Delegation Still Not Working? 5 More Mistakes You Might Be Making

Delegation Mistakes That Are Keeping You Stuck (Part 2)

Delegation is supposed to free up your time - but if you feel like you're working harder than ever, something’s going wrong.

In Part 1 of our delegation mistakes articles, we covered five of the biggest mistakes business owners make when delegating, including:

• Not setting clear decision making boundaries.
• Skipping SOPs and clear instructions.
• Holding onto too much control.
• Not giving deadlines (or tracking progress properly).
• Fixing mistakes instead of setting up better systems.

But those are just some of the problems with delegation I see small business owners make.

In this post, we’re getting into five more delegation problems - ones that could be stopping you from getting real freedom in your business.

Mistake #6: Delegation Feels Like More Work Than It’s Worth

The Problem

You started delegating because you wanted to free up time. But instead of making things easier, it feels like:

• You’re constantly answering questions.
• You have to double check everything.
• It’s taking longer to hand things over than it would to just do it yourself.

At this point, delegation feels like more hassle than help.

Why This Happens

If delegation feels like extra work instead of a time saver, one (or more) of these issues is probably the reason:

1. You’re only delegating tasks, not full processes. Instead of handing over ownership, you’re giving them one small task at a time - so everything still comes back to you.
2. You haven’t defined decision making authority. Your VA or team member keeps checking in because they don’t know what they can handle on their own.
3. You haven’t put the right systems in place. If you’re explaining everything from scratch every time, delegation will always feel like extra work.

Delegation shouldn't make things harder for you in your business. If it does, something needs to change.

How to Fix It

Delegate Entire Processes, Don't Just Delegate Tasks

• Instead of handing off a single task, give them responsibility for an entire workflow.
• Example: Instead of “post this on social media,” delegate the entire content scheduling process, including selecting images, writing captions, and posting.
• The goal is to remove yourself from the process entirely - not just from a single step.

Use the OKP Framework

If your VA keeps coming back with questions, ask yourself:

• Outcome: Have you told them exactly what success looks like?
• Knowledge: Do they have the SOP, tools, and context they need?
• Power: Do they know what decisions they can make without checking in with you?

If you’re missing any of these, read my OKP delegation of authority framework guide here.

Give Them Decision Making Power

If your team needs approval for every tiny decision, delegation will always feel like more work than it’s worth.

• Use Delegation Levels to gradually increase their decision making authority.
• Example: Instead of asking for approval on every refund, your customer service rep can approve anything under $100 without checking in.
• Not sure how to implement this? Read my guide to Levels of Delegation for more info on how to delegate authority.

Set Up Check-Ins (But Not Micromanaging)

Checking in isn’t micromanaging - it’s how you make sure things are getting done without everything bouncing back to you.

• Daily check-ins: Quick updates on what’s been done, any issues, and what’s next.
• Weekly reviews: A bigger-picture look at progress, improvements, and any roadblocks.
• Tracking in a task manager (Asana, ClickUp, Trello): So you don’t have to chase people for updates.

If you’re not checking in, you’re not delegating - you’re doing the dump and disappear.

How to Delegate Better Without Extra Effort

• Hand over full processes, not just tasks.
• Use the OKP framework to ensure they have everything they need.
• Increase decision making power with delegation steps so they don’t have to check in constantly.
• Implement structured check-ins to keep things on track without micromanaging.

When done right, delegation doesn’t create more work for you -  it saves you time. Put the right systems in place, and you’ll finally see the benefits.

Mistake #7: Your Team Member Doesn’t Take Initiative

The Problem

You hired help so you wouldn’t have to think about every little thing. But instead of taking charge, your VA or team member:

• Only does exactly what they’re told - nothing more.
• Doesn’t try to problem solve or think ahead.
• Asks for approval on things they should be able to handle.

It feels like you still have to be involved in every decision, which defeats the whole purpose of delegation.

