I have been an Executive Assistant for twenty years, and I have made some genuinely spectacular mistakes. Every EA has. The difference between this role and most others is that we have built our professional brand on precision, anticipation, and flawless execution, which means that when a ball drops, it doesn't just feel like a mistake. It feels like a full identity crisis.
Allow me to share my three most mortifying screw-ups from my long career with executive leadership.
- The Letter. My executive received a handwritten letter from a mentor congratulating him on a promotion. He asked me to make a copy for his files, then he would get the original framed. I made the copy. It wasn’t until the next morning when I realized what I'd left the original on the copy machine and raced back to retrieve it. But the original was gone. No one in the office remembered seeing it on the copier and I had to assume it had been scooped up and thrown away with the trash. I had to tell my boss. I made a second-generation copy and got it beautifully framed for him. He loved it, but every time I saw that second-gen letter hanging on his wall, I felt a deep, internal cringe.
- The Recording. My boss asked me, explicitly and with direct eye contact, to record a crucial meeting for the committee chair who couldn't attend due to a family crisis. I spent the hour before that meeting in full command of every detail: the room setup, the dial-in links for remote participants, the printed and electronic materials distribution, the catering. I was totally on top of it. But I forgot to toggle the record button. I did not realize this until the meeting ended, everyone filed out, and my boss asked me to send her the file. I died inside. My meeting notes had to do.
- The Flight. My executive was flying to a critical, million dollar closing dinner with a client's CEO. I spent days mapping out the itinerary, the ground transportation, and the briefing materials. I was totally on top of it. What I wasn't on top of was noticing a short-duration connection in one of the busiest airports in the country. The weather delayed my executive’s arrival, and she made it to her connecting gate only to find her flight had already departed. My oversight left her stranded at a hub airport. I had to partner with the airline's executive desk to rebook her flight and coordinate with the client’s administrative team to re-schedule the dinner, all while managing the immense weight of knowing my oversight caused the chaos.
No one died from any of my mistakes, no client cancelled their relationship with us, and no initiative imploded. But in each of these moments, I experienced what I can only describe as a specific, acute, full-body mortification that hits an Executive Assistant who has built her entire brand on perfection and yet has just, very publicly, not achieved it. We know, rationally, that we are human. We know, rationally, that mistakes happen. Yet when we make a mistake, we feel quite irrationally like our professional credibility has just been fed through a shredder.
So, as a seasoned EA mistake-maker, here is what I've learned about how to handle it.
- Own it quickly and without turning it into a performance.
The impulse to apologize at length, or to explain the circumstances that led to the mistake, is understandable, but both miss the point. What your executive actually wants to know is whether this experience can be turned into data to prevent it from happening again. Prolonged remorse forces them to manage your feelings on top of the actual problem. Excuse-making signals an inability to analyze and diagnose. Neither reaction is useful. Instead, say what happened, then say what you've put in place to prevent it going forward. Something like: "I see how this happened. Here's what I've done to correct it." Then stop talking.
2. Get curious instead of derailed.
Every mistake has an earlier moment where something in the chain failed, where there was some signal in the system that you missed. Finding that moment is more useful than replaying the mistake over and over. The question isn't just "how did this happen" but "what does this tell me about where my process needs shoring up?" The mistake becomes data.
3. Do the post-error work.
Update the system that failed. Edit the handbook. Look honestly at your margins and ask whether you've been running too wide open or too razor thin. Name what the mistake actually revealed about your capacity, your process, or the conditions you were working in. Then reset, not by white-knuckling your way through the next month in a state of anxious over-correction, but by returning to the steadiness that got you here in the first place, just now a bit wiser.
What I have learned after twenty years supporting leadership is that what they are actually watching, usually unconsciously, is what we do after the mistake is made. Our response is data: it tells them exactly how much authority we’re capable of managing. An EA who gets flustered over a missed connection is not one they're going to send to a meeting as their proxy, represent them in a difficult conversation, or make independent decisions on their behalf. But the EA who handles an error with composure, who owns it, fixes it quickly, and moves forward in good humor and without making it anyone else's problem is exactly the person they want at their side. More responsibility is, admittedly, a very EA kind of reward. But the alternative is being the person they silently stop trusting with the high-stakes work.
For the EA, the way we handle a mistake tells us something important about ourselves. Composure after an error is evidence of our emotional intelligence, our capacity to stay functional under the specific kind of pressure that comes with this very unique role. The knowledge we earn from a mistake hones our capacity to anticipate, refines our systems, and builds a confidence that cannot be fast-tracked or pantomimed.
A mistake, handled well, broadcasts the excellence you're made of.
Note on my use of pronouns: For most of recorded history, assistant-to-power roles belonged exclusively to men. Today, 94% of EAs are women. I intentionally use she/her pronouns to speak directly to the 2.78 million women who inherited this legacy and now sit in the seat of executive proximity.