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10 Employee Onboarding Challenges & Solutions

A warm welcome goes a long way! 

Research shows that first impressions can really convince new hires to stay (or not) with the organization long-term. 

An effective employee onboarding process speaks volumes about the organization and management and sets the tone for the days, months, and years to come. It shows that you care about your new employees and want them to flourish. After all, today’s new joiners are tomorrow’s star performers! 

But when onboarding at scale, some inevitable challenges emerge. As an HR leader or hiring manager, you must combat the obstacles and maintain consistency in onboarding. 

And we’re here to help you identify those challenges and provide potential solutions. 

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10 Onboarding Challenges and Solutions

Let’s dig deep into the 10 onboarding challenges companies face and ways to address them. 

1. Improper job description 

The biggest onboarding mistake is one you can eliminate at the root—posting vague job descriptions. Rehashing old job postings is not a good idea because chances are, a lot has changed since your last hire. 

Without enough clarity on what the role entails, must-have skills and qualifications, and compensation, you may attract the wrong talent pool. In such cases, you’ll have to restart the hiring process from scratch, which is expensive and time-consuming. 


  • Collaborate with the higher management: HR leaders or hiring managers can collaborate with departmental heads to outline what the company is looking for in a potential hire and develop a job description accordingly 
  • Include all relevant information: Ensure the job listing includes the following: a clear job title, responsibilities and expectations, must-have and nice-to-have skills, qualifications, salary and benefits, mode of working, and a short introduction to the company 
  • Update documents: If you have to use an old job description, update it thoroughly to meet the organization’s present vision and needs

2. Excessive manual paperwork

When a new employee joins, the standard onboarding program acquaints them with the company’s systems, regulations, tools, legal documentation, working methods, and employee benefits. 

It often involves too much manual paperwork, leading to a poor onboarding experience. Because let’s be real, no one likes to get bombarded with heaps of documents on the first day of their job—it’s overwhelming and puts unnecessary pressure on the employee. 


  • Go paperless: Cut down on messy paperwork and go digital with employee onboarding software for both remote and in-office roles. Compile all onboarding documents in a secure, centralized repository and share them with new joiners as and when required
  • Start early: Don’t wait for the joining day—send over the necessary onboarding documents a day or two before as part of the welcome package. The new hire will get some time to go through the papers, understand their role better, and clarify any queries beforehand
  • Share role-specific documents: Instead of sharing the entire list of documents during preboarding, provide only relevant information (such as department-specific tools, training modules, SOPs, and team structure) to keep things organized from the get-go and create a positive employee onboarding experience

Netflix is a great example of this. Cecili Reid, who joined Netflix as a software engineer, shares his onboarding process at the company in a personal Medium post:

“When I opened my email on the first day, I received an onboarding plan from my onboarding buddy. An onboarding buddy is a dedicated person on my team who shows the new hires the ropes as they are onboarded. The onboarding plan was customized for my team and me and consisted of materials I should read or required things I should do to get my credentials and environment set up or suggestions to make my onboarding smoother. I worked through the plan on my own time in between team meetings or onboarding sessions and met with my onboarding buddy daily.

My buddy and plan were essential for helping me to decide what I really needed to focus on in my onboarding.”

3. Not explaining your onboarding software 

Your employee onboarding software unifies the multiple moving pieces of the onboarding process. It irons out the “first-day jitters” an employee might face, helps them ease into their new role, and allows hiring managers to track progress. 

HR leaders often assume that the employee is familiar with the onboarding tool, but this may not always be true. Without guidance on using the software, employees feel confused and fail to make the most of it, and hiring managers cannot get a clear picture of the joiner’s progress.


  • Provide training: Offer pre-recorded materials or in-person training to walk your employees through the onboarding software. Give them some time to toy with the tool 
  • Explain the nitty-gritty: Go in-depth into the tool and explain every minute detail. Ensure everyone—irrespective of their technical expertise—understands the software like the back of their hand
  • Address challenges: Encourage new joiners to ask questions regarding the tool, if any, and help them out when they stumble upon an issue 

4. Information overload in the first few days 

HR leaders can overwhelm new employees with information during the acclimating process without even realizing it. This happens during the first few days or weeks of joining. With too much on their plates, new joiners find it difficult to absorb what’s being handed to them. 

While it’s important to deliver key information that will help employees understand and carry out their responsibilities, drowning them in information will only make the transition complicated. 


