Delegation Problems? Fix These 5 Mistakes Small Business Owners Make

Ever feel like delegation is supposed to make your life easier, but instead, it just adds to your workload?

You know you need to delegate if you’re going to grow your business and actually have time to breathe. But every time you try, it feels like:

• More work instead of less.
• Like you have to micromanage every little thing.
• Or worse, like “there’s just not good people out there.”

Here’s the thing: delegation isn’t just about handing over tasks. It’s a skill - and like any skill, you have to learn it, practice it, and refine it.

Otherwise, you’ll keep running in circles, stuck between doing everything yourself and wondering why your VA isn’t magically reading your mind.

And yes, delegation can go wrong. A lot.

• Maybe you’ve handed something over and it came back half-done - or done completely wrong.
• Maybe you feel like you’re micromanaging because your VA keeps asking endless questions.
• Or maybe you’ve hired help, but somehow you’re still drowning in work.

Here’s what I know: if delegation isn’t working, the first place to look is at how you’re delegating.

• What part have you played in things not getting done properly?
• Have you actually given clear instructions? Or any instructions?
• Does your team know what decisions they can make without checking in with you? Or are you still the bottleneck?

In this post, I’ll walk you through the first five of the ten biggest delegation mistakes I see business owners make, why they happen, and - most importantly - how to fix them so you can finally start handing things over properly.

Then in Part 2 (coming next week!), we’ll cover five more mistakes - including some of the biggest delegation traps that no one talks about.

One more thing: This isn’t a blame game. If you’re making some (or all) of these mistakes, that’s normal. Delegation is a skill you build over time. But once you get it right, it’s going to change your business totally.

Let’s get into it.

Mistake #1: Your VA Keeps Asking Questions About Every Little Thing

The Problem

You’ve delegated a task, but instead of freeing up your time, your VA keeps coming back with endless questions.

• “What do I do if XYZ happens?”
• “Is this okay to send?”
• “How should I reply to this?”

It’s frustrating. Instead of getting things off your plate, you feel like you’re micromanaging even more than before.

Why This Happens

If your VA needs constant clarification, it’s usually because:

• You haven’t clearly defined their decision making authority. They don’t know what they can do without checking in with you first.
• They don’t have enough context. They might understand the task but not the bigger picture, so they hesitate.
• You’re accidentally reinforcing the habit. If they’ve learned that asking you is easier than figuring it out, they’ll keep doing it.

How to Fix It

Use the OKP Framework

Before delegating, check that your VA has all three:

• Outcome: Do they know what success looks like?
• Knowledge: Do they have all the information and tools they need?
• Power: Do they know what decisions they can make without asking you?

If you’re not sure, go back and fill in the gaps. Need a refresher? Check out my guide to OKP here.

Set Clear Decision Making Boundaries

Your VA should know exactly when they can make a call and when they need to check in with you. Try this:

• For simple, repeatable decisions: Give them full control. Example: “If a refund is under $50, approve it automatically.”
• For mid level decisions: Have them check in, but provide a recommendation. Example: “If a refund is over $50, let me know what you think we should do before I approve.”
• For big decisions: These should still go through you, but your VA should know what details to provide so you can make a quick call.

Want more info on how to do this? Read my article on how to delegate decision making, here. 

Use a Daily Check-in

Instead of answering questions all day, have your VA note them down in a daily check-in. This way, they learn to work through problems instead of interrupting you constantly.

The check-in can be as simple as:

• What did you get done today?
• What went well?
• What challenges did you run into?
• How did you handle them (or what’s your plan)?

This small shift teaches problem solving instead of dependency.

Encourage "Don't Bring Me Problems, Bring Me Solutions" Thinking

If your VA has a question, get them into the habit of suggesting a solution before asking for help.

Instead of: “What should I do about this customer complaint?” → They say: “The customer wants a refund. Since it’s only slightly over my approval threshold of $50, I’d like to approve it. That okay?”

This builds confidence and reduces the need for your input over time.

The Bottom Line

If your VA keeps asking questions about every little thing, it’s not just them—it’s a delegation issue.

• Make sure they have clear OKP (Outcome, Knowledge, Power).
• Define decision making boundaries.
• Use daily check-ins instead of answering questions all day.
• Encourage problem solving instead of dependency.

