Ultimate Guide to Outsourcing in Online Business

Welcome to the ultimate guide to outsourcing for your online business! I started this post with the idea that I’d list a number of things you can outsource for your business and how to get started,  but it grew and branched out like a mighty oak from that acorn of an idea.

At over 4,000 words, I’ve created a resource that should serve you for many years to come.

The first time I hired for my business, I went with a virtual assistant service based overseas (in order to get the lowest possible hourly rate). Typically, these services charge a one-time fee on a packaged number of hours, and then a dedicated virtual assistant is assigned.

I first considered this approach way back when I read The Four Hour Workweek by Tim Ferriss, but if I’m honest, I jumped the gun and bought my first virtual assistant package after reading (and laughing through) Where’d You Go, Bernadette? 

It proved to be a complete waste of money; the virtual assistant was faraway and unfamiliar with both the industry and my work. I spent more time trying to come up with things she could do, and without a long-term commitment or nondisclosure agreement, I certainly wasn’t going to share passwords or other sensitive materials.

This first arrangement actually derailed and distracted me from my goals, but I learned so much because of it. Through trial and error, I’ve since perfected hiring down to a science.

When it comes to staffing, I have a different outlook than most. As a creative business owner myself, I know it’s hard to give up control on the little details that make up the work you do every day. It can also be nerve-wracking to take on the added expense. Today I’ll show you how to hire in a way that alleviates both of those concerns.

Ultimate guide to outsourcing online business

The next time I hired, I was much more established in business. I was looking to hire an assistant who would eventually become a virtual office manager for my business. I created a detailed outline of whom I was seeking, letting all who saw the want ad know what the work would entail and who would be the ideal candidate.

In truth, there was a specific someone I hoped to hire: a Luminaries Club member named Kara (AKA the Insta-famous Boho Berry). I wrote the help wanted ad with her in mind. She was the first to apply, and the one who ultimately got the job.

Then, I wrote the material for what would become Mistakes in Hiring, Chapter 2. During my first experience with hiring from the virtual assistant service, everything was too vague and generic. While I had a much better jumping off point the second time around, my training plan was way too specific and over-detailed.

When I hired Kara, I spent weeks training her on the backend of my entire operation. I mean, I went over everything.  Within a few months, we parted ways (in the most mutual and loving agreement). We did meaningful work together during that time, but I’d wasted weeks training her on unnecessary aspects of my business.

As the saying goes, third time’s a charm. Next, I’m going to teach you everything I’ve done right since then.

A quick disclaimer

Too often you get caught up in doing for doing’s sake in online business. For instance, you might make products even though your current inventory’s not moving (making for making’s sake), post status updates online even though what you’re saying isn’t connecting (marketing for marketing’s sake), email because you know you’re supposed to (emailing for emailing’s sake), and research everything you can find online to try to make what isn’t working work already (training for training’s sake).

This is not an article about hiring for hiring’s sake … never hire because you heard you should –or– it seems like everyone else is –or– you’re simply overwhelmed by a lack of schedule –or– you’re never sure what you should be doing next, so you’re doing everything for doing’s sake, and you want to delegate some of the doing to somebody else.

If you’re at all lost in logistics, or if you find yourself chasing different business advice all over the map, it’s too early to hire. Save your money and the enormous chunk of time and energy it takes to feed your hire’s position (more on this to come!), and focus on your future strategy for success.

Create a customized task list

Here’s the way to create an extremely customized outsourcing list for your operation. To start, think of every task you do each week—your responsibilities in both your personal and professional life.

Next, organize all of your weekly tasks into one of three categories:

  1. Work that creates income
  2. Busywork to maintain your business
  3. Your household responsibilities

Then, decide which items you want to continue and which you’d like to eventually delegate. Here’s a sample of my weekly tasks, organized into the 3 columns:

Life and business task list: ultimate guide to outsourcing

As you can see, I organized everything that is my responsibility into the three aforementioned categories. In this bullet journal spread, I decided which tasks I want to continue (marked with a closed dot), which tasks I would like to give up (marked with an open dot), and which tasks I’ve already delegated (marked with an x).

Your first hire

I love what I’m going to say next! I’m bursting at the seams to share this indulgent advice because you are so worth the valuable time and energy it’s going to free.

Contrary to a lot of advice on hiring, I suggest you first delegate the tasks that are easiest to give up, such as the housecleaning. The hiring process for household help is simple—at most, it’s an interview, a reference check, and a brief discussion about what areas need covered. It gives you a chance to communicate and manage terms of employment. And from there, you let the pros do their thing.

No training necessary.

Training an assistant for your business is time-consuming. Even worse, you’ll have to walk away from income-generating responsibilities at the very moment you take on a new expense. It’s not the most comfortable transition; again, why I love the housekeepers! Let them free up a few extra hours of your time each week, and use it to work ahead and cover your absence before you hire for business.

