How To Hire a Freelancer: 26 Business Experts Reveal The #1 Mistake Companies Make When Hiring Consultants & Contractors

Most business leaders would likely agree that one of most important management goals to have when growing a business is knowing how to attract and hire great talent. This is true regardless of the size of your business and what industry you’re in, and it is also true whether you’re hiring a permanent employee or a contractor. But the nature of hiring contractors is a unique process all on its own that is different from other hiring processes, which is why many businesses fail to do it well.

Whether it is proper vetting and due diligence, clear communication, workflow management, team dynamics, legal matters, or a number of other factors, there are many challenging variables that come into play when hiring contractors that can potentially turn a great client-contractor relationship into a disaster.

As a company that works closely with hundreds of business contractors and companies who hire business contractors, we at Zintro wanted to learn some helpful business tips for the business contractor hiring process, and specifically, how companies interested in hiring contractors can avoid the most common (and avoidable) mistakes that might interfere with all the great benefits of having a contractor work for your business. To do that, we asked 26 business professionals and business contracting experts the following question:

What’s the single biggest mistake companies make when hiring contractors?

We’ve collected and compiled their expert advice into this comprehensive guide to help companies hire contractors successfully. See what our experts said below:

Meet Our Panel of Business Contracting Experts:


Emil LamprechtEmil Lamprecht

Emil Lamprecht is the CMO and Creative Director at CareerFoundry, a vocational training platform for Web Developers and UX Designers. Prior to CareerFoundry, Emil was a contractor for 7 years, and as part of his job would hire remotely contracted teams all over the world for work in media, web development and design.

Whether it is in planning, listing, and clarifying exact expectations (including what happens when things don’t work), the biggest mistake people make when hiring contractors make is…

Not preparing properly.

In the same way its easy to be a bad teacher, and hard to be a good one; being a good teacher takes planning, patience and a perfect instructions. Its very easy to take a loose idea, pitch it to a contractor who will then build/write/design it based on their own general impression, which employers then hope to, after the fact, change and mold to their own. Needless to say, this is frustrating and time consuming for contractors who are often working on a project basis and thus not paid or angry with the extra work. An ill situation if there ever was one.


Carisa MiklusakCarisa Miklusak

Carisa Miklusak is the CEO of her own firm, www.CarisaMiklusak.com, and has over 10 years experience in marketing as a strategist working with over 200 of the Fortune 500 companies. She is also a public speaker and a subject matter expert in emerging media focusing on social media. Carisa has been running her own, successful business for over three years.

I would say the single biggest mistake companies make when hiring contractors is…

Not talking to the contractor about their goals and aspiration (with your company or outside of it) as you would with a full time employee.

Despite the fact they are only working with you part-time, it’s still critical to build this type of relationship, understand their overall ambitions and how your part-time opportunity/ contractor work fits in, etc. This is positive for both your company (as you know what to expect) as well as the contractor and helps to keep everyone aligned and working toward the same goals whenever possible.



Henrik DillmanMattias Guilotte

Henrik Dillman and Mattias Guilotte

Henrik Dillman, CEO, and Mattias Guilotte, CMO, are the founding members of Coworks.com, an invite-only marketplace for outstanding freelancers. The Coworks platform matches clients looking to hire independent contractors with handpicked digital creatives.

When it comes to hiring contractors, the greatest challenge is aptly navigating the exploding contingent workforce and innumerable options available. The single biggest mistake companies make when hiring contractors is…

Failing to understand the scope of management required for a remote team.

When enlisting the help of experts, companies must have a clear understanding of the value of what they need as well as ample tools and capacities to communicate clearly and consistently. The right management for a remote project makes all the difference in streamlining workflow and maximizing productivity, ensuring that an experience with a contractor is as fruitful as possible.


Jennifer MartinJennifer Martin

Jennifer Martin is a Business Coach and Work/Life Balance expert who helps small business owners worldwide understand how to build a thriving business and life they love. Learn more about Jennifer’s work at Zest Business Consulting.

