Reflecting on 5 Years of Remote work: The Onboarding Pitfalls

Explore common onboarding pitfalls in remote work and learn how to create a supportive and strategic onboarding process.

When the COVID-19 pandemic hit in 2020, companies pivoted to remote work nearly overnight – a seemingly temporary solution that has since become a fixture of modern work life.

As remote work remains integral in today’s hybrid workplace, it is more important than ever to instill thoughtful onboarding processes to help remote employees feel connected, supported, and fully integrated into the organization from day one.

Yet, many organizations still treat onboarding as a one-off checklist rather than a strategic driver of employee success – a viewpoint that can be especially detrimental to remote employees.

Onboarding plays a crucial role in helping new hires feel integrated, confident, and productive. However, in many organizations, onboarding remote employees remains an afterthought, reliant on outdated methods that do not translate to today’s modern, digital environment.

As a result, it is no surprise that 63 percent of remote workers feel undertrained when compared to just 38 percent of on-site employees. In fact, remote employees are 117 percent more likely to plan to leave their employers soon, making onboarding a potentially significant lever for better retention.

In the early days of the pandemic, companies sought to replicate office routines in a digital setting. But in this transition, onboarding processes – typically built around in-person interactions – suffered. Although virtual onboarding sessions and remote team check-ins have certainly become more common, remote onboarding is a lasting struggle for many organizations.

Remote onboarding challenges today

According to a recent Gallup report, only 12 percent of employees strongly agree that their organization does a great job of onboarding new team members.

This gap has serious implications: A Harvard Business Review study found that 33 percent of new employees start looking for a new job within their first six months, and inadequate onboarding was cited as a leading factor.

Remote employees are especially vulnerable during onboarding. Lacking face-to-face interactions, they miss out on organic learning moments like spontaneous conversations, shadowing a colleague, or grabbing lunch with a teammate. These informal interactions are essential to understanding not just what to do, but how things are done in a particular company.

Common remote onboarding pitfalls include:

  • Lack of clear communication and expectations: In a physical office, questions can be answered as they arise. Remotely, unclear communication can leave new hires struggling with undefined workflows and unstructured communication channels.
  • Insufficient access to training and knowledge resources: In many remote onboarding programs, training materials are scattered across email chains and cloud folders, forcing new hires to spend hours searching for answers instead of absorbing the knowledge they need to succeed.
  • Underutilization of technology: Many companies still rely on Zoom calls, PDFs, and basic PowerPoints instead of adopting more cutting-edge technology solutions. These text-heavy methods for onboarding often contribute to low employee engagement during the onboarding process, leading to lower knowledge retention.
  • Lack of personalization: Traditional onboarding programs often take a one-size-fits-all approach, assuming that every new hire learns the same way. Today’s workforce is diverse – not just culturally, but also in terms of experience levels, roles, and learning preferences. Without personalization, onboarding fails to meet individuals where they are.

Best practices for remote onboarding in 2025

There has been a significant evolution in remote onboarding practices over the last five years. While early pandemic-era efforts were marked by improvisation and reactive processes, today’s most forward-thinking organizations are investing in scalable, tech-enabled onboarding strategies that are both engaging and personalized.

These companies recognize that onboarding is not just an administrative step – it is a foundational driver of long-term employee success.

What has improved since 2020?

Five years after the widespread adoption of remote work, companies that lead in employee experience have transformed onboarding into an intentional, data-driven process that goes well beyond the first week, with these notable key improvements:

  • The mainstream adoption of AI and digital onboarding tools that centralize resources, automate tasks, and track progress.
  • More emphasis on personalization and accessibility, with content tailored by role, geography, and experience level.
  • Greater leadership involvement in onboarding, as executives recognize its impact on engagement and retention.

Let’s take a closer look at each core focus area:

1. AI and digital platforms for more engaging and interactive experiences

In 2025, AI-driven video platforms and learning tools are not a novelty – they are an essential tool for high-quality onboarding. AI-generated training videos, personalized onboarding paths, and virtual onboarding assistants help companies deliver consistent, scalable, and engaging experiences to remote hires around the globe.

AI platforms enable organizations to create interactive onboarding videos at scale, eliminating the need for significant resource investments. AI-powered tools can promote interactivity and accessibility through branching scenarios, multiple-choice quizzes, and automatic translation to dozens of languages.

These tools enable teams to create videos in minutes that introduce company culture, explain key tools, and walk new hires through day-to-day workflows, all in a format that is far more engaging than text-based manuals.

2. Comprehensive onboarding programs structured by role

The ad hoc onboarding processes of the early remote work era have given way to structured, end-to-end programs that are consistent, measurable, and repeatable.

A comprehensive onboarding journey typically spans the first 90 days – and sometimes up to six months – ensuring that new employees build confidence and competence gradually over time.

Key components of structured programs include:

  • Preboarding: Access to key documents, tech setup, and welcome messages before day one.
  • Role-specific learning paths: Customized content that reflects the tools, processes, and performance metrics for each job function.
  • Cultural immersion: Stories from leaders, introductions to team rituals, and opportunities to connect with peers early on.
  • Milestone check-ins: Regular one-on-ones to track progress and address concerns proactively.

Standardizing onboarding also makes it easier to assess what is working well. With the help of learning management system platforms and onboarding dashboards, HR teams can monitor new-hire engagement, course completion rates, and satisfaction metrics in real time, enabling data-driven improvements.

3. Continuous support across the business and effective feedback mechanisms

Successful onboarding does not end after the employees’ first week or even the first month in their new role. In high-performing organizations, onboarding evolves into continuous learning and support that helps employees adapt and grow within the company.

This includes regular pulse surveys, mentorship programs, peer-learning platforms that encourage knowledge sharing, and performance feedback loops built into onboarding timelines.

When onboarding is seen as a continuous journey, not a fixed timeline, employees are better equipped to navigate their roles and contribute meaningfully to the organization.

The opportunity ahead

In 2025, remote onboarding is no longer about translating in-office practices to digital formats. It is about reimagining how people learn, connect, and thrive from day one, regardless of location. By embracing AI-powered platforms, structured programs, and continuous support systems, companies can close the gaps that still plague remote onboarding today.

Organizations that succeed in this space will not only boost retention and productivity but also build cultures of inclusion, adaptability, and lifelong learning, qualities that are essential for the future of work.