The Operator: The Comfort of Control

Part 4 of the 7 Founder Personalities series. Read the overview here.

A founder once made me take a course on how to use emojis in Slack.

I need to explain this carefully because I can feel you thinking “surely you mean guidelines” or “maybe a brief style note” and no. No. I mean a course. With modules. With a quiz. With a certificate of completion that I have framed on my wall because I failed the first time and I needed proof that I eventually passed so I could look at it late at night when the doubts come.

Module One was called “Emoji Frequency and Professional Calibration.” Too few emojis, I learned, signals disengagement and possible depression. Too many emojis signals that you are either having a stroke or are “not a culture fit,” which is HR-speak for “we find you unsettling.” There is a correct number of emojis. The correct number is three to five per day. I do not know who determined this. I assume there was research. I assume the research was conducted by someone who has never experienced joy.

Module Two covered “Emotional Registers.” This is where I learned that the thumbs-up means “acknowledged,” the raised-hands means “celebrating,” and the eyes emoji means “I have seen your message and I am choosing not to respond with words and you should be concerned about what that means.” There was a chart. The chart had a grid. The grid cross-referenced emoji selection with “recipient seniority” and “message urgency” and “time of day” because apparently a party emoji at 9 AM means something different than a party emoji at 4 PM. The 9 AM party emoji is “genuine enthusiasm.” The 4 PM party emoji is “passive-aggressive.” I did not know this. I have been 4 PM party-emoji-ing people for years. I have enemies I did not know about.

Module Three—and I need you to understand that I am not making this up, I have the PDF, I will show you the PDF, I will show it to a judge—Module Three was called “The Semiotics of the Thinking Face.” It was eleven pages. It included a decision tree. The decision tree helped you determine whether the thinking-face emoji means “interesting point, tell me more” or “I disagree but lack the emotional bandwidth to type words” or “I am performing thoughtfulness while actually checking Twitter.” There were seventeen possible interpretations of the thinking face. Seventeen. For one emoji. One small yellow circle with its hand on its chin. I have spent less time analyzing actual human facial expressions. I have spent less time analyzing tax returns. I have spent less time analyzing the terms of a lease. A cartoon face with its hand on its chin required more documentation than most legal contracts, and I say this as someone who has read legal contracts.

I took the quiz. I failed. I got a 64. You needed a 70 to pass. I missed it because I said that the fire emoji was appropriate for “good job on the presentation” when actually the fire emoji is reserved for “exceptional cross-functional collaboration that advances key OKRs.” I did not know fire had criteria. I did not know fire was exclusive. I thought fire just meant “good.” I was naive. I was young. I was sixty-four percent correct, which is apparently not correct enough to communicate with my coworkers.

I retook the quiz. I passed. I got the certificate. The certificate is signed by the founder. The founder is very proud of the emoji course. The founder mentions the emoji course in investor meetings. “We take communication seriously,” he says. The investors nod. The investors are impressed. The investors do not know about Module Three. They have not seen the decision tree. If they saw the decision tree, they would take their money back. They would run. They would never return. They would tell other investors. There would be a support group for investors who have seen the decision tree. The support group would communicate exclusively in words, because nobody in that group would ever trust an emoji again.

The company had eleven employees. Three of them quit that year. I am not saying it was because of the emoji course. I am not saying it was not. The exit interviews were confidential. The exit interviews probably contained an appropriate number of emojis.

This is the Operator.

Why Operators Exist

Operators emerge from trauma. Specifically, the trauma of having worked somewhere where nobody knew anything about anything and everything was on fire all the time and the fire had a Slack channel and the Slack channel was also on fire.

I need to tell you about a company I worked at. I will not name this company because they might still exist and also because I have blocked out the name as a coping mechanism.

At this company, we discovered—eight months in, eight months of everyone working very hard on things—that we had two completely different product roadmaps. Two. Different documents. Different priorities. Different features. Different universes. The engineering team was building one product. The sales team was selling a different product. Marketing was promoting a third product that did not exist and had never existed and showed no signs of existing in the future. Three products. One company. Zero of them the same. This is not “misalignment.” This is three companies wearing one company’s trench coat.

