How to Hire Someone You Don’t Fully Know (Without Ruining the Relationship)
Hiring is always a risk.
Hiring someone you already have a personal relationship with is an even bigger one.
Recently while attending the CoolVu franchise dealer conference, Kado asked me a direct question:
“When you hired me, what was going through your head from a risk assessment standpoint?”
It’s a fair question.
Because on paper, it looked risky.
We had a good relationship.
We’d worked together before.
We’d seen each other at events.
There was mutual respect.
But we didn’t actually know each other in a day-to-day business setting.
And he was about to shut down his existing business to come onboard full-time into a role that wasn’t even fully defined yet.
That’s not a small move.
So here’s how I thought about it.
The real risk wasn’t business. It was personal.
Most people assume the biggest risk in hiring is financial.
It isn’t.
The biggest risk is relational.
If you hire someone you’re friends with and it goes badly, you don’t just lose money.
You lose the relationship.
That mattered to me more than the paycheck.
I didn’t want to create a situation where six months in, things weren’t clicking and now there’s tension, resentment, or awkwardness.
So the first thing I asked myself wasn’t:
“Will this make money?”
It was:
“How do I structure this so it doesn’t damage the relationship?”
The mistake most owners make: “Let’s see how it goes.”
When someone is making a big move — like shutting down a business to join you — the worst thing you can say is:
“Let’s see how it goes.”
That creates pressure immediately.
Pressure on them.
Pressure on you.
Pressure on performance.
And pressure kills performance.
If someone knows they can be cut loose in six months, they don’t operate with clarity. They operate with fear.
And fear distorts behavior.
So instead of “let’s see how it goes,” I proposed something different.
The three-year commitment
I told him:
“This is a three-year deal.”
Not six months.
Not a trial period.
Not “we’ll revisit.”
Three years.
Here’s why.
He was making a major sacrifice to join.
He was stepping into uncertainty.
The role wasn’t fully structured yet.
I knew the first month would feel chaotic.
I knew the first few months might feel uncomfortable.
I knew performance might dip early because of that pressure.
So I removed the clock.
Three years gives space.
Space to learn.
Space to adapt.
Space to build.
Space to make mistakes without panic.
That changes everything.
The private question I asked myself
Before I committed to that term, I asked myself something simple and honest:
“If this went absolutely horribly… could I afford to pay him for three years anyway?”
Not emotionally.
Not optimistically.
Literally.
Could I write that check for three years even if the outcome was terrible?
If the answer had been no, I wouldn’t have done it.
But the answer was yes.
That meant I wasn’t hiring reactively.
I was committing intentionally.
That clarity matters.
Removing pressure improves performance
I made the three-year commitment transparent.
Not as a trap.
Not as leverage.
Not as control.
But as clarity.
“You’re here for three years.”
That means:
You don’t have to worry about month three.
You don’t have to worry about month six.
You don’t have to wonder if you’re getting fired next quarter.
Now the focus shifts.
Instead of:
“Am I safe?”
It becomes:
“How do we build something meaningful over three years?”
That’s a completely different energy.
And energy drives execution.
Hiring isn’t about capability alone
This only works if the person is capable.
If someone is lazy or incompetent, no contract fixes that.
But capability wasn’t my concern.
I already knew he was capable.
The real question was structure.
How do we structure the risk so both sides can operate clearly?
Most owners try to reduce risk by shortening commitment.
In many cases, that increases risk.
If you’re unsure, add a term
A lot of hiring mistakes happen because the expectations are vague.
“Let’s try it.”
“We’ll see.”
“We’ll figure it out.”
That creates ambiguity.
Ambiguity creates insecurity.
Insecurity creates bad decisions.
If you’re uncertain about a hire, instead of hiring “forever” or pretending it’s casual, try this:
Put a term on it.
One year.
Two years.
Three years.
Not as a threat.
As clarity.
It defines the runway.
It tells both parties:
“This is the window. Let’s build something inside it.”
That makes decisions cleaner.
Risk is real. Structure reduces chaos.
Hiring always involves risk.
You cannot eliminate it.
But you can structure it.
In this case, the structure was:
A defined term
Financial commitment I could actually afford
Transparency about expectations
Removing short-term pressure
That made the risk manageable.
Not safe.
Not guaranteed.
Manageable.
And in business, that’s usually enough.
The takeaway
If you’re hiring someone:
Don’t default to “let’s see how it goes.”
Don’t hire out of emotion.
Don’t commit to something you can’t afford.
Instead, ask:
What’s the real risk here — money or relationship?
Can I afford this commitment even if it underperforms?
How do I remove unnecessary pressure from the first 6 months?
Would a defined term create clarity for both sides?
Hiring is not about avoiding risk.
It’s about understanding it and structuring it intentionally.
That’s what makes it sustainable.