generalist Chief of Staff

The Generalist Chief of Staff creates leverage by connecting dots across multiple people, entities, and initiatives. They maintain momentum on cross-family priorities and act as a trusted advisor and internal stabilizer. They're less about domain expertise and more about system-level thinking—seeing how the pieces fit together and ensuring nothing falls through the cracks.

This profile often emerges from operational or general management backgrounds. They might have run complex projects, managed cross-functional teams, or served in roles that required navigating competing priorities and stakeholders. What distinguishes them is organizational intelligence: they understand how to make complex systems work, even when they don't have deep expertise in any single domain.

The Generalist Chief of Staff is most valuable when:

• The family enterprise spans multiple generations or branches with competing interests
• Complexity is primarily social and organizational, not technical
• Family governance initiatives keep stalling for lack of follow-through
• The principal needs someone who can maintain relationships across the family
• There are multiple residences, entities, or initiatives that need coordination

In a multi-generational family or governance-heavy single family office, the Generalist Chief of Staff becomes the connective tissue. They're the one who remembers that the family retreat discussion about next-generation involvement needs follow-up. They're the one who notices that the Miami property manager and the Aspen property manager are solving the same problems separately. They're the one who can have a difficult conversation with a family member that the principal doesn't want to have directly.

The risk with the Generalist Chief of Staff is hiring someone who is excellent at coordination but lacks the judgment to know when to escalate, or someone who becomes so embedded in family dynamics that they lose objectivity.

Why This Distinction Matters

Both types are real Chiefs of Staff. Both create genuine leverage. But they fail when hired into the wrong context.

A Technical Chief of Staff hired into a governance-heavy family office may struggle because the leverage gap isn't about synthesizing investment information—it's about maintaining momentum on initiatives that require navigating family relationships. They'll feel underutilized and frustrated, and the principal will wonder why this obviously smart person isn't solving the problem.

A Generalist Chief of Staff hired into an investment-heavy family office may struggle because the leverage gap requires understanding the substance of what's being coordinated, not just that it needs coordination. They'll schedule meetings between the PE manager and the tax attorney without understanding why those meetings matter or what questions should be asked.

The purpose of this distinction is to prevent the assumption that "Chief of Staff" automatically means a strategy consultant or mini-CEO. It explains why some Chief of Staff hires feel smart but ineffective—they're the wrong type for the context. And it improves hiring accuracy by forcing clarity about what kind of leverage you actually need.

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When the Friction Points to Something Else Entirely

There's a third possibility worth naming explicitly: sometimes what looks like a Chief of Staff need is actually a COO need.

The distinction matters because it's easy to confuse them. Both operate across the family enterprise. Both require autonomy and judgment. Both exist to close gaps that the principal can't address themselves. But they solve fundamentally different problems.

A Chief of Staff creates leverage for the principal. They extend the principal's reach, synthesize information the principal needs to decide, and maintain momentum on priorities the principal has set. The principal remains the decision-maker; the Chief of Staff makes them more effective at it.

A COO creates leverage independent of the principal. They build and run the operational machinery of the family enterprise—the systems, processes, vendor relationships, and infrastructure that need to function whether or not the principal is paying attention. The principal sets direction; the COO makes the enterprise actually work.

The diagnostic question is this: Is your friction about decision-making capacity, or operational infrastructure?

If you're struggling to synthesize information across advisors, maintain momentum on strategic priorities, or extend your reach across family governance initiatives—that's Chief of Staff territory. The bottleneck is your bandwidth as a decision-maker.

If nothing moves unless you push it, if tribal knowledge lives in two people's heads, if you have twenty vendor relationships and no one accountable for managing them, if your technology is fragmented and cybersecurity is an afterthought—that's COO territory. The bottleneck is operational infrastructure that doesn't exist.

Many family enterprises experience both simultaneously. The principal is overwhelmed (a leverage problem) and the enterprise lacks the systems to function independently (an infrastructure problem). In those cases, sequencing matters. A COO without adequate principal support will struggle to get direction. A Chief of Staff without operational infrastructure will spend their time on work that should be systematized, never getting to the strategic leverage the role is meant to create.