The many benefits of outsourcing

Regardless of whether you hire a housekeeper to add a few extra hours to your schedule each week or jump right in and find your first assistant, hiring should greatly increase your profits.

As your business grows, so will the income you earn with every hour invested. The typical start-up mentality (“I must do everything myself!”) can quickly bottleneck your business’ growth, as it did mine. This means that something you create is very valuable to your customer (thereby generating a substantial income), and you’re trying to do it and everything else on your business to-do list, all by yourself.

Using your life and business task list …

Identify your #1 income-generator, and then calculate how much you earn per hour you spend on that task. When the amount you earn on your #1 income-generator exceeds the cost of outsourcing other tasks, it’s time to hire.

For example, my number one income-generator is content (in the form of courses, books and training). Consultation is a close second. When I’m doing either of these, I generate substantial hourly wages. Content is my zone of genius, and all the busy work that dominates my day is better delegated so that I’m free to create more of it.

Outsourcing forces you to prioritize your task list and focus on profits and gain. We are in business, after all. It’s not just about loving your work and pursuing your calling. To do more of what you love, your business has to always earn a healthy profit.

When you hire, you take on a new expense that will force you to look at your to-do list with new eyes. In online business, we often get so caught up in the day-to-day agenda that we fail to calculate projections for future growth. More often than not, you probably find yourself flying by the seat of your pants.

Even my most successful, six-figure earning clients admit to doing this!

When I finally hired my long-term assistant and right-hand woman, Jennie, the first thing I did was sit down with the “money list.” It was a detailed itinerary of all the things we were going to complete together in order to make my business more money this year.

Another benefit of outsourcing is that you’ll create constant progress toward completion. In my early trial and errors with hiring, I’ve let the assistant get ahead of me on the work load. I quickly found myself racing to catch up so that I could give her more work to do, which always left me wondering, “With the way I have this set up, who’s working for who?” It truly felt like I was always working to give the assistant more work!

The way we’re set up now, Jennie always knows what to work on next. She follows the money list.

Things to Outsource

Here’s just a sample of the many tasks you can outsource for your business …

  • shipping and handling (products)
  • blog setup
  • storefront setup and updating
  • video editing and production
  • promotional graphics
  • webinar moderation
  • accounting
  • customer support
  • text editing
  • product creation
  • photography
  • transcription
  • tax preparation
  • branding and website design
  • website development
  • office organization and cleaning
  • business management
  • social media management
  • show and event planning

Important to note: All of this requires training on your very specific operation, I know. If this is a new concept to you, teaching another person #allthethings you do probably feels overwhelming, and even maybe not worth it … right? Wrong.

I’m here so you can make your training as efficient and productive as humanly possible while avoiding all the costly mistakes I made while learning how to make training as efficient and productive as humanly possible!

When Jennie started, I trained her on one very specific topic at a time. We started with webinar setup and moderation. I take a screen recording of our training sessions, and we store them in a Google Drive shared folder. Should Jennie and I ever need to part ways, I’ll know the exact duties of the replacement and have all of the training materials at the ready.

In fact, Jennie and I aim to build somewhat of a new employee manual to have at the ready should I experience another unexpected growth spurt that causes us to expand. With the training library we’ve built, Jennie can train the new hire, and I won’t miss even an hour of income generation!

The Hiring Process

The first time I hired, I wrote an in-depth want ad on my blog. I chose a self-published announcement (blog post) versus sifting through virtual assistant search results because I was determined to hire someone who already had a working knowledge of (and mutual passion for) my mission.

If you look at the ad, it very specifically states my desires and needs. I wanted the post to be shared around because I was open to hiring someone who didn’t yet know my work, but who was willing to do the necessary research before applying.

When you hire, you’ll likely seek a very detail-oriented applicant. Secretly test for that virtue during the application process to save time!

The next part of my application required 3 things:

  1. To apply, submit your application through the linked form
  2. Let me contact you if I want to request an interview
  3. (In the form) Tell me two things you’ve taken away from my articles/products

I will only hire people who can follow simple instruction and work independently, so if they didn’t follow the first two simple instructions + prove they were familiar with my work by answering the third requirement, I wouldn’t even consider their application.

My friends, I can’t tell you how many people saw the post and promptly emailed to ask me how to apply. Or wrote to tell me why I should hire them. You wouldn’t believe how many people left the specific questions about my work unanswered on the application—I mean, it only takes a few minutes to do the research!

This process told me so much more about my potential hire than any interview ever could. I highly recommend creating the same application process for your business.

Example Working Relationship

As I said, Jennie and I structure our year around my “money list.” Here are a few items that have been recently completed from that list …

Jennie works 20 hours per week on my business. When she started, I asked her for a typical schedule: what hours can I expect you to be working on my business each day? While I’m somewhat flexible, this helps me understand when she’s available to me (should I need a fast answer) and when I should expect work or progress updates from her.

