If You’re Firing Your New Assistant in Less Than Six Months, You’re Burning Cash
Six months. That’s how long the assistant lasted.
She read the books the executive recommended before day one. She showed up in-office every single day — the only employee required to be there. She tried to get time with the executive to understand the business, the systems, the team.
But by week two, they still hadn’t had a real meeting.
By week four, she still didn’t have access to key systems.
There were no consistent weekly check-ins. No written expectations. No structured onboarding.
No partnership.
Within six months, she was called into a room and told: “This isn’t working.”
The executive’s conclusion? “She wasn’t effective.”
Let’s talk about what that decision actually cost.
The Financial Reality of a 6-Month Firing
Let’s use conservative numbers. Say you hired an Executive Assistant at $85,000.
Six months of salary: $42,500.
Gone.
My recruiting fee is 18%. Most firms charge 25–35%.
At $85,000, that’s: $15,300
Gone.
Add payroll taxes and benefits — conservatively 20%: Roughly $8,500
Gone.
Now we’re at over $66,000 — and we haven’t even touched productivity yet.
How many hours did you spend:
Reviewing my candidates’ details
Interviewing candidates
Debriefing with colleagues
“Onboarding”
Re-interviewing when it failed
Even 30–40 hours is conservative.
If your time is worth $400–$800 an hour, that’s another $12,000–$32,000 in executive opportunity cost.
Now we’re well over $80,000–$100,000 burned.
And that’s before we calculate:
Lost momentum
Team disruption
Emotional drag
Reputation damage in the EA market
The cost of starting over
HR research consistently estimates replacing an employee costs 1.5–2x their annual salary when you account for ramp time and lost productivity.
At $85,000, that’s potentially $127,000–$170,000.
Because you didn’t invest properly in the first six months.
The Part Executives Miss
Your assistant isn’t learning the job.
They’re learning you.
Your communication style.
Your decision patterns.
Your priorities. Your goals.
What you say versus what you actually mean.
How you handle pressure.
What matters. What doesn’t.
When did you really know your partner or spouse well enough to make big decisions on their behalf? Was it 30 days in?
Did they fully understand you at 90 days?
Of course not.
Why would you expect an assistant, whose job is to anticipate your needs, to understand you deeply enough to act autonomously after 4 or 6 weeks?
That level of anticipation doesn’t come from osmosis. It comes from time, conversation, observation, and feedback.
If you’re not spending time with your assistant in the first 30–60 days, you are delaying that ramp.
And then you’re disappointed they’re not “one step ahead.”
Why Assistants Are Getting Fired in Six Months
You’re Not Investing in the Relationship
Some executives subconsciously believe assistants plug into the wall and turn on like lamps.
They don’t.
Assistants plug into you.
If you are not providing:
Context
Access
Time
Feedback
Clarity
They cannot operate at full capacity.
If everything lives in your head and you won’t sit down and transfer it, you are forcing them to guess, and then penalizing them when they guess wrong.
If you are not consistently meeting with your assistant in the first 30–60 days, this will fail.
Not “might.”
Will.
You Expect Year-One Autonomy in One-Month’s Time
There is a stage in every strong executive–assistant partnership where the assistant anticipates, filters, and thinks ahead.
That stage is powerful.
It is also earned.
It usually doesn’t show up at day 30.
It often doesn’t fully show up by day 90.
Sometimes it takes six to nine months of consistent interaction.
If you expect intuition without investment, you are expecting magic — not professionalism.
Stop expecting perfection at day 30.
Stop expecting anticipation at day 45.
Stop expecting “mind-reading” at day 60.
You Confuse Discomfort with Incompetence
When a new assistant asks:
Why are we doing it this way?
Can we streamline this?
What’s the priority here?
That’s not resistance.
That’s engagement.
But if you’re not used to being challenged, that discomfort can feel like misalignment.
So you conclude: “Not a fit,” and you start over with the same structural issues.
You Never Defined What “Great” Looks Like
I often ask executives who have fired an assistant within six months:
What did great look like at 30 days?
At 90?
At six months?
Very few can answer with more than just “she needed to be proactive and really start cleaning things up.”
If success was never defined, how exactly did you measure failure?
The Hard Line
You’re not firing incompetence…
You’re firing a system you didn’t build correctly…
And you’re paying six figures — directly or indirectly — to rebuild it.
If this is your second or third assistant in two years, pause before posting another job description.
The problem may not be the talent pool.
It may be how you lead in the first six months.
If You Want to Stop Burning Cash
Schedule a non-negotiable weekly 1:1 for the first six months.
Grant access within 48 hours.
Define success at 30, 90, and 180 days — in writing.
Stop expecting year-one intuition in month one.
Decide whether you want compliance or partnership.
Partnership requires investment.
If you want a strategic partner, be one.
P.S. I can help with that. Learn more about my recruiting and executive coaching services here.