Why This Happens

If your team isn’t taking initiative, there’s usually a reason behind it:

1. They’re not clear on their role. If they don’t fully understand what they’re responsible for, they’ll play it safe and wait for direction.
2. They don’t know what decisions they can make. If you haven’t defined their level of authority, they’ll check in for approval instead of acting independently.
3. You haven’t set expectations for proactive thinking. If you only give step-by-step instructions, they’ll assume that’s all you want from them.
4. They might be the wrong fit. Some people naturally take initiative, while others prefer to be given tasks and follow instructions. If you’ve done everything right and they’re still hesitant, they may not be the right person for the role.

If you’re frustrated by a lack of initiative, the first step is to figure out which of these is causing the issue.

How to Fix It

Make Sure They Understand Their Role

• Clearly define their responsibilities - not just tasks, but the overall purpose of their role.
• Explain how their work contributes to the bigger picture of the business.
• Ask them to re-explain their role in their own words to confirm understanding.

Use Levels of Delegation to Increase Their Decision Making Authority

• Start at a lower level (e.g., gathering information) and gradually give them more responsibility.
• Be explicit about what they can decide on their own vs. what needs approval.
• Example: Instead of "check with me on customer refunds," try "approve refunds under $100 without needing my input."
• Not sure how to do this? Make sure to read my guide to Levels of Delegation here.  

Encourage Problem Solving Instead of Just Answering Questions

• If they ask for help, don’t just give them the answer - ask, “What do you think we should do?”
• Implement a “don’t bring me problems without solutions” rule.
• Example: If they have an issue, they should come up with at least two solutions before asking for your input.

Recognise & Reward Initiative

• Acknowledge when they take initiative and make good decisions.
• Give positive reinforcement - if they feel like their ideas aren’t valued, or worse, they'll get in trouble, they won’t bother next time.
• Example: If they solve a problem without checking in, let them know you appreciate their proactive approach.

Assess Whether They’re the Right Fit

• Some people are naturally proactive, while others aren’t wired that way.
• If they consistently avoid taking initiative despite guidance, training, and clear expectations, they may not be the best person for the role.
• Be honest about whether they need extra support - or if you need to find someone else who’s a better fit.

How to Get Your Team to Take More Initiative

• Clarify their role and responsibilities so they know what’s expected.
• Use Levels of Delegation to gradually increase their independence.
• Encourage problem solving instead of just giving them the answers.
• Recognise and reward initiative to reinforce proactive behaviour.
• If nothing changes, consider whether they’re the right fit.

When you set clear expectations and create the right environment with your delegation process, your team will feel more confident stepping up and taking ownership. And that means fewer decisions landing back on your plate.

Mistake #8: They Keep Making the Same Mistake

The Problem

You’ve explained it. You’ve shown them how to do it. But somehow, they’re still getting it wrong.

Maybe it’s:

• A task that keeps coming back incomplete.
• Mistakes that should have been fixed by now.
• A process that never quite runs smoothly, no matter how many times you go over it.

By this point, you’re frustrated - and wondering if they’re even paying attention.

Why This Happens

If the same mistakes keep happening, there’s always a reason. Here are a few possibilities:

1. Your instructions weren’t clear enough. Maybe you thought they understood, but there were gaps in what you explained.
2. The SOP is missing something. If the process isn’t documented properly, they’re left to guess.
3. They didn’t get proper feedback. If they don’t know exactly what went wrong, they might not even realise they’re doing it wrong.
4. They’re too afraid to ask for clarification. If they feel like they should already know the answer, they might keep doing it wrong instead of admitting they need help.
5. They’re not the right fit for the task. If they lack the necessary skills, training alone might not solve the issue.

Before you assume they’re just not paying attention, take a step back and figure out which of these could be the real problem.

How to Fix It

Check Your Instructions & SOPs

• Look at how you first explained the task. Was it clear? Did you assume they already knew certain things?
• Review your SOP - does it actually include every step?
• If you don’t have an SOP, that’s the problem. Create one using my SOPs Made Simple Bot.