For a deeper exploration of when a COO becomes necessary—and what that role actually involves in a family enterprise context—we've written separately on why family offices struggle without a Chief Operating Officer.

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How to Know When You Need a Chief of Staff

The need for a Chief of Staff typically emerges from one of several pressure patterns. Understanding which pattern describes your situation is essential to making the right hire—and to determining which type of Chief of Staff you need.

Coordination Failure

You're operating across multiple entities—investment vehicles, operating businesses, family trusts, philanthropic structures—and information isn't flowing properly. Decisions get made in silos. Your tax attorney doesn't know what your investment manager is planning. Your estate planner isn't aligned with your family governance initiatives. You find yourself spending significant time just keeping advisors coordinated—time that should be spent on higher-value work.

This is classic Chief of Staff territory. The solution requires someone who can move across the family enterprise, synthesize information from multiple sources, and ensure that what needs to connect actually connects. An EA, no matter how talented, typically can't solve this because the work happens outside your immediate orbit.

The question is whether the coordination failure is primarily technical or organizational. If advisors aren't coordinating because they speak different professional languages and no one is translating, you need a Technical Chief of Staff. If advisors aren't coordinating because no one owns the follow-through and nothing has momentum, you need a Generalist Chief of Staff.

Information Synthesis Gap

You're making decisions with inadequate information. Not because the information doesn't exist, but because no one is synthesizing it for you. Your investment managers provide performance reports, your attorneys send legal updates, your accountants deliver tax summaries—but no one is integrating these into a coherent picture you can act on.

This pressure pattern often points toward a Technical Chief of Staff. The value isn't just in collecting information or scheduling meetings where information is shared. The value is in interpreting that information, understanding what matters, and presenting it in a way that enables decision-making. This requires someone who understands the substance, not just the process.

In MFOs and complex SFOs with multiple investment verticals, fragmented reporting, or heavy deal flow, the Technical Chief of Staff becomes the integrator of intelligence—translating technical detail from specialists into decision-ready insight for the principal.

Execution Gap

Decisions are being made, but follow-through is inconsistent. Family governance priorities get announced but don't translate into sustained action. You have capable advisors, but no one owns the work of ensuring that what was agreed actually happens across the family enterprise.

This can be a Chief of Staff problem, but only if the execution gap spans entities or requires authority beyond a single domain. If the gap is within a specific area (investment operations, property management, philanthropic grants), you likely need a stronger operator in that function, not a Chief of Staff. If the gap is in your own follow-through on decisions and commitments, an exceptional EA with strong project management instincts might be the better fit.

When the execution gap is organizational—things stall because no one maintains momentum across people and entities—a Generalist Chief of Staff is often the answer. They create leverage not by doing the work themselves but by ensuring the work gets done.

Overload and Fragmentation

You're drowning in volume. Your calendar is a war zone between family obligations, investment meetings, and personal commitments. You're context-switching constantly between your children's needs, your portfolio, and your philanthropic work. You can't protect time for the decisions that matter most. You feel perpetually behind.

This is almost never a Chief of Staff problem. It's an EA problem, or a systems problem, or a boundaries problem, or a delegation problem. Hiring a Chief of Staff to solve overload is like hiring a CFO because you're behind on expenses. The capability doesn't match the need.

The honest answer for many principals experiencing overload is that they need a significantly better EA or Family Office Manager than they currently have, combined with clearer boundaries around what actually requires their attention.

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Questions Worth Asking Yourself

Before deciding on a Chief of Staff, sit with these questions honestly:

What's actually breaking, and what are the consequences? Not what's suboptimal, but what's genuinely failing. Where is value being destroyed or left on the table? "I'm busy" isn't a failure mode. "Family governance discussions keep getting postponed" is. "I'm missing co-investment opportunities because I can't get to the analysis in time" is. Be specific about the cost of the current state.

