Learn how to handle difficult workplace conversations without destroying trust. Research-backed strategies to navigate challenging discussions effectively.
What if the way you're avoiding difficult conversations is actually making them harder and destroying more trust than if you simply had them?
Difficult conversations are among the most challenging leadership responsibilities. Research shows that 70% of employees avoid difficult conversations at work, hoping issues will resolve themselves. Yet avoidance consistently makes problems worse. More importantly, research reveals that difficult conversations don't destroy trust if they're handled correctly. In fact, when managed skillfully, these conversations can strengthen relationships, clarify expectations, and build the foundation for high-performing teams. The difference lies not in avoiding difficult conversations but in how leaders approach them—building trust during the conversation rather than before it.
Research by coaching firm Bravely found that 70% of employees avoid difficult conversations. Of these, 53% handle toxic situations by ignoring them entirely, hoping the problem will resolve itself. This avoidance carries significant costs:
Problems escalate rather than resolve
Resentment accumulates over time
Misunderstandings become entrenched
Team cohesion suffers
Trust erodes through silence rather than honest dialogue
The irony is powerful: people avoid difficult conversations to protect relationships, yet avoidance damages them more severely than the honest conversation would.
Recent qualitative research examining managers' perceptions of difficult conversations found that difficulty isn't determined primarily by content. Instead, interpersonal relationships are the biggest factor in how challenging managers perceive these conversations to be.
Key findings:
Content is surprisingly not the main driver of perceived difficulty
Relationship quality determines difficulty more than topic
Over 35% of managers confess discomfort delivering direct feedback if they believe the subordinate might react negatively
Managers struggle most with face-to-face conversations and addressing difficulty directly
The paradox: managers who avoid face-to-face conversations experience them as more difficult. Those who engage directly experience them as more manageable.
Research shows that when handled well, difficult conversations:
Strengthen collaboration by creating space for joint problem-solving
Clarify organizational values and explicit expectations
Enhance bonds between employee and manager
Build psychological safety by normalizing honest dialogue
Improve decision-making by surfacing hidden concerns and diverse perspectives
One of the most counterintuitive findings in organizational research concerns how negative feedback affects trust. A longitudinal study tracking groups over time found critical insights:
Hypothesis: Negative feedback damages trust and creates conflict.
Finding: This is only partly true. The critical moderator is whether trust already exists.
A landmark longitudinal study of groups receiving negative performance feedback found:
The Direct Effect: Negative feedback increases task conflict in the short term. This is expected—when someone receives critical feedback, disagreement often emerges.
The Buffering Effect: However, groups that had established high trust before receiving negative feedback experienced significantly less escalation of task conflict into relationship conflict (the destructive form).
The Implication: Trust established before a difficult conversation acts as a buffer. When trust exists, people interpret critical feedback as "this person cares about performance and my development" rather than "this person is attacking me."
Research on trust and feedback mechanisms reveals the psychological process:
Trust signals benevolent intent: When trust exists, the feedback recipient interprets the feedback-giver's motives as benevolent. They assume the conversation is about improving performance, not personal criticism.
Reduced defensive reactivity: Rather than immediately defending themselves or dismissing feedback, people who trust the source are more receptive to challenging information.
Openness to feedback content: Trust enables people to hear the actual feedback rather than getting stuck in emotional reactions about delivery or intent.
Reduced fear of negative consequences: In trusting relationships, employees believe honest feedback won't be used against them in future evaluation or opportunity decisions.
Empirical evidence: Studies of feedback reception found that receivers know feedback comes from benevolent motives if the feedback-giver maintains consistent trust behaviors over time. When trust exists, people are more receptive to feedback that challenges their own beliefs.
Rather than pretending a difficult conversation is a normal chat, acknowledge it directly:
What to say: "I want to have a conversation with you that might feel a bit uncomfortable. But I think it's important, and I want us to talk about it directly. Does that work for you?"
Why it works:
Reduces surprise: People prepare mentally for difficulty rather than experiencing it as ambush
Sets honest tone: Acknowledging awkwardness signals you're being real, not performing
Demonstrates respect: Giving advance notice shows you respect their time and emotional preparation
Empirical support: Research on difficult conversations found that when awkwardness is explicitly acknowledged, it loses potency. People feel more prepared and the conversation becomes less charged.
