The Shape of Trust
On blurred lines, and the difference between being helped and being known
For a couple of years I flew to San Mateo every few weeks to meet with the team at NetSuite. I booked the flights myself, usually on Tuesday nights, squinting at options while half-listening to a podcast. I thought of my schedule as flexible, and of myself as responsive. I believed the adaptability was part of what made me effective.
I had a new executive assistant, and it was jarring when she sat me down and told me, plainly, that I was wasting everyone’s time. Mine, hers, and the company’s. If I just standardized the trip to every third week, the meetings would land better, the travel would cost less, and she could actually plan around it instead of scrambling every time I decided on a Tuesday night that I needed to be in California by Thursday.
I pushed back. I thought the flexibility and adaptability were important. She gave me a look that suggested she’d be willing to fight me over it, and then pulled out her phone and blocked the third week of every month for San Mateo. She later set up recurring holds with the people I usually met there, and rearranged the surrounding weeks so nothing piled up while I was gone. She refused to book it any other way.
Everything improved - meetings landed more reliably, travel costs dropped, and my family appreciate the routine. The NetSuite team started expecting me, which made the conversations richer. I stopped spending Tuesday nights making decisions that, apparently, we not as effective as I thought.
The outcome surprised me, and so did the discomfort it uncovered. Someone else had started shaping the rhythm of my weeks. The structure she imposed fit better than anything I’d built for myself, and that was the part that struck. I thought I was delegating travel booking. Turns out I was delegating parts of how I lived.
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One of my earlier EAs sent me an executive profile questionnaire to start our relationship. Standard onboarding stuff: communication preferences, scheduling habits, dietary restrictions. Near the bottom was a line for my standard coffee order.
I stared at it for an unreasonable amount of time. I’d tell a friend how I take my coffee without thinking twice. I’d shout it across the kitchen at a family gathering. But writing it on a form for someone whose job included acting on it felt demanding. Pretentious. Like I was the kind of person who expected a rider.
I filled it in eventually. And she used it, of course; it saved both of us small, repeated friction. The information was trivial after all. My discomfort with stating it, however, was a lesson for me. It turns out I was more uncomfortable being helped than I was being known, and those two things were tangled together in ways I had only started to notice.
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Founders talk about giving away your Legos. The phrase usually means operational pieces: hiring, customer calls, product decisions. You hand them off as the company grows. The discomfort is manageable because you understand the trade. Control for leverage.
The Legos I struggled to release were tied to identity. How reachable I was. How spontaneous I believed myself to be. How central my personal involvement felt. Those were stories I told about the kind of leader I was, and my EA was quietly editing them without either of us explicitly acknowledging it. The coffee form, the travel schedule, the meeting cadence she restructured while I was still pretending I preferred chaos. Each one was a small confrontation with a self-story that turned out to be mostly decorative.
It’s banal to point out that having an EA made me more effective. I expected that. What I did not expect, though, was that it would make me a better leader. Learning to state preferences clearly, to trust someone else’s judgment about my own patterns, to let go of the performance of being indispensable. Those lessons came from the relationship, from having another person close enough to see through the stories I was telling myself.
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And they do see through you. That is the part nobody prepares you for.
I’m comfortable with proximity in professional relationships. I’ve employed friends, and I’ve employed family. But an EA occupies a different kind of closeness. They know everything in real time, in a way that even employees who were best man at your wedding do not. They know when an investor is furious before you’ve told anyone. They see the therapy appointment on the calendar. They learn the gap between the version of you that walks into a board meeting and the version that sits in the car afterward.
It is a kind of surveillance that the person being surveilled has consented to and pays for. And the person doing the surveilling has no safe way to act on most of what they see. That asymmetry creates something unusual: intimate knowledge held by someone with less organizational power and few channels to use it. The look my EA gave me about the travel schedule was her using that knowledge. She understood my patterns well enough to override them. I’ve often wondered how many times she held back.
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That closeness can tip into something unhealthy, and the tipping point is hard to see from the inside because it looks so much like dedication.
An EA I knew once offered her CEO, in the same tone you’d use to confirm a hotel preference, that she could arrange drugs or companionship for him while he was traveling. She was remarkably effective - identify the potential need, remove the friction, withhold judgment. She had internalized the role so completely that potentially illegal behaviour registered as logistics.
