How To Craft a Tailored Onboarding Experience for Independent Contractors

Nahla Davies
August 16, 2023
min read
September 19, 2023
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Learn how to create a tailored onboarding experience for independent contractors. Enhance skills, provide visual learning, and foster a supportive environment for success.
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An independent contractor's onboarding experience should differ from the process a full-time employee will follow when starting with your company. This is natural, as both workers will have different requirements and needs before the working relationship becomes official. 

For example, you don’t owe them employer contributions when you hire independent contractors. The contractor often manages tax requirements, too, meaning there’s less financial paperwork to sort and organize. 

According to Statista, 31.9 million people worked as independent contractors in 2022, a substantial increase from 15.8 million in 2020.

As this type of employment is becoming more common in the United States, your business must be prepared to onboard and integrate these workers into your organization effectively. Here’s a look at how to create a tailored onboarding experience for each independent contractor. 

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Steps to enhance independent contractors’ onboarding experience

Most businesses that use independent contractors will already have a generic onboarding process that they follow to increase efficiency. Using this same process for each new hire can make onboarding quicker, but it fails to build a tailored experience that helps the new contractor get the most out of the experience. 

Although it’s wise to follow checklists and use pre-made contract templates with features such as payment terms and project details to help structure your onboarding, there are things you can do differently to help create a more bespoke process. 

Conduct a skills assessment

You need to stop treating all your contractors similarly to get the most out of your onboarding. To onboard an individual effectively, you must create a plan that suits them and their needs. A great way to do this is to start the onboarding process with a skill assessment. 

A skill assessment will allow businesses to identify key areas where there is a skills gap and spend more time in the onboarding process to train these skills so that a contractor can hit the ground running. 

In today’s modern work environment, 80% of new hires leave a job within six months if it’s not matching expectations. This means there’s not much time to get new hires up to speed, so the onboarding process needs to be efficient. 

By using a skill assessment, employers can better customize a training plan that will be more beneficial to the contractor. Instead of wasting time using a generic training program that teaches them what they already know, you can develop a bespoke training process focusing on the areas needing improvement, using programs like Scribe to facilitate this training. 

Show, don’t tell

Research shows that around 65 percent of the population are visual learners, meaning most of your new independent contractors will learn processes and information better if delivered visually. 

If your onboarding process requires your new hires to read many dense documents to learn how things operate and work in your business, that will be a poor-quality experience. Instead, focus on building a paperless onboarding process that visually shows your new contractors how to follow standard processes. One of the best ways to do that is with Scribe. 

This tool allows you to easily create step-by-step guides that onboarding contractors can follow and refer to in the future.

Its technology can capture your desktop, allowing you to visually capture processes and methodology so that it’s easier to share with new hires. The best part is that Scribe can create these guides automatically, making it easier for you to create engaging onboarding material for your contractors. 

If you find that many of your contractors are asking the same questions, you can also train teammates by creating FAQ videos and guides. 

Provide feedback

When onboarding a contractor to your business, you want to foster a supportive environment where the contractor feels they can learn and improve. One of the best ways to create that environment is by providing feedback. This lets the contractor understand if they’re meeting their requirements and gives them an indication of their performance. 

Many businesses that use independent contractors will give them an overall score based on their output, such as a star rating. Although this is a good starting point, businesses can do more when providing feedback to ensure that it’s always motivating and makes the contractor a better worker for your business. 

You can give regular feedback by scheduling catch-up sessions where the contractor can speak directly with a staff member. This type of communication has the added benefit of helping the contractor feel part of the business, as it also allows them to offer their thoughts, which a company can use to improve the onboarding experience in the future. 

You can unlock their full potential and foster long-term success during this partnership by providing good feedback that prevents contractors from feeling in the dark about their performance. Feedback should continue well after the onboarding process, and from this feedback, businesses can recommend continued training to the contractor to ensure they can maintain high performance and grow. 

An example of a real-life onboarding process

One of the best ways to implement an effective onboarding process is to follow the template laid out by an already successful business. In this case, Uber is a great example to follow, as it is one of the biggest and most successful businesses that utilize independent contractors in the US. They achieve this by focusing heavily on education when onboarding their workers. 

When becoming an Uber driver, there’s a specific process drivers need to follow to ensure that they’re embedded into the process and are set up for success. This process is slightly different depending on the country that they’re in, but in most cases, the process begins with an e-learning course to teach new workers how the app works and its features. 

Offering your independent contractors educational material is a great addition to your onboarding process, as it plugs any skills or knowledge gaps. Offering this training digitally makes it more convenient for the contractor to complete. When creating educational material for onboarding, focus on covering your specific software and processes to facilitate a smooth transition into the work. 

Following this educational course that must be completed, new Uber contractors will then have a physical appointment where their documents are checked. This can be considered a reasonably robust screening process and is something that you should include in your onboarding process to ensure that you’re working with reliable individuals. Since you’ll be holding sensitive information when screening, it’s important to implement good data security and privacy practices so that contractor information isn’t compromised.

Following this screening step and in-person introduction, Uber workers can start accepting trips once the final documents are signed and their banking details approved. When signing documents with your own contractors, make sure to use digital signatures instead of e-signatures, as they offer a higher level of security and authenticity. A digital signature uses cryptographic technology to ensure the integrity of the document and the identity of the signer, providing stronger legal protection and reducing the risk of fraudulent activities on both sides.


The onboarding process is one of the most critical parts when hiring a new contractor. A good process can facilitate a smooth transition into the role and limit performance issues in the future. 

Many businesses offer all their new contractors the same onboarding experience, but that fails to address the specific needs of each new hire. Instead, you should try to make the onboarding bespoke for each individual, using assessments and a tailored learning plan so that they can thrive. 

Focus on making your educational material visual for the best effect, using Scribe to create compelling and efficient guides.

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