The Most Embarrassing Mistake I Made at Microsoft
What an awkward moment taught me about presence, perception, and giving yourself grace.
Early in my career, I made a mistake so embarrassing that everyone in the room noticed except me.
It was one of my first broader staff meetings at Microsoft, my first time inside a real big tech conference room. My background up to that point had been warehouses, factories, and night shifts. I knew how to run a floor. I did not know how to read rooms filled with senior leaders wearing Patagonia vests and discussing quarterly priorities.
So I did what anyone does when they do not know the rules: I guessed.
I showed up early, walked into a large conference room, and grabbed an open seat at the head of the table. It seemed logical. It was open, it had a good view of the screens, and no one was there yet. I did not realize that this was the seat people informally held for the executive who led our organization.
I had no idea. None.
A few minutes later, the executive walked in. He paused behind me. Then he stood next to me. Then he leaned in slightly. All subtle cues that I should move.
And I did not notice any of them.
I was not being bold or trying to make a statement. I was simply unaware. I did not understand how these rooms worked. I knew the rules of a warehouse floor. I did not know the unwritten rules of a corporate conference room.
After the meeting, one of our senior leaders pulled me aside. He did not embarrass me. He did not speak to me like I was in trouble. He simply said, quietly and directly:
“Just so you know, that seat is usually where our exec sits. When he stood near you he was giving you a chance to move. It is totally fine. You will get used to this.”
I will never forget how calm he was. He treated it as a learning moment, not a moment of judgment. His approach earned my trust for years.
The executive whose seat I took eventually became an important mentor. But in the moment I wanted to sink through the floor.
And I learned something I still carry with me.
That moment crystallized something I had felt but could not yet name: corporate environments run on invisible rules, and nobody explains them until you break one.
Presence, awareness, and perception are skills just as much as coding, understanding financial markets, or marketing. None of them are automatic, you learn them through real and—sometimes painful—experience. People early in their career are often not taught this, especially first generation professionals or anyone coming from hands on roles. You do not understand the social rules of corporate life until you trip over a few of them.
After that meeting, I started paying attention more intentionally. I noted where leaders sat and how they entered rooms. I noticed that our VP always arrived exactly two minutes after meetings started, not late enough to disrupt, but late enough that everyone was already seated. I realized that it wasn’t carelessness, it was deliberate.
I listened to how they handled small talk, how they behaved at happy hours, and how they presented themselves on work trips. I observed when they spoke and when they stayed quiet. What they wore and why. What seemed normal and what seemed unusual.
I was not trying to become someone else. I was trying to understand the environment well enough to figure out how I wanted to show up.
Here is a cheat code for your career: Watch how people who have earned respect navigate the culture. Not to become them, but to understand the rhythm of the environment so you can build your own style.
Here are a few lessons I wish someone had given me earlier:
1. You will screw up. Publicly.
It is unavoidable. Do not let it define you.
2. Say sorry once and then move on.
Over-apologizing creates more awkwardness than the original mistake.
3. Let people tease you about harmless mistakes.
When someone ribs you about sitting in the wrong seat or mispronouncing a colleague’s name, lean into it. Self-deprecating humor builds trust and belonging. But learn the difference between teasing that includes you and mockery that diminishes you. The first brings you closer to the team. The second pushes you out.
4. Before work trips or offsites, ask questions.
What is the dress code?
Is there anything I should know about ordering a drink?
Is there any guidance around expectations?
It is not naive. It is proactive. The people who have been there before want to help you. Let them.
5. Read your company’s policies.
Things like reimbursements, gifts, alcohol, and travel expectations are small details that can prevent big mistakes. Err on the side of conservative actions (not having another drink, not taking a gift, not reimbursing unnecessary items).
6. Presence is quiet and perception is subtle.
Learn to read cues. Who sits where. Who has influence. Who speaks last. Who people look toward for reactions.
These are the details that separate people who stay stuck from people who accelerate.
And the most important part. Give yourself grace.
That Microsoft meeting was uncomfortable and humbling. I wanted to disappear. But it made me better. It taught me to observe, pause, and understand the room before jumping in.
Your career will be full of moments like this. Do not avoid them. Do not overthink them. Learn from them.
They become stories you carry forward. And years later, you laugh about them with the people who helped you grow.
Rooting for you,
Justin
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