We found out during a board meeting. The board asked a question. The CEO pulled up the roadmap. The VP of Sales said “that is not what I have been telling customers.” The VP of Engineering said “that is not what we are building.” The VP of Marketing said nothing because they had left to get coffee and would later claim this was “coincidental timing.” It was not coincidental timing. They knew. They always knew. Marketing always knows. Marketing’s entire skill set is knowing things and leaving the room before anyone asks them about it.

The slide deck had contradictions on consecutive slides. Slide 14 said we were focused on enterprise. Slide 15 said we were focused on SMB. Slide 16 had a graphic that said “FOCUS” in large letters, which was, in retrospect, ironic—the kind of irony you only appreciate later, the way you only appreciate a tornado warning after the tornado. The board was confused. We were confused. The CEO tried to explain. The explanation made it worse. The CEO used the phrase “strategic optionality” eleven times, which is a phrase that means “we do not know what we are doing” in the same way that “reorganization” means “layoffs” and “transitioning” means “fired.” The board knew what it meant. We all knew what it meant. The meeting lasted four hours. Nothing was resolved. The contradictions remained. They remain to this day, presumably, haunting that conference room like ghosts who can’t agree on what they’re haunting.

The Operator looks at this kind of chaos and thinks: never again. Never again will there be two roadmaps. Never again will nobody know who is responsible for what. Never again will Marketing escape to get coffee at a convenient moment.

And they are not wrong. Structure is good. Documentation is good. Knowing who does what is good.

The problem is when the Operator shows up too early. When they bring the structure before there is anything to structure. When they build the organizational equivalent of a mansion for a family that does not exist yet and might never exist—complete with a nursery, a guest wing, and a home office with custom shelving, all for a family of zero.

The Premature Organization

I once consulted for a company that had an employee handbook. This is normal. Companies have employee handbooks. This is fine.

The handbook was thirty pages.

The company had eight employees.

I need you to do the math here. Thirty pages. Eight employees. That is 3.75 pages of handbook per employee. That is more handbook per capita than most Fortune 500 companies. That is an amount of handbook that suggests someone had a lot of feelings about policies and no one in their life willing to tell them to stop.

The handbook covered, among other things:

• Inclement weather policy (the company was fully remote; inclement weather affected nobody; the policy existed anyway)
• Guidelines for reserving conference rooms (they had one conference room at a co-working space they rented twice a month; you could see if it was occupied by looking at it with your eyes)
• Dress code (again: fully remote; I assume this was for the benefit of anyone who was attending Zoom meetings naked, which I choose to believe was nobody but which someone apparently felt needed to be addressed in writing, which means there was an incident, which means I do not want to know)
• A section called “Kitchen Etiquette” that was four pages long and included subsections on “Refrigerator Shelf Assignment” and “Microwave Time Limits” and “The Philosophy of Shared Spaces” (THE PHILOSOPHY. Of SHARED SPACES. Four pages. Of philosophy. About a refrigerator.)
• Holiday schedule for the next three years (the company would not exist in three years, but the holidays were planned; Christmas 2027 was going to be on a Thursday; they were ready)

The handbook had been reviewed by legal. Twice. The company had spent, by my estimate, $15,000 on legal review for a handbook governing eight people, seven of whom had never read it and one of whom had written it and was very defensive about the refrigerator shelf assignments. The shelf assignments had a dispute resolution procedure. The dispute resolution procedure had an escalation path. The escalation path went to the founder. The founder was the final arbiter of refrigerator disputes. This was in the handbook. In writing. Reviewed by an attorney.

This is the Operator gift. This is also the Operator curse. They see chaos—or the possibility of chaos, or the ghost of chaos, or a vague premonition of chaos that might occur in a future that will never arrive—and they cannot rest until it has been documented, systematized, and assigned a Notion page with custom properties and a color-coded status indicator.

The Green Dashboard

I need to talk about dashboards.

If you have ever worked at a company with dashboards, you know. You already know. You are nodding. You might be crying a little. That is okay. This is a safe space. The dashboard cannot hurt you here.

