I remember how I approached some of my first hires.
I was excited, but I was also in a hurry.
The business was growing. There was more work than I could comfortably handle myself. I needed help, and finding someone felt like the obvious next step.
So I focused heavily on whether someone could do the work.
Did they have the experience?
Did they know the tools?
Could they handle the responsibilities?
Could they start quickly?
Those questions mattered.
But they weren’t enough.
Looking back, some of my earliest hiring mistakes had very little to do with choosing people who lacked skills. The bigger problem was that I was still learning what I actually needed from the people I brought into the business.
And I was learning it while already running the business.
One of my first mistakes was hiring for the role instead of hiring for how I wanted the business to operate.
That sounds like a small distinction, but it isn’t.
I would look at a job description and think, “I need someone who can do these things.”
So I searched for people who matched those things.
But I didn’t spend enough time asking what kind of person could actually operate well inside the environment I was building.
Someone can have the right experience and still require too much direction.
Someone can have the right technical skills and still communicate poorly.
Someone can be impressive on paper and still create friction once they’re actually inside the business.
I learned that the hard way.
I also underestimated how much clarity matters before hiring.
There were times when I brought someone in while I was still figuring out the role myself.
I knew I needed help.
I knew roughly what I wanted them to handle.
But the actual expectations weren’t fully defined.
So naturally, the person had questions.
And I didn’t always have clean answers.
That created a strange situation where I expected someone else to bring structure to something that I hadn’t structured properly myself.
That wasn’t really a hiring problem.
That was a leadership problem.
I just didn’t recognize it at the time.
Another mistake was assuming that a capable person would automatically know what “good” looked like.
This one took me a while to understand.
You can hire someone intelligent, experienced, and responsible, but if your standards aren’t clear, they’re still operating based on their own interpretation.
What does a good update look like?
How quickly should something be escalated?
When should someone make a decision independently?
What level of detail do I expect?
What should never be left unresolved?
These things seem obvious when they’re inside your head.
They aren’t obvious to someone else.
I learned that standards have to be communicated, not assumed.
I also made the mistake of trying to solve everything through hiring.
If I had too much on my plate, I thought I needed another person.
If a process felt inefficient, I thought another person could help.
If I was spending too much time on something, I thought I needed someone to take it over.
Sometimes that was true.
Sometimes the real problem was that the process itself was unnecessarily complicated.
Adding a person to a messy process doesn’t necessarily make it better.
Sometimes you just create another person who has to deal with the mess.
That realization changed how I think about hiring now.
Before I add someone, I try to understand whether the problem is actually capacity or whether the system needs to change.
I also hired too quickly when I felt pressure.
This is probably one of the biggest lessons I took from those early experiences.
When work starts piling up, waiting feels painful.
You have clients waiting. You have deadlines. You have things you need to get done.
So when a candidate seems good enough, there’s a temptation to move.
I did that.
And sometimes “good enough” turned into more work later.
More supervision.
More corrections.
More follow-ups.
More time spent managing a problem that I was originally trying to solve.
A temporary capacity problem is uncomfortable.
The wrong hire can become a permanent source of friction.
I understand that difference much better now.
Another mistake was focusing too much on what someone could do and not enough on how they thought.
Experience is useful.
Skills are useful.
But remote work taught me that how someone operates can matter just as much.
Can they figure things out?
Can they communicate when something goes wrong?
Can they take ownership without waiting for someone to tell them every next step?
Can they handle an incomplete situation without freezing?
Those questions became much more important to me over time.
Because when someone works remotely, you don’t get the benefit of constant physical visibility.
You need people who can carry responsibility without someone standing over them.
I also learned that being nice is not the same as being clear.
This one was uncomfortable for me.
There were times when I saw a problem with someone’s performance and waited too long to address it because I didn’t want to create tension.
I would tell myself they just needed more time.
Maybe things would improve.
Maybe I wasn’t explaining things well enough.
Sometimes they did improve.
Sometimes they didn’t.
But waiting too long rarely helped either side.
Clear feedback is kinder than prolonged ambiguity.
If something isn’t working, the person deserves to know.
And the business deserves a chance to correct it.
I also had to learn that not every person who is good is right for the business.
That sounds obvious now.
It wasn’t always obvious to me.
You can meet someone who is talented, professional, and genuinely good at what they do.
And still realize that the way they work doesn’t fit the environment you’re building.
Maybe they need more structure than you can provide.
Maybe they prefer constant collaboration while you need more independence.
Maybe their communication style creates unnecessary friction.
That doesn’t make either person bad.
It just means the fit isn’t right.
I stopped taking that so personally.
Perhaps the biggest mistake was thinking hiring would immediately give me freedom.
Sometimes it did.
But sometimes it created a different kind of responsibility.
Now I had another person’s work to think about.
Another person’s development.
Another person’s output.
Another person’s expectations.
Hiring doesn’t remove responsibility.
It changes where the responsibility sits.
And if you’re not prepared to manage that properly, you can end up with more work than you started with.
That realization made me much more intentional about who I bring into the business.
Over time, I started thinking about hiring less as filling empty seats and more as protecting the way the business operates.
Every person changes the system.
They affect communication.
They affect standards.
They affect speed.
They affect how much attention the founder needs to give the business.
That last one matters to me a lot now.
A strong hire should eventually reduce unnecessary involvement.
Not because they never need support, but because they become capable of carrying their part of the work.
That’s the kind of person I look for now.
I still make hiring mistakes.
I don’t think there’s a point where you suddenly become perfect at this.
There are still people I misread.
There are still situations where I move too quickly.
There are still roles that become clearer only after someone is already doing them.
That’s part of building.
But I don’t make the same mistakes in quite the same way anymore.
I’m more deliberate about defining the role.
I’m more careful about assessing how someone thinks.
I’m more direct about expectations.
And I’m much less willing to hire simply because I’m overwhelmed.
Looking back, my first hires taught me something I couldn’t have learned from a hiring book.
The point of hiring isn’t simply to get more hands.
It’s to build a business that can operate with greater clarity, consistency, and ownership.
That takes more thought than I originally gave it.
And honestly, I’m glad I learned that early.
The mistakes were expensive in time and energy.
But they changed the way I build teams now.
I don’t just ask, “Can this person do the job?”
I ask a much more important question.
What will the business feel like with this person inside it?
That question has saved me from making a lot of the same mistakes twice.