When you put the right systems in place, delegation actually works - without everything bouncing straight back to you.

Mistake #2: Tasks Aren’t Done Correctly

The Problem

You hand off a task, expecting it to be done a certain way… but when you check, it’s wrong. Or half done. Or just not what you had in mind at all.

• Maybe your VA sends emails with errors or missing details.
• Maybe invoices keep getting coded to the wrong categories.
• Maybe they’ve done the task, but it’s not at the standard you expected.

So now, instead of saving time, you’re either redoing their work or fixing mistakes - which makes delegation feel pointless.

Why This Happens

If tasks aren’t being done correctly, chances are:

• You haven’t provided clear instructions. What’s obvious to you might not be obvious to them.
• There’s no SOP. If they’re figuring it out as they go, there’s room for error.
• They don’t know what ‘done’ actually looks like. You know what “good” is, but have you defined that for them?
• They don’t have the right skills. Sometimes, it’s a training issue - or the wrong hire for the job.

How to Fix It

Create a Clear SOP

If you want a task done right, every time, an SOP (Standard Operating Procedure) is a non negotiable. It removes guesswork and keeps tasks consistent - no matter who’s doing them.

Not sure where to start? Use my SOPs Made Simple Bot to create one in minutes.

Be Super Clear About Expectations

Vague instructions lead to vague results. Instead of:

Example of unclear instruction: “Schedule a newsletter.”

Clearer instruction: “Schedule the newsletter in ConvertKit, using the template from last week. Send it to the ‘Customer’ segment on Thursday at 10 AM.”

Make sure you’ve answered:

• What needs to be done? Be specific.
• How should it be done? Any steps, preferences, or must dos.
• When does it need to be done? Deadlines are essential.
• What does ‘done properly’ look like? Clear success criteria.

Point Them Back to the SOP Instead of Fixing It Yourself

If something’s wrong, don’t just fix it - coach them through it.

• Instead of saying, “Leave it with me and I'll sort it,” say: “Check the SOP under Step 3 and let me know what’s unclear.”
• If the SOP is missing something, have them update it so the mistake doesn’t happen again.
• If the same mistake keeps happening despite clear instructions, retrain or reassess whether they’re the right fit for the role.

Set a Review Process (But Not Forever)

For critical tasks, start with a review phase. Have them submit the first few versions for feedback before fully taking over.

But don’t get stuck here. The goal is to gradually step back as they get it right.

How to Make Sure Tasks Are Done Right Every Time

• Use SOPs. Don’t expect them to figure things out.
• Be clear and specific about what ‘done’ actually looks like.
• Guide them back to the SOP instead of fixing mistakes yourself.
• Start with a review process, but don’t micromanage forever.

Get these right, and you’ll save time instead of spending it fixing things.

Read more about common mistakes business owners make when writing SOPs here. 

Mistake #3: Your Team Member Isn’t Doing Enough

The Problem

You hired a VA to take work off your plate. But somehow, they don’t seem to be doing much.

• Maybe they’re waiting for you to tell them what to do.
• Maybe they’re sitting idle because they don’t have enough tasks.
• Maybe they’re only working in short bursts, then waiting on your approval before moving forward.

With any of these, you’re left thinking, Why am I paying someone who isn’t actually making my life easier?

Why This Happens

If your VA isn’t getting enough done, it’s usually down to one (or both) of these reasons:

1. You haven’t delegated enough. They don’t have enough tasks to fill their time.
2. You’re still the bottleneck. They’re waiting on you for approval, decisions, or next steps.

In other words, it’s not necessarily that they’re “not working” - it’s that they can’t work efficiently because of gaps in how you’re delegating.

How to Fix It

Make Sure You’ve Actually Given Them Enough Work

Take a step back and ask yourself:

• Do they have a full list of repeatable tasks, or just one off assignments?
• Are there clear priorities, or are they sitting around waiting for you?

If you haven’t given them enough, create a list of 3-5 additional tasks they can take off your plate immediately.

Need ideas on what you can hand over? Grab my Big List of Business Tasks You Can Delegate for a list of tasks you can start handing over today.

Give Them Full Processes, Not Just Tasks

If they’re only doing small tasks and stopping after each one, it’s time to hand over a full process.

