How I Failed a New Hire (And Fixed It at 2AM)

In this candid and behind-the-scenes post, I share a hard lesson learned as a leader: how I dropped the ball with a new team member—and what it took to fix it. From poor onboarding to unclear expectations, I walk through the specific mistakes I made that left my new hire overwhelmed and under-supported. The turning point? A 2AM wake-up call—literally and figuratively—that pushed me to course-correct fast. I break down the exact steps I took to rebuild trust, reset expectations, and create a better onboarding process so no one else has to feel the way that hire did. Whether you’re growing a team or just want to be a better leader, this post is packed with takeaways you can use to avoid the same pitfalls.

Recently, we brought on a new team member.

Bright.
Eager.
Ready to go.

And as I started walking them through our SOPs, something happened...

I got that feeling in my gut.You know the one.

Where you realize you’ve been preaching clarity but living in chaos.

Nothing made sense.

The docs were everywhere.

No straight lines.
No KPIs.
No metrics.

Just... fluff.

And suddenly it hit me:I was the problem.

I’ve been running with the same crew for years.

They know my shorthand.

They read my mind - well at least Ale Diaz can.

But this new hire?

They didn’t stand a chance.

And here’s the part that hurt:I thought I was leading.

In reality, I’d just gotten comfortable.

Rusty.
Lazy.

Sure, I gave them a detailed onboarding.

Sure, I talked about the role.

But I didn’t give them a scoreboard.

The scoreboard I preach to clients.

I wasn't doing myself in this new role.

We have KPIs for every other position.

Every other department.

But this role? Nada.

No black and white indicators.
No clear outcomes.

And that’s when I sat down…

Looked in the mirror…

And whispered the hardest truth a leader can say:

"This is on me."

I can’t expect someone to just "figure it out."

That’s not leadership.
That’s abdication.

So I did what every real leader eventually has to do:

I rolled up my sleeves.

I opened the old systems folder from seven years ago.

And I sat down until 2am… rebuilding everything.

Seven. Hours. Straight.

Sweating out the fog.

Translating what was in my head into something trainable.

Because here’s the deal:

Nothing great lives in your head.

If it can’t be taught, it can’t scale.

And if it can’t scale, it will die with you.

Now—I want to give you something.

A framework.It cost me and Neil Morton $15,000 when I first started this business.

And I’ll tell you right now, it was worth ten times that.

Whenever you feel stuck…

Whenever your VA or new team member isn’t "getting it"…

Use this:The 5-Part SOP Framework:

What – What is the task or role?

How – Step-by-step, how do we do it?

Why – Why does this matter to the business - and what are the ramifications of not doing it this way?

The Impact – What does success look like? What’s the result?

Action Summary That Drives Results – What do we expect done and by when?

This isn't fluff.

This is the blueprint for clarity, accountability, and scale.

Because like I said:

We are the leaders.

And the direction of our team?

It lives and dies with us.

So if you’ve got someone underperforming…

Before you point the finger—check the mirror.

You just might find the bottleneck staring back.

Still with me?

Good.

Now go fix it.

Because leaders don’t wait to be saved.

They set the standard.

Cody

Founder of Sheridan St.

Host of The Re Agent Podcast

Ready to meet the Sharidan St. Team?

What could be better than a knowledgeable, lively group of people who have a passion for what they do and are good at it, too? We have put together an extraordinary team of innovative, committed members who put client success first.