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Four Reasons Why You're Struggling To Delegate As An Entrepreneur


Barnaby Lashbrooke

Founder and CEO of Time etc, author of The Hard Work Myth

8 minute read

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When you’re just starting out as a business owner, you probably accept that wearing many hats is part of the job. You might be doing admin tasks, client outreach, social media management, and even customer support. But as your business grows and new projects pop up, more tasks demand your attention.

You’re only one person, and you only have so many hours each day. It’s at this point that the only way out, and up, is by delegating.

But handing over tasks can be daunting. After all, what you’ve been doing so far has worked well, and you already have processes in place to deal with most of your daily responsibilities. But on average, entrepreneurs lose over 30% of their week to low-value tasks such as email management, scheduling, document management, and data entry.

These tasks may be essential for your daily operations, but they’re not directly correlated to growth. In his bestselling book Deep Work: Rules for Focused Success in a Distracted World, author and computer science professor Cal Newport categorizes this as “shallow work”, or “non-cognitively demanding, logistical-style tasks, often performed while distracted. These efforts tend to not create new value in the world and are easy to replicate.”

To get your business to the next level, it’s crucial to direct your energy away from “shallow work” as much as possible.

In the words of author John C. Maxwell, “If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.” But why are so many entrepreneurs reluctant to start delegating tasks, even when there is such a wide range of proven benefits?

Here, you’ll find out the four main reasons business owners struggle to delegate. Once you can identify them, it will be much easier to overcome them and open yourself up to the possibilities that delegation offers.

These are all common issues that can hold anyone back, but with this guide as your reference, we want to help you reclaim control of your time and energy so you can achieve the success you’re working so hard for.

“I Don’t Know What To Delegate”

Possibly the most common hurdle we see that stops people from delegating is figuring out which tasks to assign to an employee or assistant.

As the needs of both you and your business are unique, what works for one individual might not work for another. So while we won’t tell you exactly what you should be delegating, we can certainly offer some guidance to help get you started.

If a task has any of the following qualities, you should at least consider delegating it.

Your own individual expertise isn’t required

Can this task only be completed by you? Or, in theory, could anyone complete the task successfully with the right instructions?

You can try our free to-do list optimizer to help you discover how much (or how little) of your regular workload actually needs to be done by you.

It’s repetitive and/or completed routinely

Think of minor tasks that pop up periodically—for instance, clearing up your inbox, maintaining documentation, or updating a social media calendar. These might not look complicated, but their recurring nature means they will continue to demand your time unless you bring in someone to take care of them.

If handling these tasks takes up as much of your time as a part-time job, it’s a good sign they need to come off your plate.

It eats away your time without an adequate return on investment

“Does this get me closer to my goal?”

“Does this make money?”

“Does this make my life easier?”

When your schedule is full and everything and everyone seems to demand your attention, every task can feel just as pressing. But just because a task is urgent, it doesn’t mean it’s important.

The Urgent Important Matrix (also called the Eisenhower matrix) is a useful tool to make sense of all your obligations, giving you a sense of direction and more clarity about what you need to do yourself and what could be delegated.

In it, you group your tasks in a grid with four spaces divided into urgent and important tasks. Urgent tasks are reactive—they force you to shift your attention to them and away from other, more productive activities. In contrast, important work takes your focus back to your goals. Unlike urgent tasks, important tasks are intentional and require planning.

Any task in the non-important quadrants could be delegated or removed from your schedule altogether.

You don’t enjoy doing it, so you often put it off until it becomes critical

When was the last time you updated your company’s blog? Or updated internal documentation? These take time and may be outside your area of expertise, so they’re the first to go on the back-burner, waiting for you to find the time or get in the right mood to complete them.

These neglected tasks are great candidates for delegation, having someone else with more skills, experience, or interest take over will ensure that they’re done and done well.

You do enjoy doing it, but it’s not essential and is often neglected

You might have second thoughts about delegating these, but with so many other pressing things to do, they also get continually postponed to a hypothetical future when you’ll have enough time to do them.