Another time, at a conference a few years back, I watched it play out differently. We were standing in the empty hallway as people sat in sessions - the carpet that particular shade of corporate burgundy that all conference centres share. Behind a nearby closed door, her executive was mid-briefing with an analyst. She pulled me aside, voice low, and told me she and her partner were thinking about trying to have a baby.
She wanted to talk about timing. But the timing she meant had nothing to do with her own life. She was working through when her executive could best absorb the disruption. Which quarter would be least painful. How far in advance she’d need to have a plan in place so he’d barely feel the gap. I remember the hum of a session starting on the other side of the wall. The way she kept glancing toward that door, as though even this conversation was borrowed time from his schedule.
One was willing to blur legal lines on her executive’s behalf. The other was planning her family around her executive’s calendar. Both were rewarded for it. They were good at their jobs because they put their executive’s needs at the centre of their decisions. The blurring felt less like a personal failing and more like a feature of the role itself. Loyalty, in that context, meant letting someone else’s priorities colonize your own. This is what happens when trust and dependency and ambition grow together in a confined space, without anyone pausing to draw a line.
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The vulnerability in these relationships runs both ways, though the shapes differ.
The executive grants access and surrenders information. They allow another person to influence patterns and decisions that used to be private. It can feel generous, even brave.
The assistant ties part of their livelihood to a single person’s temperament. They absorb emotional turbulence without organizational power to change its source. A bad week for the executive becomes a bad month for them. They can be let go with a single conversation. The power sits unevenly no matter how well the relationship functions day to day.
What made it work, when it worked, was that both sides carried real exposure. The trust had weight because something genuine was at stake for each of us. Remove that mutuality and you have something else entirely: service, or performance, or mere efficiency.
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I work with AI-powered agents now - they’re good and getting better every day. They schedule, summarize, prioritize, and draft. They handle the coordination overhead that used to consume large parts of an EA’s mindshare.
They are also completely invulnerable. Software risks nothing in the relationship. An agent has no livelihood tied to your mood, no life that might become inconvenient, no judgment it’s quietly forming about whether you deserve its loyalty. And I’ve noticed it changes how I show up. With a person, there was slack in the system. Small talk before the agenda offered a moment to be human before being productive. We write software to be efficient, and so it expects efficiency in return. And so I meet it there. The experience reminds me of the difference between video calls and meeting in person. On a video call, people apologize for starting sixty seconds late. In a room, people shake hands, find seats, pour a glass of water. The human parts live in that slack, and I miss them.
When I handed my calendar to a person, I was entering a relationship that shaped us both. When I hand it to software, I’m optimizing a process. One made me more effective. The other, over time, made me more aware of what I owed the people around me.
Software can make me faster. I’m less convinced it can make me deeper.
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I stopped flying to San Mateo a while ago. The role changed, the company changed. But every now and then I catch myself blocking the third week of the month for travel, and I can still picture the look on her face when I tried to book a different week.
A Note on Practice
This one actually started with BABYMETAL concert tickets, of all things.
A close friend who’d also been an employee - I was buying tickets for both of us, and they called me on it. They didn’t like me defaulting to paying, as it felt like obligation. Like the old power dynamic from work was showing up uninvited.
Which, fair. But also, the concert was pretty out there. I’d bought two tickets knowing I might end up going alone. That was my cost of admission to maybe having company on a weird night out. In my head I wasn’t being generous, I was hedging.
We actually talked about it, which almost never happens with this stuff. And I kept turning it over afterward. How the power dynamics in these blended relationships just sit there. Quietly. Even when both people are trying to be honest about them. That’s where this essay came from.
If you’ve worked closely enough with someone that the lines got strange, this might land. If so, I’d appreciate you sharing it with someone who’d recognize the feeling.
In The Margin
A few books and one article that shaped how I think about trust, proximity, and what service roles do to the people in them.
“Give Away Your Legos” and Other Commandments for Scaling Startups, First Round Review The origin of the Legos metaphor. Practical and honest about why founders struggle to let go.
The Remains of the Day, Kazuo Ishiguro. A butler reflects on a lifetime of devotion to his employer and realizes what it cost him. The best novel I know about loyalty consuming identity.
The Managed Heart: Commercialization of Human Feeling, Arlie Russell Hochschild. The book that coined “emotional labor.” Hochschild studied flight attendants and bill collectors to show how organizations require workers to manage their own feelings as part of the job. Explains the invisible work that EAs do every day.
Convenience Store Woman, Sayaka Murata. A woman builds her entire identity around her role as a convenience store worker. Short, strange, and hard to shake.