Remote Developer Onboarding Checklist: How to Start Working with a Contractor

Hiring a contractor may be easier and faster than in-house hiring, but the onboarding process for a contractor should be as meticulous as for a new employee. Contractors may require as long as one month to become fully engaged because they need to get to know the team and learn the product code.

Onboarding begins as early as the interview stage when asking developers to discuss how they overcame challenges or contributed to the success of projects and if they’re able to perform expected tasks.

The importance of a contractor onboarding process

Companies often worry that a contractor may encounter difficulties within the first few weeks—even if they interviewed brilliantly. However, when hiring a contractor through a marketplace or outsourcing agency, the responsibility for onboarding and retention still falls on the employer. This is because they have to familiarize the new engineer with the project code to ensure effective teamwork.

From day one on a new project, onboarding directly impacts the developer’s effectiveness. Therefore, companies should allocate time to involve the contractor in the workflow and organize Q&A and feedback sessions. That way, they’ll feel engaged and have a clearer understanding of the company’s needs.

This article provides a checklist of activities that can help a company overcome challenges during onboarding. It also discusses how the Customer Success department at YouTeam helps businesses and contractors overcome challenges, build relationships, and complete projects on time.

Remote developer onboarding checklist

Preparing for a contractor’s first day

It would be embarrassing not to have a workstation or training instructions for a contractor’s first day at the office. Programmers who work remotely may be less aware of “gaps” during the first few days of onboarding. However, they may still notice a lack of account access or technical documentation.

Here’s a checklist of onboarding activities to get ready for a new contractor:

  • Prepare a guide with the company’s most vital information. This may include blog posts about company milestones, the CEO’s video diaries, an online onboarding portal, or a glossary of company acronyms.
  • Choose a dedicated mentor who’ll be responsible for the developer’s onboarding. A new contractor who is not yet familiar with all of the company departments is more comfortable asking their trainer questions.
  • Consider a developer’s goals for the first 30, 60, and 90 days of work.
  • Prepare technical documentation.
  • Set up a new email account for the new hire and provide access to company software and communication tools.
  • Send a welcoming email, start with a warm welcome, explain how the first day will go, and attach a necessary handbook.


Welcome emails and pictures for new team members are sometimes accompanied by an overwhelming number of introductory calls and technical documentation. An “all at once” approach can often intimidate a new team member—it’s best to pace the process to avoid frightening off the newcomer.

Regular feedback helps new contractors feel heard and appreciated. Furthermore, addressing uncertainties and misunderstandings early on can prevent more severe problems from developing. The following checklist will help organize the first few weeks of working with a new developer:

  • Introduce the contractor to the team.
  • Schedule a video call to show presentations of the company and the project.
  • Assign a technical specialist to introduce the developer to the project code.
  • Divide team roles and responsibilities. Sometimes, existing team members may feel threatened or jealous that a new hire may take over their duties. Therefore, it is good to clarify the  new contractor’s position with other team members whose work is closely related. This will improve interaction and help tackle the project.
  • Tell the developer what is expected of them during their training period and for the first few months. The developer’s goals may include acquiring a more profound familiarity with the stack and operational footprint—designing, implementing, and releasing new features to the company’s platform/product. Employers should set milestones for newly hired developers.
  • Begin with simple tasks so as not to overwhelm the developer with information and evaluate their work regularly.
  • Organize pair programming sessions to ensure the developer stays on track.
  • Arrange regular Q&A and feedback sessions during onboarding (not just at the end of the trial period but throughout the process).

You can also ask current remote employees to share their onboarding experiences and answer specific questions about how to make the process smoother for new contractors.

Post-onboarding activities

  • Get regular feedback from the contractor and in-house team. This can motivate and encourage the developer to improve teamwork and perform better over time.
  • Be honest with the contractor about long-term goals. Be aware of the developer’s mood before monotonous work forces them to change projects. For example, maybe the data structures and algorithms they practiced for a year to join the project are all forgotten within three months of doing maintenance and attending meetings.
  • Schedule regular meetings to check how tasks are going and adjust the developer’s workload.

How YouTeam can help you during the onboarding of a new contractor

If you hire a contractor through YouTeam, we provide a list of guidelines for getting started with a contract developer. After signing the hiring agreement, we ask for a manager on the client’s side who will be responsible for the onboarding process. According to Stack Overflow, 46% of professional developers call a coworker or friend when they get stuck on a problem, so your team should be ready to help.

YouTeam’s Customer Success managers conduct feedback sessions with the developer and the client throughout the collaboration. These calls begin two weeks after the contractor starts working on a new project.

In conversations with clients, we try to determine whether they are satisfied with the developer’s performance. The most common problems during the trial period are unmet expectations and progress uncertainty. Customer responses help us examine issues in detail and improve cooperation with the developer.

Feedback from developers is also important—they often need more attention to feel valued. YouTeam’s feedback sessions with developers can help you see gaps in your team’s communication and engagement. For example, a developer might point out that the environment is not challenging enough. In this type of situation, you could give this developer more ambitious tasks and find another candidate for routine work.

Developers might not receive enough communication during their first few weeks, so they may not feel supported by management. That’s why YouTeam’s calls with the developer are aimed at understanding how comfortable they feel, whether they are satisfied with the team and tasks, and whether they see themselves on that project in the near future. Sometimes it is more convenient for a developer to talk about their experiences with Customer Success than to share them with the project manager.

YouTeam’s developer feedback sessions address the following questions to help our customers avoid problems early on:

  • Are you used to working on such types of projects?
  • Are there any challenges or blockers in your work?
  • Is communication with your manager effective?
  • Do you get enough attention?
  • Have you received any feedback from a customer?
  • Can you see yourself working on the same project in 6 months?

Final thoughts

For companies to be successful at contracting and onboarding, they must delve into the nuances of their business goals and team culture.

Suppose you need engineering contractors who can speak their minds and generate ideas, work with tight deadlines, and know how to ask for help. In that case, your team should be willing to meet with contractors to understand their expectations as well: welcome input and discussions, set clear realistic goals and revisit them often, and dedicate time and people to educating the new teammates about the business and product. All in all, building great things isn’t easy, but it sure is more fun when we take the time to know each other and appreciate each other’s “unique features”.

You should additionally read our blog about creating a newcomer handbook for software developers.

Written by
Artem Vasin

Artem Vasin is a content writer at YouTeam, blending a unique educational background from both the scientific and creative fields. He holds a bachelor's degree in Mathematics and secondary music education. The author's journey in writing began with a focus on business intelligence and OSINT. At YouTeam, Artem delved into topics surrounding recruitment and software development.

His pursuit of knowledge is reflected in his completion of courses like Reuters' Digital Journalism Foundations and Ravensbourne University London's Digital Marketing and Communication.

Artem's literary preferences include Philip Kotler's Marketing anthology, Daniel Goleman's Emotional Intelligence, and Isaac Asimov's Robot series.

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