Want to know the truth about whether executive assistant jobs are hard? Let me tell you about the most cringe-worthy moment of my entire EA career that answers that question perfectly.
You know that sinking feeling when you realize you've just made a mistake that could ruin everything? That stomach-dropping moment when you watch trust dissolve right before your eyes?
That was me, sitting on a Zoom call, watching my perfect client relationship crumble because of ONE poorly handled conversation.
The Reality: Yes, Executive Assistant Jobs Are Hard (But Not For The Reasons You Think)
When people ask "are executive assistant jobs hard," they usually think about the workload, the scheduling chaos, or managing multiple executives. But here's what they don't tell you: the hardest part isn't the tasks – it's the communication.
And I learned this lesson the most painful way possible.
My Most Embarrassing Executive Assistant Mistake
I had this amazing client – we talked every week, she trusted me with everything, our working relationship was honestly perfect. We had built this incredible foundation over months of consistent communication and flawless execution.
Then I went and destroyed it all with one email.
Instead of having a normal conversation about raising my rates (which, hello, we literally talked every single week!), I just... sent her an email out of nowhere saying "hey, my prices are going up."
Like, WHO DOES THAT?!
I still cringe thinking about it. Maybe it was because things were going too well? You know that feeling when everything's smooth and you subconsciously sabotage it? That was definitely me in that moment.
What Makes Executive Assistant Jobs Challenging: The Human Element
Here's the thing about executive assistant work that makes it genuinely difficult: it's not just about managing tasks, it's about managing relationships.
My client was NOT happy about my email approach. And honestly? I don't blame her at all.
So there I was on this Zoom call, watching her tell me how hurt and confused she was, and I could literally see the trust leaving her eyes. You know that feeling when your stomach just drops? That was me, realizing I had just torpedoed months of relationship building.
She said, "I thought we had better communication than this," and I was sitting there like... yeah, we do. Or we DID. Until I decided to be weird about it.
The worst part? I had to sit there and admit, "there's literally nothing I can say to fix this right now, I just have to prove to you that I can do better."
Then I spent the next few days feeling like absolute garbage, replaying it over and over thinking "why didn't I just TALK to her?!"
But here's what this embarrassing experience taught me about what makes executive assistant jobs truly challenging:
I expected her to be a mind reader, but I wasn't giving her any insight into MY thinking either.
Think about it – we're always complaining when our executives don't communicate with us, right? When they expect us to just "know" what they want without telling us? But I literally did the exact same thing to her.
The Hidden Difficulty of Executive Assistant Work
This is why executive assistant jobs are hard: it's not about the technical skills – it's about the communication skills.
We need to be:
- Proactive communicators, not reactive responders
- Mind readers who also share our own thinking process
- Professional relationship managers, not just task executors
- Trusted advisors who know how to navigate difficult conversations
How to Avoid Communication Disasters as an Executive Assistant
After nearly losing my best client, I realized how many conflicts we could avoid if we just knew how to read the signs better. If we understood our executives' communication styles, their triggers, their preferences.
You don't know what you don't know, you know?
Here's what I wish I had done differently (and what every EA should master):
1. Know Your Executive's Communication Style
Some executives prefer email, others want face-to-face conversations for important topics. Some need data and reasoning, others just want the bottom line. Figure this out early.
2. Create Frameworks for Difficult Conversations
Don't wing it when it comes to raises, challenging feedback, or changing processes. Have a structure you can rely on.
3. Practice "Managing Up" Techniques
Learn how to guide conversations upward, anticipate needs, and communicate proactively rather than reactively.
4. Build Trust Before You Need It
Consistent, small communications build the relationship foundation you'll need when bigger conversations arise.
What Makes a Great Executive Assistant: Communication Mastery
The difference between an average EA and an exceptional one isn't organization skills or technical abilities – it's the ability to navigate human relationships professionally and effectively.
If I had known my client's communication style better, if I had frameworks for managing up and having tough conversations... that awkward Zoom call never would have happened.
The Happy Ending (And Why This Matters)
Oh, and that client? We worked it out. But only because I had to completely change how I approach these conversations. It took months to rebuild that trust, and it was completely unnecessary stress for both of us.
Your Next Steps: Don't Learn This the Hard Way
So are executive assistant jobs hard? Yes, but not because of the workload – because of the relationship management.
The executives who succeed in this role understand that we're not just administrative support; we're communication bridges, relationship builders, and trusted partners.
Don't be like me and learn this lesson the hard way. Start building these communication frameworks now, before you need them.
Remember: A good executive assistant manages tasks. A great executive assistant manages relationships.
Looking to master the communication skills that separate exceptional EAs from the rest? The EA Blueprint to Starting a New Job includes frameworks for managing up, having difficult conversations, and building unshakeable professional relationships from day one. Don't let a communication misstep derail your career like it almost did mine.