Navigating Difficult Conversations with Confidence (Part 2)
By Sophie Makonnen
Last week, we explored how difficult conversations often catch us off guard. You think it’s a routine exchange—until suddenly, it isn’t.
In international organizations, difficult conversations often involve additional layers. People bring diverse cultural norms, communication styles, and expectations to the table. Stakeholders may have different priorities or agendas shaped by their roles, work contexts, or institutional mandates. Geographic distance, language differences, or hierarchical structures can amplify power dynamics. This can make having an open, honest dialogue harder, especially when high stakes and trust are still being built. Preparation, empathy, and clarity are even more critical in these settings.
In Part 2 of this series, we’re focusing on the conversations you know will be challenging from the start. These are the moments when you’re preparing to deliver feedback that might trigger pushback, communicate an unpopular decision, or step into a discussion where there’s already tension, distrust, or high expectations. Conversations like these demand thoughtful preparation, emotional intelligence, and clarity. And most importantly, they require confidence—the kind that comes from knowing you’ve done the work to show up grounded, clear, and ready to lead.
In their book Difficult Conversations: How to Discuss What Matters Most, Douglas Stone, Bruce Patton, and Sheila Heen describe three layers that make conversations challenging: the "What Happened?" conversation, the Feelings conversation, and the Identity conversation. This framework offers insight into why these discussions often go wrong—and how to approach them differently.
In this post, we shift from reaction to intention. You’ll learn how to approach high-stakes conversations with a plan, balancing empathy with clear leadership—even when uncomfortable.
Here’s what we’ll explore, building on Stone, Patton, and Heen’s framework:
🔸 Clarify your purpose—Why this conversation matters and what outcome you’re aiming for.
🔸 Understand their perspective—How to prepare for different viewpoints and manage expectations.
🔸 Manage emotions (yours and theirs)—Staying grounded when things get tense.
🔸 Structure the conversation—How to lead with empathy, stay clear, and avoid unnecessary conflict.
Taking time to prepare mentally will help you remain calm, increase the chances that the conversation will go smoothly, and improve the solution.
Before stepping into a tough conversation, take a moment to check in with yourself. If you’ve already labelled it “difficult” in your mind, you’re probably carrying some stress or apprehension before it even begins. That’s completely normal—but it can also influence how you show up. Instead, try reframing the situation. What if this isn’t a difficult conversation but an opportunity for clarity, collaboration, or problem-solving? For example, instead of thinking, I have to confront a colleague about missing deadlines, you might say, I’m opening a conversation to understand what’s getting in the way and how we can move forward together. Or, rather than dreading, “I have to deliver bad news about a project delay,” consider, “I’m providing transparency so we can find the best path forward.” Shifting your mindset in this way can ease tension and help you enter the conversation with greater confidence and focus.
In last week’s example, we explored a tense exchange between Tara, the M&E lead at headquarters, and Rose, the project manager in the field. Tara was focused on implementing a standardized survey to evaluate impact, while Rose pushed for more qualitative input from the community. Their conversation became stuck, and both felt unheard and frustrated. We’ll use the ongoing conversation between Tara and Rose to illustrate how these steps could play out.
Clarify Your Purpose
Before you enter a difficult conversation, take time to define your purpose. What do you need to achieve? What’s the ideal outcome—not only for yourself but for the relationship? Without this clarity, it’s easy to get sidetracked by emotion or defensiveness. A clear purpose keeps you grounded.
Stone, Patton, and Heen emphasize clarifying one's purpose before engaging in a difficult conversation. Are you trying to prove one’s right, or are you seeking to understand and solve a problem together? Being clear on this can prevent one from unintentionally escalating conflict.
In the case of Tara and Rose:
Rose could have clarified that her goal wasn’t to block the survey but to enhance it by integrating community insights. This would help her focus on advocating for a complementary solution rather than venting frustration over being left out.
Tara could have clarified that her priority was maintaining methodological consistency but that she was open to enriching the evaluation if it could be done without compromising standards. This clarity would have allowed her to listen differently.
Understand Their Perspective
Before the conversation, consider the other person’s point of view. What concerns might they have? What pressures are they under? What matters most to them? This step doesn’t mean you agree with them—it means you’re prepared to engage with empathy and avoid unnecessary defensiveness.
Remember, your perspective is just one way of seeing things. The other person likely feels just as strongly about their point of view as you do about yours.
Be mindful of assuming your perspective is the obvious one. Phrases like “clearly” or “obviously” can unintentionally suggest that other viewpoints aren’t valid. This can leave others feeling dismissed or unheard. Instead, recognize that different perspectives exist and create space for more open, constructive dialogue.
In her book Unlocking Leadership Mindtraps, Jennifer Garvey Berger describes a common challenge leaders face: becoming trapped by our own sense of rightness. She explains that humans are wired to feel confident about our point of view. The sensation of “rightness” often feels like certainty, and our brains reward us with a sense of satisfaction when we believe we are correct. However, as Garvey Berger points out, that feeling of certainty isn’t necessarily an indicator that we are right.
When we fall into this mindtrap of rightness, we tend to:
🔸 Hold tightly to our perspectives, dismissing or undervaluing alternatives
🔸 Close off curiosity, convinced we already have the answer.
🔸Struggle to listen genuinely, focusing more on proving our point than understanding the other person’s perspective.
This dynamic can push us to convince others more forcefully, blind us to important insights, and ultimately undermine trust and collaboration.