The reciprocity principle—we mirror what others give us—applies powerfully in difficult conversations. If you approach with formal detachment, the other person becomes defensive and guarded. If you approach as an authentic human being, they reciprocate with openness.
Specific tactics:
Have the conversation in person when possible (or high-quality video)
Eliminate distractions—phones away, door closed
Maintain eye contact and engaged body language
Never attempt difficult conversations over email, text, or asynchronous communication
Research on trust and presence found that focused attention and physical presence signal that you value the person and the conversation, which builds trust even during challenging moments.
Stories open minds in ways facts cannot. When sharing your own experiences or lessons learned, you:
Demonstrate vulnerability (building connection)
Help the other person see themselves in your experience
Show you've faced similar challenges
Create space for their own story
Rather than approaching as "the authority with answers," acknowledge what you don't know:
"I want to understand your perspective because I might be missing something important"
"I'm noticing tension in our working relationship and I want to address it, but I want to hear your side"
"I'm uncertain about the best path forward, and I need your input"
Admitting uncertainty is not weakness. It signals genuine interest in the other person's perspective and builds psychological safety.
Before discussing the specific issue, establish shared understanding of why you're having the conversation:
What to clarify:
Your positive intent: "I'm bringing this up because I value our working relationship and want to address this before it becomes bigger"
The goal: "I want us to understand what's happening and figure out how to move forward together"
The stakes: "This matters because it affects the quality of our work and our team"
Your assumption of good intent: "I'm assuming there are good reasons for what's happening, and I want to understand"
Why this matters empirically:
Research found that when people understand the conversation goal is collaborative problem-solving (not judgment or punishment), receptivity increases significantly. Framing the conversation as "we're in this together to solve a problem" rather than "I'm correcting you" fundamentally changes the dynamic.
Difficult conversations are easier when trust already exists. This means:
Daily relationship investment: Regular positive interaction, genuine interest in the person, follow-through on commitments
Consistency over time: Behaving trustworthily when it's easy makes the difficult conversation credible
Demonstrated competence: People are more receptive to feedback from those they believe actually have relevant expertise
Warmth and competence: Research shows that warmth (good intentions) + competence (capability to help) are what signal trustworthiness
When trust is limited, acknowledge this directly: "I realize we haven't had much opportunity to build a relationship yet, so I want to be especially clear about my intent here."
Rather than launching into feedback, create a container for honest dialogue:
Useful phrases:
"Can we talk about something? I think it'll be uncomfortable for both of us, but important"
"I want to give you feedback. Are you in a good headspace to receive it?"
"Something's been on my mind about our working relationship. Is now a good time?"
This accomplishes three things:
Respects autonomy: The other person chooses to engage rather than being trapped
Prevents ambush: People prepare themselves
Signals collaboration: You're asking, not commanding
Vague feedback destroys trust. Specific feedback (even critical) builds it. The difference:
Vague (relationship-damaging): "You have a bad attitude" or "You're not a team player"
Specific (trust-building): "In the last three team meetings, I've noticed you've challenged decisions immediately after they're made, rather than asking clarifying questions first. I'm concerned this might affect how others view your input"
Specific feedback:
Shows you've paid attention
Provides clear behavioral data
Enables the person to understand what needs to change
Prevents defensive arguments about interpretation
Observable, not interpretive:
❌ Interpretive (damages trust): "You're defensive"
✅ Observable (preserves trust): "When I mentioned the budget adjustment, you immediately said 'That won't work.' Can you help me understand your concerns?"
Research on difficult conversations consistently shows that leaders do most of the talking when they should be listening most.
What to listen for:
Context you're missing: Why did the person behave this way? What pressures or challenges were they facing?
Their perspective: What's true from their viewpoint?
Underlying concerns: What are they actually worried about?
Their needs: What would actually help?
Specific listening techniques:
Ask open-ended questions: "Help me understand what was happening when..." rather than "Why did you...?"
Pause after asking questions and let silence work—people fill silence with honesty
Reflect back what you hear: "So what I'm hearing is that you felt unsupported in that decision. Is that right?"
