Revisiting Conversational Leadership
When a workplace culture starts to falter, leaders often reach for more structure.
More rules, more checklists, more metrics…
Often, what’s really needed isn’t another form to fill out. It’s a conversation.
Clients who know me will be surprised by this advice: This is not a performance review, and it’s not a staff meeting agenda. It’s a real conversation: the kind that requires courage, presence, and a willingness to be changed.
This is conversational leadership—the practice of creating culture not through edicts, but through intentional dialogue. My history and experience as a founding faculty member for the Institute of Conversational Leadership and Invitas (with poet David Whyte) taught me that as we inhabit a conversational nature of reality, we are balancing listening and telling, leaning in and leaning back. In challenging times, it’s one of the most powerful tools a leader can use to restore trust, build connection, and move the team forward.
Why Conversational Leadership Works
Leadership is not a position—it’s a relationship. There’s no relationship without relating, or without being in conversation. So, relationships are built, strengthened, and sometimes repaired through those conversations. Not just the "How's your weekend?" kind (though those matter, too), but the kind that invites meaning, perspective, and vulnerability.
A well-timed, well-held conversation can shift morale, reset expectations, and reignite a sense of shared purpose. And yet, many leaders avoid these moments. Why? Because they feel messy. Unpredictable. Emotional. And they are.
But they’re also the heart of a thriving culture.
When you create space for people to share their truth—and when you meet that truth with respect—you lay the groundwork for psychological safety. And when people feel safe, they are more likely to take risks. They innovate. They speak up. They stay. That’s more than a million-dollar idea right there!
Be Fearless and Fair
One of the frameworks we work with and provide tools for is fearless and fair communication.
It means:
Tell the truth with courage
Listen and act with respect
Fearless doesn’t mean harsh. It means truthful. It means saying what needs to be said—even when it’s hard—with the intention of creating clarity, not blame.
Fair doesn’t mean you always agree. It means you approach the other person with dignity and care. You don’t weaponize honesty. You extend it like a bridge.
These conversations require preparation, but not scripts. They require heart, not spin.
Start with curiosity:
What’s really going on here?
What might I not be seeing or understanding?
How can I express what matters to me while honoring what matters to them?
And most importantly: Am I willing to listen, not just respond?
Yes, And: The Leader’s Superpower
Another favorite tool of mine, borrowed from the world of improv, is the principle of Yes, and…. In conversation, “Yes, and” doesn’t mean agreement—it means acknowledgment.
Yes, I hear that this change is frustrating…
And here’s why it’s necessary for our future success.
This approach validates the experience of the other person without abandoning your own leadership stance. It keeps the conversation alive, collaborative, and open.
Contrast this with “Yes, but”—which shuts things down and signals defensiveness. One word can change the entire tone of a conversation. Sometimes, we need to make our exchanges but-free!
You Don’t Need to Engineer Psychological Safety
It’s tempting to try to formalize psychological safety with initiatives, training, or policies. But the truth is, people don’t feel safe because of a slide deck. They feel safe when they’re seen, heard, and treated like their presence matters.
That happens one conversation at a time.
So start small:
Invite input—and listen fully.
Acknowledge hard truths—and stay open.
Speak your truth—with heart.
Make room for humor, honesty, and even disagreement.
This isn’t about perfection. It’s about practice.
Real Culture Lives in Real Conversations
Culture doesn’t live in your employee handbook. It lives in the moments between people:
In the courage it takes to speak up.
In the grace it takes to listen well.
In the stories we share—and the ones we’re still willing to write together.
What sort of challenges are you facing in your work culture? For now, let go of the checklist. Instead, ask yourself: What conversation is waiting to be had?
Then, take a breath.
Lead with heart.
And begin.
Reach out for more guidance on how to fine-tune these concepts to your specific needs by posting your questions in the comment section below, or for a more intimate conversation, connect with me here.
