Uploaded August 2026 | Updated September 2026, 2 weeks ago
I’ve made some horrible hires.
Not “small learning lesson” horrible.
More like, “Wow, I somehow paid money to make this more confusing and time consuming” horrible.
And looking back, I don’t think the issue was always the person.
A lot of the time, I was hiring out of pain.
I was busy.
I was overwhelmed.
There were gaps in the business.
And my solution was basically:
“I just need another set of hands.”
Which sounds reasonable.
Until those hands enter a business with no clear role, no systems, no defined outcome, and no real way to measure success.
Then everyone is frustrated.
They’re frustrated because they don’t know what winning looks like.
You’re frustrated because they’re not magically fixing the mess.
And now it’s easy to say, “Hiring doesn’t work.”
But sometimes the uncomfortable truth is:
The hire didn’t fail the business.
The system failed the hire.
That one stings a little.
A good person still needs direction.
They need to know where things live.
What matters most.
Who owns what.
How decisions get made.
What a good job looks like.
Hiring doesn’t fix a big ol' mess.
It exposes it.
And I am certainly still learning this, but before I ask, “Who do I need to hire?”
I try to ask:
“What system am I bringing them into?”
--
Comment "pod" and I'll send you my podcast that covers topics like this every Friday.
I’ve made some horrible hires.
Not “small learning lesson” horrible.
More like, “Wow, I somehow paid money to make this more confusing and time consuming” horrible.
And looking back, I don’t think the issue was always the person.
A lot of the time, I was hiring out of pain.
I was busy.
I was overwhelmed.
There were gaps in the business.
And my solution was basically:
“I just need another set of hands.”
Which sounds reasonable.
Until those hands enter a business with no clear role, no systems, no defined outcome, and no real way to measure success.
Then everyone is frustrated.
They’re frustrated because they don’t know what winning looks like.
You’re frustrated because they’re not magically fixing the mess.
And now it’s easy to say, “Hiring doesn’t work.”
But sometimes the uncomfortable truth is:
The hire didn’t fail the business.
The system failed the hire.
That one stings a little.
A good person still needs direction.
They need to know where things live.
What matters most.
Who owns what.
How decisions get made.
What a good job looks like.
Hiring doesn’t fix a big ol' mess.
It exposes it.
And I am certainly still learning this, but before I ask, “Who do I need to hire?”
I try to ask:
“What system am I bringing them into?”
--
Comment "pod" and I'll send you my podcast that covers topics like this every Friday.
