Starting as an executive assistant can feel overwhelming. You’re supporting someone who makes important decisions, manages multiple projects, and expects you to keep everything running smoothly. Many new EAs make the same mistakes in their first few months, but the good news is that these problems are easy to fix once you know what to look for.
The Biggest Problem: Thinking Too Small
The most common mistake new executive assistants make is treating the job like it’s just about checking boxes and following instructions. They focus on tasks instead of thinking about the bigger picture. But here’s what successful EAs understand: your job is to make your executive more effective, not just to do what you’re told.
This mindset shift changes everything about how you approach your work.
Mistake #1: Being Afraid to Ask Questions
When you’re new, you might think asking questions makes you look inexperienced or unprepared. So you try to figure things out on your own, make your best guess, and hope it works out. This almost always backfires.
Why this doesn’t work: Your executive would rather spend five minutes explaining what they need than dealing with work that misses the mark. Wrong guesses waste everyone’s time.
What to do instead: Ask clear questions upfront. Before you start any new task, find out:
- What’s the end goal?
- When does this need to be done?
- How important is this compared to other projects?
- What would make this successful?
Stop worrying that questions make you look unqualified. Smart questions show you’re thinking strategically.
Mistake #2: Not Understanding Relationships Matter Most
New EAs often think their job is just scheduling meetings and organizing files. But that’s missing the point. Your real job is protecting the relationships that help your executive succeed.
Here’s the truth: Every email you send, every phone call you take, and every meeting you schedule reflects on your executive. People form opinions about your boss based on how you treat them.
What to do instead:
- Learn people’s names and remember details about them
- Pay attention to how different people prefer to communicate
- Notice if there’s any tension or history between people
- Think about timing—is this a good time to schedule this conversation?
Keep notes about the important people in your executive’s world. When someone mentions their daughter’s graduation or their recent vacation, write it down. Remembering these details builds trust and strengthens relationships.
Mistake #3: Treating Everything Like It’s Urgent
When you’re new, everything feels like an emergency. Someone says “urgent,” and you drop everything to handle it immediately. But not all urgent requests are actually urgent.
Learn the real priority levels:
True emergencies: Major problems that could hurt the business, legal issues, or serious stakeholder concerns (handle immediately)
Important and time-sensitive: Things that directly affect your executive’s main goals (handle today)
Regular business: Normal work that keeps operations running (handle within a day or two)
Can wait: Administrative tasks that need to get done but won’t cause problems if they take a few extra days
What to do instead: When someone says something is urgent, ask “How does this fit with today’s other priorities?” This simple question helps you make smart choices about what to tackle first.
Mistake #4: Keeping All the Information in Your Head
Some new EAs think that being the only person who knows where things are or how things work makes them valuable. Actually, it makes you a problem.
Why this backfires: What happens when you’re sick or on vacation? Everything grinds to a halt because no one else can find what they need or figure out how things work.
What to do instead: Create systems and write things down:
- Use shared calendars that everyone can access
- Keep files organized in folders others can navigate
- Write down how you do regular tasks so someone could cover for you
- Make sure contact information and vendor details are accessible
Your value comes from managing things well, not from being the only person who understands the system.
Mistake #5: Spending Too Much Time Making Things Perfect
It’s natural to want your work to be flawless. But many new EAs waste hours perfecting documents that were already good enough. They miss deadlines trying to make everything look perfect, or they research every possible option instead of presenting the top three choices.
The business reality: In the executive world, getting something good delivered on time often beats getting something perfect delivered late.
What to do instead: Before you spend extra time polishing something, ask yourself: “Will this extra work actually change the outcome?” If not, it’s time to move on. Aim for excellent work that gets done on schedule.
Mistake #6: Not Understanding What “Confidential” Really Means
New EAs sometimes think discretion just means keeping secrets. But it’s actually about knowing what information to share with whom, when, and how.
Real discretion means:
- Not discussing your executive’s schedule with people who don’t need to know
- Understanding that most meetings are private
- Learning how to politely redirect questions without giving information
- Protecting your executive’s time to think and make decisions
The golden rule: When you’re not sure if something should be shared, keep it private and ask your executive directly about their preferences.
Mistake #7: Stopping Your Own Learning
Some EAs think that once they learn the basic administrative skills, they’re done learning. This is a major mistake. Your learning needs to keep pace with your executive’s growth.
