CEO Chatter: When Your Business Outgrows the Way You’ve Been Running It

By Francheska “Fancy” Felder

Bringing someone new onto your team is exciting. You start thinking about the work you can finally share, the ideas you'll have time to explore, and the things that might move a little faster with another person helping.

Then you realize you have to explain how everything works.

The things you do automatically now need instructions. The standards you carry in your head need to be communicated. And the person you brought in to help needs you to make time to help them, too.

That's a part of growing a business we don't always talk about. We talk about needing a team, but preparing someone to work alongside us is a responsibility in itself.

What's Clear to You May Need Explaining

Running SwagHer has given me a rhythm. I know what needs to accompany an article, how I want a caption to read, and what should happen after publication. But someone coming into the business doesn't arrive with all that information.

They need systems and processes they can follow.

For example, publishing an article involves more than putting words on the website. There's a promotional graphic, a caption, credits, and making sure the right people receive those materials. If I only say, "Get this article published," I may be leaving out several steps that feel obvious to me.

That means I have to slow down enough to explain the whole process.

I'm realizing that part of building a team means getting information out of my head and into something another person can actually use. A checklist, a written guide, or a recorded walkthrough gives them a place to start—and a place to return to when they forget a step.

It also gives me a chance to notice where the process itself needs work.

Patience Has to Be Part of the Plan

Of course, instructions don't eliminate every question or mistake.

People need room to learn. They may miss something, misunderstand a direction, or need to try again. As business owners, we have to make space for that without treating every mistake as proof that bringing someone on was a bad decision.

That takes patience, especially when you already have a full day.

You may have hired someone because you needed more time, but in the beginning, training them requires some of that time. You have to be available when they need assistance. Sometimes that means stopping what you're doing to answer a question or walking through a task you thought you had already explained.

I can see how easy it is to get frustrated. But I also have to ask myself: Did I explain this clearly? Did I show them an example? Have they had enough practice to do this confidently?

I want someone to feel comfortable asking for help before a small misunderstanding becomes a bigger problem. Creating that comfort is part of my job, too.

Give the Training Somewhere to Live

This is where AI and tools like Loom and Google Meet can be helpful.

AI can help me put a process into clearer language, organize my notes into steps, or develop a simple visual guide. I still need to review it and make sure it reflects how we actually work, but having help with the wording can make documenting everything feel more manageable.

Recorded training sessions are useful for the same reason. A new hire can refer back to a walkthrough instead of trying to remember every detail from one conversation.

Sometimes seeing a task done makes more sense than reading about it. Sometimes a short checklist is all someone needs. Having those resources available gives people more ways to learn and gives our conversations a stronger starting point.

The goal is to make the work easier to understand and repeat.

Growing Into the Next Version of the Business

I'm learning that bringing someone on board also asks me to grow.

I have to become clearer in my directions, more intentional about training, and more patient with the learning process. I have to make time now for the support I hope to have later.

There's excitement in that, even when it's demanding. Each process I document and each task someone learns, creates more room for the business to function beyond what I can personally handle in a day.

If your business is reaching this stage, it may be time to look at what you're asking someone to learn—and what you've given them to learn from.

I'm starting with the things I do so often that I barely think about them anymore. Those may be the very things someone else needs me to explain.