  • Employee handbook: Design an employee handbook (a document containing the company policies and guidelines) to communicate what’s accepted in the workplace and what’s not. This should serve as a go-to resource to answer queries related to team communication, workplace safety, use of company resources/property, dress code, and disciplinary rules. 

If you’re feeling adventurous, try the Nordstorm way—their employee handbook is a company philosophy summed up in a single, powerful sentence: “Use good judgment in all situations. There will be no additional rules.”

While their complete handbook is about 7500 words long, they do a great job of capturing their core philosophy with wit and brevity.

  • Onboarding checklist: Keep an onboarding checklist handy while welcoming new employees to the company. This checklist will ensure a consistent onboarding experience, eliminate errors, and ensure everything runs smoothly. You can also use onboarding templates to simplify this process
  • Give them time: Share the employee handbook a few days before the joining date (along with the onboarding documentation) and allow new joiners some time to familiarize themselves with the company’s ethos. The day they join, you can get straight to orientation and introduce them to their teammates

5. Not collecting feedback 

Chances are, not all employees feel the same about the onboarding journey. One of the best ways to prevent initial hiccups is to ask new employees about their onboarding experiences. 

New employees are most engaged in the first few weeks and are likely to be more transparent in their feedback. Collecting and collating feedback over time can give you an accurate picture of what employees appreciate and what you can do better. This can help you fine-tune the onboarding journey. 


  • Put them at ease: Employees who feel welcomed and cared for find satisfaction in their roles. Create an atmosphere where constructive feedback is appreciated and worked on so employees know their opinions matter
  • Have one-on-one sessions: You can try a more personalized approach by having one-on-one sessions with new employees. This allows HR teams to ask specific questions and use the feedback to improve the onboarding journey
  • Conduct surveys and polls: Quantitative surveys give you a holistic picture of onboarding experiences at scale. Ask questions on resources and milestones to know what stands out for employees and run brief polls to understand how they’re settling into their jobs

At ClickUp, we seek to constantly improve our onboarding processes with helpful feedback from new hires. New hires fill out dedicated survey forms to share how they’re feeling during onboarding. They also share their suggestions for improvements to the program. We also use dashboards to visualize this data and track the areas to refine and create a better overall onboarding experience.

6. Not setting clear expectations 

A new employee joining your team brings a lot of changes—for both the employee and the company. One of the biggest mistakes HR teams can make is not setting clear expectations early on. 

Clarity about the job, the expectations, and the day-to-day operations can make a massive difference in the onboarding experience.


  • Create expectations: Before communicating expectations to a new hire, create and refine a list of expectations. This prevents miscommunication and streamlines hiring. The list should include the values and performance expected of the employee as an individual and team member and the resources a new hire should expect from the company
  • Communicate expectations: Set examples by notifying when a candidate should hear from you. During the hiring phase, take a few minutes to explain what is expected of the employees
  • Manage and track expectations: It’s not easy to enforce the expectations and see if they’re met. To help employees get comfortable in the role and track their progress, you can create a 30-60-90 day plan, which highlights the onboarding goals and expectations broken down into smaller phases

7. Not contextualizing onboarding

In complex organizations, a new hire often feels like a fish out of water. Things move too fast for them, and they feel clueless. 

It becomes a bigger issue if you use a cookie-cutter onboarding journey that doesn’t consider the new employee’s skillset and expectations.


  • Bin the introduction: Contextualized hiring experiences are engaging, which is the opposite of watching an introductory video. It wastes time and contradicts the next step in the process

Reid highlights that none of the onboarding sessions at Netflix were boring. 

“No one wants to sit in a room (or in my case in front of a computer) for an hour or two watching someone read from the slides. Each one has been interactive in some way and tied in very interesting concepts or themes from Netflix which has been refreshing. For example, a presentation included a game with Kahoot! to test our knowledge.”

  • Create contextual hiring flow: The best way to make sure new employees feel connected to their role is to have an interactive onboarding journey that’s contextualized to their department and profile
  • Explain the process: A contextualized onboarding flow is most effective when a new employee knows how to use it. HR teams should explain the setup beforehand so employees can make the most out of it

8. Low employee engagement 

According to Gallup, only 23% of employees are engaged in their work globally. Disengagement stems from a lack of clarity about work and career, bad experiences with managers, and a lack of sense of belonging at a company. 

