Top 10 Onboarding Challenges and How To Solve Them

Organizations spend a significant amount of time and resources attracting and hiring qualified talent. Once new hires join the team, effective onboarding is essential to ensure workers smoothly integrate into their new jobs and continue to feel excited about contributing to the business. However, onboarding can be complex and many organizations face common challenges with enabling successful onboarding.

Learn about why onboarding is important, key benefits, and onboarding best practices to overcome top challenges and support a positive experience.

The importance of onboarding

Onboarding is the process of welcoming and training workers when they join a company. While onboarding, new employees are introduced to the organization’s culture, people, processes, and environment, and are expected to learn about what they need to succeed in their new roles.

A successful onboarding strategy also offers the opportunity to make a positive first impression on new team members, which is critical to engagement and retention. According to a survey of more than 300 talent acquisition and HR leaders conducted by Aptitude Research, 86% of respondents believe new hires make the decision whether to stay at a company within their first 90 days.

Key benefits of effective employee onboarding include:

• Faster ramp-up and time to productivity
• Increased employee engagement and retention
• Decreased employee turnover
• Reduced training costs
• A better understanding of company culture, values, and processes
• Enhanced teamwork and collaboration
• Improved safety and risk mitigation

Top onboarding challenges

Despite the importance and benefits of effective onboarding, many organizations have room for improvement with their overall processes and experience. According to a survey of 1,002 employed Americans conducted by Paychex, only 52% of respondents feel satisfied with the onboarding experience at their current job.

Addressing common employee onboarding challenges can help your organization maximize the outcomes of your efforts and set new team members up for success.

Top challenges include:

1. Lack of a defined onboarding process
2. Ineffective communication
3. A one-size-fits-all approach
4. Failure to set clear expectations
5. An overwhelming amount of information
6. Inadequate training materials
7. Overlooking company culture
8. Limited engagement and interaction
9. Insufficient feedback methods
10. Lack of ongoing support

1. Lack of a defined onboarding process

The absence of a defined onboarding program can lead to inconsistent experiences, confusion, and frustrations for new team members. Disorganized onboarding can also result in slower time to productivity and turnover risks for your organization.

While developing and implementing a defined onboarding process may require time and effort up front, doing so can help ensure consistency and clarity for everyone involved.

The following best practices can help your team develop a standardized onboarding plan and process:

• Defining overall onboarding goals and objectives
• Mapping out an onboarding checklist for all hires, as well as specific steps for different roles or departments
• Gathering required new-hire paperwork, such as job offer letters, employment contracts, employee handbook and company policy acknowledgments, and tax forms
• Aligning with your IT team to streamline access and training for internal systems and technology
• Establishing timelines and milestones throughout onboarding starting with day one
• Developing an internal onboarding team and assigning roles and responsibilities
• Producing standardized onboarding materials and resources
• Leveraging employee onboarding software and related technology to centralize information

After you implement a standardized employee onboarding process, continue to evolve and improve it over time—whether this means incorporating feedback from workers, integrating new technology, or identifying ways to make onboarding more efficient and impactful.

2. Ineffective communication

Similar to lack of a defined process, ineffective communication can complicate the onboarding process for new team members. On the other hand, effective communication can help workers get off to a successful start, understand expectations, and quickly feel motivated to make positive contributions to your organization.

The strategies below can help your team support effective communication during onboarding:

• Developing a defined communication plan that includes an overview of onboarding information, communication channels, and frequency of communication throughout the process
• Sending initial communication about onboarding before the first day, also known as pre-boarding, so new team members know what to expect
• Assigning one point of contact or a small team for general onboarding questions and information
• Responding to questions from new hires in a timely manner
• Providing a list of frequently asked questions (FAQ) about onboarding
• Setting expectations to help new workers understand internal communication processes and frequency
• Leveraging technology for virtual communication, including email, messaging apps, video conferencing software, and project management tools
• Encouraging asynchronous communication to streamline collaboration across time zones and schedules and minimize the amount of time spent in meetings

3. A one-size-fits-all approach

A standardized onboarding process and communication plan can drive efficiency and support an engaging employee experience for new team members. However, leaving room to adapt onboarding steps and resources based on each worker and their role is important.

As an example, in-house workers may require different onboarding steps than independent professionals. And individuals on different teams and in various roles across the organization may require specialized training relevant to their roles, as well as personalized goals.

