Gardener

Elder

Maker

Leadership Practices

Tough Conversations

Navigate conflict, bridge divides and foster transparency through effective dialogue

Table of Contents

Introduction

We’ve all experienced awkward conversations. They often make us cringe. Whether you are raising a sensitive topic, addressing an issue that you have ignored or avoided for a while, or resolving a conflict, engaging in tough conversations is a critical leadership practice that fosters trust, innovation, and growth within teams. By embracing open dialogue, leaders can navigate conflicts constructively, leading to more cohesive and high-performing organizations.

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When to use this practice

Tough conversations are essential in the following situations:

When resolving interpersonal conflicts;
When it’s necessary to raise sensitive issues;
When addressing poor performance or unwelcome behavior;
When implementing organizational changes.

Proactively engaging in these discussions prevents issues from escalating and promotes a culture of transparency and continuous improvement.

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How to develop this practice

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1. Know your style

Understanding your conflict management style is the first step. The Thomas-Kilmann Conflict Mode Instrument outlines five approaches:

Competing (high focus on own needs, low focus on others’ needs)
- If you naturally assert your views forcefully, you may struggle to listen and seek win-win solutions.
- Try this: Before the conversation, challenge yourself to list at least three alternative perspectives. Enter the discussion with curiosity instead of certainty.
Collaborating (high focus on both own and others’ needs)
- If you aim for mutual benefit, you might risk over-complicating things or avoiding difficult trade-offs.
- Try this: Set a time limit for the conversation to avoid endless discussions. Focus on clear decisions rather than perfect consensus.
Compromising (moderate focus on both own and others’ needs)
- You likely seek middle ground, but this can sometimes lead to superficial solutions.
- Try this: Ask yourself, “What would be a bold but fair solution?” Challenge the other person to co-create something better than just ‘splitting the difference.’
Avoiding (low focus on both own and others’ needs)
- If you tend to sidestep conflict, you might delay necessary conversations, allowing issues to escalate.
- Try this: Commit to initiating one tough conversation this week. Start with small, lower-stakes situations to build confidence.
Accommodating (low focus on own needs, high focus on others’ needs)
- You may prioritize harmony over addressing real issues, which can build resentment over time.
- Try this: Prepare a simple script to state your needs assertively (e.g. "I need to discuss something important that affects me. Can we find a solution that works for both of us?")

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2. Prepare mentally and emotionally

Before diving in, assess where you and the other person stand (and how you feel about that) using the Okay-Not Okay Matrix:

You = Okay, Other = Not-Okay (e.g. addressing poor performance)
- You may unconsciously take a superior stance, making the other person feel defensive.
- Tip: Approach the conversation with inquiry, not judgment. Ask open-ended questions like, “What challenges have you been facing?”
You = Not-Okay, Other = Okay (e.g. feeling undervalued or unheard)
- You might feel like a victim, unintentionally seeking sympathy rather than resolution.
- Tip: Reframe your position: "I have a concern I’d like to address so we can work better together." This keeps the focus on a solution, not blame.
You = Not-Okay, Other = Not-Okay (e.g. unresolved tension or resentment)
- The conversation can become emotionally charged and unproductive.
- Tip: Acknowledge the tension early: “I know this is a difficult topic for both of us. Let’s focus on finding a way forward.”

Decide your priority: relationship vs. result

Steve Jobs famously said that he had to learn over time to take the long perspective on other people. Strong leadership is sometimes associated with being tough on others, and holding people to high standards. But that style has significant costs. Whether it is a colleague or a family member, in many cases the relationship between two people who work together is more important than the issue at hand.

If the relationship is more important, focus on understanding first. Listen more than you speak and validate their perspective, even if you disagree.

If the result is more important, be clear about the outcome you need and why it matters. But be prepared to negotiate so the other person doesn’t feel bulldozed. Only in extreme cases, be prepared to terminate the relationship.

