Navigating a Bumpy Start: How to Handle Onboarding Challenges with Confidence

No matter how strong your recruitment process is, onboarding can still present unexpected challenges.  

In a recent LinkedIn poll, we asked hiring professionals to weigh in on the most common onboarding hurdles. The top response? Clarifying expectations. It was closely followed by challenges around candidate engagement, cultural integration, and managing logistics. 

If you’ve ever experienced a rocky start with a new hire, you’re not alone. The good news? These early bumps in the road don’t have to derail the entire journey. Here’s how to proactively navigate common onboarding challenges and set the stage for long-term success. 

Clarify Expectations Early, Clearly, and Continuously 

Misaligned expectations are a leading cause of early-stage frustration for new hires – and it’s easy to see why. Without a clear understanding of their role, responsibilities, and how their contributions will be measured, new employees can feel adrift, leading to disengagement and self-doubt. 

What you can do: 

• + Set Up a Comprehensive 30/60/90-Day Success Plan: Beyond simply outlining tasks, clearly define measurable goals and deliverables for each milestone. This provides a roadmap for success and allows both the new hire and their manager to track progress and celebrate achievements. 

• + Foster Two-Way Dialogue: Encourage new hires to articulate their understanding of their role and expectations. Ask open-ended questions like, “What do you see as your primary contributions in the first month?” or “How do you envision success in this role?” This allows for immediate course correction and ensures genuine alignment. 

• + Connect to the Bigger Picture: Help new hires understand how their role contributes to the overall success of the team and the organization. This provides context and meaning, boosting motivation and engagement.  

Keep Candidates Engaged Before Day One 

If there’s a long gap between offer acceptance and the first day, engagement can wane. Just as candidates can “ghost” employers, the reverse can also happen, leading to a diminished sense of excitement and connection before the employee even starts.  

What you can do:  

• + Initiate a Personalized Communication Strategy: Keep the excitement alive with proactive updates about the team or company. These small gestures demonstrate that they’re already a valued part of the team.  

• + Share Essential Information in Advance: Provide “need-to-know” onboarding materials, FAQs, or a digital welcome packet ahead of time. This allows new hires to feel prepared and reduces first-day anxiety. 

• + Introduce Them to the Team Virtually: Consider an informal virtual “meet and greet” with their immediate team before their official start date. This helps put faces to names and makes the first day feel less daunting.  

Integrate Culture Intentionally 

Company culture can be tricky to effectively articulate, especially in a hybrid or remote work environment. Without a strong, intentional introduction to your culture, new hires might feel like outsiders looking in, struggling to connect and truly belong.  

What you can do:  

• + Pair New Hires with Experience Employees: These “culture ambassadors” can share unwritten rules, introduce them to key people, and help them navigate the social dynamics of the workplace. 

• + Include Interactive Culture Sessions: Design onboarding sessions that encourage real conversations about your company’s values, norms, and how they manifest in daily work. Case studies, group discussions, and storytelling can be incredibly effective.  

• + Create Diverse Opportunities for Connection: Facilitate both formal and informal interactions. This could include virtual team lunches, dedicated “water cooler” Slack channels, interest-based groups, or even organized virtual team-building activities. 

Get the Logistics Right for a Seamless Start 

Nothing undermines a new hire’s initial confidence more than logistical hiccups. A late laptop, delayed system access, or a missing welcome kit can send a clear, albeit unintended, message: “we weren’t quite ready for you.” These seemingly small issues can create unnecessary frustration and signal disorganization.  

What you can do:  

• + Implement a Cross-Functional Onboarding Taskforce: Establish clear communication channels and coordination protocols between HR, IT, hiring managers, and any other relevant departments as soon as an offer is accepted.  

• + Develop a Detailed Pre-Arrival Checklist: Use a comprehensive checklist to ensure all necessary equipment (laptop, monitor), software licenses, system access, and login credentials are ready well in advance of the new hire’s start date. 

• + Designate a Clear Onboarding Point Person: Assign a single, accessible point of contact who can proactively troubleshoot any logistical issues that arise during the new hire’s first few days or weeks. This person should be empowered to resolve problems quickly and efficiently. 

• + Automate Where Possible: Explore onboarding software or platforms that can streamline tasks like document signing, benefit enrollment, and IT provisioning, reducing manual errors and improving efficiency.  

Beyond the Checklist: The Human Connection 

Onboarding isn’t just a process – it’s a critical moment of trust-building between employer and employee. It’s about making someone feel valued, supported, and confident in their decision to join your team.  

Even when the start is less than smooth, there’s always an opportunity to reset, realign, and re-engage. A positive and proactive approach to addressing challenges demonstrates your commitment to your employee’s success and fosters a resilient, adaptable workplace culture. 

Need Help Finding the Right Candidates? 

At Smart, Savvy + Associates, we are passionate about helping companies find and hire the marketing, communications, and creative professionals they need, from coordinators to C-suite. Based in Vancouver, BC, our team of marketers-turned-recruiters deeply understand the roles you need to fill, and the right mix of skills and experience required to ensure the best possible fit.  

Need help filling a role (or two) on your team? Contact our team to start the recruitment process today.