The Issues with Delegating Work Nobody Else Understands

Suffering due to delegating work

The nightmare of (not) delegating work

Delegating work sounds so simple that it’s almost funny to have a blog post about it. What’s there to it? Just tell them what tasks you need doing and how. Duh.


We know you’ve come across this attitude. Those who have it are almost never CEOs or other high-level executives. If they were, they’d know the pain.

You know what I’m talking about, though. It’s the endless hours spent slaving away at your desk, tying up admin chores because Stephen proved himself to be utterly incompetent at working with spreadsheets. That kind of pain.

Just tell them what tasks you need doing and how.” Yeah, sure, buddy.

We, however, do understand you. Throughout our experiences, we’ve become intimately familiar with the struggles high-level executives face with delegating work. In this post, we’d like to show you how much we understand you and offer you some help. Free of charge.

The catch? You’ll have to do some soul-searching along with us.

But first, the

Tiers of Tears

Forgive the pun, but I really couldn’t resist. The point of this section is to give you an overview of how we see your troubles. They’re divided into two tiers. One of them is pre-awareness, before an executive realizes delegating work is an option. The second tier, post-awareness, are all the mental and practical hurdles that prevent you from hiring a VA even after you’ve found out about them.

Baby in Brown and Black Hooded Top crying because of delegating work

Tier 1: Pre-awareness

Woe 1: “I’m so overworked!”

But it’s okay, right? Since you’re in love with your job and all. At least, that’s what we tell ourselves sometimes to cope with the relentless onslaught of stressful tasks. Free time is for losers, after all, and those who want to actually enjoy some leisure.

We both know it’s not black and white, but what’s the alternative? You can’t just stop working. Well, you can… but then everything falls apart. You’d give anything for just a little bit of help with the seemingly endless to-do list.

Woe 2: “My family hasn’t seen me in three months!”

An exaggeration, yes. Sadly, not a big one. We know what it feels like, and it’s not simple. You love your job—of course you do, but you also love your family and friends. You’re faced with an impossible choice: career or relationships?

It seems that no matter what you choose, one of them needs to suffer. If only there was a way to take a bit of work off your shoulders so you can free up some time for your loved ones…

Woe 3: “Literally all I want is just five minutes of peace.”

Peace can mean a lot of different things, depending on whom you ask. Me, personally? I like to meditate. For you, it might be kicking back with a martini or even playing your favourite video game. The point is, winding down is an important part of any person’s life.

What? Oh. You’ve forgotten what that feels like. Yeah, figures… that’s what happens when you’re spending all your time putting out fires and making sure the colossal machine that is your business doesn’t dismantle itself. The decline of your mental health soon follows as all peace is replaced by stress.

Ouch. I’m no expert but that doesn’t sound good. I mean it hurt me just to write this.

Gray Monk Statue in Between Plant Pots

Tier 2: Post-awareness

Woe 1: “I don’t want to waste even more time!”

So, it finally happened. You stumbled over one of our blog posts and learned about VAs. We understand. It’s inevitable. It happens to everyone. Our SEO is just that good.

But now what? Delegating work may sound simple, but is it really? I mean, just think of all the explaining and onboarding you have to do! In the end, it can easily seem like getting an assistant ready to take over some of your tasks will take more time than simply doing them yourself. If only you could find someone skilled and proactive.

Woe 2: “They probably won’t do as good a job…”

Of course. You’re the one who primarily does the work so you know how to do it best, right? It’s also your company. You know in which direction all tasks should ultimately lead.

Some foreign VA who’s just come into your company can’t possibly do your tasks as well, let alone better than you. Not to mention all those VAs out there who slack off and try to convince you they’ve been working. You might end up with more free time, sure, but can you risk letting your business suffer because of it?

Woe 3: “My money’s better spent elsewhere!”

Okay, great, VAs can help you, but they aren’t free. Nothing good ever is. And, let’s face it, some companies and freelancers can charge quite a fee for their services. What if they mess up? You still need to pay them, right? For what? For wasting your time?

You might as well rest, really. Even if you lose some money, you’ll have at least not spent it on something else. Worse yet, what if a VA costs you money through some unfortunate blunder? Hiring a VA can easily seem like a questionable investment.

Person Holding Black Desk Calculator

Woe 4: “What if we don’t click as people?”

This is a valid concern. After all, a VA is presumably someone you’ll be interacting with a lot. What if you hate them? What if they’re annoying and have terrible communication skills? What if their vibes are rancid?

Finding someone compatible with your personality isn’t easy. It’s even more difficult when you add on the requirement of being good at their job.

Woe 5: “Can I trust them?”

We usually don’t even trust our partners with sensitive login info (unless it’s that fake Facebook account with only three friends). Who’s to say a VA won’t misuse your accounts? What if you wake up one day with pictures of your underwear (don’t ask me how the VA got those…) all over your company’s Instagram page?

Delegating work is already sensitive. Having VAs use your accounts is almost dangerously intimate. Trustworthiness and integrity are necessary.

Woe 6: “I probably can’t even find a VA for this task…”

Just out of curiosity, what task is it? We’ve heard about some pretty crazy ones in the past. If someone can find a VA to keep track of his wife’s and mistress’ birthdays and buy them gifts accordingly, I’d really like to know what insane colossus of a labour you have for your proverbial VA Hercules.

Jokes aside, it totally makes sense. After all, VAs all get boring administrative chores and the like. If you have something more… spicy, it can easily seem like it’s way too out there. But you don’t know for sure though. It can be so difficult or awkward to ask. Maybe you’re the only one who’s ever had this issue?

Man Changing a Car Tire

Okay, great… now what?

It can definitely seem like this post is a pessimistic landscape of hopelessness.

And it is.

…Up until this point, at least.

Look, we haven’t just been listing the troubles we know you have with delegating work for no reason. Through our long experience in working with clients, we at Remote Bob have steadily been working on tackling these issues. We may not have worked out all of the solutions perfectly, but I daresay we’ve done a pretty good job so far, and we’re still working on them.

Since we know that you can relate to the heartaches we’ve listed here, here’s what we recommend you do next: email us at business@remotebob.co.uk with the subject line “tips” to sign up for our mailing list. You’ll regularly receive our newsletter with advice on how to deal with these issues.

Did we mention it’s free?

Yes, we did. It’s in the first section.

Wait. Who are you?

I’m the VA ghost. I’ve come to tell you that you’ve rambled on long enough and that you need to end the post.

Oh… well, okay… if that’s how you feel.

It’s how all of us feel.

Well, okay then! And, you, reader—I promise I’m not crazy (except maybe about helping you)! Don’t let my sanity go to waste and leave your email if you crave answers! You can always unsubscribe if we turn out to be useless.

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