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The Overworked Entrepreneur’s Guide to Efficient Outsourcing

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You started your business to do what you love, right? To take charge of your schedule, be your own boss, and focus on the work you’re most passionate about.

And maybe it’s all been great so far – except for the part of entrepreneurship where you’re spending late nights and early mornings catching up on the administrative tasks you’re not passionate about: invoicing, payroll, scheduling, answering customer service emails...the list goes on and on.


Three cheers for being your own boss? Not exactly.


Too many of us start our own businesses to do the work we’re most uniquely qualified to do, but then end up bogged down by the details of running a business, not doing the work we’re most passionate about.
Sound familiar? This was me just three years after starting my business and it might be you, too.


Everyone deserves to have help, and despite popular belief, asking for help doesn’t make you any less of a superhero. Whether that’s by hiring a housekeeper or hiring a virtual assistant, seeking out qualified support makes room in our lives to do the things we love and be with the people we care about. This is especially important for entrepreneurs, because your job isn’t just about what you do between the hours nine and five. It’s about the time you get to spend with your family, the adventures you get to have, and the difference you get to make with your work.


I have some good news for you – getting started with delegating all the things you’re not uniquely suited to do is easier than you think.


1. Build outsourcing into your business plan
You may not be in a place to hire a virtual assistant right away, but if you want to grow your business in the future, I recommend planning to outsource from day one.

Rather than trying to organize your projects and tasks as you onboard a new assistant, build systems as you go. Use collaborative tools that will allow you to hand off tasks easily and document your processes so they will be simpler to teach them to someone down the road. Create secure passwords for accounts you may need to give access to and store them in an online password tool like LastPass or 1Password.


This will eliminate the need to compile everything at the last minute when you’re ready to hire somebody.


2. Set a budget
Business owners often ask me how they’ll know when they’re ready to hire someone. Unfortunately, it’s not a one-size-fits-all answer. You might need someone today, but you might not have the money or the time to get started. Since the goal with hiring is to make more time in your life, I always say that a good indicator of when you’re ready to hire someone is when you can afford it.


Of course, being able to afford something or not has a different meaning for everyone. Just keep in mind that you’ll always get what you pay for. If you want your work done fast, good, and cheap, well, unfortunately you can only pick two out of the three. Choose the two that are most important to you and set your budget accordingly.


Establishing a monthly budget for support will enable you to comfortably invest in buying back time for your business and your future. You might want to enlist the help of a finance or accounting professional to assist in this process. Make sure you're able to plan for growth, or at least stability, in your revenue so that you'll be able to fund a long-term business engagement with your assistant.


3. Take time to find a good match
I always recommend going to your network first when looking for a virtual assistant. Talk to other business owners, post on social media, and try to get a personal recommendation. This will help you feel more comfortable that the person is capable and trustworthy.

If you can’t get a personal referral to a virtual assistant, try searching on LinkedIn or using a virtual assistant agency to find a great match.


When you’ve got a few solid candidates with impressive resumes lined up, consider conducting at least one video interview to get a better feel for their personality and professionalism. Test their skills with a sample assignment that represents the type of work you'll be offering. Between the virtual face-to-face interview and the test project, you’ll be able determine whether they can actually do what they say they can do.


Test projects could be anything from a sample blog post to a sample travel itinerary. Just make sure it’s something you would actually assign to your assistant and make sure you have a rubric against which to grade their work.


Finally, you might want to consider paying for these test projects because it’s an important way to show goodwill toward your future assistant and get better quality applicants, even if you don’t end up hiring everyone who went through the process.


4. Invest the time to train
In general, virtual assistants are highly-motivated, self-starting people who enjoy learning how to do new things. But you can’t hire someone and expect they’ll know how you want things done right off the bat.


You have to invest the time in training your new virtual assistant, especially if you’re someone who – like me – appreciates having things done a certain way for a certain reason.


I always recommend creating training videos and process documents that you can use in the future. This enables your assistant to follow the trainings and processes on their own time (watching and re-watching if necessary), while also preserving this valuable knowledge so it’s easier to train the next assistant if your virtual assistant ever moves on or ends up not being the right fit.


5. Develop a strong relationship
One of the biggest issues I see when it comes to developing a successful virtual assistant relationship is that a business owner usually knows they need help, but they’re afraid to give up their control. It’s understandable. When you hire any kind of assistant, they might be handling your customer information, your schedule, and maybe even other confidential details like financial information.


That’s why it’s so important to find a virtual assistant who isn’t only good at their job, but is a good match for you, personally.


Building trust in a virtual relationship can be a challenge, especially because you’re not sitting next to each other every day making small talk and learning about each other’s work styles. As a result, you need to be more deliberate about cultivating that relationship. Take the time to get to know your assistant, provide ongoing feedback, and be sure to ask them how you can make their life easier as a manager.


Don’t underestimate the cost of not hiring help
If you had five more hours in your week, where would you invest them? Would you complete more billable work, up your creative output, or dig deeper into the projects you’re passionate about?


How much more revenue could those hours create?

How might they help you grow your business and increase your impact on the world?

Alternatively, if you don’t need the support for your business, how much more balanced could your life be?


Whether you’ve worked yourself to the point of health problems (guilty!), constantly checked your email on date night (guilty again!) or are simply staring at a sunny Sunday morning wishing you could go for a hike rather than sending invoices, you know the cost of not asking for help when you need it. It doesn’t have to be difficult and it doesn’t have to be scary. Remember: The amount that you’re able to grow depends on the amount you’re willing to let go.

About This Author
Jess Tyson is the proud Director of Calm at Don't Panic Management, the first virtual assistant agency to embody a people-first approach to virtual assistant success. Since 2011, she's been making matches between chaotic, overworked entrepreneurs and focused, calm virtual assistants. Offering services that span from administrative assistance to marketing support, she finds deep joy in making a difference through service. When she's not speaking, writing, or researching productivity hacks, you can find Jess trying new recipes, tasting wine, searching for the next great music festival to attend, or playing with her labradoodle, Hummus.