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3. Engage

Establish psychological safety:
- Be aware of the broader context that the other person may be in. Have there been other conflicts? Did you communicate other controversial decisions? Is there a power relationship between yourself and the other person? Context matters when you want to have a genuine, trust-based conversation.
- Set the tone upfront: “I want to have an open and honest conversation, and I value your perspective.”
- Show neutral body language (uncrossed arms, steady eye contact) to avoid triggering defensiveness.
Provide context:
- Explain why the conversation is happeningxample: “I want to discuss X because it’s impacting Y. My goal is to find a solution that works for both of us.”
Manage emotional responses:
- Expect emotional reactions—yours and theirs. Instead of reacting, pause, acknowledge and name the emotion (“I’m feeling frustrated right now” or “I sense you’re upset—do you want to talk about that first?”). Use the old ‘count to ten’ or ‘breathe in, breathe out’ techniques to regulate yourself, and feel free to take a pause when you or the other person gets stuck or hijacked by a difficult emotion, whether it is anger, shame or guilt.

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4. Have the conversation

Difficult conversations can quickly derail if they feel like personal attacks. Using the Nonviolent Communication (NVC) framework helps keep the discussion constructive by focusing on facts, emotions, needs, and requests.

Observations (facts, not opinions)
Describe specific behaviors without judgment. Keep it neutral and avoid loaded language.
- Don't say, "You always interrupt people and dominate meetings." (This sounds accusatory and invites defensiveness.)
- Do say, "In the last three meetings, you’ve spoken over team members multiple times." (This is factual and easy to verify.)
- Tip: Stick to concrete examples—avoid saying "you never," "you always," or "you’re being difficult." Instead, state what happened in a way that the other person can recognize and acknowledge.
Feelings (how it affects you or others)
Share how the behavior impacts you or the team. This helps the other person understand the emotional consequences of their actions.
- “This has led to frustration among the team and hesitation to share ideas.”
- Tip: Use I-statements instead of blame. Saying “I’ve noticed people withdrawing from discussions” is much better than “You make people feel uncomfortable.” The goal is to share impact, not accuse.
Needs (the deeper concern or principle at stake)
Frame the issue around a shared value or principle, rather than making it about personal conflict. This helps align both parties toward a common goal.
- “We need an environment where everyone can be heard so we can make the best decisions.”
- Tip: Connect your need to something bigger than the immediate issue. For example, instead of saying “I need you to stop interrupting me,” say “We need everyone’s input so we can make smarter decisions as a team.” This shifts the focus from individual fault to collective success.
Requests (clear next steps or adjustments)
Ask for a specific, actionable change, not just an agreement to “do better.”
- “Can we agree on giving everyone space to speak before responding?”
- Tip: Make your request realistic and measurable. Instead of “I need you to be more respectful,” say “Can we take a 3-second pause before responding in meetings?” This gives the other person a clear way to move forward.

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5: Find a resolution

Collaborative solutions: Work together to develop mutually beneficial outcomes.
Negotiated agreements: If immediate solutions aren't feasible, agree on interim measures and set a timeline for reassessment.
Agree to disagree: In cases where consensus isn't possible, acknowledge differing perspectives and outline how to proceed despite disagreements.

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Benefits of this practice

Practicing the art of having tough conversations will lead to the following outcomes:

Resolved conflicts: Addressing issues directly leads to timely and effective solutions.
Restored trust and commitment: Open communication rebuilds trust and reinforces team cohesion.
Deeper connections: Navigating challenges together strengthens relationships and fosters a sense of belonging.

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How to take this further

Continue learning: Engage in workshops and training focused on conflict resolution and effective communication.
Seek feedback: After tough conversations, solicit input on your approach to identify areas for improvement.
Reflect regularly: Assess past conversations to understand what worked and what didn’t, refining your skills over time.

Embracing tough conversations as a leadership practice not only resolves conflicts but also cultivates an environment where innovation and collaboration thrive. By developing this skill, leaders can more effectively guide their teams through challenges, leading to sustained growth and success.

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