HR teams need to put more effort into revitalizing engagement metrics. And what better way to do that than by making a lasting first impression?


  • Create a strong internal culture: New hires observe how other employees operate and visualize themselves in their positions. If you can cultivate a collaborative and encouraging internal space for employees, new hires will feel more engaged at work
  • Recognize the wins: New employees appreciate peers and managers recognizing their work. It’s a massive boost of confidence and encourages employees to put more effort into their work
  • Check-in frequently: When the manager or someone from HR drops by occasionally, it shows people are concerned about the new employee. All these little efforts go a long way in promoting employee engagement

9. Not addressing differences

You may notice some stark differences of opinion between new and old employees. These could stem from generational, cultural, or temperamental differences. It’s normal to have conflicting views, but there has to be a certain level of alignment between employees. 

Without initiative from the HR leader or the hiring manager, it can be difficult to keep the team on the same page and work toward shared goals. 


  • Lead by example: Treat every employee with equal respect during the onboarding process. Rather than trying to mold everyone into the same shape, leave room for celebrating differences
  • Create a collaborative space: Encourage both new and old employees to collaborate among themselves, get to know each other, resolve conflicts constructively, and work as a unit
  • Set up mentorship programs: Senior team members can mentor new joiners for a specific period to help them understand their responsibilities. These programs allow new employees to learn and bond with the higher-ups in the team

10. Not using a buddy system 

Joining a new organization is a massive change. Despite how smooth the onboarding process is, it feels daunting. If the employee finds adjusting to their new workspace difficult, their motivation dwindles, and they may even consider switching jobs. 

Besides a mentor, they’ll also need the support of a peer who’ll walk them through (virtually or in person) their new workplace. It’ll help them understand the nuances of the role. Without this, the entire onboarding system will miss out on the essential human touch. 


  • Offer an onboarding buddy: Make it a standard practice to pair your new employee with an onboarding buddy—a friend who’ll make the first few days at the workplace feel less intimidating (and more productive!)

According to Microsoft, the frequency of meetings between onboarding buddies and new hires significantly impacted the new hires’ perception of their productivity.

Among those who met with their buddy at least once within the first 90 days, 56% felt the buddy accelerated their progress towards becoming productive in their role. This number rose steadily with increased meeting frequency.  For those who met two to three times, the percentage rose to 73%, and it climbed to 86% for those with four to eight meetings.

Notably, a whopping 97% of new hires who met with their buddy more than eight times in the first 90 days credited their buddy with helping them achieve rapid productivity.

  • Boost confidence: The onboarding buddy will be the employee’s support system, educate them on the company’s processes, and keep up their confidence 
  • Encourage making new connections: The buddy can introduce the employee to other team members. This makes them feel comfortable to open up and build connections in the workplace
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Tools for Dealing with Employee Onboarding Challenges

If unresolved, onboarding challenges lead to low employee satisfaction. The tips we discussed in this blog post will allow you to simplify the onboarding process. 

From the moment you put out a job listing until the employee joins the workforce and gets in the groove, implementing small changes will create a bigger impact in the long run. 

To tie up all the steps into a centralized hub, you need a comprehensive HR tool. What better option than ClickUp’s Human Resources Platform

Improve the onboarding process with the ClickUp HR platform

  • Stay on top of employee performance, engagement, and development with the customizable ClickUp Dashboards
ClickUp’s Dashboard
Get real-time reports on tasks assigned or completed, time spent on tasks, completion dates, and more with ClickUp’s Dashboards 
  • Collect feedback using polls, surveys, and requests with customizable ClickUp Forms. They help you track employee response data and glean insights to improve the onboarding process 
ClickUp Forms
Collect feedback on the onboarding experience using ClickUp Forms
  • Create company wikis to get new hires up to speed using ClickUp Docs. Add nested pages, edit in real time, and keep information up-to-date. Also, add comments to get departmental teams to pitch in where necessary  
 ClickUp Docs
Add information, edit, and collaborate on company wikis with ClickUp Docs
ClickUp Comments and ClickUp Tags
Allow new employees and the leadership to communicate on tasks using assigned ClickUp Comments and ClickUp Tags

ClickUp allows you to personalize your HR system by creating custom statuses and fields. You can curate a consistent onboarding experience while adding role-specific elements to contextualize the process. 

