As someone who spent 19 years in corporate America (14 as an EA), I've seen firsthand how the right executive assistant can transform a leader's effectiveness—and how the wrong one can create chaos that extends far beyond a messy calendar.
If you're thinking, "I just need someone to answer phones and schedule meetings," we need to talk. Today's executive assistants are strategic partners who can either multiply your productivity or become an expensive burden.
Let's break down what a mis-hire actually costs you (spoiler: it's more than you think) and how to avoid this expensive mistake.
The Hidden Price Tag of a Bad EA Hire
Financial Costs You Can Measure
When calculating the cost of a bad hire, most executives consider only the obvious expenses:
- Recruiting costs: Job board fees, time spent interviewing, background checks
- Onboarding expenses: Training time, reduced productivity during ramp-up
- Salary and benefits: Direct compensation before parting ways
- Termination costs: Severance, potential unemployment claims
According to the U.S. Department of Labor, a bad hire can cost at least 30% of the employee's first-year earnings. For an EA making $65,000, that's $19,500 down the drain.
But that's just the beginning.
The Invisible Costs That Really Hurt
The most damaging expenses don't show up on your P&L statement:
1. Your Precious Time
Every minute you spend fixing your EA's mistakes, redoing their work, or explaining the same process for the third time is time you're not:
- Closing deals
- Developing strategy
- Mentoring your team
- Growing your business
As one executive told me: "I hired an assistant to save time, but I spent more time managing them than doing the work myself."
2. Opportunity Cost
While you're distracted by admin chaos:
- Important emails are buried
- Critical meetings are scheduled incorrectly
- Client follow-ups fall through the cracks
- Strategic initiatives stall
One missed connection or delayed response can cost you a major opportunity. How much is that worth?
3. Team Morale and Productivity
A struggling EA affects your entire team:
- Other staff pick up slack or fix errors
- Team confidence in leadership diminishes
- Office tension increases
- Overall workflow disruptions multiply
4. Your Professional Reputation
Your EA is often the first point of contact for:
- Clients and customers
- Investors and board members
- Industry partners
- Internal stakeholders
Their performance directly reflects on you. Unprofessional communication, scheduling errors, or poor follow-through damages relationships you've worked hard to build.
As one client confided: "I started avoiding scheduling meetings with that executive because dealing with their assistant was so frustrating."
5. Your Mental Health
Never underestimate the daily stress of:
- Constant uncertainty about whether tasks are being handled
- Anxiety checking (and double-checking) your calendar
- Managing a tense working relationship
- Making the difficult decision to let someone go
This invisible cost affects your leadership, home life, and wellbeing.
The Math Doesn't Lie: Total Cost Calculation
Let's put real numbers to this:
The total? Easily $50,000-$150,000 for just three months with the wrong EA. And that doesn't include the costs of rehiring.
How to Avoid This Expensive Mistake
1. Get Crystal Clear on What You Actually Need
Before posting a job description, ask yourself:
- What are my biggest time drains?
- Which tasks do I consistently postpone?
- What communication inefficiencies exist in my workflow?
- Do I need someone who's technically skilled, people-oriented, or both?
- Am I looking for task completion or strategic partnership?
Pro Tip: Track your activities for a week. What could someone else handle? This becomes your EA's initial responsibility list.
2. Write a Job Description That Attracts Top Talent
Your job posting is your first filter. Make it work harder by:
- Being specific about required skills (not just "good communicator")
- Describing your working style honestly
- Listing concrete responsibilities, not vague expectations
- Including compensation range (yes, really—it saves everyone time)
- Highlighting growth opportunities and autonomy
Pro Tip: Ask current successful EAs to review your job description before posting.
3. Look Beyond the Resume
Resumes tell you about past experience, not future performance. Evaluate candidates with:
- Skills assessments (writing samples, scheduling exercises)
- Behavioral interview questions ("Tell me about a time when...")
- Realistic job previews or paid trial projects
- Reference checks that ask specific questions about work style
Pro Tip: Ask candidates to complete a small project related to the role (like organizing a mock calendar or drafting correspondence) to see their work quality.
4. Use This EA-Specific Interview Checklist
Great executive assistants share certain traits. Look for evidence of:
- Proactive problem-solving (ask for examples)
- Attention to detail (test this with assignments)
- Emotional intelligence (observe interactions with everyone they meet)
- Adaptability (ask about handling changing priorities)
- Discretion (discuss confidentiality scenarios)
- Communication skill (assess written and verbal clarity)
- Tech savvy (verify experience with relevant platforms)
- Organization systems (ask how they track multiple projects)
Red Flags to Watch For:
- Difficulty providing specific examples of impact
- Focusing solely on tasks rather than outcomes
- Inflexibility about work processes
- Complaining about previous executives
- Poor communication during the hiring process
5. Set Up for Success
Finding the right person is just the beginning. Prevent future problems by:
- Creating a structured onboarding plan
- Establishing clear communication protocols
- Setting expectations and priorities
- Scheduling regular feedback sessions
- Investing in relationship-building early
Pro Tip: Develop a 30-60-90 day plan with clear milestones and check-ins.
The Bottom Line
A great executive assistant is an investment that pays dividends in productivity, peace of mind, and professional growth. A bad hire is an expensive drain on resources, energy, and opportunity.
By understanding the true costs at stake and following a deliberate hiring process, you can find an assistant who becomes your greatest asset rather than your biggest headache.
Looking for qualified EA candidates without the usual hiring headaches? Post your job on the Find An Admin job board to connect directly with pre-vetted administrative professionals who understand the strategic value they bring to executive partnerships.