Where does the friction live? Is it in your personal sphere (your calendar, your preparation, your capacity to stay on top of what matters), the organizational sphere (coordination failing across entities, execution inconsistent, information not flowing between advisors), or the external sphere (investment manager relationships suffering, philanthropic engagement slipping)? The answer determines whether you need an EA or a Chief of Staff.

Is the friction primarily technical or organizational? If you need someone to synthesize complex information, translate specialist detail into decision-ready insight, and act as a filter between advisors and the principal, you need a Technical Chief of Staff. If you need someone to connect dots across people and initiatives, maintain momentum on cross-family priorities, and act as a trusted advisor and internal stabilizer, you need a Generalist Chief of Staff.

Does the solution require authority across the family enterprise, or excellence within your orbit? This is the crucial test. If someone operating primarily in your world (managing your time, your communications, your preparation) could solve the problem, you need an exceptional EA or Family Office Manager. If the solution requires someone who can independently engage other parts of the family enterprise, make decisions without checking with you, and drive outcomes across entities, you're in Chief of Staff territory.

How much ambiguity can you genuinely delegate? A Chief of Staff will encounter situations daily where the right answer isn't clear and they'll need to use judgment. Are you prepared to give someone that latitude and live with decisions you might have made differently? If you want to approve everything, you don't want a Chief of Staff. You want an EA who's very good at escalating.

What would you stop doing? This reveals whether your need is for protection (keeping things away from you) or extension (doing things on your behalf). Both are valid, but they point to different solutions—and different profiles.

Is there enough organizational complexity to justify the role? A Chief of Staff creates leverage by navigating complexity. If your family office is small enough that you have direct relationships with all your key advisors, or simple enough that coordination happens naturally, the role may not have enough to do. This often applies to single family offices under $100 million, family offices with primarily passive investments, and situations where the principal is still close to all the key decisions. A Chief of Staff in a simple family office becomes overhead, not leverage.

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What's Actually Possible

Done well, a Chief of Staff hire can fundamentally change how you operate. But the nature of that change depends on what you're solving for—and which type of Chief of Staff you hire.

For the Complex Single Family Office

Consider the principal of a $2 billion single family office with direct investments across private equity, real estate, and venture capital, plus operating business interests, a family foundation, and multi-generational dynamics. The coordination challenge is immense: managing relationships with dozens of fund managers, overseeing direct investment due diligence, coordinating estate planning across multiple jurisdictions, and navigating family governance with the next generation.

This situation might call for either type of Chief of Staff—or potentially both over time. If the primary friction is that investment information arrives fragmented and the principal can't synthesize it fast enough to make good decisions, a Technical Chief of Staff becomes the integrator of intelligence. They take the quarterly reports, the deal memos, the tax projections, and the estate planning updates, and they synthesize these into briefings that enable faster, better decisions.

If the primary friction is that initiatives keep stalling—the family retreat never gets planned, the next-generation education program loses momentum, the reporting consolidation project dies after the first meeting—a Generalist Chief of Staff becomes the connective tissue. They ensure that decisions translate into action across all entities.

The leverage equation is straightforward: every hour the Chief of Staff spends on synthesis, coordination, or cross-entity work is an hour the principal can spend on the irreducibly principal-level work that no one else can do. Key relationships, investment decisions, family matters, and the moments that require the principal's judgment specifically.

For the Multi-Family Office Executive

Now consider a different archetype: the CEO or managing partner of a multi-family office serving fifteen to twenty client families. Their value is generated through client relationships, investment strategy, and the judgment they bring to complex family situations. They're managing multiple client relationships while also running an organization with its own operational complexity.

The leverage need here is both personal and organizational. What's breaking might be the operational texture around high-stakes client work—traveling between client meetings, preparing for quarterly reviews, managing the administrative complexity that accumulates around senior client-facing roles. But it's also likely to include coordination challenges across the firm: ensuring consistent service delivery across client families, driving strategic initiatives that span the organization, and maintaining information flow between investment, client service, and operations teams.