Garvey Berger suggests a different approach. She encourages leaders to acknowledge their perspective as one possibility, not the truth. By staying curious about other points of view and shifting from a mindset of “I’m right” to “What am I missing?” leaders open the door to more meaningful conversations. Rather than trying to win, they can invite others into co-creating richer and more inclusive solutions.
In the case of Tara and Rose:
When Rose insists on including qualitative data from community members, she’s acting from a deep belief that this perspective is essential for an accurate evaluation. From her point of view, it seems obvious that numbers alone can’t capture the full impact. If Rose isn’t careful, this conviction can lead her to dismiss Tara’s priorities as rigid or disconnected from reality.
Similarly, when Tara defends the standardized survey methodology, she likely operates from a sense of rightness grounded in institutional expectations and professional standards. Her certainty may prevent her from genuinely listening to Rose’s concerns. If Tara believes her approach is beyond doubt, she risks ignoring curiosity and missing valuable insights that Rose brings from her field experience.
Both are vulnerable to Garvey Berger’s “trapped by rightness” mindtrap. If either one can step back and say, This is one valid perspective, but what might I be missing? it opens the door to deeper understanding and collaboration. Rather than trying to "win," they shift toward co-creating a solution that respects both methodological rigour and community voice.
Manage Emotions—Yours and Theirs
High-stakes conversations stir up emotions, whether we acknowledge them or not. To stay grounded, take time before the discussion to reflect on what feelings may come up for you—and how you’ll manage them. During the conversation, pay attention to emotional cues from the other person and adjust your approach to maintain calm and connection.
This directly relates to what Stone, Patton, and Heen describe in their framework as the "Feelings" conversation. Unexpressed emotions don’t disappear—they leak into the conversation, often manifesting as defensiveness, blame, or withdrawal. Naming and addressing emotions is key to staying grounded and helping others feel heard.
Express Feelings Without Blame
It’s completely normal to feel upset when something feels unexpected or unfair, but pointing the finger at someone for how you feel can make them defensive and shut the conversation down. For example, if a teammate decides without consulting you, saying ,Why did you leave me out of this as a team member?, can quickly escalate things. A more constructive approach might be I noticed I wasn’t included in the response, and I’d like to understand more about how that decision was made. This opens up a dialogue and invites a more straightforward, collaborative conversation.
In the case of Tara and Rose:
Rose felt dismissed and overlooked. Had she taken a moment to acknowledge and manage those feelings before the call, she might have entered the discussion more calmly, choosing words that fostered collaboration instead of conflict.
On her side, Tara might have noticed Rose’s rising frustration during the call and slowed things down. She could have said something like, I want to ensure I fully understand your concerns. Would you mind walking me through what feels missing? This approach could have diffused some tension and created a more productive exchange.
By staying aware of their own emotions and tuning in to each other’s, Rose and Tara could have created a conversation that prioritized understanding over defensiveness, paving the way for a better outcome.
Structure the Conversation for Clear Communication and Empathy
Even in difficult conversations, you can structure the exchange to foster understanding. Start by naming shared goals. Be clear and transparent, especially if you’re making an unpopular decision, but do it respectfully. Frame the issue as something to address together rather than as a personal shortcoming.
Stone, Patton, and Heen remind us that the identity conversation always runs in the background. Defensiveness rises when people feel their competence, goodness, or worth is under threat. The key to effective leadership is structuring the conversation to preserve dignity while being honest.
In the case of Tara and Rose:
Rose could have started by stating their common ground: “We both want this evaluation to reflect the true impact of the project.” She could then state her concern clearly but respectfully: I worry that without community input, we’re missing an important part of the story.
Tara, in turn, could have responded by affirming Rose’s role: Your connection to the field gives you insights we can’t get from the data alone. Let’s see how we can integrate those voices without compromising the data structure we need.
By doing this, both would have protected the “Identity conversation” Stone, Patton, and Heen describe—acknowledging one another’s expertise and role while working toward a co-created solution. Jennifer Garvey Berger emphasizes that when leaders move beyond the need to be correct, they open space for shared ownership and richer outcomes.
Bringing It All Together
When you prepare for difficult conversations with clarity, empathy, and emotional intelligence, you create constructive and productive exchange conditions. These conversations aren’t about avoiding disagreement—they’re about advocating for what matters in a way that builds understanding and moves things forward.
By being aware of your own emotions and those of your colleagues, understanding different perspectives, and clarifying your goals, you’ll have the confidence to engage with purpose and resolve. Preparation allows you to stand your ground on important issues while fostering mutual respect and collaboration.
Not Every Conversation Can Be Saved
Adam Kahane, in Collaborating with the Enemy: How to Work with People You Don’t Agree with or Like or Trust, introduces the concept of stretch collaboration—the practice of working with others even when it’s difficult, uncomfortable, and full of uncertainty. He encourages us to stay engaged with people whose perspectives challenge us, to let go of the need for control or certainty, and to approach collaboration with humility and openness. It’s about stretching beyond our comfort zones and co-creating solutions, even without full agreement or trust.
But Kahane also reminds us that collaboration isn’t always possible—or appropriate. His framework presents four potential responses to complex situations: collaborating, adapting, forcing, or exiting. While this blog focuses on building the skills for meaningful collaboration, it’s equally important to recognize when the wisest course of action is to adapt, assert a decision, or walk away altogether. Developing this discernment—knowing when to stretch and when to step back—requires confidence in your own judgment. The confidence to engage wholeheartedly and the confidence to set boundaries when necessary.
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