The biggest mistake that business owners make when hiring a contractor is…

Not being entirely clear about what they expect to get from their contractor and figuring it out on their own dime.

Here are some tips to help you get more of what you actually want from your subcontractors.

1. Be very clear about your desired end result. Write down your goal and if you can find pictures that display what you want, all the better. The more senses (see hear, touch, etc.) you can bring on board to help tell your sub-contractors about what you want, the better.

2. If you have had someone else do this piece of work in the past and you were happy with their results, see if you can interview them before you start interviewing anyone new. See if they can tell you what the biggest challenges were and what they wish you would have told them or done to make their work easier.

3. Be clear about how much you can afford to spend to have the work complete and know what your end dates are to have the contracted work complete.

4. Have a contract ready to go.

5. Be prepared to oversee someone new. Make sure that you are prepared to manage another person on the team. They are likely to have some questions and if you want to make your time frame they are going to need some of your support.

6. Give some thought to the 3 most important things are that someone who is coming aboard needs to know about being successful working with you. If you don’t have time for a 20 minute conversation and you just like the facts, let them know.

Then consider the 3 most important things they need to know about being successful working for your organization. If you are a stickler for detail and getting things done on time, your subcontractor needs to know what your “non-negotiables” are.

7. Ask for references. Just because someone tells you they can do the work or their willing to take on the job isn’t a good enough reason to hire them. Make sure you do your homework.

8. Determine what you are going to offer and what you aren’t to help your sub get the job done. Can they work from your office? Are you planning on providing drafts, samples, or guidelines to help them get the job done? Make your subs life as easy as possible by providing them everything you can to help make it easier for them to do their job well.

9. Have reasonable expectations. This is a biggie. Make sure that you are asking for someone else to do something that is possible. Set your cub up for success. It’s good for them and good for you.


Karin HurtKarin Hurt

Karin Hurt, CEO of Let’s Grow Leaders, is a leadership consultant, speaker, writer, and MBA and executive education professor. A former Verizon Wireless executive, she was recently named as a Top 100 Thought Leader in Trustworthy Business Behavior by Trust Across America. She is author of author of “Overcoming an Imperfect Boss: A Practical Guide to Building a Better Relationship With Your Boss” and “Parent’s Guide to Leadership.” She has an award winning blog that has achieved a strong international following.

In my experience, the biggest mistakes companies make when hiring contractors are…

1. Not spending enough time up front sharing vision and big picture. Just like employees, when contractors understand the bigger context there work will be of better quality in less time.

2. Due to co-employment concerns, many companies are skiddish about integrating the contractors into the team. Contractors are still human beings who yearn for inclusion and connection. Even if they are there for a short time, be sure they feel like a welcomed member of the team.


Paris VegaParis Vega

Paris Vega is the CEO of The Web Craftsmen.

The biggest mistakes that business owners make when hiring a contractor is…

Hiring contractors too quickly, and then firing bad ones too slowly.

This will kill your project, and eventually, your business. Invest your time in making sure a candidate is perfect for the job. Especially if you’re hiring a remote contractor, take whatever steps necessary to confirm their identity and follow up with any references they can give you. Nothing is worse than having the wrong team for the job, but nothing is better than having the right team.

After hiring that perfect candidate, if they don’t measure up to expectations, don’t waste your time, or your project’s budget, hoping a contractor will improve performance eventually.

The right way to hire & fire a contractor:

1) Communicate your expectations clearly up front.
2) Allow for a reasonable learning curve so they have a chance to prove their effectiveness.
3) Schedule a review date.
4) After the first review period, be honest with yourself and the contractor. If you don’t think they are going to work out long term tell them so in the review. Tell them when the contract will end, so they can start lining up new work.
5) Start looking for their replacement.

Don’t wait until you’re so frustrated that you explode one day, firing them in the middle of a critical moment in your project when no one is their to take over their responsibilities. This hurts your project and your reputation.

You don’t have to waste your project’s budget nor a contractor’s time. If they aren’t fitting into your team and mutually agreed expectations it’s time to move on.