Example: Instead of saying:

Unclear instruction: “Can you post on Instagram?”

Clear instruction: “Each Monday, create and schedule three Instagram posts. Use our content calendar for ideas, write captions, and schedule them in Later. Check engagement on the previous week’s posts and flag any DMs that need my response.”

This way, they’re not waiting on you after every tiny step - they’re responsible for a whole workflow.

Stop Holding Up Their Work

If they’re always waiting for you, look at where the delays are happening.

• Are they waiting on approvals? If so, define what they can approve on their own.
• Are they unsure about decisions? If so, use Levels of Delegation to clarify their authority.
• Are they missing information? If so, make sure they have an SOP, tools, and resources upfront.

Set Clear Deadlines & Checkpoints

If they’re working too slowly, they might not know what the expected pace is.

• Assign clear deadlines for everything you delegate.
• Use a task manager (ClickUp, Trello, Asana) so they can track progress.
• Do daily check-ins to keep things moving without micromanaging.

How to Keep Your VA Productive

• Give them enough work - don’t expect them to “find things to do.”
• Hand over full processes, not just tasks.
• Remove bottlenecks so they can keep moving without waiting for you.
• Set deadlines and track progress in a task manager.

If you’ve been wondering why your VA isn’t doing enough, start here. Once you fix these gaps, they’ll be able to work independently - and you’ll finally get the support you need.

Mistake #4: Deadlines Are Missed Repeatedly

The Problem

You delegate a task, expecting it to be done by a certain time - but then the deadline comes and goes, and… nothing.

• Your VA or team member hasn’t finished it.
• Or they’ve done it late, throwing off your workflow.
• Or worse, they didn’t even realise it was urgent in the first place.

Now you’re frustrated, questioning whether they even take their work seriously.

Why This Happens

When deadlines aren’t met, it usually comes down to one of these issues:

1. You didn’t actually set a deadline. You assumed they’d just “know” when it needed to be done.
2. You weren’t clear on urgency. They didn’t realise this task was a priority.
3. You didn’t build in accountability. There was no system to track progress or check in before it was overdue.

If you’re finding out about a missed deadline only when it’s too late, that’s a delegation issue - not just a team issue.

How to Fix It

Always Set a Clear Deadline (Not Just "ASAP")

If you’re saying things like “Get to this when you can” or “ASAP”, that’s not a real deadline.

• Be specific: “This needs to be completed by Wednesday at 3 PM.”
• Clarify the urgency: “This is a priority because it affects next week’s launch.”
• Confirm understanding: Ask them to repeat back the deadline so there’s no miscommunication.

Use a Task Manager (Not Just Email or Slack)

If you’re handing out tasks over Slack or email, things will slip through the cracks. Use a task manager like ClickUp, Trello, or Asana to:

• Assign tasks with clear deadlines.
• Set reminders so nothing gets forgotten.
• Track progress at a glance - without having to chase people.

Schedule Quick Check-Ins to Keep Things on Track

Deadlines shouldn’t be a surprise. If something’s due in a week, don’t wait until the deadline to check progress.

• Daily check-ins: A quick update at the end of each day keeps tasks moving.
• Weekly check-ins: A structured meeting to review tasks, priorities, and any roadblocks.

If Deadlines Are Consistently Missed, Find Out Why

Occasionally missing a deadline? That happens. But if it’s a pattern, you need to dig deeper.

• Is the workload too much? If they’re overloaded, tasks will fall behind.
• Are they unsure about the task? If they don’t fully understand what’s needed, they’ll procrastinate.
• Are they prioritising the wrong things? If so, you need to be clearer about what’s most important.

A missed deadline is a symptom of a bigger issue. Fix the root cause with better communication, and you’ll prevent it from happening again.

How to Make Sure Tasks Get Done on Time

• Set a clear deadline - not just “soon” or “ASAP.”
• Track tasks in a project management tool, not scattered across emails.
• Use check-ins to catch potential delays early.
• Fix the real issue if missed deadlines are a pattern.

Delegation works best when everyone is clear on expectations. Once you put these fixes in place, you’ll stop chasing tasks - and start getting them completed on time.