In many MFOs, the Chief of Staff is an investment professional who has stepped into an operating role—someone who understands the substance of what the firm does and can synthesize information upstream. They might prepare the executive for client meetings (understanding the portfolio context, not just the logistics) while also ensuring that insights from those meetings flow to the relevant teams. This Technical Chief of Staff profile is particularly valuable when there are multiple investment verticals and reporting is fragmented.

Alternatively, if the friction is primarily organizational—client service quality varies across families, strategic initiatives lose momentum, the team isn't aligned—a Generalist Chief of Staff who can connect dots and maintain momentum might be the better fit.

For the Simpler Single Family Office

Now consider the more common situation: a principal with a $150 million family office, primarily invested in public markets and real estate through external managers, with a small philanthropic program and straightforward family dynamics. The organizations are small enough that formal structure feels unnecessary, but the complexity of the principal's life—personal, philanthropic, and financial interests intertwined—can be enormous.

The instinct is often to hire a Chief of Staff to manage this complexity. But the nature of this family office work usually points toward a different profile: someone with exceptional discretion, deep personal loyalty, and the ability to navigate the ambiguity of a role that spans professional and personal domains. This is quintessentially EA or Family Office Manager work, even if the scope and compensation exceed what most people associate with those titles.

The exception is when the family office is large enough to function like a true institutional investor, with a team managing significant assets across multiple strategies and geographies. In that context, the coordination and execution challenges may justify a Chief of Staff—but the role will look quite different from a Chief of Staff at a corporate enterprise.

For the Family Office Advisor

Family office advisors—whether wealth managers, family governance consultants, or specialized service providers—face their own leverage challenges. A senior partner at a family office advisory firm managing relationships with a dozen ultra-high-net-worth families operates in a demanding environment where client relationships are everything.

The leverage need here is typically in the personal and external spheres: managing the operational complexity of high-touch client relationships, preparing for meetings that require deep context about multiple family situations, and handling the administrative burden that accumulates around senior client-facing roles. This is usually EA work, requiring someone who understands the family office world deeply enough to catch nuance and operates with the discretion required for sensitive family and financial information.

A Chief of Staff becomes relevant when the advisor also has significant firm leadership responsibilities: leading a practice area, driving firm-wide strategic initiatives, or managing a team of professionals. In those cases, the role extends beyond personal leverage into organizational leverage.

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Defining the Right Profile

Once you've determined that a Chief of Staff is genuinely what you need—and whether you need a Technical or Generalist profile—the question becomes: what specific capabilities matter most?

The Technical Chief of Staff: Detailed Profile

Background: Often an ex-investment professional, management consultant with financial services experience, or operations person who has worked across multiple asset classes. What distinguishes them is domain expertise—they understand the substance of what the family office does.

Core capabilities: Interpreting complex information, translating technical detail into decision-ready insight, acting as a filter between specialists and the principal, evaluating opportunities and synthesizing due diligence, understanding how different domains (investment, tax, estate, operations) interact.

How they create leverage: By synthesizing information upstream so the principal can make better, faster decisions without drowning in technical detail. They don't just collect reports—they interpret them. They don't just schedule meetings between advisors—they understand what questions should be asked.

Best fit for: MFOs with multiple investment verticals, investment-heavy SFOs, situations with significant direct investment activity or complex alternative exposure, family offices with heavy deal flow, contexts where reporting is fragmented and specialists speak different "languages."

Risk factors: May lack the interpersonal skills to navigate family dynamics. May want to be a principal investor rather than a force multiplier. May over-index on analytical sophistication at the expense of organizational awareness.

The Generalist Chief of Staff: Detailed Profile

Background: Often from operational or general management backgrounds. May have run complex projects, managed cross-functional teams, or served in roles requiring navigation of competing priorities and stakeholders. What distinguishes them is organizational intelligence—they understand how to make complex systems work.

Core capabilities: Connecting dots across multiple people, entities, and initiatives. Maintaining momentum on cross-family priorities. Acting as a trusted advisor and internal stabilizer. Navigating family dynamics with emotional intelligence. Building trust across different family members and generations.

