When I hired my first team member, I thought I was buying back time.
In reality, I was stepping into an entirely new job I hadn’t prepared for: leading.
If you’re a solo entrepreneur or small business owner trying to grow beyond yourself, you probably know the feeling. You’re stretched too thin, juggling too much, and thinking,
“If I could just find the right person to take a few things off my plate, everything would get easier.”
Sometimes it does. But often, it doesn’t—at least not at first.
Looking back, I can clearly see what I got wrong—and what I’d do differently today. This post is for the version of me who was just getting started building a team. Maybe it’ll help you avoid a few landmines on your own path.
I Waited Too Long to Hire
Like many founders, I wore every hat—strategy, operations, marketing, admin, even IT support.
But by the time I was finally ready to hire, I wasn’t just busy—I was overwhelmed and reactionary. That meant I hired reactively instead of strategically.
What I learned:
Hire before you’re desperate. When you wait too long, you hire to stop the bleeding—not to build the future.
Even one part-time hire can change the game if it’s planned well.
I Didn’t Define the Role Clearly Enough
My first hire was smart and capable. But I gave them a vague job description and expected them to “figure it out.”
They couldn’t—and that was on me.
What I should’ve done:
- Defined the exact outcomes I expected
- Documented key workflows
- Clarified ownership vs support tasks
Lesson learned:
If you can’t describe what “done” looks like, your new team member will drown—or default to you for every decision.
Clarity isn’t micromanagement. It’s leadership.
For help building out processes, start with this step-by-step SOP guide.
I Confused Delegation with Abdication
When I finally handed off tasks, I did it all at once—and then disappeared.
I thought I was being hands-off. I was actually being unavailable.
When things didn’t get done right, I took the work back. And that eroded trust on both sides.
What I learned:
Delegation isn’t just handing something off. It’s creating the structure, training, and feedback loops that allow someone else to succeed.
Now, I treat every delegation like a handoff, not a dump. I explain the “why,” confirm understanding, and check in with a simple status rhythm.
Learn how to delegate effectively without micromanaging in this practical guide.
I Didn’t Realize Leadership Requires a New Skill Set
I was good at my craft. That’s what built the business.
But leading people requires entirely different skills—communication, coaching, prioritization, and trust-building.
I had to learn:
- How to give feedback that improves outcomes
- How to set expectations and boundaries
- How to create shared goals and celebrate wins
And perhaps most importantly:
How to stop solving problems and start developing people.
That was the hardest shift—and the most rewarding.
For a deeper dive on this transition, read From Founder to Leader.
What I’d Tell My Past Self (And Maybe You)
If you’re a founder stepping into leadership for the first time, here’s my short list of hard-won advice:
- Hire slowly—but start early. Even 5–10 hours a week of the right help frees your mental bandwidth.
- Don’t hire “a helper.” Hire someone with a clear scope and ownership.
- Set expectations on day one. Document, explain, and confirm.
- Coach, don’t rescue. Let people struggle a bit. Growth happens in the stretch.
- You don’t have to get it perfect. You just have to get it clear, and be willing to adjust.
Leadership Is Learned. And It Starts With Letting Go.
Scaling your first team won’t feel natural. That’s normal.
You built this business by executing. But now your role is changing. You’re not just the builder anymore—you’re the architect.
And if you want your business to grow, you need a team who can build with you.
You don’t have to figure it out alone.
🤝 Let’s Build a Team That Works Without You Doing Everything
If you’re stuck in the weeds, struggling to delegate, or unsure how to scale your systems—I help business owners build the team, structure, and clarity they need to lead with confidence.
📅 Schedule a Free Discovery Call →
Or learn more about how I can support your growth on the Leadership Development Services page.