The 5 Key Signs Your Business Needs Executive Assistance

While running your own business is certainly rewarding, it’s no secret that it’s also a ton of work. For starting and growing business owners like you, there’s so much to do that each day ends with heads spinning. Here are 5 key signs that will tell you it’s time to get some executive assistant to run your business.

1. Too Many Mistakes

Whenever we get overworked, the first thing that suffers is our work. We rush things that need time, forget what we’ve already done, or overlook key aspects of the business. 

This can lead to:

  • missed invoices, which means less money
  • duplicated invoices, which looks bad to customers, or worse
  • accounting mistakes or failed communication, which can cost you time, money, and perhaps even your reputation

One of the possible reasons for this is the lack of the right processes in place. Another probable reason is work overload, not only for you but for all your subordinates as well. You or your staff may have too many things in their hands which resulted in overlooking small but critical aspects of the business. 

Pro Tip: Administrative support will allow you to hand some of these tasks over to your Executive Assistant. The EA’s entire job will focus on ensuring these tasks get done correctly. Delegating tasks to your EA will save your time, free up more time for other tasks and will reduce the number of mistakes.

2. You Can’t Find Stuff

Another tell-tale sign you need some administrative support is: you’re having trouble locating important files or communications. As your business grows, you will start creating more spreadsheets, workflows, tools, and messaging boards to keep track of everything. Poor organization of these files and platforms spell disaster for the business.

Keeping all of these well-organized takes time. An Executive Assistant is expected to organize and locate these files for you. Imagine how nice it would be if you needed a file, and instead of spending twenty or thirty minutes digging it out, you could shoot a message to your EA and just ask for it.

Pro Tip: Time well spent would lead to a more profitable business.

3. Simple Things Take Too Much Time

Another good determinant you need administrative assistance for your business is the time spent doing simple tasks. Perhaps you’re still doing payroll by yourself, or booking reservations while placed on hold over the telephone. You might still be doing routine tasks such as posting to social media, which takes way longer than you think they should be. 

Pro Tip: If you’re thinking this might be the case, we encourage you to start writing down the tasks that you consider “time wasters.” Afterward, carefully consider how having an EA solely dedicated to complete this task would make the process much more efficient. 

4. You’re Wearing Too Many Hats

Businesses succeed when personnel focuses on their specialized tasks. Working within their lanes whilst complementing each other pushes the business forward. Hence, it counterproductive if personnel with specialized skills are forced to do other things.

Doing other things other than your specialization consumes more time, fills up unnecessary space in your schedule and prevents you from doing what you do best. This is wearing too many hats. 

It would be a great activity if you ask yourself, “what do I bring to the business that’s unique?” Then, calculate how much time you spend in a given day actually working on this task. 

If the answer is half or even two-thirds of your time is being dedicated to this core function, there’s a pretty good chance you need to bring in some administrative help and delegate certain tasks to others. 

Pro Tip: If you’re doing this, it’s quite likely your other employees are experiencing something similar. Talk to them frequently to find out if they’re being pulled in so many different directions and if this hinders them from doing their jobs.

5. Long-Term Strategy Seems a Distant Thought

Lastly, while it’s important to have your finger on the pulse of your company’s day-to-day operations, getting too caught up in the minutia will cause you to lose sight of your long-term vision for the business. Failing to plan for the long-term could leave you in a position where your competitors leave you and your company behind.

You need to be constantly innovating and optimizing. Running the business daily consumes so much time which makes it hard to find time to brainstorm and plan for new innovations. This is another factor to consider that spells the need to get help.

It’s Not Too Late

For some, it takes a while before they realize that they can’t run a business on their own.  Many business owners allow systems and processes to get out of control before seeking help, which leads to wasted time, too many mistakes, and a delay in the growth of your business. 

If you are one of these budding business people, it’s not too late. You can still assemble a team that can handle other aspects of the business. Additionally, you need to learn how to delegate to these teams

Getting an executive assistant for your business definitely will benefit not only the business but yourself as well. Leading a team and growing a company is already hard.  Getting overworked, dealing with too much stress and running the risk of experiencing burnout is much harder. 

We recommend spending some time looking at your business to see if it’s exhibiting any of these signs. Go out and get the assistance you need to turn your business into everything you’ve always dreamed it could be. 

For more information about hiring a well-vetted distant executive assistant, fill out this form and we will be in touch. 


Bottleneck would like to thank Olivia Diaz from for writing this article.

Jaime Jay

About Jaime Jay

Meet Jaime Jay – a man who wears many hats, and wears them all admirably. He's a master connector, an entrepreneur extraordinaire, and a published author who knows how to get things done.

Before he found his way to the business world, Jaime served his country as a brave paratrooper in the U.S. Army. But that's just the beginning of his many accomplishments.

He's the founder of the renowned Bottleneck Distant Assistant Services firm, and his book "Quit Repeating Yourself" has become a must-read for entrepreneurs everywhere.

When he's not busy building his empire, you can find him on his beloved Harley Davidson, cruising through the countryside and taking in the invigorating effects of Uitwaaien – a Dutch practice that involves facing the wind to boost health and relieve stress.

He enjoys spending his free time outside building stuff with his wife, Nikita the dog and their two kittens (for now at least) Tommy and Tater.

He is ‘over-the-moon’ happily married to his wonderful wife Sara, his amazing daughter, Jessica, who is serving our country as a United States Army soldier. Jaime and Sara are the proud grand parents of two beautiful little girls.


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