Leading with Connection in a Hybrid World: Lessons That Still Resonate

I just wrapped up a virtual meeting with our Administrative and HR Staffing team here at Hollister—and it struck me how far we’ve come. Who would have imagined back in 2020, when we were thrust into remote work, that we could not only run a virtual sales and service organization, but thrive in it? For many of us, this world was unfamiliar. But over time, we’ve adapted, grown, and redefined what it means to stay connected in a hybrid environment.

That first virtual meeting at the onset of the pandemic taught me powerful lessons—lessons that still hold true today. As we continue navigating the evolving workplace, these principles remain essential for leaders who want to foster engagement, well-being, and trust.

1. Transparent and Frequent Communication Is Non-Negotiable

At Hollister, we’ve always led with heart. Our culture thrives on human connection, so the physical distance of hybrid work initially posed a challenge. But what we learned quickly is that silence breeds uncertainty. Frequent Zoom check-ins and transparent updates—even when we don’t have all the answers—build psychological safety and keep momentum alive. Leadership isn’t about always knowing what’s next; it’s about committing to honesty and presence.

2. Working from Home Requires Rhythm, Not Perfection

Hybrid work isn’t just a logistical shift—it’s a behavioral one. Early on, our team wrestled with everything from setting up home offices to wondering if they needed to announce a coffee break. Those concerns were valid. What helped? Open forums where people could ask questions without judgment and share best practices. Creating space for candid dialogue allowed us to normalize the uncertainty and support each other through it.

3. Lead with Compassion, Always

The emotional toll of constant change is real. Our teams speak with job seekers navigating career transitions, clients facing hiring freezes, and others managing personal loss. Amidst this, we’ve found that leading with empathy—and even a bit of levity—can be grounding. We can’t control external chaos, but we can choose to lead with kindness, understanding, and perspective. This choice not only reduces stress but fosters deeper human connection.

4. Listen Deeply to What Your People Need

Leadership isn’t just about providing answers—it’s about listening. When our team expressed a desire to bring back meditation sessions virtually, we acted on it. These sessions have become a meaningful way to reduce anxiety, restore focus, and reinforce community. The lesson? Ask, listen, respond. Simple gestures rooted in listening can have profound impact.

5. Acknowledge What’s Real

Sometimes the most powerful thing you can do as a leader is name what’s true. Acknowledging fear, uncertainty, and even grief gives people permission to process and move forward. During those early days—and even now—our team shared stories of challenge, resilience, and unexpected joy. By naming what we’re collectively experiencing, we strip fear of its power.

6. Inspire Through Storytelling and Presence

This isn’t the first crisis I’ve led through, but it is perhaps the most defining. And one truth stands out: People don’t just want a plan—they want to feel something. They want stories. They want hope. They want to see that their leaders are human and still choosing optimism. I believe challenge sharpens us. We are more agile, more intentional, and more connected because of what we’ve been through. We are not who we were in 2020—we are better.

To our fellow leaders: your people don’t need you to have all the answers. They need you to show up, to listen, to be honest, and to lead with heart. That’s what will carry your culture forward—today, and into whatever comes next.

Wishing you continued health, connection, and success.

Onward,
- Kip Hollister