The Operator dashboard has metrics. The metrics are green. All the metrics are green. Every single metric on the dashboard is green, and you have never seen a metric that was not green, and you are beginning to suspect that the dashboard cannot display any other color—that someone built this dashboard and forgot to include red, or deliberately excluded red, the way you might exclude an ex from a wedding. Red is not invited. Red does not exist here. This is a green place.

The dashboard says: Tickets closed: green. Meetings attended: green. Slack response time: green. Alignment score (this is not a real thing, but it is on the dashboard, so): green. Velocity (this is also not a real thing): green.

The dashboard does not say: Revenue: not on dashboard. Customer satisfaction: not on dashboard. How many employees are actively interviewing at competitors: not on dashboard. Is the company going to exist in six months: NOT ON DASHBOARD.

Three engineers updated their LinkedIn profiles that week. That was the canary in the coal mine. That was the smoke before the fire. That was the thing that meant they were about to leave and everyone knew it but nobody was talking about it because it was not on the dashboard. If it was not on the dashboard, it was not real. The dashboard was reality. The dashboard was green. Everything was fine.

The building is on fire. The dashboard is green.

The Post-it Note Incident

Here is a thing that actually happened, at an actual company, where actual humans worked:

Someone ordered too many Post-it notes.

I need you to sit with this. Someone—and to this day, nobody knows who, the identity has been lost to history like the builders of Stonehenge or the person who first decided to put pineapple on pizza—someone ordered Post-it notes. And the quantity of Post-it notes was deemed, by someone else, to be excessive.

How many is excessive? Nobody remembers. Was it fifty packs? A hundred? A thousand? Was this person building a Post-it note castle? Were they starting a Post-it note-based religion? Were they preparing for a Post-it note emergency that the rest of us were too naive to foresee? We do not know. The knowledge is lost. The Post-it note incident occurred in 2019. It has passed into legend. It is this company’s founding myth. Other companies have “two guys in a garage.” This company has “someone ordered too many Post-it notes and now you need three approvals to get a pen.”

But here is what remains: a process.

The company built a fifteen-step approval workflow for office supply purchases. Fifteen steps. For Post-it notes and pens and paper clips and all the other things that cost less than a sandwich.

You need a pen. You are a grown adult human being who has been hired because someone believed you could make good decisions. You need a pen because your other pen ran out of ink. This is what pens do. Pens run out of ink. It is their whole thing. It is the only thing pens are known for, besides occasionally ending up in someone’s mouth during a meeting, which is disgusting but not currently covered by a policy, though give the Operator time.

You cannot simply get a pen. No. You must: Log into the procurement portal. Navigate to Office Supplies. Select Writing Instruments. Choose Pens Non-Specialty because God forbid you need a specialty pen, that is a different workflow with its own approval chain and a committee that meets monthly. Specify quantity. Provide justification—justification, for a pen, a justification for why you need an object whose sole purpose is to make marks on paper, which is something humans have been doing for 40,000 years without a procurement portal. Submit for Level 1 approval. Wait for your manager—who sits eight feet away—to log in and click approve. Wait for Level 2 approval from the department head, who does not care about your pen. Wait for Budget Code Assignment. Wait for final approval. Receive email with pickup instructions. Pick up pen from supply closet—the supply closet is twelve feet from your desk; you can see the pens; the pens are right there; the pens have been right there this entire time; the pens are watching you navigate the workflow; the pens feel nothing because they are pens, but if they could feel, they would feel pity.

A senior engineer at this company—a person who makes $180,000 a year—once spent two hours navigating this process to acquire a $4 notebook. The process cost forty-three times more than the thing the process was protecting. If you paid the engineer their hourly rate for the two hours they spent acquiring the notebook, the notebook cost $177. It is the most expensive notebook in corporate history. It is a notebook that costs more than most laptops. The engineer could have bought a laptop and typed their notes and it would have been cheaper, but the laptop procurement process is twenty-two steps and requires VP approval, so that wasn’t really an option either.

The engineer gave up. The engineer wrote their notes on their hand. Like a feral child. Like someone who has been broken by bureaucracy and reduced to their most primitive state. The pen was twelve feet away. The pen might as well have been on the moon.