How they create leverage: By ensuring that what needs to connect actually connects, and that initiatives maintain momentum even when the principal's attention moves elsewhere. They're not the doer; they're the one who makes sure things get done.

Best fit for: Multi-generational families with complex dynamics, governance-heavy SFOs, situations where complexity is primarily social and organizational rather than technical, family offices with multiple residences or entities requiring coordination, contexts where family alignment is harder than advisor alignment.

Risk factors: May lack the domain expertise to know when something technical is going wrong. May become so embedded in family dynamics that they lose objectivity. May be excellent at coordination but lack judgment about when to escalate.

The Family Dynamics Navigator: A Specialized Variant

For some principals, the primary leverage need is internal to the family rather than the enterprise. They need someone who can navigate multi-generational dynamics, facilitate family governance processes, and manage the interpersonal complexity that comes with significant shared wealth. This requires a particular combination of emotional intelligence, discretion, and the ability to build trust across different family members and generations.

This is a specialized variant of the Generalist Chief of Staff profile—someone for whom organizational intelligence extends specifically to family systems. They become a trusted facilitator who can hold confidential conversations, synthesize family perspectives, and help the principal navigate delicate interpersonal terrain.

This profile is most relevant in family offices where the family itself is the source of complexity—where getting alignment across generations or branches of the family is harder than getting alignment across advisors or entities.

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The Leverage Outcome

When the hire is right, the effects compound quickly.

Decision velocity increases. Not because decisions are rushed, but because the preparation for decisions improves. For a Technical Chief of Staff, this means information arrives synthesized rather than raw—investment opportunities are framed with context about how they fit the portfolio, risks are identified before the meeting, and specialist recommendations are translated into language the principal can act on. For a Generalist Chief of Staff, this means decisions actually lead to action—the meeting ends with clear next steps, someone owns the follow-through, and momentum is maintained.

Execution becomes more consistent. Initiatives that previously stalled after the initial family discussion now maintain momentum because someone owns the connective tissue. Follow-through stops being the principal's responsibility to personally enforce across every advisor and entity.

Attention gets protected for the work that matters most. The calculus of what requires the principal's direct involvement changes when there's someone capable of handling significant complexity independently. The threshold for what escalates to the principal rises.

Perhaps most importantly, the principal's thinking improves. A good Chief of Staff doesn't just execute. They challenge, pressure-test, and surface considerations that might otherwise be missed. A Technical Chief of Staff becomes a thought partner on investment and strategic questions—someone who can engage with the substance. A Generalist Chief of Staff becomes a sounding board on organizational and family questions—someone who sees the system as a whole. Both extend the principal's capacity to think, not just their capacity to do.

The net effect is that the principal's leverage becomes non-linear. Their impact is no longer bounded by their personal bandwidth. The family enterprise can move faster, handle more complexity, and execute more consistently than the principal could enable alone.

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When It Goes Wrong

Chief of Staff hires in family offices fail for predictable reasons. Understanding these patterns can help you avoid them.

Misdiagnosis of the Problem

The most common failure is hiring a Chief of Staff to solve a problem that doesn't require one. If your actual need is for better time protection and calendar management, a Chief of Staff will be underutilized and frustrated. If your need is for a specific functional capability (better investment analysis, better tax coordination, better property management), a Chief of Staff is the wrong shape for the hole.

The solution is rigorous honesty about what's actually breaking before you start the search.

Wrong Type for the Context

The second most common failure is hiring the wrong type of Chief of Staff. A Technical Chief of Staff in a governance-heavy family office will struggle because the leverage gap isn't about synthesizing investment information—it's about maintaining momentum on initiatives that require navigating family relationships. A Generalist Chief of Staff in an investment-heavy family office will struggle because the leverage gap requires understanding the substance of what's being coordinated, not just that it needs coordination.

This explains why so many Chief of Staff hires feel "smart but ineffective." They often are smart. They're just the wrong type for the context.

