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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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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Culture Matters in Hiring But Clarity Comes First
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 doingIt 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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Why AI Will Make Argentina Shine Even More
There’s been a lot of talk about how AI is changing outsourcing. I’d like to share what I’m seeing. For years, outsourcing meant sending low-complexity tasks to the cheapest countries: – Data entry. – Basic support. – Repetitive work. The kind of labour that was time consuming, and could be done with little judgment. AI is wiping that model out and the countries that built their economies on routine, high-volume work are feeling it first: – Philippines, – India, and – Bangladesh. And then there are the less prominent outsourcing countries that I believe will now shine more than ever. What countries are those? There are tasks where AI can do 80% of the task, but the remaining 20% require something completely different: – reasoning, – communication, – clarity, and good judgment. And that is exactly where Argentina shines. When I first started working with Argentina, I didn’t know what to expect, and what I found was something AI can’t replace: – creativity, – sharp thinking, and a level of – cultural alignment that makes collaboration effortless. What used to be “outsourcing” has become something different: Smart outsourcing. People who supervise AI, not compete with it. People who can make decisions, solve problems, and communicate clearly and use AI to 10x their output. That’s why I am so excited about the future of Argentina because the people in Buenos Aires, Córdoba, and Rosario are not “cheap talent.” They’re exceptional talent in a world where exceptional matters more than ever. AI is changing outsourcing and as it does that, it’s also revealing something important: The future belongs to countries with judgment, adaptability, and talent density. And Argentina is one of the strongest examples I’ve ever seen.
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