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The first time I hired an assistant did not go as planned.   I was busier than ever, and naturally I thought there would be tons for them to do. After hiring the assistant, I was at a loss. I had no clue what tasks would be best to hand off and had trouble letting go of my hold on my work.   Fast forward ten years and I’ve worked with myriad assistants: on-site, onshore, offshore, full-time, part-time, dedicated, task-based. We’ve hired through eLance, UpWork (formerly oDesk), Indeed, Craigslist: basically any and every job board in the world that doesn’t charge $800 a posting.   My eventual success with that first assistant (and every assistant that’s come since) was a result of shifting my mindset. I want to share with you what I’ve learned so that you can bypass the problems I had.  

Lesson #1: Realize you’re already outsourcing.

You outsource things every day. You trust an accountant to do your taxes, an attorney to handle your legal matters, a doctor to take care of your health, a cook or chef to make your food. You might not think of these people as “assistants,” but reframing your perspective on what you already outsource will help you get comfortable with outsourcing more.   “Sure,” you might say, “but those people are experts. It’s different hiring someone to do something I already know how to do.”   Is it?   Would you hire someone to clean your house? What about to drive you around?   Most people know how to do those things but aren’t bothered by hiring a cleaning service or booking an Uber. Hell, your Uber driver might actually be a worse driver than you. And that’s exactly the point.   Trusting someone to do a good enough job is what frees you up to focus on more important things. Which brings me to…  

Lesson #2: Get over your ego.

It’s easy to see the value in hiring someone who’s better than you at doing a task to do that task. Where most people struggle is hiring someone who’s worse than themselves. We get hung up on wanting every detail to be perfect and lose sight of the big picture in the process.   If you want to understand what’s to be gained by getting out of your own way, visit the kitchen of a successful restaurant. Is the head chef better at slicing onions or making a red sauce than everyone else in the room? Yes. But they aren’t wasting their time with that. The head chef is the head chef because they have vision. They put their creative energies into inventing dishes and developing menus, and they let their staff handle the implementation.   As long as someone can do your work 70–80% as well as you can, that’s good enough to let it go. The tradeoff for that 20–30% imperfection is more time to focus on the visionary work that only you can do.  

Lesson #3: Walk before you run.

The first two steps will help you reframe your mentality and open your mind to the possibilities of what can be outsourced. That said, there are bound to be bumps in the road when it comes to hiring an assistant for the first time. Dumping a host of complex, high-stakes tasks on your first assistant is an invitation for disaster.   Starting slow is actually less about whether or not you can trust your specific assistant to do quality work and more about building your trust in the process of outsourcing. If your first experience goes poorly, you’ll be tempted to give up on the whole idea of an assistant and continue grinding yourself down with menial work.   Start small with internal, non-customer facing tasks: CRM data entry, or compiling spreadsheets for sales reports. The first thing you’re going to realize is that you need to do a lot of teaching. Initially this is going to feel like more work—you hired an assistant take things off your plate, not so you could hold their hand through everything!   But it will force you to create processes for your work. Once you start recording how you work (I like video captures, but pen and paper checklists work just fine, too), you’ll realize how many things you’ve tricked yourself into believing only you could do (see Lesson #2).   Over time, you’ll start learning to record tasks and bundle them off to your assistant after the second or third time you do them, rather than waiting until the fifteenth or twentieth time.   As you and your assistant get comfortable working together, you’ll get better at providing them with the right tools for their success and you can start handing off more complex tasks, including those that involve interacting with customers.  

Lesson #4: Remind yourself why you’re doing this.

If you’ve been with your business from the ground up, every little thing you’ve done has been vitally important, making it hard to let go. But you didn’t work hard to watch your business stall out at its current level of success.   There’s no way to retain control of everything and keep growing. The mindset shift around hiring an assistant is so difficult precisely because it marks a new stage of growth in the life of your company.   Take a step back and remind yourself of your primary goal. My push towards efficiency is always about one thing: living a life I’m in control of. Paradoxically, that has meant learning to let go of more and more.   (Remember letting go doesn’t mean not paying attention. To learn more about feedback loops and keeping track of things post-outsourcing, take a look here.)

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