Some ways to personalize the onboarding experience include:

• Scheduling recurring one-on-one meetings with new team members as early as the first week to welcome them to the organization
• Sharing an organizational chart with all new workers and highlighting additional details about an individual’s direct team members, roles, and responsibilities
• Training individuals on processes, technology, and other resources they need to succeed in their specific roles
• Creating personalized learning and development paths for each worker depending on the skills required for the individual role
• Highlighting potential career paths for each new team member
• Offering different onboarding and training resource formats, such as on-demand training sessions, live training sessions, written materials, and team building exercises

4. Failure to set clear expectations

While initial onboarding may involve completing administrative paperwork and receiving access to systems and technology from IT, setting goals and expectations is essential to driving engagement and productivity among new hires.

A survey of 1,000 full-time U.S. workers distributed by Workhuman found that 93% of respondents have a good understanding of where they stand with their performance. However, 60% of those who don’t know where they stand feel constantly stressed at work—which can lead to disengagement and employee turnover. Setting clear expectations from the start can improve the effectiveness of onboarding.

As part of initial onboarding, encourage managers to meet with each new team member to collaboratively identify SMART goals, which stands for specific, measurable, attainable, and time-bound.

Examples of SMART goals during a worker’s initial onboarding include:

• Business development specialist. Complete the company's sales training program, earn required certifications within the first 30 days of employment, and schedule five customer demos within the first 90 days.
• Customer support representative. Complete customer service training, demonstrate proficiency with the company’s customer relationship management (CRM) software, and independently handle a minimum of 20 customer support tickets in the first 45 days.
• Social media specialist. Understand the broader marketing strategy, tools, and channels, and develop a social media content calendar for the next quarter within the first 60 days.

Once SMART goals and expectations are in place, managers can also schedule check-ins at each new worker’s 30-, 60-, and 90-day mark to discuss where they stand with goals and share feedback. During this time, individuals can also ask questions to clarify expectations.

5. An overwhelming amount of information

Between completing the required paperwork and learning about the company culture, processes, technology, and individual roles, new hires can face information overload during onboarding. Too much information at once can lead to stress and have a negative impact on individuals’ ability to absorb important details.

While some may perceive onboarding as a short-term process that is complete within a matter of days or weeks, successful programs typically take a more phased approach. In fact, a consultant for Fortune 500 companies shared with Harvard Business Review that the most successful organizations onboard new hires for the entirety of their first year.

Consider the following tips to avoid overwhelming new workers with too much information:

• Create an onboarding schedule, broken down by days or weeks, so workers don’t feel as though they need to learn everything at once
• Set time aside each day for onboarding tasks to help workers balance onboarding and their day-to-day work
• Foster an open, transparent work environment by encouraging new hires to ask questions and clarify onboarding details
• Centralize all company documents in a shared drive or company intranet so important information is easily accessible
• Regularly check in with workers about the pace of onboarding and whether they need any additional support

6. Inadequate training materials

While training is critical to effective employee onboarding, many organizations fall short of new workers’ expectations and needs. The Paychex research cited above found that 52% of respondents reported feeling undertrained following onboarding and 80% of those who feel undertrained plan to leave their organizations soon.

All workers should complete training on general technology and processes across the organization, while training for role-specific training and skills will vary depending on each new team member, their position, and their existing skill set.

Leveraging the latest technology can help centralize materials, highlight training progress, and offer access to comprehensive training resources to both in-person and remote workers.

Technology resources to consider using during the onboarding process include:

• Onboarding platforms such as ClearCompany, Click Boarding, and Enboarder
• Online learning platforms like LinkedIn Learning, Udemy, and Skillshare
• Talent assessment tools including eSkill, Plum, and pymetrics

7. Overlooking company culture

In addition to providing training and resources to drive success in day-to-day roles, incorporating your company culture into onboarding can help workers get acclimated to your organization. Understanding company culture enables team members to work together toward common goals, feel a sense of purpose and belonging, and effectively collaborate with one another.

According to a survey of 1,565 U.S.-based office workers distributed by BambooHR, 96% of respondents want an overview of a company’s mission and values during onboarding.

