Your Onboarding is a Dress Rehearsal for Your Next Job
The first impression is the real one, revealing a company’s true values.
The hum is the first thing you notice. Not the people, not the art on the walls they mentioned in the interview, but the low, monotonous drone of the server room down the hall. Your desk is particle board and cold laminate. There’s a stapler with no staples, a phone that isn’t plugged in, and an impressive amount of dust. This is it. Day one.
Someone from HR, whose name you’ve already forgotten, drops a folder on the desk. “Your laptop should be ready in a day or two,” she says, avoiding eye contact. “IT has a backlog of 48 tickets. In the meantime, you can review our culture deck. It’s all in there.” The folder contains a printout of a 108-slide presentation last updated in 2018. Slide 8 declares, “We are a fast-paced, agile, people-first organization.”
Cognitive Dissonance
The truth is immediate and physical.
The cognitive dissonance is immediate and physical. You feel it in your gut. Nothing about this experience is fast, agile, or people-first. It’s slow, rigid, and deeply impersonal. This isn’t a minor administrative hiccup. This is the truth. This is the most honest thing the company will ever tell you.
We love to talk about onboarding as a process, a checklist of forms and training modules. I used to think that way, too. In a previous role, I was responsible for bringing a new analyst onto my team. I was buried in a project with a punishing deadline. I did the bare minimum: I pointed him to the shared drive, introduced him to two people, and gave him a login. I thought my job was to get him access; his job was to figure it out. He quit in under 8 months, taking a job at a competitor. For years, I told myself he just “wasn’t a culture fit.” What a cowardly, self-serving lie. The truth is, I didn’t onboard him into our company; I onboarded him into a state of quiet desperation that made our competitor’s LinkedIn message look like a life raft. I taught him that at our company, you are utterly on your own. It was my single greatest management failure.
The Onboarding Paradox
Administrative Preamble
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The Job (in miniature)
Onboarding isn’t the administrative preamble to the job. It is the job, in miniature.
It’s a living demonstration of the company’s real values, not the ones on slide 8. It reveals how the organization handles complexity, how it treats its people, and how much of a gap exists between its marketing and its reality.
Onboarding is the company’s first promise. And its first lie.
I was complaining about this to a friend, Sam A., who designs escape rooms for a living. I expected sympathy. Instead, he got a strange look in his eyes. “So, the new player gets a key, but it doesn’t fit any lock they can see. They’re in a room with a puzzle that’s missing a piece, and the clock is ticking. What do they learn?” he asked.
I must have looked confused. “They learn that the game is broken,” I said.
“
“Exactly,” he replied. “You’re not giving them a broken game. You’re giving them the wrong game. You tell them they’re playing chess, but you’ve handed them a single, useless checker.”
– Sam A.
He explained that a good escape room doesn’t just present a series of disconnected tasks. It builds a world and teaches you its rules through interaction. The first puzzle teaches you the logic you’ll need for the last one. It builds confidence and agency, one small discovery at a time.
The Onboarding Escape Room
A company’s onboarding should be its best-designed escape room.
I’ve seen research from a group of 238 companies showing that structured onboarding programs result in 58% greater employee retention after three years. But I’m convinced “structured” is the wrong word. It implies rigidity, a checklist. What Sam was describing was something else entirely. It was architected, not just structured.
Structured
Rigid, checklist, disconnected.
Architected
Designed, integrated, contextual.
The Day One Mission
He would design a “Day One Mission.” The goal: get a piece of code you wrote into the staging environment. Seemingly simple, but the mission would be designed to fail without help. To get your laptop, you don’t file a ticket; you have to find Sarah in Ops, who has it at her desk. Her name isn’t on a list; you have to ask your assigned ‘buddy’ who knows that Sarah is the unofficial queen of hardware. To get database credentials, you need to talk to James, but he only responds on the company’s messaging app, teaching you the primary communication channel. The mission forces you to navigate the company’s actual social and technical systems. It’s a tutorial for the real world, not a PDF about it.
We get so obsessed with efficiency that we strip the humanity out of everything. The systems we build at work are often clunky, outdated, and profoundly frustrating. You file a support ticket to get access to a shared folder and wait 28 hours for a response. The friction is maddening, especially when we contrast it with our personal lives. We can set up entire home entertainment networks with minimal effort. We expect a setup as smooth as a good Meilleure IPTV, a system that just works from the moment you plug it in, yet at work we are handed a broken process and told it’s our fault for not understanding it. This dissonance is exhausting.
I used to be a fierce advocate for new hire autonomy. “Don’t micromanage them,” I’d argue. “Let them find their own way. That’s how they’ll learn to be resourceful.” Now I see that as another sophisticated form of neglect. It’s an abdication of responsibility disguised as a management philosophy. Sam’s escape room approach isn’t micromanagement; it’s the opposite. It’s a guided tour of resourcefulness. It provides the map and the compass, then sends the explorer on a very specific, low-stakes treasure hunt. It respects the new hire enough to give them a game that is challenging but winnable.
The final puzzle in Sam’s ideal onboarding isn’t about finding an object. It’s about earning a key. After 18 days of these missions, the new hire presents a small project they’ve completed to a panel of 8 people from different departments. Upon approval, they are granted full production access and an autonomous project budget of $8,888. They don’t just get a job; they ‘unlock’ the company. They’ve proven they know the rules of the game by playing it.
Unlock the Company
Earn the key by playing the game, proving you know the rules.
Most companies don’t do this. They hand you the employee handbook from 2018 and a broken key. And then they act surprised when, six months later, you use that key to lock the door behind you on your way out.