Hiring your first team member is a huge milestone — especially if you’ve been doing everything solo. But delegation isn’t a magical cure for chaos. In fact, it can make the chaos louder.

This week’s story is from a bootstrapped founder who learned that leadership isn’t just about giving up tasks — it’s about clarity, context, and learning how to manage someone when you’re barely managing yourself.

I brought on a part-time ops generalist.

I was drowning in admin, customer support, internal tools — and I thought, “If I can just get this stuff off my plate, I’ll have time to actually build the product.”

Spoiler: I ended up busier than before.

Because I didn’t really delegate, I dumped.

No onboarding. No process docs. No clear outcomes.

I gave her my chaos, and she didn’t know what to do with it.

I kept thinking, “Why isn’t she just taking initiative?”

She kept thinking, “What exactly am I responsible for?”

One afternoon she Slacked me:

“Hey, I just want to check — is this what you meant by revamping the onboarding email flow? Or should I be doing something else?”

It hit me: she wasn’t asking for approval. She was asking for direction.

I had brought someone in to give me breathing room. But I was making her operate in a vacuum.

That night, I spent two hours writing a 1-pager.

Not a Notion wiki. Not a task list.

Just:

She messaged back the next day:

“Thank you. This helps a lot. I’ve been wanting to contribute more, but I wasn’t sure where the edges were.”

Things got better immediately.

I check in with her twice a week.

Not just to assign tasks — to talk about context, blockers, what we’re actually aiming for.

She’s still part-time. But output-wise, it feels like I unlocked a second founder.

I also realized I was hiring for relief, not readiness.

The next person I hire, I’ll make sure I’m actually ready for them — not just desperate for help.

Delegating without direction isn’t leadership. It’s offloading guilt.