Productive Empathy: Caring for Your Team and Your Business
I was recently talking with a leader who found themselves in a bind: after the most recent U.S. presidential election, their team members were distracted and wanted to take the time and space they felt they needed to process. While the leader understood their team’s concerns, they also faced the reality that business needs weren’t on pause—their clients still required support.
They asked me: How might I be both empathetic to my team and realistic about our business constraints?
This is a common leadership challenge. Whether your title is "CEO" or "parent," navigating the sometimes conflicting needs of our people and performance of our business is one of the toughest aspects of leadership.
Leading Humans, Not Machines
Leaders set the boundaries of their teams' workdays—determining what success looks like, what meetings are essential, and what opportunities are available. It’s inevitable that personal needs will arise, sometimes as minor conflicts (a doctor’s appointment overlapping with a key meeting) and sometimes as major life changes (a new career interest, relocation, burnout, or external crises).
This is the tradeoff for the creativity, passion, and engagement humans bring to their work. You can’t bottle that magic without making space for the people who create it. As a leader who shapes both the goals of your business and the boundaries of your organization’s culture, you have both the opportunity and the responsibility to anticipate these challenges and navigate them thoughtfully.
Designing the Field of Play
Leaders can proactively prevent many conflicts by designing a flexible and humane work environment. It’s not just about formal benefits like PTO or parental leave—it’s about structuring the team in a way that makes those benefits accessible in practice. Here’s how:
Model Balance
Take time off and be vocal about it. Don’t just announce you’re OOO—share that you’re excited to unplug. Make it clear you won’t be available (except for true emergencies) and that you trust your team to handle things in your absence.
Build Redundancy for Resilience
Efficiency is often the enemy of resilience. Efficiency helps you capture more value, but resilience creates flexibility for your team and durability for your business. If only one person knows how to handle a key function, the system breaks down when they step away. Redundancy doesn’t mean duplication—it means structuring your team so that flexibility is built in.
Research from McKinsey emphasizes that organizations with built-in redundancies and cross-functional collaboration are more adaptable during crises, big and small. The ability to quickly absorb and respond to pressures from your organization or in the business landscape depends on leaders designing structures that allow for flexibility without sacrificing productivity.
You can build your organization’s resilience in a few simple ways:
Ensure everyone can speak to what others on the team are working on through regular round-robin updates, buddy systems, or stand-up meetings.
Set cross-training as a formal development goal for each team member so at least two people understand every major role on the team.
If you lead leaders, ensure they understand their peers' roles well enough to step in when needed. (Tip: Great leaders see talent across the organization as their responsibility, not those within their function. A deeper understanding of peer functions helps these leaders collaborate and lead more effectively across the business.)
Make Space for the Personal
Acknowledging employees as whole people fosters trust and engagement. You can do this in small and big ways:
Dedicate time in meetings for real connection. In one-on-ones, go beyond "How are you?" and follow up on personal details they’ve shared before.
Support development goals beyond their current role. Show genuine interest in their long-term aspirations—even if they lead elsewhere—by helping them find ways they can progress within and outside of their current role.
Pause for major events that impact the whole team or organization. During the height of the COVID-19 pandemic, one organization I worked with paused work to host extended town hall meetings, bringing together 1,200 employees for open dialogue about the extraordinary hardship everyone was under. These were spaces to process, share, and learn—acknowledgments that the external world impacts the workplace. The gesture reduced bottled-up anxiety, strengthened trust between employees and leadership, and demonstrated that the organization saw its people as whole human beings, not just workers.
Meeting People Where They Are
Sometimes, employees' needs won’t align with what the business can accommodate. Ethical, caring leaders want to support their people—but sometimes, full alignment isn’t possible. It’s natural for team members to feel frustrated when they don’t get the support they need. "We can’t help" sounds harsh in moments of distress.
Gallup research shows that employees who feel heard and supported are more engaged and productive, even when business constraints prevent full accommodation of their requests. It’s critical that leaders are able to genuinely validate employee concerns while co-creating solutions. In short, your response matters. A lot. But you aren’t without options when faced with these challenges.
Validate Their Frustration
Harvard Business Review has published extensively on how psychological safety in organizations fosters trust and reduces workplace stress. Acknowledging emotions without attempting to correct or minimize is necessary for strengthening trust and can help make employees more open to compromise.
When an employee is struggling with your response, acknowledge their emotions without trying to change them. You don’t have to agree with their perspective, but their experience is still valid. Trying to convince them otherwise will only erode trust.
Get Creative
Even if you can’t meet their request exactly as they’d like, explore alternative solutions together. What’s possible within the constraints you face?
Use the Power of "And Yet..."
When an employee faces an unfair challenge and the answer they want isn’t possible, this phrase can be transformative.
After listening and validating, say: “And yet, this is where we are.” Then, lay out the facts and the support you can offer. Then, invite them into solution-building with you.
A Conversation Example
Employee: With everything happening in the news, I’m overwhelmed and need time away to process and take action.
Leader: That makes sense. Can you share more about how it’s impacting you?
Employee: I’m worried about friends and family, and I feel like being informed is the most important thing for me right now. It’s hard to focus on work when so much is happening. I think I need extended time off.
Leader: I’m so sorry you’re going through this. It sounds incredibly tough. I’d love to give you as much time as possible, but our customers need support right now. I can offer a couple of days.
Employee: That’s frustrating! How am I supposed to ignore what’s happening?
Leader: I get it. I wish I could offer more, and it’s frustrating that I can’t. And yet, this is the reality we’re in. Our customers are depending on us. If you need more time, we can shift things around. You’re an essential part of this team, and I want to support you and our work. What other options could we explore together?
By the end of this exchange, the employee feels heard, understands the business realities, and is engaged in crafting a solution.
Leading with Productive Empathy
Leadership is about balancing empathy with the realities of business. The goal isn’t to eliminate tension—it’s to navigate it well. When employees’ needs and business constraints diverge, the most impactful leaders:
Build a resilient culture that makes space for the humans who work there.
Build redundancy in the structure and the work so flexibility is possible.
Meet employees where they are, even when they can’t give them everything they want.
Use "And yet…" to acknowledge reality while inviting agency.
How do you handle situations where personal and business needs collide? What strategies have worked—or backfired—for you?