On the other hand… Your specific project or business may not have a deep reservoir of contractor talent waiting to jump aboard. Or maybe you’re in a crunch and don’t have time to find the “perfect” candidate. In that case, give yourself a timeline. Hire that best candidate you’ve found by the end of that timeline and keep going. Don’t let your ship sink because you didn’t find the perfect patch to mend the hole.

Be picky (when you can). Hire slow (if you can). Measure performance. Fire fast. Get back to work.


Jillienne-allgauerJillienne Allgäuer

Jillienne Allgäuer is a certified Senior Professional in Human Resources and has over twelve years of experience in Human Resources and Chamber of Commerce member business development. She holds a Bachelor’s Degree in Business Administration from the State University of New York at Geneseo and currently serves as an HR Consultant for Paychex in West Palm Beach, FL.

Many times, the single biggest mistake companies make when hiring contractors is…

Not considering the most fundamental question one can ask in this scenario: Should this worker be considered an independent contractor or an employee of the enterprise?

Many times, it is taken for granted that when someone is labeled a consultant or services are outsourced, the individual is considered a “1099” or contractor, without taking certain factors into account which may influence the terms of the relationship.

When a true independent contractor relationship exists, an employer engages a worker for the specific expertise they have. This expertise is typically unique and distinct from the core functions of the business and the work that the regular employees of the business are performing. If the worker is determined to be an employee, additional considerations including employee benefits, training, workers’ compensation coverage and withholding of payroll taxes will normally apply.

Correct classification is critical. This is partly because agencies including the Department of Labor (DOL) and Internal Revenue Service (IRS) have a vested interest in the correct classification of workers, both from the perspective of enforcing regulatory protections that apply to employees, and from the perspective of assessing fines, penalties and lost revenue associated with misclassification.

Employee versus independent contractor status can be clarified by applying different tests to the employer/worker relationship, which center around how much direction and control is asserted by the employer over the individual. These tests, available through both the DOL and IRS, should be used by the employer to determine classification status, rather that the worker’s preference to be considered an employee or independent contractor.

As misclassification can be a costly mistake for employers, the relationship of service partners as contractors versus employees must be carefully considered.


Michael J. VignaMichael J. Vigna

Michael J. Vigna is the President of Staffing at Mainz, a firm that finds, hires, and trains exceptional receptionists, office managers, and executive assistants.

By far the single biggest mistake is…

Not treating them as employees from day one.

In most, if not all, cases contractors make the same impact to a companies performance as full time hires, so why not give them the same perks as your full time employees (i.e. – using the company gym, etc).


Anna D'AurioAnna D’Aurio

Anna D’Aurio is HR Recruitment Specialist at the Pennsylvania College of Health Sciences. Anna has 8 years of experience in recruitment and employee relations, with extensive experience in hiring independent contractors.

The biggest mistake I’ve seen companies make when hiring contractors is…

Not including an assignment end date in the contract.

As a result, the contractor stays on the company payroll indefinitely. Contractors should not be treated as temps; they are primarily project-based professionals. There should absolutely be an approximate end date for the assignment they are hired for.


Jeffrey CampJeffrey Camp

Jeffrey Camp is the CEO of Cinium Financial and the COO of Ox Bonding, a leader in credit and bonding services. The firm offers traditional commercial surety bonds to the millions of American business who are required to post a bond under the terms of their licenses.

Ideas and talk are a dime-a-dozen. One thing that many companies forget when hiring a contractor of any type that is so important is…

Asking for real-life work examples and results.

This will help you see what type of outcomes a contractor has a proven track record of producing. In addition, be sure to ask for 3 happy clients/customers to reference and actually follow up with them about their experience!


christy-delehantyChristy Delehanty

Christy Delehanty is the Content Lead at PandaDoc, a platform that helps you build, track, and sign any doc on the fly. Christy is dedicated to processes that help people communicate in simpler and better ways.

The biggest mistake you can make in hiring a contractor is twofold:

Not communicating your expectations clearly and not putting your agreement in writing right off the bat. The good news is that one resolution can solve both problems: Always start with a signed contract.

