Written by: Kary Glawe, WISE Sr. VA Lead and Project Manager

In 2020, many of us learned a great lesson: We can’t do it all. As much as we may think “I’ve got this,” we often get a healthy dose of “nice try” back from the universe. Learning to focus on which parts of your business truly require your active involvement can be the key to growth. Do what you value, what you excel at, and what is vital to the core of your business success. The rest can be outsourced. 


Are you thinking, “That sounds great! I do need to outsource...but how do I do that?” 


Many people don’t know where to begin, but, you’re in luck - it’s one of our favorite topics. One of the highlights of my role at WISE is taking business owners from “how exactly do I do that” to “I’m rocking this outsourcing” stage.  


Here are a few actionable steps to get you started so that you can outsource successfully this year. 


Determine Your Why


The very first step to successful outsourcing is determining why you want or need to outsource. 

  • Do you want to earn your time back? 
  • Do you or your team lack certain skills? 

Imagine your ideal scenario and write down some tangible goals. 


Start Small


You don’t need to overwhelm yourself thinking about all of the items that you can outsource. 

Start with a list of 3. Just three. Once you are in the groove of outsourcing, you can add more. However, it’s always best to start small with a few obtainable goals. 

When you create that list, consider the following:

  • What tasks do you need to accomplish that are outside of your skillset? If there are multiple, that’s okay! Prioritize your list by looking at which ones are the most important or timely, which take up most of your time, and which would be the easiest to pass on. 
  • Do you need help with ongoing tasks or is there one project that you’d like to tackle?
  • Are there any repetitive tasks that take time out of your day/week/month? Anything that’s predictable and recurring is VERY outsource-able. This is your “low hanging fruit” and a great place to start. 


Determine Your Budget


You need to know your budget for outsourcing. It can be a range, but you do need a tangible number each month that is aligned with your financial goals. 

This is an area that can stump even the most experienced business owner. If you’re stuck on this step, don’t give up. Our team offers Advising services and can help you develop your plan. 


Choose Your Team


There are a few things to consider when choosing a team to outsource. Regardless of who you choose, you should always ask for references, read reviews, request a portfolio of work, and have a discovery call. (A discovery call is a tool used in sales to establish a relationship with a potential client." I think it would be awesome if there were a description of what a discovery call actually is in the copy.)

Consider if you’d like to go with an agency or hire individual freelancers

Many of our clients choose to work with us because our agency offers a full package. WISE manages the project and team members. 

When considering individual freelancers, it’s important to be very honest with yourself. Do you like managing people and do you have the availability to communicate with an additional number of people each day? 

The Balance Small Business gives some great tips on outsourcing success, and many of them highlight the importance of selecting your team. Making your selection can be crucial to the success of your project. 




Once you have determined what tasks to outsource, have chosen your team, and signed a contract that fits within your budget you’ll need to onboard your contractors. This can be another area where business owners can “freeze.” 

In this situation, hiring an experienced agency can be a huge “hidden value” to your business. A team with onboarding experts can take you from the contract phase to the implementation phase with ease. 


Set Expectations


During onboarding, it’s vital to set expectations. 

Expectations can be for work and due dates of course, but it’s also vital for all team members to understand:

  • The scope of work
  • How communication will flow
  • Who is responsible for each task 

It’s very helpful to explain your goals so that the team completing the work understands exactly what you are looking for and the purpose of the work. 


Grow, Pivot, Grow, Succeed


Outsourcing is a continuous activity. The word “outsource” is a verb, after all. Once you have successfully outsourced your list of 3 items it’s time for a review. 

Consider what’s going well, what can be improved, and what other items you can outsource to strategically grow. 




If you’d like to continue the discussion on Outsourcing, wikiHow has a very informative piece with some great tips. 

If you aren’t ready to outsource, but you are struggling because your email is out of control… then it’s time for a change!

Download this Email Inbox Clean Up Guide and go from overwhelm to “Oh, Ya!” Take your email inbox from overflowing to owning it!


As we continue into the unknown of 2021, remember to consider why you want to earn your time back, starting small with just three items to outsource, determining your budget and team, and setting expectations when considering outsourcing. Next on your to-do list will be to schedule a Discovery Call with a WISE Expert today! 


Headshot Kary Glawe 1500x150

Kary Glawe

WISE Sr. VA Lead and Project Manager
Kary, a Project Manager at WISE, has over 12 years of administrative experience. She utilizes her office management experience to help our clients refine and stick to processes that set them up for success. Kary has recently earned her Project Management Professional (PMP) ® Certification and thrives on creating clarity in the chaos for small business owners. Kary enjoys exploring each new duty station that the Air Force provides, with her husband, son & two cats. She's currently learning to speak Spanish and has recently developed a love of running.