How to effectively manage work being done remotely by independent contractors

Jimmy Sheehan, Contracting Plus
Jimmy Sheehan, Contracting Plus

Opting for contractors expands the talent pool keeps business agile and affords more attention to markets further afield, says Jimmy Sheehan of Contracting Plus



17 April 2020 | 0

Now, more than ever before, people are choosing to work remotely. The recent Coronavirus situation has forced people into a remote working scenario. While this was not their choice it is likely that both companies and workers will see the benefits of this and may opt for more of this type of working arrangement in the future.

The number of professional contractors has been steadily growing year on year. In periods of economic uncertainty, the number of professional Contractors typically sees a spike as companies err on the side of caution – they choose independent workers and a project based approach rather than taking on an employee whom they hope to be able to keep busy with future projects.

Opting to use independent professional contractors expands your available pool of talent, keeps your business agile and allows you to expand your national or global presence with less overheads and administration. They are highly skilled and as such have little or no ‘bedding-in’ period and can hit the ground running.




Follow these five tips to ensure you get the best possible output, avoid friction and work effectively with your remote independent professionals.

Be in the same boat

Make sure your independent contractor knows what success looks like. If it’s the first time you’ve worked with them make sure you’ve spent some time sharing some examples of what’s worked for you in the past and ask them, where possible to try and work in a similar manner (remember, they’re not employees so these will be discussions on approach and not a dictate. You can’t make them work a certain way).

Open communication, clear expectations from both parties and an alignment of goals will ensure minimal frustrations.

Have a clear communication strategy

Everyone has preferred communication methods. Personally, when remote working, I prefer video. It’s true an email update or quick phone-call may seem easier, but you miss those visual cues that so often are key to helping us understand how a person is reacting to the information.

By agreeing methods and frequency of communication in advance you will help avoid project delays and ensure issues can be discussed and resolved quickly. Factor in time-zones and be conscientious of each other’s work hours.

Set deadlines and stick to them

This may seem a bit obvious but making sure there are never delays on your side will act as a show of intent. It will keep the project and the independent contractor on track.

Where possible break your project into milestones and dates on which these milestones should be met. Where there is accountability there is ownership. This also allows both parties stay true to the scope of work. Any scope-creep may lead to adjustments in the timelines and/or the cost of the project.

Remember this is a B2B relationship

Effective collaboration with your independent contractors is a fine balance between too much over-sight, and not enough.

As independent contractors are self-employed and not under your direction or control, they have the responsibility of managing both the process and the outcome to meet their contracted obligation. This of course does not prohibit them from adhering to standard company-wide operating procedures.

A written contract or Statement of Works should be where you turn for clarification on setting expectations and discussing expected outcomes.

What you are measuring is their performance by the quality of work they produce, so your interactions are more about ensuring the project remains within agreed timeframes.

Independent contractors are not employees

You should try to speak to independent contractors in a different way you might speak to employees. It is not your responsibility to oversee what your remote independent worker is doing with every hour of their day. You are interested only in managing output/deliverables (and this is really the way everyone should be managed).

How independent contractors, remote or otherwise, are managed is where some companies fall down. It is not difficult to compliantly engage independent contractors. However all too often employees managing project teams which are made up of both employees and independent contractors, can innocently cause irreparable damage to your business reputation.

Compliant engagement of independent contractors is vital. Despite the best written contracts or a robust independent contractor engagement policy, the Revenue Commissioners will ultimately look at the relationship of the worker to the work being done. If the worker ‘looks’ like an employee by virtue of you managing and communicating with them a certain way, then your business runs the risk of additional taxes, fines and reputational damage.

Proper classification and management of your independent contractors is essential in protecting your business. This should be followed through in engagement style also.

With the use of remote and contingent workers likely to increase, a little preparation and some foresight on how you can compliantly incorporate remote independent talent into your workforce will deliver long-term benefits.

Request your free copy of How Tech Companies Successfully Engage Independent Workers by sending an e-mail to

Jimmy Sheehan is commercial director with Contracting Plus

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