Get your hands on a good business agreement template and customize like crazy to get all of your expectations down on paper in one place. (Here’s a good one from PandaDoc, for example: https://www.pandadoc.com/business-contract-template.) But remember that the important part isn’t the signature. The purpose — and beauty — of a thoroughly customized contract is to get you and your contractor communicating about expectations in concrete terms before the work is even underway.

It’s a formal process, sure, but it also has the power to enable authentic communication early in your relationship with a contractor. And nothing is more important than that.


Amara MillerAmara Miller

Amara Miller is part of the Talent Services team at Talencio and partners with clients to provide recruitment strategy along with recruiting and related services. She works closely with clients to customize proven recruiting processes to fit the unique needs of their organizations. She provides clients with a short list of candidates that exceed their skills requirements, and align with their company culture and values.

The biggest mistake companies make when hiring contractors is…

Hiring too quickly and poorly, which ends up being costly and time consuming.

At times, when companies have made the decision to hire contractors, the need has been present for some time. They need help, and they need it now. However, making a quick hire just to fill the need yesterday, can have it consequences. It is much better to fully vet the potential contractor for both skills and culture fit. You don’t want to waste time and money on training if this isn’t a good fit.


Rod-Brown-Oncelogix-picRod Brown

Rod Brown is a seasoned, innovative entrepreneur, motivational speaker, coach, and radio show host that is responsible in part for the startup, growth, and development of several thriving companies. He is the COO of OnceLogix, LLC, a software company that specializes in web-based solutions for the Health Care Industry, and also the Chief Idea Officer/Founder of The Lyndell Group (TLG).

The biggest mistake companies make when hiring contractors is…

Turning the contractors into employee’s/staff members too fast, which is costly and time consuming.

Implement a trial period in which you can ensure quality work and professionalism. Also, you might not need them long term, so don’t over sale yourself in the initial contract. Use contractors on as as-needed basis because your company may have down time in slower seasonal months.


Jill Van NostranJill Van Nostran

Jill Van Nostran is a Freelance PR and Digital Marketing Consultant for mobile technology companies. Learn more about Jill’s work at http://www.jillvancommunications.com/.

In my experience as a PR and marketing contractor, the single biggest mistake companies can make is this:

Hiring a contractor who may have some general experience in your industry or niche, but is not specialized in your industry or niche.

Specialists can solve problems quicker and more efficiently. Generalists will take more time and possibly even cost more money as a result. Companies may not often feel they need a specialist — and some companies don’t. But for the most part, hiring a specialist who is well versed in your unique industry and on how to solve your problem will save a lot of money and a lot of headaches.


Victora RiveraVictoria Rivera

Victoria Rivera is the Office Manager at VIATechnik, responsible for HR, finance, and marketing among other things. VIATechnik serves the construction, engineering, and architecture markets, and provides affordable and high quality services from design to engineering. Using a highly skilled team, VIATechnik delivers CAD work, engineering services, and business process solutions efficiently to their clients.

In my firm’s experience, the biggest mistake that a client makes when hiring contractors is…

Not having a clear scope sheet and pricing tied to that scope.

Not knowing what you want can certainly cause a lot of miscommunication and can also affect the outcome of your final project. Coming prepared to a meeting and having set goals and a straightforward vision helps a business like ours pinpoint what exactly needs to be done. It also enables us to work quickly and efficiently in order to satisfy every client’s need of needing things to be finished “as soon as possible”.


Marius_FermiMarius Fermi

Marius Fermi is the Director of Online Communications at Tactical Sales Training where his focus is growing the brand’s presence online and focusing on increasing business through digital marketing strategies.

Thanks to the powerful world of freelancing and the ease of access to professionals and contractors you’ve got plenty of talent to choose from. I myself have spent a lot of time and money hiring web developers to take on work that require a certain expertise or skill set that I may not currently have and unfortunately this is where the problems start. The biggest mistake I’ve made every time that I have had to learn from has been…

Not being clear enough as to what to expect from the contractor and the project.

