Hi Reader!

Hey hey, it’s my birthday! Thank you for all the sweet messages! I took some time off this weekend to relax and am headed to the Art Institute and out for gelato as soon as I hit publish on this email!

So let’s get to it! Today, we’re continuing our October content theme around outsourcing. Specifically, we’re talking about best practices for actually WORKING with your freelancer or new employee. The biggest thing I had to learn when I started outsourcing was how to get my *ish together enough to effectively communicate my needs to my assistant. So here are a few things I learned along the way!

I hope that’s helpful for you! Happy reading while I’m off to the museum!!

Most of the time, at least as a small business owner, we outsource because we’re all over the place, and we need some help getting our *stuff* together. The ironic part is that in order to effectively work with a freelancer or virtual assistant, we need to have our stuff together!

That is by far the hardest thing about getting help, or using the help you have. You need to tell them how to help you. They can’t read your mind! Outsourcing takes a lot of planning, and it’s not going to magically solve all your problems. But when handled well, it’s worth it. I’ve learned this first hand, so I have some tips on what’s helped me have a great working relationship with my assistant.

Decide their responsibilities

The very first thing you need to do is figure out exactly what you’ll be outsourcing. You probably had a vague idea of this when you were hiring, but now is the time to get specific. What tasks will they actually be doing?

This step can be difficult when you’re SO overwhelmed and there’s SO much on your plate that you can’t think straight. Well, friend, you need to set aside some time to think straight. Sometimes you need to slow down to speed up, and this is exactly one of those times.

Prepare their access

Once you’ve decided what you’ll be delegating, you need to figure out what kind of access they’ll need to complete their tasks. Which programs and accounts will they need access to? Will they be getting their own username and password, or are you giving them yours?

This will take a second, but set aside the time to get all of these things in order. Set up a document or a portal with all the necessary information they’re going to need. Actually think through the task - are there any programs that you forget that you use? Create a shared drive for them. It’s going to seem like a lot, but trust me, it’s MUCH easier to do this on the front end than for them to be stuck waiting on you to give them access when you’re busy doing something else. You don’t want to be the bottleneck – it only hurts you and your business!

Create a standing meeting

Set up a standing meeting, whether it’s daily, weekly, or biweekly, to cover what you need. Treat this like any other business meeting with a client - after all, you are your freelancer’s client. Having a standing weekly meeting with my assistant has been a complete game changer, not just for us working together, but for my business as a whole. Not only does it facilitate regular check-ins and give her a chance to ask questions or clarify things with me, it also gives me a deadline for when I need things prepared for her. This keeps me more on top of my stuff, and it keeps us both on the same page.

And here’s another tip: if you don’t have time to think through your assignments before your meeting (which is a semi-regular problem for me), take the time DURING the meeting to talk it out. If you’ve hired the right person, collaborating in real time can sometimes create even better ideas than what you would have come up with on your own.

Communication, communication, communication

Open lines of communication are by far the most important part of any working relationship. I would advise determining the best method of communication between you and your assistant, which may be different for different circumstances.

It’s important to set healthy boundaries around this, on both sides. No one wants to feel bombarded, and no one wants to feel like they’re bombarding someone else. When do you both prefer email vs. text? When is a phone call better? Do you (or they) prefer a lot of little emails or one email that has everything in it? Start by communicating ABOUT communication, and then keep it going from there.

One last thing I’ll mention, specifically in the area of social media and content creation: be very clear about when you want final approval on things and when you don’t feel like you need it. This may change over time, but it’s important to be upfront about it.

Finding the right assistant or freelancer can be one of the best things to happen to you as a small business owner, but there can be a steep learning curve if you don’t know how to handle the working relationship. I hope these tips are useful as you continue your outsourcing journey!

What other recommendations do you have for people who want to work with freelancers? Let me know your thoughts!

More insight into working with freelancers...

• ​How to Build an Amazing Working Relationship with Your Virtual Assistant​
• ​LinkedIn's thoughts on the topic​
• ​6 Ways To Develop A Good Relationship With A VA​
• ​7 tips for getting the most from your virtual assistant​

2235 N Saint Louis Ave, Unit 2, Chicago, IL 60647
​Unsubscribe · Preferences​