Ask clarifying questions: "When you say 'difficult,' what does that mean specifically?"
The empirical finding: The more you listen, the more the other person feels heard and respected. Feeling heard is a primary driver of whether someone experiences a difficult conversation as trust-building or trust-damaging.
Negative feedback is the highest-stakes difficult conversation. Here's how research shows to handle it:
Ensure trust exists: If trust is low, invest in relationship-building first
Get specific: Not "You're not meeting expectations" but "Your project delivery has been 3-5 days late on the last four assignments"
Consider timing: Not when someone is already stressed or exhausted
Plan your listening: Prepare to listen to their context and perspective
Lead with intent: "I'm bringing this up because I value you and want you to succeed"
Deliver feedback specifically: Observable behaviors, not character judgments
Pause for response: Let them react before continuing
Listen to their perspective: They may have information you lack
Collaborate on solutions: "What would help you meet these timelines?" rather than "You need to do better"
Studies of feedback reception found that negative feedback is received best when:
It's specific (not vague character attacks)
Intent is clearly benevolent
The feedback-giver demonstrates genuine interest in the person's success
The person has opportunity to share their perspective
Solutions are developed collaboratively
Many leaders see the difficult conversation as the endpoint. Research shows the follow-up is critical:
What to do after:
Summarize what you discussed: Send a brief note confirming what you discussed and what you agreed to
Check progress: Follow up on agreed actions with timelines
Acknowledge difficulty: "I know our conversation last week might have felt uncomfortable, and I want you to know I appreciate how you engaged with it"
Look for improvement: Notice and acknowledge progress, even small steps
Adjust if needed: "I realize my feedback about X might not have been clear. Let me clarify..."
The trust-building mechanism: Follow-up demonstrates that you were serious about the conversation and genuinely invested in improvement, not just criticizing.
Sometimes difficult conversations damage trust. This happens when:
You lose your temper or become judgmental
You deliver feedback that feels personal rather than behavioral
You listen defensively rather than genuinely
You make it clear you've already decided the person is the problem
If this happens, repair is possible:
Acknowledge it directly: "I want to come back to our conversation last week. I think I handled it poorly"
Identify what went wrong: "I came across as judgmental rather than curious about your perspective"
Take responsibility: Don't blame the other person or the situation
Clarify intent: "My intent was to address a real issue, but I went about it in a way that probably felt like a personal attack"
Commit to doing it differently: "I want to restart that conversation. Can we do that?"
Research on trust repair found that acknowledging harm directly and taking responsibility is far more effective than pretending nothing happened.
The counterintuitive truth is this: handled well, difficult conversations build trust rather than destroy it. They demonstrate that you're willing to be honest, that you care enough to address issues, and that you value the relationship enough to risk discomfort.
The opposite approach—avoiding difficult conversations—silently signals that you don't care, the relationship isn't important enough to invest in, and you don't trust the other person to handle honesty.
By acknowledging awkwardness upfront, being authentically human, clarifying intent, asking permission, listening deeply, and following up, you transform difficult conversations from relationship threats into relationship strengtheners. These conversations become the moments when trust either deepens or repairs—the moments that matter most.
Organization Learning Labs offers workshops and coaching designed to help leaders develop the communication skills, emotional regulation, and psychological frameworks needed to navigate difficult conversations with confidence and integrity. Our evidence-based approach helps leaders build trust through honesty rather than avoiding truth.
Work Bravely. (2017). Understanding the conversation gap: Why employees avoid difficult workplace discussions and the effects of avoidance
Work Bravely. (n.d.). The cost of the conversation gap on workplace health.
Smith, R., & Addicott, C. (2022). A systematic literature review of difficult conversations in the workplace.
Overton, A. R. (2013). Conflict management: Difficult conversations and teamwork outcomes. PMC.
Bradley, G. L., & Campbell, A. C. (2014). Managing difficult workplace conversations: Goals, strategies, and outcomes. International Journal of Business Communication.
Sue Belton. (2022). How to have difficult conversations at work.
Difficult conversation (n.d.). Wikipedia.
Reciprocity (social psychology) (n.d.). Wikipedia.
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