Steps you can take to promote company culture during onboarding include:

• Sharing the company's vision and strategic business objectives
• Providing a formal company handbook that includes processes and expectations at your organization
• Tying each new worker’s goals to company values or strategic business objectives
• Planning meet-and-greets with leadership team members or sharing pre-recorded videos from leaders discussing the company culture
• Scheduling team-building and collaborative activities with both new and existing team members
• Encouraging workers to recognize each other for embodying company values
• Showcasing worker success stories and testimonials
• Highlighting company traditions, events, and celebrations
• Encouraging participation in employee resource groups (ERGs) to enable workers to build relationships and connections around shared interests, communities, or identities

8. Limited engagement and interaction

If new hires are simply required to read through onboarding materials and watch training videos, this can lead to a poor onboarding experience and disengagement. Interacting with other workers at the organization—including fellow new hires, direct team members, and individuals across departments—can help drive employee engagement and support relationship-building as part of onboarding.

The BambooHR research cited above also found that new hires desire authentic connections to feel like part of the team during onboarding, with 93% of respondents saying they want to shadow a colleague and 86% appreciating support from an onboarding buddy.

Here are some ways to encourage engagement and interaction during onboarding:

• Offering job shadow opportunities for new workers to learn directly from team members
• Using interactive training methods such as role-playing, simulation, or knowledge-sharing sessions
• Assigning an existing team member to each new hire as an onboarding buddy to help learn about the company
• Asking tenured workers to set up casual meet-and-greet conversations with new employees
• Scheduling multiple team members to start on the same day or week, when possible, so an onboarding group or cohort can get adapted to the company together
• Assigning initial collaborative projects to encourage workers to start making an impact on the business and begin collaborating with team members during onboarding

9. Insufficient feedback methods

A proactive approach to sharing feedback can help workers effectively integrate into the company and drive improvements in the onboarding process over time. Implement methods for both managers to give feedback to workers and new team members to provide their input about the onboarding process.

In addition to formal check-ins to discuss 30-, 60-, and 90- day goals as highlighted above, encourage managers to schedule recurring one-on-ones—either weekly or biweekly—with new team members to share ongoing feedback and answer any questions.

Also consider asking your HR team to distribute surveys, schedule one-on-one feedback sessions, or conduct focus groups following onboarding to learn more about what’s working and what’s not with the process. Based on this feedback, your team can make adjustments to improve onboarding.

Questions to consider asking include:

• How satisfied are you with the overall onboarding experience?
• How well did the onboarding process prepare you for your role?
• How well did the onboarding program introduce you to the company culture?
• Were the training materials and resources provided during onboarding clear and helpful?
• How well did your direct manager support you during the onboarding process?
• What did you find most useful or beneficial about the onboarding process?
• What do you see as the top areas for improvement with onboarding?
• Would you recommend the company to someone you know based on your onboarding experience?

10. Lack of ongoing support

Onboarding is just the first step in comprehensive employee training. An ongoing approach to talent development is critical to engagement, productivity, and employee retention. In fact, an analysis of over 21,000 exit interviews across 175 companies conducted by Work Institute found that a lack of career opportunities or development is the top reason workers left their jobs in 2023.

Because each team member has a different learning style, offering a variety of support and development opportunities and resources is important. Examples include:

• Recurring one-on-one meetings
• Regular performance reviews
• Ongoing access to online learning sites or platforms after onboarding
• Internal growth opportunities through succession planning and other talent development strategies
• Stipends or reimbursements for relevant certifications, degrees, professional development events, resources, and upskilling courses
• Worker feedback and recognition programs
• Stretch assignments and experiential learning
• Dedicated time during the workday to focus on training and development
• Team or company-wide training and development sessions
• Mentoring and coaching opportunities

Key takeaways

Onboarding sets the stage for a new team member’s experience and success with your company.

By addressing common challenges, implementing a standardized onboarding process, and evolving and improving the process over time, your organization can develop positive working relationships with new team members and drive long-term engagement and retention.

Solve onboarding challenges with Upwork

Identifying and solving top onboarding challenges can seem daunting and requires time and thoughtful consideration. Experienced onboarding professionals are available on Upwork to share onboarding best practices, identify areas for improvement, and ensure each new worker’s onboarding experience is as engaging as possible.

Get started—log in or create an Upwork account and search for skilled onboarding specialists who align with your goals, requirements, and budget.

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