Realistically, I should have listed instructions and goals like I were speaking to a 5 year old child as this way there leaves little room for guess work, little room for error and ultimately it’ll be as close as to what you have in your mind as possible.

Each time I haven’t been specific with instructions the project has gone completely the opposite way of what I expected and had as a vision, trying to combat these issues generally leaves you with either a larger bill or a headache which can only be solved by hiring another contractor and this time ensuring you list everything, clearly and definitively.


Rebecca Staton ReinsteinRebecca Staton-Reinstein

Rebecca Staton-Reinstein, Ph.D., is the President of Advantage Leadership, Inc., and works with companies around the world that want strategic leaders and engaged employees to increase bottom- and top-line results and delight customers. Advantage Leadership, Inc. helps clients achieve their goals through strategic planning and leadership, management, team, and organizational development. Her team works with you to craft highly customized, successful solutions to your complex business problems in all economic sectors.

The single biggest mistake companies make when hiring contractors is…

Focusing on features not benefits.

The typical dog-and-pony-show presentation often focuses on the contractor and his or her resume, customers, and all the things he or she will do for you. The problem is the company may not have a clear business problem statement about what results are needed as a result of working with the contractor. Combined with an overemphasis on the features is an overemphasis on one particular feature, price. Because the company is not clear about the problem to be solved, it really has no good way to decide if there is a good exchange of value. The end result is to try and get a lot of features for as low a price as possible. The company and the contractor are now on the road to dashed expectations, unhappiness, and even legal action.

The only solution is for the company and consultant to spend time defining the business problem and the beneficial solution and then seeing if they agree on the value exchange. For example, a company does not need to train people how to manage. The company needs managers who demonstrate great effectiveness through employees who are engaged while accomplishing and exceeding goals.

There are many tactics to get these benefits. The ideal consultant will demonstrate he or she understands the company needs and has a track record in designing and implementing a systematic way to assure these results.


Nellie AkalpNellie Akalp

Nellie Akalp is a mom of four, serial entrepreneur and CEO of CorpNet.com where she helps entrepreneurs start, grow and maintain their business ventures.

The single biggest mistake companies make when hiring contractors is…

Keeping on a contractor who is not a good fit for that business or job.

Yes, it is hard to fire people, but when I first start working with contractors I always start with trial run. During that trial, a few weeks, I know if that person will be a fit for my business or not. If they are not, I don’t waste any more of my time or money on them and move on. This will cause a bit more time upfront to find that right person, but once you find them you’ll have a go-to contact for projects moving forward. Most contractors I work with now have been with me from the beginning, it took time them to find them, but it saves time now because I know right who I need to call and they get the project done the right way.


DDavid Shiffman

David Shiffman is Co-Founder and Brand Elevater at Brandamos, and is a creative strategist with over 10 years of experience developing marketing strategies and guiding business development. Shiffman has worked with companies such as Paramount Pictures, Universal Pictures, Absolut Vodka and Polaroid Fotobar. His internet marketing strategies and execution have resulted in millions of dollars in revenue for clients and his personal experience gives an advantage in elevating brands both offline and online.

The biggest mistake business owners can make when hiring a contractor is…

Not having a contract.

The internet has made it very easy to hire contractors on a project basis, however, it’s easy to forget simple things like outlining expectations and timelines.


sJulia Angelen Joy

Julia Angelen Joy is the Founder of Z Group PR, which she founded as a freelance consultancy after years working with communications teams and public relations agencies. Now, with 18 years of experience, a second marketing degree, and MBA on the way, Julia is confident that she can solve client PR issues faster than you can say “Super PR Lady!”

The biggest mistake companies make in hiring contractors is…

Not asking enough questions.

Everyone wants to bask in the glow of the great ideas and the new beginnings, but details such as specifics on hours, deliverables, and access are left out. Generally, the company is not aware of its internal processes, hurdles and brick walls and therefore does not know how to properly on-board the contractor. On the other side, contractors need to be very specific in terms of responsibilities, tasks, strategies and work process.


