Drowning in To Do's? How to Figure out What to Outsource

I’m drowning in To Do’s. I need to figure out what to outsource stat to keep my sanity and grow my business.  I can’t get to the big stuff to bring in new clients, create courses and all the publicity things I should be doing (hello, interviews and guest writing).  I’m ready to hire out, because something’s gotta give.

How do I look at my business To Do list with a critical eye and figure out what to outsource?  

Flashback to your English class days and the 5 “W” and a “H” questions (Who, What, Where, When, Why and How) give you all the information you’ll need. Who knew it could be so simple!

Here’s another approach you can use if you want something more complex that focuses specifically on sales and operations.

First we’ll start with WHAT do you need help with and WHY. Dive next into WHO is the best type of expert or organization to help with it and WHERE do you need them to be, WHEN are you going to need support and how much, and finally HOW you’d prefer to work.   

How to figure out what to outsource and what to hire out


WHAT would you hand off to someone else to do and WHY will it help your business.  Before you hire a single person to do anything for you, know what you’ll want them to do and why it’s important to either saving money or time, increasing sales or quality.  If it saves you time, estimate how much.  Does it mean you’ll never miss collecting payments from any of your clients? How about more visibility and revenue from pitching places to interview, guest post or connect for a JV webinar.  

The WHAT is as important as the WHY to figure out what to outsource.

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This is the really the foundation of hiring and contracting the right talent.  If you don’t know what activities you need expertise and support with, and why it’ll benefit your business, you’re just throwing cash in the wind. Throwing cash in the wind means your chances of success are worse than roulette which is nearly 50/50 so you might as well just hand it to a stranger on the street.


Once you have what to outsource outlined and why it’s important for your business, it’ll point you in the direction of WHO is the best type of expert for the job.  Obviously there’s the easier things like finances. If you barely keep up tracking your sales and expenses with a half completed spreadsheet and a stash of crumpled receipts, you should look into hiring a bookkeeper or at least getting a bookkeeping system.  

What about some of the tougher things? Making your launches more effective to generate more sales. Managing your team is sucking hours of your day. Making changes to graphics or creating templates. Onboarding and offboarding your fabulous clients with TLC so they feel special. Here’s where it gets tricky.  

Consultants & Coaches:

If you look at your list of what to outsource and see things where you need someone’s brain for strategy (aka figuring ‘how’ to do things better), a coach or consultant is the best way to go.

Online Business Managers (OBM):

If you need someone to take on overall management (keeping your business run like a well oiled machine) for all parts of your business including your day to day team, consider an OBM, Online Business Manager. It’s like a ‘mini me’ who directs the operations “behind the curtain” so it looks and feel easy for you.

Virtual Assistants (VA):

If you need straight up, get it done, execution support, a VA or virtual assistant of the general or specialized variety might be what you need.  How to find the right type of VA? Group WHAT to outsource into common skill or theme categories.  Group together activities for customer service or business administration like onboarding, offboarding, invoicing, payments and contracts. Group writing and scheduling activities like emails, newsletters, social media and blog posts.  Public relation activities like guest posts, interviews, joint venture webinars have a similar nature and skill.   

By grouping activities into similar activity categories will help you get headed in the right VA direction. You’ll need to keep asking questions because some VAs have expertise in more than one area and others only specialize in one. You might find a VA who does social media and customer care and a VA that only does newsletters.


You know what to outsource and who would be the best type of expert to tackle those things slowing you down from growing. Next, think about WHERE you need your experts to be located.

Think about timezones and the way you work.  Outsourcing abroad might be a good fit if you are you looking to save on expenses and work mainly by email.  Do you need to be able to connect by video or phone to chat live frequently? Look for experts closer to your own timezone to avoid calls in the wee hours.  If you like to meet in person regularly, you’ll need to look for experts in the same state or even city.  Think extra hard about what you’re outsourcing and if it really requires someone to be physically close to your location. It does limit your options and likely, it’s a ‘nice to have’ not a ‘must have’ requirement.


Yes, you’ll need to know WHEN you need the work done. Is it a single project with a due date or continuous help with a certain number of hours every week or month? If you’re not sure how many hours you might need, pull together your ‘what to outsource’ list for that role with details or samples of what would need to be done and ask how long it should take.   Asking about available hours or deadlines will be an important question to ask when you evaluate potential contractors. If they have longer than usual timelines or so many clients they only have 2 hours available a month,  you’ll need to go back to your list of potential contractors.


Your working style. HOW do you like to work with other people. Jot down how you expect to work with potential team members.  Make a note if there are differences based on the role they play. You may need to have discussions less frequently with your web designer than with your VA or OBM who’s providing hours every week.  

Even if you’ve never hired out work before, consider if you like talking by video, phone or emailing more.  Do you like to use systems and tools to manage your work. Will you expect a potential contractor to work in your project management system.  Write down how you like to work and share it during the evaluation process and again when you hire.  Knowing how you work will making your contractors experience more success.


  • what to outsource

  • why it’s important to your business

  • who’s the right expert for the job

  • where do these experts need to be located

  • when will you need them; and

  • how will you work together.

So get to work and stop drowning in your To Do’s! A solution is ready for you on what to outsource to make life feel easier and help your business grow.

Leave a comment where I can help you with what to outsource or any of the other "W" and "H" questions.

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