An Executive Assistant with eight years of experience at a Fortune 500 company applied for a role with one of our clients.
Resume was flawless. References were excellent. Interview was polished. On paper, this was the best candidate in the pool by a mile.
Hired.
Started.
Failed.
It didn’t work.
Within six weeks, both sides threw in the towel.
Here’s what happened:
The EA came from a 1,000-person finance company. Structured hierarchy. Formal communication. Clear processes for everything. Every task had a playbook. Every decision had a chain of approval.
The client was a 30-person startup. Priorities shifted every 48 hours. Half the tools were held together with duct tape. The founder made decisions on the fly and expected everyone to keep up.
The EA wasn’t bad. She was trained for a completely different environment.
She waited for processes that didn’t exist. She looked for approval chains that weren’t there. She drafted formal memos when the founder wanted a 2-line Slack message. She was uncomfortable making decisions without explicit permission — because in her previous world, that’s how you got fired.
In the new world…that was just the norm. Expected, even.
And the founder was confused. “She has 8 years of experience. Why can’t she figure this out?”
Because experience isn’t transferable across environments the way people think it is.
Take note:
An EA who thrived in corporate structure can be awful in startup chaos. And an EA who thrives in startup chaos might feel sloppy and undisciplined in a corporate setting.
Neither one is wrong. They’re just…wired for different worlds.
When you’re hiring for this role, stop matching the resume to the job description. Match the person to the environment.
This example can apply to any role across any type of company.
The trick to all of this is to just make it clear from the start. Spell it out. Make sure all candidates know the score. It may still be that the right person doesn’t have the experience. But you need to prepare them.
Nobody likes being handed a live grenade 2 seconds before it goes off.
For help figuring out these problems and getting the role right from the get-go, click here to book a free discovery call with the HireUA team:
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