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The Virtuous Cycle of Caring for Our Employees: How Employee Wellness Can Benefit Everyone

Part 2 of 2: System Perspective

Part 1 of 2: Employee Perspective was released in December of 2022 under the title “Moving Beyond Mandatory Use of PTO: Are You Supporting or Inhibiting Employee Wellness?”


  • Leaders are privileged when it comes to choosing to take time off, delegating coverage authority, and being able to quickly resume in our role upon return. It is important to recognize that members of our teams are not as privileged and might not feel comfortable honoring time off in the same way we do.

  • As leaders, we can work with members of our team to support and provide thorough, thoughtful coverage that allows them to unplug and recharge.

  • There are many system-level benefits to covering others’ time off, including:

    • Increased partnership and introspection on what matters (and what doesn’t).

    • Increased team communication, trust, and reliance on others.

    • Fraud prevention and inviting discussions on employee overload.

    • Increased understanding and empathy into others’ work.

    • Investment in employee development, growth, and improved operations.

In today’s post, I’ll explore the system benefits to investing in our people and supporting their time off through actions and not just words.

Background: Leaders Are Privileged. Assuming Our Privilege Extends to Our Employees Could be a Recipe for Employee Burnout.

As leaders, we are in a position of significant privilege. It can be easy to forget this when asking our people to take time off. When leaders take time off, we have access to a lot of flexibility:

  • We can designate a trusted senior executive to serve in our absence.

  • We can time our PTO (or even major organizational initiatives) carefully to avoid significant work events that need our participation.

  • We can take time off essentially whenever needed throughout the year.

  • Our teams are willing and expected to support our needs and preferences.

At this stage of our career, our work is not as focused around deadlines and churning through production as it is around leading our teams, company vision, strategic direction, and organizational culture and tone. The work is crucial and demanding, but its timing and output requirements may be far more flexible than those of our direct reports.

Without our support, it may be difficult for our direct reports (or theirs) to exercise this level of flexibility. As a result, they might feel that the upside of time off is not worth the downside they’ll return to after.

In addition, many executives have experienced firsthand downsides to time off that negatively reinforce the notion, such as:

  • A lack of systemwide planning, delegation, or fully honoring time off that leads to numerous drop-everything calls while they’re away.

  • A lack of foresight, flexibility, and cross-training that leads to a last-minute emergency only they can handle, requiring that they cancel their scheduled time off.

All this is a recipe for burnout and employee turnover.

As leaders, there are actions we can take to better support our team. When done thoughtfully, these actions can benefit everyone.

Five System Benefits to Supporting Your Employees’ Time Off

Rather than encouraging your employees to take time off only for them to return to a mountain of delayed work on top of their already growing pile (or to political or cultural blowback), leaders and teams can support their people by providing coverage to truly allow them to recharge.

Although coverage might be daunting, it’s good for everyone. Five system benefits are discussed below.

Benefit 1: Understanding and Respecting People’s Needs Leads to Increased Partnership and Introspection on What Matters (and What Doesn’t)

When I was CEO, I had some exceptional direct reports who, in addition to being dedicated and skilled, were grounded counterparts to my ideas and thought partners for brainstorming solutions to big challenges. We developed relationships where we were able to be open and honest, as well as challenge each other.

As I wrote about last month, one of those honest moments was regarding honoring work-life balance. The concept had been more-or-less a platitude to me—I didn’t value it and came from prior systems that didn’t value it either. It wasn’t until my direct reports shared their values that I could open my mind to its benefits.

In honoring my team’s boundaries, I was given the important opportunity to really consider whether my urgencies reflected genuine time sensitivity, or just impatience or poor planning.

Part of respecting team boundaries meant being more intentional about how my own “needs” affected the team. In my privilege as CEO, people would respond to my late-night emails, stay at the office late into the night with me, and drop everything when I made a request. But objectively, that’s not partnership. Though not intentional, it could be described as an abuse of power.

As leaders, are we refusing to unplug because we are that singularly essential, or is it an attempt at controlling our anxiety?

When we take time off but are fully accessible to the team, we’re not instilling confidence in them. Instead, we’re sending the inadvertent message that we don’t trust them and are unwilling to rely on them.

Understanding others’ needs and discussing our unspoken messages (or motivations) openly with our team can help us gain clarity into both the issue and the system we’ve built around it.

