Why Delegating Is So Hard and How to Overcome It

As a virtual assistant, I often hear from business owners and busy professionals who feel overwhelmed by their workload. They know they need help but find it difficult to let go of tasks. Delegating sounds simple on paper, but in reality, it can feel uncomfortable, unfamiliar or even risky.

So why is it so hard for some people to delegate? And more importantly, how can you get past that block and start making delegation work for you?

Here are some common reasons people struggle with it, and tips on how to move forward.

1. You Think It Will Take Longer to Explain Than to Do It Yourself

This is probably the most common barrier. When your to-do list is overflowing, the idea of stopping to explain something to someone else can feel like just another job. But here’s the truth: investing a little time up front can save you hours later.

Tip: Start small. Choose one repeatable task that takes up more time than it should. Record a voice note or screen share video as you complete it. That way, you only have to explain it once and your assistant can refer back to it as needed.

2. You Worry No One Will Do It the Way You Would

This is especially true for business owners and perfectionists. Your work is a reflection of you, and it's natural to want everything done just right.

Tip: Be clear about your expectations and what “done well” looks like. Create simple checklists or templates, and don’t be afraid to give constructive feedback. A good assistant will welcome it and learn your preferences over time.

3. You Feel Guilty Handing Over Tasks

Some people feel awkward asking for help or worry that they’re offloading too much. But delegation isn’t about passing on what you don’t want to do, it’s about making the best use of your time and skills.

Tip: Reframe delegation as collaboration. You’re not asking for a favour, you’re creating space to focus on the parts of your business or life that need your attention most.

4. You Don’t Know What to Delegate

Sometimes people simply don’t know what to hand over. If you’re used to doing everything yourself, it can be hard to even recognise what could be delegated.

Tip: For one week, track what you do each day. Highlight the tasks that feel repetitive, draining or outside your zone of genius. Those are ideal to delegate. Even something as small as inbox management or calendar booking can make a real difference.

5. You’ve Had a Bad Experience in the Past

If you’ve tried to delegate before and it didn’t go well, it’s understandable to feel cautious. But one experience doesn’t mean all help is unreliable.

Tip: Start again with clearer communication and a more structured onboarding process. If you’re working with a virtual assistant, set up regular check-ins and shared task lists to keep things transparent and on track.

Final Thoughts

Delegation is a skill, and like any skill, it gets easier with practice. If you can learn to trust the process and build a working relationship with the right support, it can free up your time, reduce stress, and help your business grow more sustainably.

If you’re ready to explore how working with a virtual assistant could lighten your load, I’m here to help. I offer professional, flexible support to clients both remotely and in person around Bordon and Hampshire.

Let’s chat about what you could delegate and what that extra headspace could do for you.