Imagine you just hired a designer in Cyprus to work on a project with a deadline in six months. They are excited to start working on this project. However, within a month, they start missing deadlines, and sometimes are unsure of expectations. What do you think will happen? Surely, your six months deadline project could be in jeopardy, and that means losing clients. To get the best out of international contractors, you need to be the one setting the tone. HOW?

Remember, the first 90 days with international contractors are critical. It’s your window to set the tone, build trust, and establish the foundation for a productive, collaborative working relationship. Done right, it leads to strong performance, fewer misunderstandings, and long-term loyalty.

This post walks you through what to prioritize in your first 90 days with remote contractors, especially when you're managing people across borders, cultures, and time zones.

Week 1: Create Clarity from Day One

This is your first week with a remote contractor. And this is where a lot of expectations are expected to be communicated, the right documentation signed, and whatever is needed for them to start work is available. The goal here is also to make sure your contractor knows who to talk to, what to do, and how to get started.

 Here is what to prioritize in the first week:

  • Signed agreements and paperwork: Ensure contracts, NDAs, and tax forms (like W-8BEN or W-9) are in place.
  • Clear scope of work: Provide a detailed work outline, including deliverables and key milestones.
  • Introduce your team and tools: Host a welcome call and provide access to your project management, communication, and file-sharing tools.

Week 2 to 3: Build Foundations for Communication

Communication is an important step to getting the best out of a contractor in the first three months. Time zones, cultural nuances, and asynchronous work styles can make communication tricky if not proactively managed. At this stage, you are trying to establish, and or communicate strong, respectful communication norms that fit a global team.

 To avoid issues with communication, you should focus on the following:

  • Communication guidelines: Define working hours, response time expectations, and your main communication channels.
  • Documentation culture: Encourage async-friendly updates via project boards (Trello, Asana) or shared docs.
  • One-on-one check-ins: Schedule a recurring video call (even 15–20 minutes weekly) to build rapport and surface any concerns early.

Week 4–5: Align on Deliverables and Workflows

In Weeks 4 and 5, it’s time to make sure everyone is clear on what needs to be done and how work will get done. This means agreeing on tasks, timelines, and tools. Setting up clear workflows now helps avoid confusion later. It also builds trust and keeps your projects moving smoothly. You can also do the following:

  • Role-specific training: Provide documentation or walkthroughs of your workflows, tools, and internal quality standards.
  • Define ownership: Be clear about who owns which part of a project—and who approves what.
  • Use feedback loops: Give structured feedback early and often, especially during the first major deliverables.

Week 6–7: Foster Belonging and Connection

Your contractor is technically performing well, but you realize they never speak up in group calls or and they’ve barely interacted with others. Here’s what you should do:

  • Social touchpoints: Create space for informal interaction, like virtual coffee chats or a “Friday fun” Slack thread.
  • Recognition: Publicly acknowledge good work in meetings or chat channels.
  • Cultural awareness: Learn about your contractor’s local holidays or time zone limitations, and accommodate where possible.

Week 8–9: Monitor Performance and Adjust

In Weeks 8 and 9, focus on checking how things are going. Look at the contractor’s work, give feedback, and see if any changes are needed. This is the time to fix small issues before they grow. Regular check-ins help improve performance and keep everyone on track.

  • Performance reviews: Do a mid-90-day review. Discuss wins, roadblocks, and areas for improvement.
  • Re-align on expectations: If there’s misalignment, revisit the original scope or KPIs.
  • Offer support: Ask what they need to do their job better—more context, better tools, or clearer direction?

Week 10–12: Set Up for Long-Term Success

You’ve made it to day 80, and things are going well. Now’s the time to think beyond the short term, that is if you have plans to do so.

  • Evaluate fit for ongoing work: Is this someone you’d want to keep long-term or bring on for future projects?
  • Extend or update contracts: If continuing, lock in new terms and plan ahead for capacity.
  • Create an SOP handover: Ask contractors to document their work processes—it’ll save time if others need to step in later.

Final Thoughts: Make the First 90 Days Count

The first three months with international contractors can shape the entire working relationship. By investing upfront in communication, structure, and cultural connection, you avoid missteps later, and create a team that thrives remotely.

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