How to Outsource Even If You’re a Control Freak

December 20th, 2016   |    By: Will Lipovsky    |    Tags: Recruiting

Do you find it hard not to micromanage every little aspect of your business?

Are you guilty of wishing that you could just clone yourself?

You’re not alone, but you can become far more effective when you outsource everything you don’t absolutely HAVE to be involved with. Plus, there are some tasks that — sorry — someone else could be doing much better — as challenging as that can be to admit to yourself.

Here are three essential keys to make sure that delegating part of your work is as painless (and even as enjoyable) as possible.

Choose Tasks to Delegate

These are the things that you don’t really want to do, but are scared to let go of. Some examples might include work-related minutia, like posting to social media, filtering emails, and tracking your business expenses.

Others tasks might be more personal, like doing grocery shopping or purchasing and sending out gifts to friends and family at the holidays. Now, if grocery shopping is what makes your whole world sing, by all means, keep doing it. I get it. Who can resist getting you door dinged in the parking lot at the grocery, crying babies, and seeing your neighbor who always has a lot of time for a chat?

However, if it’s a task that can be outsourced to a virtual assistant or automated without you having to take a look-over and approve it every time, then it’s a good one to release control of.

If it’s something that you know you’re going to be absolutely livid about if it’s not done exactly the way that you would have done it — or the way you have done it forever, then that one is off the list of your “assistant” giveaways.

Train Your Assistant

You’ve taken the plunge and hired a virtual assistant. Great! But you’re not done yet. You’ll want to write down how you do each task on your list of things you want done — step by step — and walk your new assistant through the process.

If you take the time to fully train your virtual (or otherwise) assistant now, you’ll be setting yourself up for success. There’s nothing more aggravating than thinking that something’s covered and then watching someone else drop the ball, especially for control freaks.

Listen — let me just repeat that again — listen — to all the questions that your assistant will ask about your processes. Have your list there in front of you, and read from it as you go along, in case you’ve forgotten a step.

Think through the process with your assistant, from beginning to end. Avoid using catchy “love language” phrases such as, “you’ve got to be kidding, you don’t know that?” and “this is so simple.”

Make sure your assistant has all the tools they need — passwords, login information, templates, links, and so forth. Consider making a quick “how-to” video for your assistant for the more detailed work you need, or for work that has to be done in a precise order every time. This way your assistant can refer back to the instructions if needed.

If you’ve been very clear on what you expect during the interview stage, from when you want them to be working on the project, about how long you think this process will take once they’ve practiced and come up to speed, to how often you’d like them to check in with you.

Yes, you control freak, you best let them know exactly how often to check in, because maybe they have never heard of personally calling someone on their cell every hour on the hour.

Seriously, do you need a beginning of day and end of day catch-up until you feel okay? Ask for this (favor) so you will really feel comfortable and be able to let go. Later, when you have some trust you will find that you’re not constantly worrying anymore that the work isn’t really being done. You really will be able to relax at some point.

Loosen Up

While it can truly be difficult for control freaks, perfectionists, and overachievers to watch someone else do things just a little bit differently than your all-knowing self would, this allowance will become one of the keys to your success.

If you’ve picked someone with similar values and a work ethic like yours, it’s now time to let go. This is going to take some personal growth and maturity on your part.

Of course, if you’ve tried to make a business relationship with an assistant’s work, and it’s just not happening, no matter what, it’s time to find someone who’s a better fit for you and your business.

In the end, you’ll hopefully find someone who makes you feel that your business is truly in good hands, and you’ll have more time to focus on the irreplaceable elements of your work that only you can make happen.

How to Outsource Even If You’re a Control Freak was originally published on Due blog by Will Lipovsky.

About the Author

Will Lipovsky

Will Lipovsky is a full-time personal finance freelance writer. His work has been published on Yahoo Finance,, the Department of Defense Technical Information Center, Lifehacker and elsewhere. His most embarrassing moment was telling a Microsoft executive, "I'll just Google it."

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