The solution is clarity about whether your friction is primarily technical or organizational before you start the search.

Unclear Mandate

A Chief of Staff without a clear mandate becomes family office overhead. They attend advisor meetings without authority, coordinate without power, and advise without impact. The role needs to come with genuine scope: either specific initiatives to own or clear authority to act on the principal's behalf.

The solution is defining the role around concrete outcomes rather than abstract responsibilities.

Principal Unwilling to Delegate

Some principals say they want a Chief of Staff but can't actually let go of anything. Every decision comes back to them. Every communication gets second-guessed. The Chief of Staff becomes an expensive note-taker.

This is particularly common in family offices where the principal has built everything themselves and is accustomed to being involved in every detail. The solution is honest self-assessment before hiring. If you're not prepared to genuinely delegate judgment and authority, you don't want a Chief of Staff.

Wrong Profile for the Context

Beyond the Technical vs. Generalist distinction, there are other profile mismatches that create friction. A corporate generalist in a role that requires comfort with the intimacy and ambiguity of family office work. Someone from a large institutional environment who expects clear reporting lines and defined processes. Someone who wants to be a principal rather than a force multiplier.

The solution is clarity about which capabilities matter most for your specific leverage gap, and discipline in hiring for those capabilities specifically—including cultural fit with the family office environment.

Family Resistance

In family offices, the Chief of Staff often needs to work with other family members—some of whom may view the role as a barrier to access or an unwelcome layer of professionalization. Spouses may resent going through the CoS to reach their partner. Adult children may feel their relationship with the principal is being mediated. The role becomes a source of family friction rather than leverage.

The solution is careful positioning of the role from the outset: clarity about what the Chief of Staff owns vs. facilitates, explicit conversations with family members about how the role will work, and a hire who has the emotional intelligence to navigate family dynamics rather than create them.

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Making the Decision

The question isn't whether a Chief of Staff is a valuable role. It clearly can be. The question is whether it's the right role for your specific situation—and if so, which type.

Start with the problem, not the solution. What's actually breaking? Where is leverage being lost? What would you do differently if you had the right support?

Be honest about scope. Does your situation genuinely require someone who can operate across the family enterprise with autonomy and judgment? Or do you need exceptional support within your immediate orbit? Both are valuable, but they're different hires.

Distinguish technical from organizational friction. Do you need someone to synthesize complex information upstream and translate specialist detail into decision-ready insight? Or do you need someone to connect dots across people and initiatives and maintain momentum on cross-family priorities? The answer determines which type of Chief of Staff you need.

Consider the tradeoffs. A Chief of Staff is a significant investment: in compensation, in the principal's time to develop the relationship, and in the complexity of adding a senior role to an environment that often values simplicity. Make sure the leverage gained justifies the investment.

Get the profile right. Once you've decided a Chief of Staff is warranted, be precise about which capabilities matter most. Technical or Generalist? Investment-focused or family-dynamics-focused? Execution-oriented or synthesis-oriented? The wrong profile creates friction that compounds over time.

And finally, be prepared to delegate genuinely. A Chief of Staff who lacks real authority is overhead. If you're not ready to give someone meaningful scope to act on your behalf, the hire won't deliver the leverage you're seeking.

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A Note on Assessment

Understanding your leverage gap with precision matters more than most principals realize. The difference between needing an exceptional EA versus a Chief of Staff—and the difference between needing a Technical Chief of Staff versus a Generalist—determines not just who you hire, but how much value that hire creates. Get it wrong, and you've made an expensive mistake that takes months to unwind—and in the intimate environment of a family office, that mistake affects not just business operations but personal relationships and family dynamics.

We've built a diagnostic tool designed to help family office principals and executives think through these questions systematically: where leverage is breaking down, whether the friction is primarily technical or organizational, what type of support addresses the gap, and what profile matches the need. It takes ten minutes and will give you a clearer picture of what you're actually solving for. If you'd like to pressure-test your own situation before starting a search, it's available here.