Once you have a list of all the tasks you can delegate, take a moment to imagine your daily life without those tasks on your plate. If it brings you a sense of relief or excitement, you know this is the right choice for you.

“I Don’t Have Time To Delegate”

If your schedule is already packed and your to-do list is a mile long, it's hard to justify carving out extra time to write out instructions, do a handover, or onboard a new employee, so you tell yourself it’s quicker to keep doing everything yourself.

But this is only a short-term gain. The initial time you invest in the beginning will be worth it for the time you’ll continue to get back in the long term.

Successful delegators view their time similarly to money. Let’s say you sell a $60 item, but it cost you $40 to buy it, you’ve made a profit of $20. Not bad, right? I’m sure most of us would be very happy to have that $20 in our pockets.

So if you delegate a 60-minute task and you spend 40 minutes explaining to someone how to do it, you’ve saved 20 minutes. Many people focus on the 40 minutes spent to explain it and feel like it would have been quicker to do it themselves, but they neglect the 20 minutes of “profit” that they’d make. And if the task is recurring, your time-profit will continue to grow. As your employee or assistant gets used to the task, they will need less instruction and input from you, which will steadily increase your time saved from that task each day, week, or month.

“I Don’t Want To Lose Control”

As business owners, it's only natural that we want to be in control of everything. After all, we've put in the hard work and dedication to grow our businesses from the ground up. As a result, we often fall into the trap of thinking that we're the only ones who have the knowledge and experience to meet our own high standards or achieve the results we want.

But delegation isn’t about handing over authority and responsibility for your business. You are still leading the company and remain in charge of its growth, vision, goals, and values.

What delegation does is bring in people with the experience and expertise to complete more tasks faster than you could, implement new processes to improve your business, and free up your time so you can focus on being a founder and make the most out of your company. Focus on results, not the processes.

“I Don’t Want To Become Less Valuable”

This can be a tough one for some people to admit, but another common hurdle that holds people back from delegating is the belief that leaving themselves with “less” work to do will reflect poorly on their work ethic. For some, “doing it all” and always being busy is their way of proving their value within their organization.

But being a committed, ambitious, and hardworking entrepreneur doesn’t mean working yourself to death.

In my personal experience, I’ve had to deal with feelings of guilt around delegating. But if I hadn’t overcome these feelings, I’d still be stuck working 100-hour weeks doing distracting and time-wasting “shallow work”, with near-zero levels of passion and enthusiasm, and my business wouldn’t be anywhere near as successful as it is today.

As the head of your business, it’s not the quantity of work you should be doing, it’s the quality.

What’s The Bottom Line?

Every business owner with a successful company arrives at a point where tasks are no longer manageable on their own, and they have to face reality—they need to bring in someone new to take care of some of the work.

It can be hard to let go of some of the work, but this is a vital step if you want to grow, or continue growing. Whatever your reason for delegating, and regardless of the tasks you choose to delegate, you owe it to yourself—and your business—to be able to make the most of your time, focus on what matters the most, and maximize your success.

At Time etc, our service was designed with hardworking and ambitious business owners in mind. Our mission is to help entrepreneurs do more, achieve more, and earn more by matching them with the best virtual assistants.

We have a wide range of experienced assistants ready to tackle those tedious and time-consuming tasks that are holding you back. Your assistant will be hand-selected by our expert team to meet your unique requirements. We’re so sure you’ll be delighted with your new assistant, we offer a complete lifetime satisfaction guarantee.

Try a virtual assistant for free or speak to our team to find out more about how we can help you.

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About the author

Barnaby Lashbrooke is the founder and CEO of Virtual Assistant service Time etc as well as the author of The Hard Work Myth, recently recommended by Sir Richard Branson. Barnaby is a Forbes Columnist on productivity and is also an accomplished entrepreneur, selling more than $35 million worth of services.

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