Benefit 2: Increased Team Communication Leads to Improved Trust and Appropriate Reliance on Others

When a member of our leadership team (including me) was scheduled to be out on vacation, we began our internal communications by huddling up about a month ahead.

We discussed and aligned on the meaningful points we could anticipate and what we could do to prepare in advance. Typical questions might include:

  • What major issues, initiatives, problems, or needs will be on the horizon around the time the leader will be out?

  • What essential or political situations might be cooking that could explode during our time off, who will be appointed to handle them, and what threshold should trigger an emergency call?

  • Who, between the person’s boss and direct reports, will cover what major functions?

  • What will need to be completed in advance (e.g., briefing, training, access) so coverage will be successful?

  • What kinds of issues or questions from the person’s team are appropriate to wait until their return?

  • What will the person worry about and what needs to happen in advance so they can let go?

  • What are our internal and external communication plans?

  • Who has delegated authority for what categories of unforeseeable urgent issues in the person’s absence?

When it was me going out, I would have similar discussions with my board chair and other key stakeholders. The leadership team would talk with their teams to ask what important things we were forgetting. We made plans for the important specifics and delegated authority where no concrete advance plans were needed.

These conversations helped us all get on the same page and minimize unforeseen disruptions or misunderstandings. Enacting the plans helped us maintain a high performing system of dedicated team members who we trusted and relied on.

Benefit 3: Fraud Prevention and Bringing Overload to the Surface

My team taught me something I didn’t know when I was part of very large systems: that covering others’ work was also an opportunity for organizations to discover fraud. Fraudulent activity can rise to the surface when people are not in the office to manage it, or when others have access to their work.

Often, those committing fraudulent acts will refuse to go out or share access to their materials, as they worry about being caught. When leaders notice resistance that doesn’t add up, this could be a sign to deepen the conversation or consider investigating warning signs, as appropriate.

There may be other issues that are not a matter of fraud, but of overload. An employee might be struggling to keep up while living on the verge of burnout, unwilling to speak up for fear of looking bad or facing negative consequences. When managers discuss (not demand) time off and face resistance, it can open the opportunity for disclosure and collaborative solutions.

Benefit 4: Better Insight, and Empathy, Into the Work

When you provide direct coverage for your people, you gain insight into what it’s like to be in their shoes at the organization. It provides deeper perspective on their frustrations or feedback they’ve shared that’s hard to understand without firsthand experience.

Just like an airline CEO occasionally flying coach to understand their customer experience, covering some of your direct reports’ functions in their absence can help you see systemic perspectives you might otherwise miss.

On one occasion when my head of finance was out, I ran into a banking issue (despite her training me in advance). It involved payroll, so it quickly rose to the level of emergency. I thought about calling her, but wanted to honor her time off and felt I could be more resourceful if I put my mind to it.

I tried all my internal resources, but it was a problem only the bank could resolve: I couldn’t remember my credentials. I called the bank, which catalyzed a comedic routine that lasted the better part of an hour. In short, their IT team helped me guess—through their prompts and my trial and error—my username and the organization’s security questions (which were set before my arrival). They never verified my identity.

There was so much wrong with this. While I appreciated their attempt to be helpful and got a laugh out of the whole thing, it was completely unacceptable from a fraud prevention and account security standpoint. I walked away with fears that anyone could have impersonated me to gain account access.

As soon as my head of finance returned, we changed banks, which came with other system and service improvements we had been wanting for a long time.

Benefit 5: Investment in Our People, Their People, and Sound Operations

Covering others serves as cross-training and an opportunity for employees at every level to step up and into responsibilities they don’t normally have. This is good for everyone.

Lean Six Sigma philosophy says that cross-training makes organizations more flexible, nimble, and helps employees avoid the drudgery of repetitive tasks, while giving them insight and appreciation into the upstream and downstream processes that surround their work.

Cross-training is financially and operationally smart in case of emergencies, but it also allows people to develop professionally and be trusted and relied on. It helps managers see their employees’ potential and helps employees grow and stretch.

Cross-training feeds good ideas, professional growth, innovation, trust, and employee satisfaction for knowing the role they play in outcomes and that the organization is invested in them.

These, and other benefits discussed in this post, are all indicators of employee satisfaction, retention, and wellness.

How does this resonate for you? Feel free to post thoughts in the comments or on social media.


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