You hired help to free up your afternoons. Now you’re paying another person, answering more questions, and still doing everything yourself.

Sound familiar?

You run a business. The client work is growing. Your to-do list is getting longer. So you finally hire an assistant.

But when an important task comes up, you think:

“It’ll take me 30 minutes to explain this. I can do it myself in 10.”

So you do it yourself.

Your assistant waits for instructions. You get frustrated because they don’t show initiative. Meanwhile, payroll goes up, but you haven’t gained a single free afternoon.

Here’s the uncomfortable question: Is your assistant failing to take initiative, or are you having trouble handing over responsibility?

In a recent BestieFinder Office Hours conversation, Dr. Lisa Richardson and Coach Nyala Allen explored why this happens—and how understanding your motivational Gifts can help you get past what they called “the trust hump.”

Hiring an Assistant Doesn’t Automatically Remove Work From Your Plate

Hiring help is one step. Learning to work with that person is another.

When you’ve built a business yourself, you know how everything works. You remember which clients need extra attention, where the files are stored, and how to fix problems before anyone notices them.

That knowledge is valuable.

But if it stays in your head, your assistant can’t use it.

You may have even written standard operating procedures (SOPs). The problem? They’re sitting in a Google Drive folder nobody has opened since onboarding.

Coach Nyala pointed out that business owners often hire someone because the work is piling up, then struggle to give that person what they need to succeed.

The assistant gets a job title but not enough information, practice, or authority to do the job independently.

And the owner keeps carrying the workload.

Your Motivational Gifts May Be Part of the Pattern

At BestieFinder, we use Gift Intelligence to understand how our motivational Gifts influence the way we work, communicate, make decisions, and respond to other people.

A Gift is a strength. But the same characteristics that help you succeed can create challenges when you rely on them without noticing how they affect others.

In this Office Hours discussion, Coach Nyala explored four Gifts that may influence the way an entrepreneur works with an assistant.

The Teacher: “I Know Exactly How This Should Be Done.”

A business owner with a strong Teacher Gift may have a clear picture of how a task should be completed.

They know the details. They’ve thought through the steps. They may even have the process documented.

But knowing something well isn’t the same as teaching someone else to do it.

A Teacher may explain a task once and expect the assistant to remember every detail. When the assistant needs another explanation, the owner may become impatient.

And when time is tight, doing the task personally can feel easier than teaching it again.

The challenge: Give someone else enough instruction, practice, and room to learn—even when repeating yourself feels inefficient.

The Administrator: “I Need These Tasks Off My Plate.”

The Administrator Gift can help an entrepreneur organize work, see what needs to happen, and move tasks toward completion.

But recognizing what needs to be done isn’t enough if every decision still runs through the business owner.

An assistant needs to know which tasks they own, what a finished result looks like, and when to ask for help.

The challenge: Turn a list of tasks into responsibilities someone else can actually manage.

The Exhorter: “I Want to Help You Succeed.”

The Exhorter Gift brings encouragement and a desire to help others grow.

That can be useful when training a new assistant.

Rather than expecting someone to work exactly as you do, you can help them build confidence, recognize their progress, and take on more responsibility over time.

The opportunity: Encourage the person you’ve hired to develop their own strengths instead of becoming a copy of you.

The Compassion Gift: “There May Be Another Way to Do This.”

Coach Nyala also discussed how a person with the Compassion Gift may bring sensitivity and creativity to their work.

An assistant with different motivational Gifts may approach a task differently than the owner would.

Different doesn’t automatically mean wrong.

The opportunity: Pay attention to what your assistant does well and give them appropriate room to use those abilities.

The goal isn’t to assign a Gift to someone based on one behavior. It’s to become more aware of your own tendencies and curious about the strengths another person brings.

Are You the Single Point of Failure in Your Business?

Dr. Lisa brought an important operations concept into the conversation: key person risk.

That’s what happens when one person holds so much essential knowledge that the business struggles to function without them.

Maybe you’re the only one who knows:

• How to fix a recurring software problem.
• Where a client’s important documents are stored.
• What to do when an order goes wrong.
• How to complete a task that happens every Friday.
• Which decisions can be made without your approval.

If you’re the only person who can handle those things, taking a vacation becomes difficult.

Getting sick becomes a business problem.

And growing the company means adding more work to your own calendar.

As Dr. Lisa explained, you can’t build a growing organization if you’re its single point of failure.

That doesn’t mean handing everything over overnight.

It means asking whether the way you’re working today will still work when your business gets bigger.

