When you’re leveraging contractors, there is not (well, should not be) any wiggle room between expectations and performance. A boss anticipates challenges and encourages success, understands and works well with all employees, partners, etc., and has a unique grasp of the business from everyday functions to end-results.


To break it down, a successful boss has the following characteristics, skills, and experience:

Efficient Communication

Have a way with words. And know how to use them efficiently and confidently. Open communication should be encouraged. Especially between a boss and contractor. These two should be on the same page at all times, specifically regarding projects that the contractor has influence on. To ensure the highest quality of work, the most efficient timing, and the best working relationship, a boss should focus on the way of communication. And this doesn’t just mean simple, daily conversations about the work. This also includes the expected voice and communication of a project deliverable to the client, as well as the preferred way of communication to the client him or herself.


Onboarding Practices

Every company and every boss takes on a different onboarding practice. And most still have not been perfected. People change, work changes, contractors change, etc.; so should your onboarding practices! Adapt to the change… by creating a reliable new-hire program. Onboarding begins with acquisition, and doesn’t end until the new employee is comfortable and on their own. The process should be consistent: reel in the best (top talent), form a working relationship with he or she, explain the business in depth on a day-to-day basis, start he or she in a training program, and encourage open communication.



When hiring a contractor, you must make sure that you don’t throw them in the ocean to see how they swim. As a boss, YOU have already designated the work he or she will perform, YOU know the common expectations of quality work, and YOU know the in’s and out’s… but does the new guy? This is not to say that a new contractor should have he or she’s hand held for the first few weeks. This is not an allowance for the contractor to “put a monkey on the boss’s back.” Just a simple reminder that you once were new as well, so treat them as such.


Skill Sets

Have an understanding of unique skill sets. And apply these skills in the best ways possible. Check out the contractor’s resume, past work and experiences, or maybe a reference letter, to nail down exactly what he or she is great at. Use these skills to your advantage. Add them to projects in which he or she’s skills will be used and enhanced to the fullest. Well-rounded skill sets are excellent and more rare to find nowadays, so be sure you are able to recognize unique skills when you come across them.


Emotional Intelligence

Gather a great grasp of emotional intelligence. A boss who can handle his or her own emotions well and understands others emotional behaviors, can delegate and oversee the work being done with a clearer head than someone of the opposite. With this, the contractors will be managed in a more effective and positive way. Communication ease increases, stress levels decrease, working relationships improve, and the boss becomes relatable.


Quality Versus Quantity

Push for and have set expectations for quality versus quantity. When a boss hires a contractor for a specific project, he or she was clearly hired for a unique reason– most likely due to this person’s track record of solid performance and great experience. So, not only ensure you are hiring the best, make sure to follow through to ensure that he or she delivers the best. Explain whom (client, manager, company, etc.) the contractor is conducting work for. Explain the purpose, the diligence, and the quality of work that is expected here.



Keep contractors updated, in the know, and accounted for. No one likes to be left behind with information or news. Plus, the less people know, the more catching up and explaining the boss must do during a time of need. Allow he or she to feel well rounded in understanding, as well as influential. Form solid communication: talk often, be open for questions, and act approachable. I promise, even those with years of experience will still have questions for their new boss.


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