Matt WaldenMatt Walden

Matt Walden is a Partner at Infinity Consulting Solutions (ICS) and has 20 years’ experience in staffing and recruiting. Matt designed the proprietary recruiting model for ICS, which boasts one of the largest talent networks in the country. The firm’s areas of specialization are IT, Legal & Compliance, Accounting & Finance, and Corporate Support which consists of Executive & Administrative Support, and Sales & Marketing.

The biggest mistake companies make when hiring contractors is…

Misclassification.

This happens with in a number of ways but the two that will cause most companies the biggest headaches and possibly fines are:

  • Misclassification of exempt vs. nonexempt employees specifically for overtime
  • Misclassification of W2 vs. Independent Contractor / Corp to Corp.


Patty-DeDominicPatty DeDominic

Patty DeDominic is the Chief Catalyst and C.O.O. of Maui Mastermind, a community of successful entrepreneurs helping business owners like you take your business to the next level.

The biggest problem companies make when hiring contractors is simple and it is…

Failure to adequately communicate your needs and trying to buy on low price only.


David W B ParkerDavid W. B. Parker

David W. B. Parker is a Founding member of PTC Computer Solutions, a full service web site design and development company operating out of Jacksonville, Florida. David has two Bachelor’s degrees in Engineering and a Master’s in IT Project Management and has been involved in a vast array of IT projects for over 25 years. PTC Computer Solutions provides a wide range services for the small and medium sized business to enhance their web presence or infrastructure, include Web Design, Web Development, Social Media Management, Design and more.

The biggest mistake companies make when hiring contractors is…

Failing to perform their own due diligence.

Performing due diligence on a contractor is perhaps the single most important function when hiring a contractor, and yet, very few companies complete this primary step.

With the world the way it is, almost anyone can offer services and even look extremely professional online and over the phone, but perform the required due diligence to ensure this is the contractor you want working on your job. Make sure to request some references and follow up with those references. Legitimize those references with cross-references from other companies they have worked with as well.

The internet allows for a wonderful world of sharing resources, but it also allows for the ability to confuse and even fool you in to a sense of comfort with a contractor without knowing all the details. Be sure to get the details and take the time to verify the contractor before going in to business with them.


Scott MirskyScott A. Mirsky

Scott A. Mirsky is Founding Partner at Mirsky Policastri LLC, a firm that focuses on employment, business, and construction disputes. Scott has experience in handling non-compete and trade secret disagreements, employment claims, intellectual property infringement cases, complex construction issues, wage disputes, and breach of contract claims. He also has over 15 years’ experience representing individuals and businesses in diverse civil matters throughout Maryland and the Washington, DC region.
There are so many pitfalls that can occur when hiring contractors, and some of the main ones are…

1. Misclassification – hiring a contractor who is really nothing more than an employee can create major problems for a business, such as overtime violations, unemployment compensation issues, payroll issues, liability issues, and others.

2. Non-compete issues – the consideration of whether the worker allowed to work for others while working for your business? And after the worker leaves your business, can they go work for your customers or a competitor?

Some of these possible pitfalls can be minimized if the worker signs a well-drafted Independent Contractor Agreement, but the true test is what the worker does day-to-day for the business and for others.


James PillowJames Pillow

James Pillow is one of the Managing Directors at Fancastle.com an online retailer with physical locations that sells college t shirts and college apparel to customers around the country.

I’ve hired several contractors for our businesses and in my experience, the biggest mistake companies make when hiring contractors is…

The failure to adequately check references.

Typically people will just look at the work examples the contractor did for another person rather than talking to the previous customer. The potential customer will not take the time to pick up the phone and ask the previous customer key questions like:

1) Was the contractor easy to work with and did you mesh well with them?
2) Did you feel the contractor reached your goals?
3) Did they cut corners during your project?

For now on I take the prior customer’s word for it rather than the long list of accolades and trophies the contractor might have won. Don’t be fooled by this. Just because they can do something well, doesn’t mean they can do it well with you.

Featured image via: Flickr

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