top of page

In-House Or Freelance? 14 Questions To Help You Decide Which Tasks To Outsource

Expert Panel, Forbes Coaches Council


Forbes Source:


As your business (and your workload) grows, you might consider outsourcing some work to freelancers. Bringing on freelance contractors has both its benefits and its drawbacks, so you will need to consider which hiring model best meets your company’s needs.


The experts of Forbes Coaches Council know the importance of expanding your business, as well as how to best manage that growth. They shared some questions you can ask yourself to determine whether you should keep your work in-house or outsource it to freelancers.





1. Do we need to reduce costs?

If you can't buy full-time talent, you may rent it. This means outsourcing to competent and excellent freelancers, which could save a company that must cut costs. The risks are that you engage someone who does not depend on you for their main livelihood and may not have the day-to-day loyalty and commitment of a full-timer. Costs controlled? Consider freelancers. - John M. O'Connor, Career Pro Inc.


2. Would our company suffer if our freelancers left? 

Freelancers are great for filling gaps. But when you find that your company is relying on them for critical, time-sensitive tasks, to the point that if they were to disappear, the company would suffer, it may be time to invest in more skilled staff or invest in training for your own staff. Great companies invest in people and your people are worth it. Let them step up, show interest and train. - Mitch Russo, Mindful Guidance, LLC


3. Do we have the margin to do this profitably? 

I see this come up frequently with overworked entrepreneurs. They're overwhelmed, behind and feel like this is the only option to move forward. But often the volume is only high because prices are too low. That's not a sustainable model for growth, long-term success or outsourcing. It's critical to evaluate processes, price and margins. A virtual assistant or short-term consultant may have greater ROI. - Laura DeCarlo, Career Directors International


4. Can our employees' time be better spent if we outsourced? 

If something can be done by someone outside of the company, for less money, it is essential to calculate what employees' time could be better used to achieve. Many organizations have many employees who have idle time. Sometimes specific tasks could quickly be done within that idle time. It is helpful to do some analysis to see where people could best utilize their time. - Dr. Diane Hamilton, Tonerra


5. Is this work consistent or variable? 

Project-based work satisfies a transactional purpose for your business—you get the work you need when you need it. However, this doesn't build the company's value or strategy. The costs can become a pass-through for your business. Ask, "What is consistent work that aligns with our values and core business?" Then ask, "What work is variable and inconsistent?" Variable work equals freelancers. - Joanne Markow, GreenMason


6. Do we need a highly specialized skill? 

One question a company can ask themselves is, "Is the skill I am looking for highly specialized?" If so, hire a freelancer! Freelancers choose to build their entire careers upon their unique strengths or skill sets. Because of this, freelancers are often passionate about the work they do and, more importantly, very highly skilled. With that combo, they can be a true pleasure to work with. - Holly Knoll, Holly Knoll Coaching and Consulting


7. Is this work core to our business? 

If the work isn't core to your business then consider outsourcing it. Be the best at what you do and let others do the rest. Work that's important yet peripheral to your business can be a drain on your time, resources and bottom line. If someone else can do it better, faster and at a reasonable cost, then consider outsourcing. - Heather Backstrom, Backstrom Leadership Strategies


8. Does the work need an ongoing internal owner? 

Consultants often have deep expertise and bring great knowledge, insights and suggestions. Unfortunately, too many consulting reports never get implemented. This might be because the outsider didn't fully grasp the culture, the circumstances or some other internal impediment. It might be because the process owner didn't "own" the answer or may not have the ongoing knowledge to make it work. - Kimberly Roush, All-Star Executive Coaching


9. Can we legally hire a freelancer? 

Before you make the choice between contracting with a freelancer or hiring an employee, ask if you have the choice from a legal standpoint. Your business attorney should advise you about the laws in your state governing labor classifications. You might also connect with an intellectual property attorney to construct an agreement and obtain copyrights to protect your company and work product. - Nance A Rosen, MBA, NanceSpeaks!


10. What will happen to our institutional knowledge when a freelancer leaves? 

Companies must ask, “When the contract ends, will there be a significant loss of institutional knowledge?” If the answer is yes, leadership should develop the skills internally or devise a creative arrangement where the contractor mentors staff, preparing them for future needs. This is a win-win-win scenario for the business, the contractor and employees who want to grow. - Vanita Bellen, True North Coaching and Consulting


11. What does our long-term organizational chart look like?

One thing to consider is the long-term vision for the company. Is this function going to one day be insourced? Why or why not? Outsourcing is more than just a financial decision. You need a vision for the company and its future organizational chart to be able to make this decision wisely. The other thing to remember is that freelancers typically are not nearly as manageable. - Josef Shapiro, Clear and Open


12. How close is the work to our customer experience?

How close is this work to embodying the foundational experience we want our customers to have of us? The experience that's going to lead to loyal, repeat customers and enthusiastic referrals. Why? Because if it's done in-house, you can instill those values into the person doing the work. With freelancers, you have less influence over how that brand experience is created for customers. - Kathryn Gorges, Essentials³


13. Do we have the time to manage freelancers? 

Do my leaders have the time? Change, including freelancers, always means more chaos. Chaos often brings more work to your leaders, because it ramps up communication needs with internal staff to ensure they understand the scope and role of the freelancer. Some teams are also more tolerant of chaos than others, so be sure your staff is well prepared to maximize the freelancer investment. - Dr. Rachel MK Headley, Rose Group Int'l LLC


14. What will best fit our employees' needs? 

Your positive culture depends on your current employees. If work is being done in-house and you wonder if it should be outsourced, meet with your team. Review mission, vision, values, strategic objectives and check in with those who are impacted by this work. What will move you forward better, faster and more affordably and best fit the needs of your team who are already committed? They already know. - Christine Rose, Christine Rose Coaching & Consulting


Article: ©2019 Forbes Media LLC. All Rights Reserved.

bottom of page