Leading From the Shadows: A Conversation with Clara Ma

Clara Ma has quietly built a reputation around one of the most misunderstood roles in startups: the chief of staff. She was the first chief of staff at Hugging Face, joining when the now-influential AI company was just ten people, and that front-row seat to how leadership actually works became the seed for Ask a Chief of Staff, a platform and global community of more than 400 chiefs of staff that helps executives find the right strategic partner to operate beside them.

What makes Clara's perspective valuable is that she sits at the intersection of founders, operators, and executives. She has seen what great leadership partnerships look like from the inside, how companies scale internally, and why the relationship between a CEO and their chief of staff can make or break momentum. This conversation is a working playbook for the role: what it is, when to hire one, and why the arrival of AI makes the human glue more essential rather than less.

The zone of genius

Clara's cleanest definition of the role is that a chief of staff is the strategic right hand to an executive, and their core mandate is to keep that executive operating in their zone of genius. The idea is simple. What is the thing only this CEO or leader can do, the thing they alone bring to the table, and how do you give them back as much time as possible to spend there? Everything else that lands on the principal's plate but does not require the principal specifically is a candidate to be absorbed by the chief of staff.

The mechanism she describes is being a body double. A good chief of staff can stand in for their principal in meetings, field the bottlenecks and roadblocks before they ever reach the executive, and troubleshoot them first. That requires holding a dual brain. One brain thinks the way the principal thinks, so you reach the same conclusions they would and can act on their behalf. The other is your own developing judgment, since many chiefs of staff are preparing to become executives themselves, and knowing when to surface a genuine disagreement is its own discipline. The best leaders she worked with also protected time for deep thinking, talking through possibilities in a session and then coming back to the decision a day or two later, after the unconscious had time to digest it.

Influence without authority

The hardest and most defining part of the role is that it runs entirely on soft power. A chief of staff has influence without authority, so the first thing Clara has every new chief of staff do is a listening tour of two weeks to a month. That means talking not just to the leadership team but to the individual contributors and managers actually doing the day-to-day work. You gather context, you hear the needs that never make it up to leadership, and you get a set of quick wins by surfacing things that can be fixed fast.

The listening tour works partly because a new chief of staff can play the "I'm new" card, when people are more willing to volunteer information and help you get oriented. The relationships and trust you build early are what make it normal, later, to grab fifteen minutes with anyone. And there is a synthesis skill underneath it. Rather than carrying one person's raw complaint to the CEO, you pattern-match across many conversations and present something anonymized and actionable, so people feel heard without their name being attached. That, more than any title, is what makes a chief of staff effective, because you rarely have the authority to do things yourself and instead have to get the whole company rowing in the same direction.

When to hire one

There is no headcount number that triggers the hire, and Clara is firm about that. She was a chief of staff at a ten-person company. Other companies add the role at fifty or seventy-five people. The role has actually always existed in some form, the generalist glue person at a startup, or the group that always seems to have the executive's ear at a larger company. The title only gained popularity in the last five to seven years, but the function is old.

The real test goes back to the zone of genius. She tells any founder considering a chief of staff to ask how much of their time is spent on things only they can do versus things they wish they could delegate but that still need to be performed at an executive level. When a leader feels that less than half their time is going to that zone of genius, that is the signal to start considering a chief of staff. It is organization-dependent and leader-dependent, not a stage you cross.

Operational debt

The concept from this conversation most worth stealing is operational debt, Clara's name for the cousin of technical debt. If you do not write down your processes and build the playbooks early, even at ten or fifteen people, then by the time you are at twenty-five or fifty that knowledge lives entirely in one person's head. That person becomes the linchpin for five or six crucial operations, and if they leave, all of it walks out the door. Documentation can feel thankless, and writing out the steps for something you could just do in thirty seconds feels like a waste, but the payoff compounds as the team grows.

There is a personal upside too, and it reframes the whole thing. Being the keeper of institutional knowledge feels important, and the constant Slack pings feel like being wanted, but that attention becomes a tax that caps your growth. The more time you spend on the things people know you can do, the less time you have to expand your scope. Clara's version of "teach a man to fish" is that writing down the playbook so someone else can run it frees you to go explore the parts of the business that actually advance your career. It echoes a manager who deliberately answered Slack only twice a day, so his team would learn to find answers themselves rather than making him the bottleneck.

What Hugging Face taught her about AI

Working inside Hugging Face during the AI boom gave Clara a thesis that has only held up: AI is a communal effort, not something built in a bubble. Even when the internal team was tiny, there were contributors all over the world building the model library and the hub. No single entity will ever control the AI space. It is always going to be many, and the progress comes from people openly sharing knowledge through tutorials, courses, and open contribution.

The practical version of this is that even a product built for a narrow audience depends on countless external inputs, from the models it is trained on to the community around it. Remembering that AI moves forward as a team sport, rather than one company pushing out a product and expecting the world to adopt it, is the lens she took from those early days and still applies.