Communication like this is key. 

Jennie has a series of daily rounds she makes for my business, and she typically takes care of these tasks first thing in the morning: ship Etsy orders, manage my various Facebook groups, and answer any customer support queries or billing issues.

I like to keep my operation lean and mean, so I’ve already built my system to operate, sell, and support my clients in my absence. If you’re hiring to help manage all of the admin you can never get on top of, you might want to reevaluate the system, resolve the reasons so many people need to contact you, or restrict or reduce access to yourself altogether.

Do you think that sounds harsh?

I liken my business to a doctor’s practice. Imagine an experienced physician—studied, trained, and skilled—answering her own phones, recording new patient information, monitoring each person’s blood pressure and temperature, taking her own notes and records, and doing the billing at the end of each appointment.

Would you respect her expertise more or less for it?

How about if you had her email address and felt entitled to ask questions, send comments, and make requests on demand? Just because you’re in online business does not mean you need to have an open-email policy. Professionals need to set boundaries and reserve their time and energy for paying clients.

But, I digress.

Jennie isn’t paid to handle a large amount of questions, requests, complaints, and customer issues because they’re a rare occurrence. I’ve built a system that delivers and satisfies. Instead, she finishes her daily tasks and works with me on income-generating projects from the “money list.”

From the above bullets, Jennie was editing Marketing Playbook while I was building sales materials for my coaching concentrate, The Summer Shift. I needed no assistance with the launch, but she’ll attend each private one-on-one session to record action items and follow-up with my clients.

Once the Marketing Playbook file was complete, she reformatted the entire thing for both the print and Kindle versions. In the meantime, I filmed a course for the The Luminaries Club. We taped the course with a live audience, and in between Marketing Playbook formatting, Jennie moderated those webinars.

As I start the next project (Your Best Year 2018), Jennie will edit the videos of all eight modules I just taped, design the workbooks, and update the course pages inside the club. By the time she’s finished, I’ll be sending her early drafts of Your Best Year 2018 to edit.

And when I don’t have a current project that takes priority, Jennie is hard at work combining some of my former classes, programs, and training into the next book I’ll launch. The last time I saw the project, it was over 100 pages already. It’s my book, it’s halfway done, and I haven’t even opened the document yet!

Imagine that.

In fact, her independence on this project has been a key ingredient to our success. Entrusting Jennie to produce one of the items on the “money list” tested both of our comfort zones. Since she’s not familiar with the material, she had to go back and gather it all, read or watch every single piece of training, and start to organize it into a new book. It’s not easy, and she was definitely overwhelmed by the idea at first. That said, there was simply no better way for her to fully immerse herself in the business and learn my process than to have her tackle a big project by herself.

In the process, I learned to trust her to figure it out (and not micro-manage or over-prepare the workload). Plus, I sleep better at night knowing she always has something to work on if I fall behind deadline.

With our system, one of us is always starting something new while the other wraps the last thing. Once Your Best Year 2018 launches, I’ll take my book that Jennie’s been building across the finish line while she sets up our upcoming podcast! It’s the perfect alchemy of production and completion.

Common Pitfalls to Avoid

Yes! This post is still going because it would be remiss of me not to include some common pitfalls to avoid. Take the following list into consideration before you hire.

Clearly define work hours, policies, and an outline of duties expected. I also recommend adding your own “money list”—let your hire know the events or projects that you’re going to roll out a year in advance. (Use Marketing Playbook to help you identify these.)

This outline will help you understand when your hire is working for you, and it gives them a checklist to refer to when they find themselves not knowing what to do next.

Be crystal clear in your delivery, expectations, and requirements. With a lot of emails racing back and forth between you two, things will become open to interpretation if you don’t specifically state what you want. Being indirect or indecisive is a recipe for disaster, so any communication that’s been misinterpreted must be corrected promptly.

I respect Jennie’s work, and I genuinely like her as a person, but I’ve always been very upfront that this is business. There’s nothing I won’t approach her about, and if I find myself thinking twice about anything she’s done, I open an email, tell her how I feel, and ask very direct questions.

I love to know where I stand with people, so in my opinion, the best thing I can do is always let other people know where they stand with me. It is all too easy for resentment and tension to creep into a relationship where there’s no communication, and there’s no room for that kind of energy in my schedule!

Do not over-prepare your hire’s workload. My best example of this is one involving my bi-weekly housecleaning crew. When they first started, the lady in charge asked me if I wanted them to change the bed sheets each week. I did, but at first I didn’t have all the fresh bedding I needed to cover the change. I used to just launder the sheets and then put them back on the beds.