The process won. The process always wins.

The Fab.com Catastrophe

Jason Goldberg raised $336 million for Fab.com. Three hundred and thirty-six million dollars—a number that stops meaning anything after a while, so let me put it differently: that’s enough to buy every employee a house, or fund the Post-it note approval workflow for roughly ten thousand years, or simply set on fire in a very large and impressive bonfire that would at least have the courtesy of being honest about what was happening.

He built the most beautiful machine. Seven hundred employees. Clear reporting structures. Defined roles. Documented processes. The org chart looked like art—clean lines, logical hierarchy, everyone in their box, every box connected to the right other box. If you judged companies by their org charts, Fab was the Rdio of e-commerce: gorgeous, meticulous, and doomed.

The org chart was magnificent. The company was dying.

Because here is what never got figured out, what got lost beneath all the beautiful structure: Why should anyone buy from Fab instead of Amazon? Nobody asked. Or rather, someone probably asked once, early on, and the question got routed through the proper channels, and the proper channels took six weeks, and by the time the question reached someone who could answer it, the company had hired four hundred more people and the question felt rude. You don’t ask “why do we exist?” after you’ve hired seven hundred people. That’s not a strategy question at that point. That’s an existential crisis. That’s a question that requires a therapist, not a task force.

Everyone was too busy building processes to ask. The machine was so well-built that nobody noticed it wasn’t going anywhere. It was a perfectly engineered car with no engine. The seats were comfortable. The dashboard was green.

Fab sold for $15 million. After raising three hundred and thirty-six. That is a 95.5% loss. That is the most expensive org chart in history. That is what happens when you mistake the appearance of a company for the existence of one.

Somewhere, that org chart still exists on a server. The org chart does not know everyone is gone. The org chart is waiting, boxes and lines and dotted-line reporting relationships, all pointing to people who have moved on and updated their LinkedIns and are now at companies that sell things that people actually want to buy. The org chart will wait forever. The org chart has nowhere else to be.

The Fix

Track outcomes, not activities. The dashboard should tell you if the company is healthy, not if people are busy. Busy is easy to measure and meaningless to know. The busiest company I ever saw went bankrupt. Their Slack response time was immaculate. Their ticket velocity was extraordinary. Their employees were so productive that they produced the company right into the ground. The dashboard was green the whole time.

Delay, delay, delay. Wait until you know what you are systematizing. Wait until the chaos has taught you what it is trying to teach you. The chaos is data. The mess is information. If you systematize before you understand, you are building a beautiful machine to automate the wrong thing. You are optimizing the process of getting lost. Do not let them create an emoji course. Especially do not let them create an emoji course.

Measure the cost of the process, not just its output. The Post-it note workflow costs more than Post-it notes. The approval chain costs more than the thing being approved. Every process has a tax, and the tax is paid in time and attention and the slow erosion of the will to live. If the process costs more than the problem it prevents, kill the process. The problem was cheaper.

Let chaos exist. This is the hardest one for Operators, and I say it with love: some things do not need to be organized. Some things are fine messy. Some conversations do not need an agenda. Some decisions do not need a framework. Some refrigerators do not need a shelf assignment policy reviewed by legal. The chaos is where ideas live before they become ideas. If you organize the chaos too early, you organize the ideas out of existence. Let the chaos breathe. Let the mess teach you. Then—and only then—build the system. The system will be better because you waited. The waiting is the work.

Next in the series: The Expert — when twenty years of experience becomes twenty years of doing it wrong.

Take the quiz: What’s Your Founder Type? — Ten scenarios. Seven types. Find out which one is killing your company.

Marc Lefton is a Fractional CMO and Creative Director who spent 30 years at places like BBDO and DiMassimo Goldstein before becoming the person founders call when the marketing isn’t working and they can’t figure out why. He writes the strategy, writes the ads, buys the media, reads the data, and does it again. One person. No agency. If something in this piece made you uncomfortable, that’s probably worth exploring. Start with a $250 Brand Check to find out what’s actually broken, or see the full menu of founder engagements.

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