Aligning the leadership team

One thing most employees never see is how much misalignment happens at the top. A leadership team can agree on a North Star, say becoming number one in some market, and still have the CTO, CFO, and COO each interpret it differently. A great chief of staff goes to each leader and asks what that North Star actually means to them, and gets genuine alignment before it cascades into OKRs, KPIs, and metrics. Without that, confusion trickles all the way down, and individual contributors end up unsure how their work connects to the goal.

The reason it stays invisible is that the leadership team disappears into a room for hours and emerges with a polished-looking plan, when in reality there was enormous back-and-forth, much of it still unresolved even after the plan is presented. Surfacing and closing that gap is quiet, unglamorous work, and it is exactly the kind of thing the role exists to do.

The role AI makes more important

Given how much operational work AI can now absorb, the obvious question is whether the chief of staff becomes less necessary. Clara argues the opposite. You still need the human balance check, because no one should be handing the full workload to an LLM and trusting the output blindly. Inputs and outputs are only as good as the prompting, and a chief of staff helps the principal think through what to feed the model in the first place. Chiefs of staff are also frequently the ones shepherding AI adoption across the company, deciding what good hygiene and best practice look like internally.

The deeper point is that AI tends to build an echo chamber. It will happily tell you your own idea is great, because you are the one who fed it that idea, and your field of vision narrows. A human sounding board who will be honest with you, not just your leadership team but a chief of staff acting as a second brain, is something AI has not been able to recreate. Her framing of the role as culture, operations, and strategy (the letters C, O, S) captures why the human sits at the center of all three.

Key takeaways

A few things worth keeping.

Protect the zone of genius. The whole point of the role is giving the executive back time to do the thing only they can do. When less than half of a leader's time goes there, it is time to consider a chief of staff.

Run the listening tour. New chiefs of staff should spend the first weeks talking to people at every level, gathering context, banking quick wins, and building the trust that makes soft power work.

Pay down operational debt early. Write the playbooks before the knowledge is trapped in one person's head. It feels thankless at ten people and saves you at fifty.

Delegate yourself out of a job. Clinging to tasks because they make you feel important caps your growth. Automating or handing them off frees you to expand your scope.

AI needs a human sounding board. Left alone, AI builds an echo chamber. The value of a chief of staff, and of any honest second brain, goes up as AI adoption goes up.

Frameworks worth stealing

The zone-of-genius test

To decide whether you need a chief of staff, audit your own time. Separate the work only you can do as the leader from the work that merely needs to be done at an executive level. If the second bucket is eating more than half your week, that is the case for the role, regardless of your headcount.

The listening tour

In the first two to four weeks, meet people across every level of the company, not just leadership. Use the newcomer's license to ask candid questions, collect quick wins, and synthesize what you hear into anonymized, actionable patterns for the leadership team. This is how you earn influence when you have no formal authority.

Operational debt

Treat undocumented process as a liability that accrues interest. Write down the playbooks while you are still small, so critical operations do not depend on a single person's memory. The thirty seconds it takes you today becomes the thing nobody else can do tomorrow.

Carrot before stick

When you need to change how an entrenched team works, lead with the reframe that what got us here will not get us there, and show people how the change lifts everyone. Reserve the "this is coming from the CEO" card for rare, genuinely critical moments, because using it often turns you into the boy who cried wolf and erodes the relationships the role depends on.

Quotes worth keeping

The lines I wrote down.

A great chief of staff should be enabling you, not babysitting you.

The best tool is the tool you're going to use.

What got us here is not going to get us there.

And the one that captures the whole ethos of the role.

There's no right way into it and no right way out of it.

Rapid fire round

Same questions every guest. No prep, no warning. Here is how Clara handled it.

Best advice you've ever received? Give time to time. From her CEO at Hugging Face. She thought back-to-back meetings all day meant she was productive, until he asked when she actually thought about things. Block real time for deep strategic thought, and take a walk to let your brain process rather than forcing a decision.

Advice you ignored or wish you had listened to? Do not hold on to tasks just because the institutional knowledge makes you feel important. Automate or delegate yourself out of a job, and use the freed bandwidth to learn more of the business.

What would you tell your younger self? A winding career with titles that do not line up neatly is fine. Hindsight is 20/20, and your story is what you make of it. Chase your curiosities, and go put in the extra hours with teams whose work you want to understand.

Ongoing challenge that keeps you up at night? Still feeling like the linchpin of her own five-person company as it scales, and building enough contingency that the business does not depend on any single team member, herself included.

Favorite spot? Raku, an udon restaurant she loves in New York, especially on a cold day. Warm soup, chewy noodles, great toppings.

Tool you can't live without? Whisper Flow, the speech-to-text tool. It lets her dictate a first draft without immediately editing herself, getting the whole thought onto the page far faster than typing into a blank screen.

---

Clara Ma is the founder of Ask a Chief of Staff, a platform and global community of over 400 chiefs of staff that helps executives find the right strategic partner and helps chiefs of staff upskill through workshops, mentorship, and coaching. She was previously the first chief of staff at Hugging Face. Find her at askachiefofstaff.com or on LinkedIn.