Address onboarding challenges with ClickUp’s templates

ClickUp’s templates offer a powerful solution to address several onboarding challenges for new team members, including information overload, knowledge gaps, excessive reliance on individual mentors, and the understanding of workflows, systems, and processes.

Using the following templates will help you tackle these issues head-on. 

1. ClickUp Onboarding Checklist Template

Organize onboarding tasks with ClickUp’s Onboarding Checklist Template

Onboarding is a long, winding process. When hiring at scale, you have to ensure you’re ticking off every step involved—from recording the employee’s personal information and discussing pay and benefits to collecting post-onboarding feedback. 

ClickUp’s Onboarding Checklist Template offers you a ready-to-use task list to keep you on track. It comes with: 

  • Step-by-step instructions on how to complete the onboarding tasks 
  • Real-time updates on task status and task progress
  • Option to set deadlines and priorities

It’s a lifesaver for busy hiring managers looking to stay more organized and maintain a uniform onboarding experience. Leadership can also use this template to monitor how the onboarding process unfolds.

2. ClickUp Employee Onboarding Template

Pave the way for smooth initiation into a new role with ClickUp’s Employee Onboarding Template

With the ClickUp Employee Onboarding Template, you can give your new employees a roadmap for what’s expected of them in the first few weeks and how they can fulfill their roles within the first 90 days of joining the organization. 

It offers employees clarity in navigating the new role without taking away their autonomy. They can easily track their progress with measurable goals and ask seniors or peers for help if needed. 

The template consolidates every little detail the employee needs to remember to carry out their job. They don’t have to juggle between multiple documents to understand their role—they can get straight to business!

3. ClickUp Employee Onboarding Template (90 Days)

Guide new hires to learn the ropes of their job within the first three months of joining with ClickUp’s Employee Onboarding Template

If you follow the 30-60-90 onboarding framework, ClickUp’s Employee Onboarding Template would perfectly fit your workflow. 

It helps you draft an action plan for the new employee, outlining what they should accomplish and what kind of employee training they should get within the first 30, 60, and 90 days after joining. 

Use the template to elaborate on the role’s mission and vision, specific role descriptions, ownership areas, key responsibilities, key stakeholders, and measurable goals. 

Let’s understand this approach better with an onboarding example

If we’re to create a 30-60-90 plan for a new marketing analyst at a marketing agency, it’ll look something like this: 

The first 30 days

  • Orientation and onboarding: Get familiar with company culture, policies, and procedures. Meet with key team members and stakeholders
  • Learn tools and systems: Understand the marketing analytics tools and platforms used by the agency
  • Study past campaigns: Review previous marketing campaigns to understand the agency’s approach, successes, and areas for improvement
  • Shadow team members: Spend time shadowing senior analysts and other team members to understand workflows and processes
  • Begin data analysis: Start analyzing data from recent campaigns to identify trends, patterns, and insights

Days 31-60

  • Deep dive into data: Continue analyzing data from past campaigns, focusing on more nuanced and contextual analysis techniques 
  • Develop reporting templates: Create standardized templates for reporting campaign performance to clients and internal stakeholders
  • Contribute to strategy discussions: Participate in strategy meetings, offering inputs based on data analysis and research
  • Begin independent projects: Take on smaller projects independently, under the guidance of senior team members
  • Work on feedback: Get feedback from peers and supervisors and identify areas for improvement and refinement

Days 61-90

  • Lead small projects: Take the lead on small-scale marketing analytics projects, from data collection to analysis and reporting
  • Present findings: Present findings from independent projects to the team and possibly to clients, showcasing your ability to derive actionable insights
  • Refine skills: Focus on refining specific skills based on feedback and self-assessment. This could include improving data visualization skills, learning advanced statistical techniques, or mastering new analytics tools
  • Contribute to strategy development: Contribute actively to the development of marketing strategies for upcoming campaigns
  • Prepare for the next phase: Reflect on achievements and challenges from the first 90 days, and implement the learnings in the next phase of your role within the agency

You can also tweak the template to meet the requirements of different roles and industries. 

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Make the Onboarding Process Easier with ClickUp

Handling common onboarding challenges is all about starting on the right foot. Prioritizing positive first impressions boosts retention and happiness and creates a culture that says, ‘You’re at home!’ 

With ClickUp’s all-in-one project management and human resource management platform, you can simplify documentation, communication, feedback collection, and progress tracking. This makes onboarding a breeze! 

Get started with ClickUp and experience it yourself! 

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