How to Lead Through Hard Conversations Without Losing Trust

By Jessica S. Andrews

When Leadership Gets Heavy

The weight of that conversation still sits heavy in my chest. In my past roles, I've had to walk into rooms filled with talented, hardworking people and deliver news that would change their lives. Three reductions in force. Three rounds of layoffs. Each one harder than the last.

As a COO, I thought the hardest part would be choosing who to let go. I was wrong. The hardest part was what came after leading the people who remained while supporting those who were leaving.

If you've ever had to navigate restructuring, downsizing, or any difficult organizational change, you know this truth: how you handle the hard conversations defines your leadership more than any strategy meeting or quarterly review ever will.

The Ripple Effect Nobody Talks About

Here's what I learned: everyone suffers, just differently.

The people leaving are dealing with feelings of inadequacy, fear about their future, and confusion about why them, why now. They're wondering how they'll explain this to their families, whether they're actually good enough for their next role.

The people staying are dealing with their own challenges:

• "Am I next? What if there's another round?"

• "Now I'm going to have to do Sarah's job AND mine."

• "Can I trust leadership anymore? They said this wouldn't happen."

• "Is this company actually stable?"

After our first reduction in May, I watched productivity drop across the board. Not because people were lazy, but because they were scared. Fear is a productivity killer. When your team is spending mental energy wondering about job security, they're not innovating or solving problems.

By the second round in October, trust was fragile. By the third in December, I was facing a full-scale morale crisis. People who had survived three rounds were questioning everything my leadership, the company's direction, their own security.

Leading with Intention Through the Storm

The most important lesson I learned? Intentional communication is everything. You can't communicate your way out of a difficult situation, but you can communicate through it with dignity intact.

Supporting Those Who Leave

How you treat departing employees sends a message to everyone watching. We allowed them to keep their work computers, paid for professional resume rewrites, conducted mock interviews, and I served as a reference. I stayed in touch even after they left, celebrating when they landed new roles.

The goal was simple: when they talked about our company, they could say, "It was hard, but they treated me with respect and set me up for success."

Supporting Those Who Stay

Your remaining team is watching everything. They need transparency, validation, and stability.

Acknowledge their reality: "I know this is scary. I know you're wondering about your job security. Let me share what I can about where we stand."

Validate their concerns: "It's normal to feel uncertain. It's normal to be sad about colleagues leaving and worry about increased workload."

Provide what stability you can: Double down on routine check-ins, maintain meeting cadences, and keep working toward your mission. Consistency in small things provides comfort during big changes.

The Hidden Challenge: Developing Your Managers

Here's what nobody prepared me for: many of my managers had never let someone go before. While I was dealing with the strategic weight of the decisions, they were facing their own crisis of confidence.

The manager who had to let go of someone they'd hired. The director questioning whether they'd failed as a leader. The supervisor terrified they'd say the wrong thing.

I realized I had two jobs: supporting the people directly affected and coaching my management team through their first experience with this level of leadership difficulty. I should have provided clearer frameworks for these conversations, emotional intelligence training, and post-conversation debriefs to help them process.

Rebuilding Trust After Multiple Rounds

By the third round of layoffs, I faced a trust problem I hadn't anticipated. The first time, I'd reassured everyone we were stabilized. The second time, people felt misled. The third time? Trust was broken.

"You told us this wouldn't happen again." "How do we know there won't be a fourth round?"

I had to own this. I acknowledged that my previous communications, while well-intentioned, hadn't been accurate. I changed my communication style from definitive statements about the future to sharing our best assessment while acknowledging uncertainty. I increased transparency about our financial position and delivered consistently on smaller commitments.

When trust is broken, you rebuild it through actions, not just words.

What Culture Really Means

I used to think culture was about perks and casual Fridays. I learned it's actually about how you show up when everything is falling apart.

Culture is defined by how you treat people when you have to let them go, how you support those who remain, whether you communicate with honesty or hide behind corporate speak, and whether you take responsibility for your mistakes.

Companies with strong cultures aren't the ones that never face hard times—they're the ones that maintain their values when times get tough.

The Long View

A year later, I'm still in touch with most of the people we had to let go. Several landed in better roles. A few have thanked me for how we handled the situation.

The team members who stayed? They're stronger and more resilient. Not because the experience was easy, but because they saw that even in the hardest moments, leadership could be exercised with integrity and care.

Difficult conversations and hard decisions are inevitable in leadership. How you navigate them isn't just about damage control, it's about who you choose to be when leadership gets heavy.

Your culture isn't built in the good times. It's built in moments like these, when everything feels uncertain and everyone is watching to see what kind of leader you really are.

What difficult conversation are you avoiding? What would change if you approached it with the same intentionality you bring to your biggest strategic decisions?