Why this matters: If your executive is expanding into new markets and you don’t understand those markets, you can’t really help. If they’re dealing with new types of clients and you don’t understand those relationships, you become less useful.
What to do instead: Keep developing your skills in:
- The industry your company works in
- Advanced software that could make work easier
- Communication and negotiation
- Basic financial concepts
- Project management
The most successful EAs become true partners by understanding the business well enough to offer insights, not just complete tasks.
Mistake #8: Taking Business Stress Personally
When your executive seems stressed, suddenly changes priorities, or seems unhappy with your work, it’s easy to assume you did something wrong. Usually, that’s not what’s happening.
The reality: Your executive deals with pressures you probably don’t see. They’re thinking about revenue goals, investor expectations, market changes, and strategic decisions. Their stress usually has nothing to do with your performance.
How to protect yourself:
- Set up weekly check-ins to ask directly: “How am I doing? What should I focus on?”
- Keep track of successful projects and positive feedback
- Remember that urgency is usually about external factors
- Develop resilience while staying detail-oriented
Mistake #9: Never Saying No
Many new EAs think being helpful means saying yes to everything. You take on every request, volunteer for extra projects, and try to accommodate every scheduling demand. This leads to burnout and makes you less effective at the important stuff.
Why this doesn’t work:
- You get overwhelmed and make mistakes
- Your executive loses confidence in your judgment
- People learn to expect instant responses even for non-urgent requests
- Your work quality drops across the board
What to do instead: Learn to manage your workload honestly:
- “I can help with that. Let me check my current tasks and get back to you with a timeline.”
- “I can do this today if we push the board meeting prep to tomorrow. What’s the priority?”
- “Taking this on means the vendor report will be delayed by two days. Does that work?”
Being known for excellent work delivered on time beats being known for saying yes but delivering mediocre results.
Mistake #10: Just Taking Orders Instead of Thinking Ahead
New EAs often think their job is just following instructions. But your executive hired you to make their life easier, which sometimes means respectfully pointing out potential problems or offering better options.
What this looks like:
- “You have three calls scheduled back-to-back with no breaks. Should we add 15 minutes between them?”
- “Last time we did a similar project, we needed legal involved. Should we loop them in earlier this time?”
- “I see two conflicting priorities this week. Which one should come first?”
The key insight: Your executive wants you to think strategically about their success. They hired you partly to catch things they might miss and offer operational insights.
Start small with observations about scheduling or logistics. As you build trust, gradually offer insights about processes and strategy.
Mistake #11: Not Learning About the Industry
Many new EAs think they just need to be good at administrative work. But the most successful EAs understand their executive’s industry, which transforms them from task-doers into strategic partners.
Why industry knowledge matters:
- You can prioritize emails and calls based on what’s actually important
- You understand the context behind urgent requests
- You can have real conversations with industry contacts
- You anticipate needs based on industry patterns
- You become capable of drafting emails and preparing briefings
How to learn quickly:
- Read the same publications and websites your executive follows
- Follow industry leaders on LinkedIn
- Attend virtual industry events when you can
- Ask your executive to explain industry dynamics
- Keep a list of important terms, key players, and major trends
EAs who understand their industry often move into business development, operations, or strategic roles.
Mistake #12: Communicating the Wrong Amount
New EAs either communicate too much (sending updates on every tiny task) or too little (assuming their executive knows what’s happening). Both create problems.
Too much communication: Your executive’s inbox gets flooded with status updates on minor tasks.
Too little communication: Your executive can’t make informed decisions about priorities and timing.
The balanced approach:
- Create a weekly summary of project updates, upcoming deadlines, and decisions that need to be made
- Use a simple system: green (on track), yellow (potential issues), red (needs attention)
- Send immediate updates only for truly urgent situations or when decisions are needed
- Figure out the best way to share different types of information
Ask your executive directly: “What’s the best way to keep you informed without overwhelming you?”
The Bottom Line
The most common mistakes new executive assistants make all come down to one thing: thinking too small about the role. When you focus only on tasks, you miss the opportunity to become a strategic partner who makes real impact.
You’re in a unique position to see how businesses work, solve complex problems, and contribute to real success. The executives who do best have EAs who think strategically, communicate clearly, and execute reliably.
Learn from these common mistakes, and you’ll build a career with unlimited potential.
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