The Art of Conversation: Leading in Unscripted Moments

Many leadership conversations happen outside of boardrooms or carefully rehearsed presentations. In fact, many don’t even lend themselves to a polished elevator pitch when you unexpectedly find yourself face-to-face with a decisionmaker or boss. They often happen in the moment where emotions, urgency, and competing priorities collide.

And yet, when leaders think about communication, they tend to prepare for the moments they can anticipate: presentations, town halls, and key messages they’ve had time to plan. They learn how to clarify their thinking, structure an argument, and persuade an audience. These skills are essential. But they’re not always designed for conversations that unfold in real time.

That pressure has only intensified in today’s environment. Leaders are navigating the constant change of shifting priorities, tighter timelines, and growing expectations to move quickly while still bringing people along. Decisions are being revisited, strategies adjusted, and conversations that once felt straightforward now carry more emotion, more risk, and more consequence.

Through our work with leaders across industries, we’ve seen this gap become increasingly clear. In the moments that don't allow for scripting or certainty, leaders need tools that help them think, listen, and respond as the conversation progresses.

It’s this reality that led us to develop The Art of Conversation, a new program designed to help leaders navigate dynamic, real-time conversations where influence is built moment by moment, not only message by message.

The conversations leaders are avoiding

In our work with clients at The Humphrey Group, we consistently hear the same challenges surface:

• Leaders avoiding difficult conversations because they’re worried about conflict
• Managers defaulting to silence, aggression, or people-pleasing under pressure
• Meetings that go in circles, get hijacked by dominant voices, or end without clarity
• Teams feeling disengaged because issues go unaddressed

The cost of these missed or mishandled conversations has operational impacts. Facing these challenges with avoidance leads to an erosion of trust, declining engagement, stalled decision-making, and even productivity loss.

Sandra Bekas, The Humphrey Group’s Senior Manager, Learning and Development, explains, “A lot of people avoid difficult conversations because they don’t have the clarity they need to really feel confident about having that conversation.”

Consider a one-on-one conversation that a leader knows they need to have. They’ve thought through what they want to say, rehearsed the key points, and committed to addressing the issue directly. But once the conversation begins, the other person reacts emotionally. In response, the leader hesitates, softens their message, or moves on entirely.

As Sandra explains, under stress, leaders often default to familiar, reactive patterns rather than intentional responses. Ultimately, the issue remains unresolved because the real-time conversation demanded something different than was anticipated. Stress, emotion, or resistance can alter a conversation, and many leaders haven't yet developed the tools designed for navigating those shifts without escalating tension or losing control of the outcome.

A different kind of framework for a different kind of moment

At The Humphrey Group, our foundational programs have long focused on persuasive communication, helping leaders clarify their thinking, articulate conviction, and inspire action through structured messages. These skills are essential, particularly in moments where leaders are expected to inform, align, or influence at scale. 

Conversations, however, operate differently. They’re dynamic and unpredictable. They’re shaped by emotion, power dynamics, competing priorities, and how present or reactive each party becomes.

The Art of Conversation starts from a simple observation: While most conversations can’t be scripted, they can be prepared for. As a complement to programming that supports planned communication, this program focuses on how leaders show up, respond, and listen when conversations unfold in real time, whether the moment is routine, complex, or emotionally charged.

That’s the role of the Prepare-Act-Listen (PAL) framework. PAL gives leaders a simple, practical way to approach conversations without relying on scripts or rigid plans.

In The Art of Conversation, leaders use this framework to learn how to prepare by getting clear on what they want to achieve in the conversation, what matters most, and where they may need to stay flexible. This preparation is not about deciding exactly what to say, but about entering the conversation with intention and focus.

As the conversation unfolds, leaders practice moving between acting and listening. They learn how to contribute their perspective clearly and confidently, while staying open to what others are saying. Rather than pushing the conversation in a single direction, leaders build the skill to respond thoughtfully to new information, emotion, or resistance as it emerges.

PAL also reinforces that preparation does not end once the conversation begins. Leaders are taught to pause, recalibrate, and adjust their approach in the moment as the dialogue evolves. This allows them to stay grounded, maintain clarity, and guide the conversation forward, even when it takes an unexpected turn.

This flexibility is intentional. The goal of PAL is not to control the conversation, but to help leaders remain present, intentional, and effective from start to finish.

Four tools for guiding conversations that drift, stall, or escalate

As conversations unfold, leaders inevitably encounter derailers: resistance, tangents, emotional reactions, competing priorities, or lack of engagement. To help leaders navigate these moments, The Art of Conversation also introduces four practical influence tools:

1. Frame. Framing makes the purpose of the conversation explicit. It answers the questions, Why are we here, and what are we trying to achieve together?  By naming the objective out loud, leaders create alignment and reduce ambiguity before the conversation veers off course.
   
   For example, a leader might open with, “I want to talk about how we move this project forward without putting the timeline at risk.” Clear framing aligns attention and reduces unproductive debate.
   

2. Summarize. Summarizing distills what’s been said and is especially helpful when multiple perspectives are in play. It demonstrates listening, surfaces shared understanding, and helps groups see patterns instead of talking past one another.
   
   In a meeting with competing viewpoints, a leader might say, “What I’m hearing is agreement on the goal, but different concerns about timing and resources.” This helps the group move out of repetition and toward a decision.

3. Clarify. Clarifying questions move the conversation forward by deepening understanding. Instead of reacting to assumptions, leaders use curiosity to uncover what’s really driving concerns, resistance, or confusion.
   
   When someone pushes back, a leader might ask, “What part of this feels most risky to you,” or “Can you say more about what you’re seeing from your side?” These questions replace assumptions with understanding.

4. Redirect. Redirecting is one of the most powerful tools in the set. It allows leaders to acknowledge contributions without validating derailment, refocus the group on the objective, and mobilize action with a forward-looking question. Instead of shutting people down, leaders know how to bring conversation back on track in a way that is both respectful and effective.
   
   For example, “That’s helpful context. Let’s bring it back to the decision we need to make so we’re clear on next steps.” Redirecting keeps momentum while preserving trust.

Conversation as a core leadership capability

Leadership today is less about delivering top-down answers, and more about holding space for dialogue. The leaders who are most effective are the ones who can stay grounded under pressure, listen without losing sight of their purpose, remain responsive without becoming reactive, and most of all, the ones who develop the skillset to guide conversations toward clarity and momentum.

More and more, organizations are recognizing that leadership effectiveness increasingly depends on what happens between prepared messages. By building awareness, intention, and skill in the moments that matter most andThe Art of Conversation equips leaders to do exactly that.

Afterall, these are the moments where leadership is felt, and where intentional development can make the greatest difference. As Sandra Bekas puts it, “Leadership doesn’t show up only in the messages you prepare. It shows up in the conversation when you’re willing and able to navigate in the moment.”

Experience The Art of Conversation

If this resonates with you or your team, join us for an upcoming open enrollment session of The Art of Conversation beginning May 7th, 2026. Experience the PAL framework and more firsthand and practice the tools that help leaders navigate real-time conversations with clarity, confidence, and intention. Space is limited, register here to secure your spot!