Mistake #5: You’re Fixing Their Mistakes Instead of Working on Your Business

The Problem

You hired a VA or team member to take work off your plate - but instead of freeing up your time, you’re stuck fixing their mistakes.

• They keep getting things wrong.
• You have to jump in and redo their work.
• It feels easier to just do it yourself.

At this point, delegation isn’t saving you time - it’s actually making things harder.

Why This Happens

If you’re constantly fixing mistakes, one (or more) of these issues is at play:

1. You didn’t give them the right tools or training. They’re guessing their way through the task.
2. Your SOP is unclear (or non-existent). They don’t have a step-by-step guide to follow.
3. You haven’t built in a troubleshooting system. When they get stuck, they come straight to you instead of solving it themselves.
4. They’re the wrong person for the job. Not every hire is the right fit, and that’s okay.

Fixing mistakes over and over again isn’t delegation - it’s babysitting.

How to Fix It

Start With a Clear SOP

If you’ve handed off a task without an SOP, you’ve set your team up to fail.

• An SOP (Standard Operating Procedure) is a simple, step-by-step guide that removes guesswork.
• If they don’t have clear instructions, they’ll either make mistakes - or keep asking you what to do.
• Need an SOP fast? Use my SOPs Made Simple Bot to create one in minutes.

Make Sure They Have the Right Tools

• Do they have the correct software, logins, and resources?
• Are they working with outdated information?
• Have they been trained properly, or are they figuring it out on the fly?

You wouldn’t expect someone to build a house without the right tools. Make sure your team has what they need to do the job right.

Stop Being the Fixer - Let Them Come Up With a Potential Solution First

Every time you fix a mistake yourself, you reinforce the idea that they can come to you instead of finding a solution.

Instead, try this:

• Point them back to the SOP. If something isn’t clear, they can update the SOP as they go.
• Use a troubleshooting checklist. Create a simple decision tree that guides them through common issues.
• Encourage problem solving. Instead of “I don’t know what to do,” ask them to come to you with solutions, not just problems.

If It’s Not Working, Re-Evaluate the Fit

Sometimes, the issue isn’t the SOP or the tools - it’s the person.

• Are they taking feedback and improving?
• Are they engaged, or are they just doing the bare minimum?
• Do they have the right skills for the job?

Not everyone is a good fit for every role. If mistakes keep happening despite proper training and systems, it might be time to reconsider whether they’re the right person for the task. Just make sure that you've checked your part in delegating properly first.

How to Stop Fixing Mistakes and Actually Save Time

• Create an SOP so they have a clear process to follow.
• Provide the right tools so they’re not working with missing or outdated info.
• Let them troubleshoot first instead of running to you every time.
• Assess the fit - if they’re not improving, they might not be the right person for the role.

Delegation works when your team can do their work without everything bouncing back to you. Put the right systems in place, and you’ll finally start seeing real time freedom.

What’s Next? Let’s Talk About the Next 5 Mistakes

So far, we’ve covered five of the biggest delegation mistakes that could be keeping you stuck in a cycle of frustration and extra work:

• Your VA keeps asking questions about every little thing.
• Tasks aren’t done correctly.
• Your team member isn’t doing enough.
• Deadlines keep getting missed.
• You’re fixing their mistakes instead of focusing on growth.

But we’re not done yet. There are five more delegation mistakes that trip business owners up - ones that could be stopping you from getting real freedom in your business.

In Part 2 (coming next week), we’ll tackle:

• Why delegation often feels like more work than it’s worth - and how to fix that.
• What to do when your team doesn’t take initiative (and how to encourage them).
• How to stop the same mistakes from happening over and over again.
• Why delegation hasn’t saved you as much time as you thought it would.
• How to keep your team engaged and motivated.

Ready for the next five? Come back next week for Part 2. 

Freebie & Next Steps

Freebie: Want a no stress, proven way to delegate successfully, every time? Grab my No Stress Delegation Checklist, here. 

Next steps: If you’ve been trying to delegate but keep hitting roadblocks, let’s chat.

I offer a free, no obligation 15 minute strategy call where we can talk about:

• Where you’re stuck with delegation.
• What systems you need.
• How I can help you make it all work!

You don’t have to figure this out alone. Click here to book your free call, and let’s get your business running like a machine - without you having to do everything yourself.