The Hidden Cost of “It’s Faster If I Do It Myself”

Imagine a task takes you 10 minutes to complete.

Teaching your assistant might take 30 minutes the first time.

If you only look at today’s calendar, doing it yourself seems like the better choice.

But what if that task comes up twice a week?

Over 12 weeks, that’s 24 times you’ve had to stop what you’re doing and handle it.

At 10 minutes each, you’ve spent four hours on that one recurring task.

A 30-minute training session may not solve everything. Your assistant may need practice, follow-up, and feedback.

But the time you spend teaching today can reduce how often you’re interrupted tomorrow.

That’s why Dr. Lisa encouraged entrepreneurs to give themselves more time when training someone.

Build in room to explain. Expect to repeat yourself. Let the assistant practice.

Training takes time. So does doing the same task forever.

AI Can Help Document Your Work. It Can’t Build Trust for You.

One interesting point from the discussion was the temptation to use AI to duplicate yourself.

AI tools can help you organize instructions, create checklists, and turn recorded explanations into draft procedures.

That can be useful, especially when you’re trying to get processes out of your head.

But Coach Nyala raised a warning: you can still be the bottleneck even when you’re using AI.

If every task, instruction, and decision still has to come from you, you’ve changed the tools without changing the way work gets done.

A checklist doesn’t help much if your assistant isn’t allowed to use it without your permission.

And a beautifully written procedure won’t free your time if you keep taking the task back.

The bigger goal is to help another person take appropriate ownership of the work.

Three Steps to Get Over the Trust Hump

You don’t have to hand your assistant your most important client account tomorrow.

Start smaller.

1. Choose One Recurring Task

Pick something you’ve done at least twice recently that your assistant could reasonably learn.

It might be scheduling client appointments, preparing a weekly report, organizing files, or sending routine follow-up messages.

Don’t start with a task that requires decisions your assistant hasn’t been trained or authorized to make.

2. Explain the Result, Not Just the Steps

Tell your assistant:

• What needs to be finished.
• What a successful result looks like.
• When it’s due.
• Which decisions they can make independently.
• When they should come back to you with a question.

If you already have an SOP, review it together instead of assuming they’ve read and understood it.

Then ask them to explain the task back to you in their own words.

You’ll quickly discover whether your instructions were clear.

3. Give Feedback Without Taking the Task Back

Your assistant may not complete the work exactly the way you would.

Before stepping in, ask yourself:

“Is the result actually wrong, or is the process just different from mine?”

If something needs correcting, explain what needs to change and why.

If the result meets the standard, let it stand.

That’s how someone gains the experience to work with less supervision.

And that’s how you begin getting time back.

What If Your Assistant Really Does Lack Initiative?

Sometimes the problem isn’t just the business owner’s reluctance to delegate.

An assistant may need more training, clearer expectations, or a different role. There may also be a genuine performance issue.

Gift Intelligence doesn’t mean ignoring those possibilities.

It means examining your own contribution before deciding you’ve found the whole problem.

Ask yourself:

“Have I given this person the information, authority, and opportunity to show initiative?”

If the answer is no, start there.

If the answer is yes, you have a clearer basis for a conversation about performance.

The Real Goal Isn’t to Hire Another You

One of the most memorable moments in Office Hours came when Dr. Lisa acknowledged what many entrepreneurs secretly want:

Someone who thinks exactly like they do.

Someone who knows the business, anticipates every need, and completes every task without explanation.

But as Coach Nyala pointed out, growing a business requires learning to trust people who bring different Gifts to the table.

Your assistant doesn’t need to become you.

They need to understand their responsibilities, have the tools to do the work, and know when they can make decisions.

And you need to recognize when your own habits are making that harder.

You hired help because you couldn’t keep doing everything yourself. Don’t let the way you’ve always worked prevent that help from helping.

Ready to Work Through Your Own Leadership Patterns?

It’s easy to recognize a delegation problem in someone else’s business. It’s harder to spot the habits that keep you doing the same thing in yours.

Business Besties gives entrepreneurs a place to work through challenges like trust, delegation, decision-making, and working with people whose Gifts differ from their own.

Over 12 months, members participate in 12 small-group coaching sessions and 12 private coaching sessions, with opportunities to examine their habits, set goals, and practice different approaches.

If you’re ready to stop carrying every decision yourself, tell us a little about yourself and schedule a time to talk.

Watch the Office Hours Conversation

Watch Dr. Lisa Richardson and Coach Nyala Allen discuss the assistant scenario, the Teacher Gift, key person risk, and how entrepreneurs can get over the trust hump.