Give Specific, Actionable Feedback

• Instead of just saying, “This isn’t right,” explain what’s wrong and how to fix it.
• Example: Instead of “Your email responses need work,” try “Your replies should follow the template in the SOP - make sure you cover all the key points.”
• Ask them to repeat back the corrected version to ensure they understand.

Add an FAQ Section to Your SOPs

• If the same question keeps coming up, update the SOP with a “Frequently Asked Questions” section.
• Example: If they keep asking, “What do I do if a customer asks for a discount?” - document the answer so they don’t have to check in every time.

Encourage Them to Ask Questions

• Let them know it’s okay to ask for clarification. The goal is to get things right - not to guess and get it wrong.
• Set the expectation: If they’re unsure about something, they should check the SOP first. If the answer isn’t there, then they can ask you. And make notes once they've got the answer.

Assess if They’re the Right Fit

• If they’re consistently struggling - even with clear instructions, SOPs, and feedback - it might not be the right task for them.
• Ask yourself: Do they have the skills needed for this role? Or would they be better suited to something else?

How to Stop Recurring Mistakes for Good

• Review your instructions and SOPs to make sure nothing is missing.
• Give clear, specific feedback so they know exactly what to fix.
• Update your SOPs with FAQs to prevent repeat questions.
• Create a culture where asking for clarification is encouraged.
• If all else fails, evaluate whether they’re the right person for the job.

When you address the root cause instead of just the symptom, mistakes stop repeating - and delegation finally starts working the way it should.

Mistake #9: You Feel Like Delegation Hasn’t Saved You Any Time

The Problem

You’ve started delegating, but somehow, you’re still just as busy as before.

Instead of freeing up time, you feel like:

• You’re still managing every little detail.
• Tasks keep bouncing back to you with problems.
• Your to do list isn’t getting any shorter.

By this stage, you’re wondering - wasn’t delegation supposed to make things easier?

Why This Happens

Delegation isn’t just about handing over tasks - it’s about handing over responsibility.

If you’re still stuck in the weeds, it’s probably because:

1. You’ve only delegated tasks, not entire processes. Your VA completes a task but still checks in with you for the next step.
2. You haven’t given them enough to do. If they don’t have enough work, they’ll might just wait for instructions instead of asking for more work.
3. You’re still the bottleneck. They can’t move forward without your approval or feedback.
4. They don’t have the knowledge, power, or outcomes (OKP) they need to work independently. If they’re missing information, they’ll keep coming back to you.
5. Your task tracking system isn’t working. If things aren’t documented properly, you’ll spend more time chasing updates than focusing on your business.

How to Fix It

Delegate Entire Processes, Not Just Tasks

• Instead of delegating piece by piece, hand over the full process.
• Example: Instead of saying, “Post this blog,” delegate the entire content publishing process - from formatting to scheduling to adding internal links.
• Use the OKP Framework to make sure they have the knowledge, power, and expected outcomes.

Increase Their Workload (If Needed)

• If your VA isn’t doing much, it’s time to hand over more.
• Use my Big List of Business Tasks You Can Delegate to come up with more ideas for what else they can take off your plate.

Give Them More Decision Making Authority

• If they keep coming back to you for approvals, you’re still the bottleneck.
• Use Levels of Delegation to clarify what they can decide on their own.
• Example: Instead of “Check with me before issuing refunds,” say, “Approve refunds under $100 automatically.”

Use a Task Manager, Not Your Inbox

• Email isn’t a task manager - things will get lost, delayed, or forgotten.
• Use ClickUp, Asana, or Trello to track tasks, progress, and deadlines in one place.

Review and Refine Your Delegation Strategy

• If delegation isn’t saving you time, ask yourself:
• Have I fully handed over the task or am I still involved in every step?
• Does my team have everything they need to do the job independently?
• Am I still the bottleneck without realising it?

How to Make Delegation Actually Save You Time

• Stop handing over single tasks - delegate entire processes.
• Make sure you've actually given your VA enough work.
• Remove unnecessary check-ins by increasing decision making authority.
• Use a proper task manager instead of emails.
• Continuously improve your delegation system so you’re not stuck in approval mode.

