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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Hiring Doesn’t Fix Chaos, It Amplifies It
Before you hire, ask yourself this: am I ready for a new team member?
A lot of founders are in pain. Overwhelmed. Buried in tasks. Stretched too thin and running on fumes.
So they do what feels logical: they hire someone. Maybe a VA, maybe an operations manager, someone to finally take things off their plate.
And here’s what I’ve seen again and again: if the foundation isn’t ready, the hire won’t save you. Most people don’t come in and build systems for you. They execute what’s already there.
So before you hire, ask yourself:
• Are your workflows documented?
• Do you know what success looks like in this role?
• Is there one central place for tasks and communication?
• Are you available to onboard and give context for the first two to four weeks?If the answer is no, even the best hire will feel lost—and so will you.
Hiring doesn’t fix chaos. It amplifies it.
And yet, this happens all the time: founders hiring to feel productive instead of getting prepared, adding people instead of fixing systems, confusing motion for progress.
Hiring isn’t about making you feel less lonely in your business. It’s about making it run better. And that only works when there’s clarity.
So the next time you’re tempted to post that job listing, pause and ask yourself: are my systems ready?
The right hire can be transformational, but only when the business is ready to receive them.
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Entrepreneurship Isn’t Rowing Harder: It’s Knowing When to Hand Over the Oars
Lake Bled looked effortless. But I bled sweat and tears.
This week in Slovakia, I visited Lake Bled with a friend. People were gliding across the water, smiling, and rowing with one hand like they were born for it. I told my friend, “Let’s rent a boat. I’ll row, I’ve got this.” The fact was, I’d never used a rowboat before—but how hard could it be?
Turns out, very hard. The oars were stiff, the boat barely moved, and I kept zigzagging across the water like a drunk duck. Halfway to the island, my arms were already aching. After what felt like an eternity—but really was only twenty minutes—we landed on the island. I was ready for a break.
But the break didn’t last long, because we had to return the boat. My friend offered to row, and I heard myself say, “No thanks, I’ve got this.” Somewhere, deep in my brain, I believed that accepting help made me weak.
I grew up with a strong mother who carried her own suitcases and fixed things in the house herself rather than asking for help. That mindset shaped me. So I rowed. And rowed. And rowed. A sweaty mess, water running down my back, trying to prove something no one was asking me to prove.
That’s when I realized: this is how I used to lead Gorilla Stationers in the beginning. Doing it all. First in, last out. Trying to earn respect by powering through everything alone. Believing that, as the boss, I had to look strong and prove it was my business.
It took me a decade to understand: entrepreneurship isn’t rowing harder—it’s knowing when to hand over the oars while still owning the journey.
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Why Reducing Uncertainty Is a Leadership Skill
One of the most underestimated leadership skills is the ability to reduce uncertainty.
Not by controlling everything.
Not by having all the answers.But by creating a sense of direction people can trust.
Most teams don’t stall because they’re lazy or unmotivated. They stall because too much feels unclear at once. Priorities shift. Decisions feel inconsistent. Context is missing.
So people slow down.
They double check.
They wait for permission.
They hesitate instead of acting.What looks like a performance issue is often an orientation issue.
Good leadership gives people a stable reference point.
What matters right now.
How choices will be made.
What success looks like in this moment.That clarity doesn’t need to be perfect. It just needs to be steady.
When leaders are consistent, teams stop bracing and start building.
When people feel grounded, they take smarter risks.
When direction is clear, momentum returns.If your team feels tense or stuck, resist the urge to push harder.
Look instead at what might feel uncertain from their side.Leadership isn’t about accelerating people.
It’s about giving them solid ground to move from.———————-
I help founders find and manage the right remote talent so their businesses can grow without burning out their teams, or themselves.
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