Hiring feels hard. We chase culture fit. We obsess over “value alignment.” And yes, they matter. But if I’m honest, I’d bet that 95% of failed hires come down to one boring thing: bad, or nonexistent, job descriptions especially in small companies.
I’ve seen it in my own businesses, and I’ve seen it when friends ask me why their new hire isn’t working out. If the role itself isn’t clear, no amount of culture magic will fix it.
Over the years, here’s what I’ve learned makes a job description actually work:
1️⃣ Purpose – why the role exists at all
2️⃣ Reporting – who they answer to
3️⃣ Company intro – why someone should be excited to join
4️⃣ Objectives – the real outcomes you expect
5️⃣ Day-to-day duties – what they’ll actually be doing
It sounds simple, but most job descriptions I see are either vague (“we just need a VA”) or contradictory (“do our marketing and fix IT”). No wonder the hires don’t stick.
So before you go looking for “the perfect cultural fit,” ask yourself: would a smart, motivated person even know how to succeed in this role? That clarity is where good hiring really starts.
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Don’t Hire a Captain If the Ship Isn’t Built
“Should I hire an operations manager?”
Maybe not.
The inbox is overflowing, deadlines are constant, and you’re still the one catching the details. The instinct is to think, “If I just find the right person, they’ll clean this up.”
I used to believe an operations manager would save me. Until the third one quit.
Here’s what I’ve seen inside my own company, Gorilla Stationers, and in many others: operations and building are two separate things. Most operations professionals are great at optimizing, but not at building systems from scratch.
If intake happens five different ways, case handoff depends on memory, and no one’s really sure who owns what, most operations managers will struggle. They first need to understand what’s going on, then build a system, and only then can they run it. When they realize it’s not about running but about building, they often leave.
So before hiring someone to run the ship, ask yourself: is the ship built?
And by built, I mean:
• Standardized onboarding
• Clear case handoff
• A follow-up system that doesn’t rely on you at 10 p.m.These are the things we as founders have to create first. In my experience, maybe one in a hundred operations managers is both good at building and happy to do it.
They’re two different jobs.
Don’t hire an ops lead to figure it out. Build the system first, then hand over the keys.
Because even the best captain can’t steer a ship that’s still under construction.
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The Identity Shift No One Talks About
The Identity Shift No One Talks About
There’s a moment every founder hits that no one prepares you for.
It’s when the business is finally “working”
but you feel more tired than ever.
Revenue is up.
The team is growing.
Opportunities keep coming.
And yet, something feels off.
That moment usually isn’t about workload.
It’s about identity.
You’re still operating like the person who had to do everything.
Even though the business no longer requires that version of you.
So you stay involved where you shouldn’t.
You hold onto decisions that don’t need you.
You solve problems that are no longer yours to solve.
Growth quietly asks you to let go of an old role
before it hands you a new one.
Most burnout at this stage doesn’t come from the business.
It comes from refusing to evolve with it.
The hardest part of scaling isn’t building systems or hiring people.
It’s redefining who you need to be now.
If your business has outgrown the version of you that built it
that’s not a failure.
It’s an invitation.
And the sooner you accept it
the lighter everything else becomes.
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