This felt like such a rich luxury, having all of the bedding changed for me! So, I went out and purchased enough sets to cover all the beds, and the next time they came, I had laid out all the replacement sheets in matching piles for every bed in my household.

This is where things get funny, but don’t laugh at me because it will happen to you, too! For every housecleaning, I had chores to do. I had to make sure all the sheets in the house were sorted and arranged in front of the appropriate beds. One time when I forgot, so did they (or thought I didn’t want them changed because I didn’t lay out the materials), and I wound up doing the work I was paying someone else to do better!

Over-prepping trains your hire that they need your involvement to get tasks done.

We had a talk, and now my housecleaning crew finds all the clean bedding in an unsorted, badly folded pile in my towel closet each visit. Now, having our bedding changed is the rich luxury I’d imagined it to be before I started over-preparing their work.

This is similar to having an assistant and researching the issue before delegating it. Your hire is more than capable of researching the issue. If that worries you, consider offering them a time cap (so researching doesn’t go on longer than necessary) and some suggestions on where you’d start.

I recently found myself in the middle of travel arrangements gone awry, fussing over the drama of the situation, losing time and money in the process, and wishing I’d put Jennie in charge from the get go. When in fact, I hadn’t involved her because it never even occurred to me to include her on the planning. Had she managed the details, it would have turned out much more pleasantly and hassle-free.

Delegating work daily, or even weekly. This is a huge mistake. Your hire will quickly catch up on your task list, and you’ll be racing to feed their position. As I’ve said, work off of a “money list” or list of priorities that only need reviewed occasionally.

Jennie and I are fortunate to live in the same state, so we meet quarterly to do big picture planning. We share project status updates, I tell her where I see us headed for the coming quarter, and we each walk away with a notebook full of plans.

Close your court to ball return. This one is vital for my wellbeing and sanity! I’ve been in professional relationships where the ball is always being hit back into my court. As in, I hire someone to do a job, explain in great detail exactly what I want, and throw them the ball.

But it keeps coming back like someone turned on the ball return machine.

I hire for two reasons and two reasons only: (1) to earn more, and (2) to buy solutions. Habitual ball returners provide neither (without tons of hassle) and cost way more than just money. This one’s hard to explain because it’s more than just conversations or examples. It’s a passive-aggressive dance. It’s a delay on promises. It’s someone making you work for them when they should be working for you.

It’s them saying, “I don’t want to work on this right now, so I’ll email you a line of questions that are unnecessary to the project’s progress to make you think I’m working on this right now.” Your hire’s job is not to return the ball like a game of tennis, but to catch it and turn it into either more money or better solutions for your business.

A ball-returning hire is the inverse of you over-preparing the workload, but with the same end result. In the first scenario, they train you to be available when they work for you, in the second scenario, you train them to need you in order to work. Both are equally bad and incredibly frustrating.

Your hire should always feel like a rich luxury that supports you. I love taking the afternoon off once and awhile, knowing Jennie has my back and can handle anything in my absence. I love going for a run when the housecleaning crew arrives, knowing that when I return my house will feel fresh and clean.

People who are hired to support you shouldn’t need your constant support.

Know your seasons. Have a working marketing calendar before bringing anyone on. Hire and train before it gets busy, and aim to get the most bang for your buck:

How can every one hour of training take at least four hours off your plate each month?

Hiring should offer a huge return on investment and bring great relief; the only way to make it so is by doing it with a game plan for highest return and maximum efficiency.

Tell Me: What’s the first thing you’re going to delegate?

Please leave me a note in the comments and tell me the first thing you’re going to delegate – OR – share the delegation you’ve already made that makes you feel most indulgent.  I can hardly wait to read your ideas!

Here’s to your success.

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7 comments

  • A year and a half ago, I hired someone to redo my site and create a new logo. She did such a good job and was so so efficient that I have continued to work with her. I can call her anytime things aren’t working on my site or if I need to change things. Hiring her to do these things is such a necessary luxury after ten years of doing all of the backend stuff on my blog myself!

    As always, this is such a good post! Thank you, Lisa for all that you do for us!

  • We recently hired someone to come in and do our shipping. It was a task that I hated doing, but couldn’t think of who we could hire because we needed someone who lived close to us and didn’t mind coming in for just a few hours a week. We found the perfect person (and she lives practically next door!) and it’s going so well that I’m feeling ready to hand off more tasks to her. Inspiring, as always. Thank you Lisa!

  • This was a really helpful post, Lisa.

    I’m a visionary but a terrible manager of people. Business is doing quite well but I’m burned out and I just cannot for the life of me work out how to hire and train the right people online through sites like Upwork.

    It always ends up being more trouble than it’s worth and I get so frustrated at bad hires that I go back to doing it all myself.

    You mentioned you do consultations? Would you be available for call/Skype briefly?

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