When you understand how to delegate responsibility, you should be able to step away - and things will still run smoothly. If that’s not happening yet, tweak your approach until it does.

Mistake #10: They Don’t Seem Engaged or Motivated

The Problem

Your VA (or team member) is doing the work, but it feels like they're just going through the motions.

• They don’t take initiative.
• They aren’t engaged in their tasks.
• They seem checked out and uninterested.

At best, it feels like they’re completing tasks with minimal effort. At worst, they’re making careless mistakes, missing deadlines, or delivering low quality work.

Why This Happens

A disengaged team member is usually a sign of one (or more) of the following issues:

1. They don’t understand how their work fits into the bigger picture. If they don’t see how their role contributes to the business, they won’t feel connected to their work.
2. They don’t feel ownership over their tasks. If you haven’t fully handed over responsibility, they might feel like they’re just checking boxes instead of making a meaningful contribution.
3. They aren’t being challenged. If they’re stuck doing repetitive tasks with no opportunities to grow, boredom sets in.
4. There’s no feedback or recognition. If their hard work isn’t acknowledged, they may feel like their efforts don’t matter.
5. You’ve delegated the wrong tasks to the wrong person. If they don’t enjoy the work or don’t have the right skills, motivation will naturally drop.

How to Fix It

Make Their Work Meaningful

• Connect tasks to the bigger picture. Help them see how their role impacts the business.
• Example: Instead of saying, “Schedule social media posts,” say, “Your work helps keep our brand visible and attracts new customers.”
• Show them the results of their efforts - whether that’s increased engagement, happy customers, or more sales.

Give Them More Ownership

• Move beyond just assigning tasks - let them take full ownership of a process.
• Use the Levels of Delegation framework to gradually increase their decision making power.
• If they’re constantly waiting on you for approval, they won’t feel a sense of responsibility for the outcome.

Challenge Them with Growth Opportunities

• If they’re capable of more, give them new challenges.
• Ask if there’s an area of the business they’re interested in learning more about.
• Give them a small project or responsibility beyond their usual tasks to keep them engaged.

Recognise Their Efforts

• A simple “great work on that” goes a long way.
• Provide feedback regularly - acknowledge what they’re doing well and give constructive guidance where needed.
• Celebrate small wins in your weekly check-ins.

Check If They’re the Right Fit

• If you’ve tried all the above and they’re still disengaged, it’s time to assess whether they’re the right fit for the role.
• Ask yourself:
• Are they capable of the work?
• Do they seem interested in growing with the business?
• Is there another role that might suit them better?
• Not everyone is cut out for every role - and that’s okay. If it’s not the right fit, you may need to restructure their responsibilities or look for someone better suited to the job.

How to Keep Your Team Engaged in Their Work

• Show them how their work contributes to the business’s success.
• Give them full ownership over their tasks, not just assignments.
• Provide opportunities for growth and new challenges.
• Acknowledge their contributions and give regular feedback.
• Make sure they’re in the right role - if they’re not engaged, there might be a better fit.

A motivated team is a productive team. When you get delegation right, your VA (or team) will be proactive, engaged, and invested in helping your business grow - without you having to chase them for every little thing.

Final Thoughts: Delegation Is a Skill - And You Can Master It

If delegation hasn’t been working for you, you’re not alone. Most business owners struggle with it at first. It’s not because you’re bad at delegating - it’s because no one ever teaches you how to do it properly.

The good news? You can fix that.

Delegation is a skill, and like any skill, it gets easier the more you do it. By avoiding these common mistakes, you’ll start handing off tasks with confidence, getting work done exactly how you want it - without things bouncing back to you.

And remember, if something goes wrong, the first step is to reflect and refine:

• Did you give clear instructions?
• Did they have everything they needed to succeed?
• Have you truly handed over responsibility, or are they still waiting on you?

Once you learn how to delegate work effectively, you'll be dishing out tasks like Oprah handing out freebies – "You get a task! You get a task! Everyone gets a task!" ...and the best part? No boomerangs – once those tasks are gone, they’re not coming back!

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.