Resolving 7 Common Onboarding Challenges

Onboarding White Paper by CTD

What to say to a new employee to successfully navigate the ups and downs of onboarding

Introduction: The Honeymoon is Over

The proverbial honeymoon period of a new employee’s introduction to your organization is over. The new employee has been with your company for at least 30 to 40 days, and she has had time to form a greater understanding of the responsibilities of her new role. She has likely experienced the typical ups and downs of becoming comfortable in an unfamiliar organization, but you start to pick up on signs that aside from typical ups and downs, the new employee is not adjusting to the company, the position and/or the new responsibilities.

The employee has been participating in an onboarding program, but her results are not on par compared to what you’ve seen from other new employees or what you expected from this new employee in particular.

Is there anything you as the employee’s , hiring manager or HR partner can do to salvage the onboarding experience?

Can you turn her into an engaged employee fully integrated in the company and its culture, and the stellar leader you saw during the pre-start period?

The answer to both questions is yes.

In the following seven challenges of onboarding, we give you sample phrases to use with an employee who is having a hard time onboarding with your organization. Sometimes the easiest way to get back on-track is by exchanging a few simple words that let the employee know someone is still willing to make their transition easier—even after they have been with the organization for over a month.

The Common Onboarding Challenges are:

  • Lack of Role Clarity
  • Challenges with Expectations and Results
  • Managing Change
  • Issues of Time Management
  • Issues with the Manager
  • Navigating the Culture
  • Handling Personal Transition and Relocation


1. Lack of Role Clarity

Not having a clear understanding of one’s role is a pervasive problem for new employees and can lead to onboarding derailment. When reality hits at about the 30-day mark, the employee may realize that her expectations of her role are conflicting with the role she thought she accepted a month ago. Use these phrases when an employee is struggling with understanding her duties in your organization:

“Your role might be different than you expected it to be, it’s important to identify the differences and talk with your manager about those gaps.”

“I understand that you feel like this is not what you ‘signed up for.’ Let’s talk about what’s different.”

“I know that your manager said _______________ in your selection process, things in the business have changed. Let’s talk about how those changes impact your role.”


2. Challenges with Expectations and Results

Some new employees simply try to take on too much too quickly. Whether it’s to impress their managers, their new coworkers or that they thought they were expected to complete an insurmountable amount of work from the get-go, not understanding how much work is expected of her can lead the employee to unnecessary work overload (or the opposite).

These phrases will help you tell an employee she can take a breather.

“Trying to do too much too soon can be too much too soon. Trying to make a good impression and being too “heroic” in expectations can be stressful and can actually lead to alienating others instead of building relationship.”

“Take on reasonable expectations.”

“Acting like you have all the ‘right answers’ can make you seem arrogant, and you will have a difficult time building relationships and gaining support for your initiatives.”


3. Managing Change

Frequently a new employee, usually someone in a leadership role, is brought into an organization with the hope that she will evoke and drive “change.” But the pressure of following through with the “change” the employee had promised during the interview process can be stressful and downright difficult. Help the new leader understand how she can follow through with her plans for the organization.

“Changes are easier to make when you have built strong relationships. Let’s talk about who you need to get to know better.”

“I understand that ‘change’ was a big theme during your selection process and that you are ready to implement some new things; however, it is important to know the best way to initiate change in our organization.”

“Your team has been through a great deal of transition lately; let’s talk about doing a working session to surface some of their concerns.”


4. Issues of Time Management

A new employee wants her manager, the HR partners and her coworkers to have a favorable impression of her and the way she manages her time. But, the way she managed time in her previous role may have been different than the way she needs to manage her time in her new role. Maybe she is keeping her schedule too full and having to cancel or neglect other activities when something more important comes up.

Show the new employee that managing her time appropriately within the new organization is something that is important to you and her managers by using these phrases.

“Prioritize and be structured, but stay flexible for unexpected demands. Don’t schedule more than about 60% of your day so that you can respond to other things. This will also reduce stress and make you more accessible.”

“Manage your time wisely, and observe how others who do this well manage their time.”

“I am concerned that you have cancelled our last few onboarding meetings. Let’s talk about how we can stay in touch.”


5. Issues with the Manager

When a new employee has problems forming a positive relationship with her manager, onboarding can be seriously affected. As soon as signs of an issue show up, an HR partner or onboarding coach may approach the new employee with these phrases to get to the root of the problem and offer advice to smooth the relationship.

“Your manager does travel a lot; maybe you can set up regular conference calls to stay in touch.”

“Your manager’s style is different from your style. What do you know about her that will help you communicate successfully?”

“Here are some things I know about your manager that might help you as you get to know each other.”


6. Navigating the Culture

Similarly to a rocky relationship with her manager, if an employee is showing signs of not fitting into the company culture, don’t waste time before approaching the problem. There is no easy-fix to make someone “fit-in”, , but acknowledging that a new employee is having issues with the culture and letting her know that you are offering assistance will certainly make it an easier transition for her.

“It can take new employees up to a full year to really “get” the culture in our organization. What are some examples of the issues that have come up for you?”

“Our culture can sometimes be tricky for new hires. What feedback have you gotten?”

“Here’s what I know about the culture you came from at _______________, and here is how I see it as different from the culture here. What do you think?”


7. Handling Personal Transition and Relocation

When the pressure of taking on a new role is combined with a family who is having their own issues moving to an unfamiliar location, a new employee can be positively stretched thin and left wondering if they made the right decision accepting a new job. These combined forces can impact onboarding negatively.

“If your family (significant other) is not happy with your transition, let’s brainstorm some solutions, and then let me help you put a plan together.”

“_______________ in the department (organization) had some experiences similar to this when he moved and started his job here. I can ask him if he would be willing to share some of his advice and experiences with you.”

“What else can I do to support you and your family?”



Onboarding programs are designed to create a smooth transition into a new role and/or organization. Even with a tried and true onboarding process in place, it’s common for new employees to experience personal ups and downs during the first few months of a job. And, after a new employee has been with a company for over a month, she or he may be less likely to speak up about issues.

Rather than avoid issues, approaching them at the first sign by using a simple phrase or two to open a conversation can be the easiest way to solve a challenge before it becomes a full-blown problem.