Why is navigating extended leave such a challenge for both employees and organizations?
From my perspective, extended leave is one of those moments where personal needs and business needs really collide. On the employee side, there’s often stress about job security, uncertainty around the leave, concerns about pay continuity, and then also just the team’s perception of the leave in general. On the employer side, leaders are usually worried about workload redistribution, compliance, the regulatory components tied to FMLA or other state leave laws, and just maintaining productivity overall.
Usually the challenge is balancing empathy for that team member with the operational realities of still getting the work done. And when organizations don’t plan ahead, they often end up scrambling, which adds additional stress for everyone involved.
Have you seen examples where organizations handled leave particularly well – or poorly? What made the difference?
One of the mid-sized SaaS companies I supported had a senior software engineer who needed to take about 10 weeks of medical leave for surgery and recovery. This employee was highly respected and had been leading a project that was critical to the product. While the organization had a formal FMLA policy in place, the leave process exposed several blind spots.
On the employee side, they were reluctant to request the leave at first because they feared disrupting the team and being seen as replaceable. They also weren’t clear on whether their role and pay would be protected beyond FMLA, and no one proactively explained that to them.
On the employer side, the manager avoided early conversations about leave planning. When the employee went out, the project stalled, stress mounted, peers became overwhelmed, there was no backup plan or designated point of contact, and very little communication during the leave.
The turning point came when we introduced a leave planning playbook. It outlined pre-leave responsibilities, coverage mapping, communication boundaries, and reintegration steps. For this engineer, the return to work was much smoother because we were facilitating the process and reinforcing that simply meeting expectations after leave was a success.
How does workplace culture shape whether taking leave feels supportive versus stigmatized? What can we do to create a positive culture?
Culture is everything. In a supportive culture, leaders typically encourage employees to take the time they need and model it themselves. Communicating this from a wellbeing perspective really comes first.
In stigmatized cultures, employees may fear being labeled as less committed. To create a positive culture, organizations need visible leadership support, consistent messaging, and systems that normalize leave. That can include manager toolkits, peer coverage plans, and post-leave check-ins that focus on re-engagement without punishing the team member for taking time off.
For example, at one of the manufacturing companies I worked with, employees on medical leave were informally labeled as unreliable. Returning employees weren’t given meaningful work or seen as effective. Morale dropped, attrition rose, and the company lost key talent during a growth phase.
The lesson from situations like this is that culture drives perception. Even when policies are compliant, stigma can kill trust. Leaders need to model support and normalize leave as part of the business continuity plan.
What kinds of leadership blind spots do you see emerge when people are navigating someone’s leave or return?
One common blind spot is understanding the importance of reintegration after a leave. Leaders may assume the employee will just pick up where they left off, forgetting the personal and professional adjustments needed for someone returning to work.
Another big blind spot is overlooking the impact on the rest of the team – especially when workload has been redistributed unevenly. This can lead to burnout or quietly erode morale, and really turn into a silent killer.
Leaders also sometimes fail to communicate the plan clearly to the team, which can create unnecessary anxiety. Instead, it’s important to foster a sense of harmony around leave, helping both the returning employee and the team transition smoothly.
How can moments of leave – whether parental, medical, or bereavement – be reframed as opportunities for team growth or resilience?
From that perspective, in terms of a positive reframe, I think people who are on leave present an opportunity to strengthen the team’s capability. When one person steps out, others often have the chance to stretch into new responsibilities, develop leadership skills or other attributes, or cross-train in new areas. With the right framing, a team can come out of the experience more resilient and versatile while supporting the leave.
It also gives leaders a chance to show that they value people as whole humans, not just as roles – reinforcing trust and loyalty. For example, at one mid-sized company I worked with, a director’s sudden bereavement leave forced the team to redistribute work. Instead of panicking, leadership framed it as an opportunity to test bench strength and gave employees stretch assignments. When the director returned, the team had grown in capability, and the business identified two employees who might be ready for promotions.
One of the key lessons is that moments of leave can reveal hidden talent and build resilience – if leaders approach them with trust and proper planning.
In your coaching practice, how do you help leaders prepare themselves – and their teams – for a successful reintegration after leave?
What I typically encourage is to use a structured yet human-centered approach. At the end of the day, that’s what we are. We care about the work we do, but we also care about our personal health. It’s about balance.
Before the leave, clarify responsibilities, identify necessary coverage, and communicate openly with the team. Let them know what’s going to happen, and even crowdsource solutions to ensure there’s an appropriate level of synchronous communication before the leave starts.
During the leave, maintain appropriate contact. Updates or check-ins should happen only if the employee wants them, but even a simple “just checking in” goes a long way. It’s also important to align on the person’s intent to return and any anxieties they may have about coming back – it can feel strange, like being a new hire again.
For the return, hold a reintegration conversation: what’s changed, what remains the same, and what support might be needed as they reacclimate. I coach leaders to manage their own expectations – don’t overload returning employees immediately – and to create space for them to adjust. Small gestures, like a welcome-back lunch or just acknowledging them with the team, go a long way in rebuilding connections. When I’ve received simple messages myself, I know how much it means – it really does.
Any final words for our readers?
Leave is not a disruption to be managed. We’re evolving in our economy and workplaces, with multiple generations working side by side and many factors to consider in order to maintain highly engaged workforces. There’s a lot happening with AI, technology, and innovation, but at the same time, it’s all about people.
Leave is a normal part of the modern workplace. With thoughtful planning and genuine care, it can actually strengthen organizations. Leaders who embrace leave as part of the employee life cycle – not as an exception – will not only reduce risk, but also build a culture where people feel valued, supported, and motivated. That, in turn, helps retain talent and further positions the organization as a highly engaging place to work.
