Ask ten executives what their Chief of Staff does, and you’ll get ten different answers. Ask ten Chiefs of Staff what makes someone succeed in the role, and you’ll hear the same word: ambiguity.
In a recent conversation with three alumni who’ve built careers as Chiefs of Staff, one thing became clear: there’s no singular profile for this role—but there are specific, learnable skills that determine whether you’ll thrive or flame out.
Three Paths, One Pattern
The Chief of Staff role has exploded across industries. It sounds like the ultimate career accelerator: C-suite exposure, strategic work, broad impact. But here’s what I hear in coaching sessions: “I think I’d be great at this, but I don’t actually know what it is.”
We gathered three alumni whose paths couldn’t look more different:
→ Jennifer McEachern ’13, Chief of Staff at VDX.tv, started as a middle school teacher. Her skill? Meeting people where they are – whether that’s 7th graders or stakeholders resistant to change.
→ Lauren Love ’20, Chief of Staff at Kodiak, spent a decade in film production. What translated? Bringing order to chaos and building from scratch – exactly what a newly created CoS role demands.
→ Andrea Sugano ’20, Chief of Staff for Vanguard’s Data Analytics Group, came from healthcare with zero financial services experience. Her edge? Rapid learning and reading organizational dynamics – essential when reporting to three different leaders in one year.
CoS success isn’t about where you’ve been: it’s about what skills you bring and how you adapt them.
The Skills That Actually Matter
These aren’t soft platitudes: they’re the specific capabilities that came up in every conversation:
• Influencing without authority: You’ll shape priorities and execution without formal power or resources. Your influence is your currency.
• Stakeholder management across competing agendas: Navigate conflicting priorities and strong personalities. Success looks like turning a skeptical VP into your champion.
• Prioritization: Not every leadership priority delivers value. Your job is knowing which ones align with strategy and helping your leader focus there.
• Agility and handling ambiguity: You’ll shape the role repeatedly as priorities shift, and toggle between strategic thinking and operational firefighting.
• Facilitation without ownership: You don’t own the P&L, but you align teams and remove blockers. You’re the conductor, not the soloist.
• Code-switching across levels: Prep the CEO for a board meeting, then dive into details with an analyst—all in the same hour.
What They Don’t Tell You (But Should)
The panelists were candid about trade-offs:
One day you’re shaping strategy for market entry. The next, you’re fixing a broken approval process. That whiplash is part of the job. If it feels energizing rather than exhausting, you’re wired right for this.
There’s also no clear “next step.” Some CoS move into GM roles, others into strategy or operations leadership, some start companies. You’ll define what’s next. That can be either thrilling or terrifying.
Before You Apply Ask Yourself These Questions
Answer these for yourself, not the interview:
→ Can you build without a blueprint? Most CoS roles are newly created. You’ll define it as you go.
→ Are you comfortable with ambiguous “next steps”? There’s no traditional path out. That’s either liberating or destabilizing.
→ Do you thrive in strategic-to-tactical whiplash? Three-year vision in the morning, process breakdown in the afternoon. Energizing or exhausting?
→ Can you influence without a title? You’ll have the CEO’s ear but no direct reports. Your power is persuasion, not position.
So, Is This Role For You?
The Chief of Staff role is defined by two things: the leader you report to and the strengths you bring.
If you can influence without authority, prioritize ruthlessly, and toggle between strategy and execution without losing your balance, this role might be exactly where you belong. But if you need clear structure, predictable career paths, and well-defined ownership, there are better paths. And that’s okay.
The best career move isn’t the one that sounds impressive. It’s the one where your natural strengths become superpowers.
Interested in exploring CoS roles further or navigating a different career path? The CDO is here for you.
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AI in the Trenches: Real Use Cases – Myth vs Reality, April 2, 12-1pm: Panelists to be announced. Registration will be on SOM Connect.
Leadership in Volatile Times: is AI Changing Your Role as a Leader? Thursday, April 20th from 12-1pm. (Panelists to be announced). Registration will be on SOM Connect.
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