Most managers would rather endure root canal treatment than address underperformance directly. The prospect of confronting an employee about missed deadlines, quality issues, or problematic behaviour triggers a cascade of anxieties: What if they become defensive? What if the conversation damages our working relationship? What if they cry, or worse, resign?
Yet avoidance carries its own costs. Unaddressed performance issues rarely resolve themselves. Instead, they metastasise—undermining team morale, creating resentment amongst high performers who shoulder additional work, and ultimately forcing more drastic interventions that could have been prevented through timely conversation.
The paradox is that difficult conversations, when conducted skilfully, don’t damage performance or relationships—they enhance them. Employees often crave clarity about where they stand, and many performance issues stem from misalignment or misunderstanding rather than malice or incompetence. Learning to navigate these conversations effectively transforms them from dreaded obligations into powerful tools for development and improvement.
Reframing the Purpose
The first obstacle to effective difficult conversations is conceptual. When we frame these discussions as confrontations or criticisms, we approach them with the wrong mindset and trigger defensive responses. Instead, reframe difficult conversations as collaborative problem-solving sessions aimed at removing barriers to success.
This isn’t semantic sleight of hand—it’s a fundamental shift in purpose. You’re not sitting down to tell someone they’ve failed; you’re meeting to identify why performance hasn’t met expectations and co-create solutions. This framing acknowledges that performance issues rarely have single causes. Perhaps the employee lacks necessary resources, hasn’t received adequate training, faces unclear expectations, or genuinely doesn’t recognise the gap between their output and standards.
When you approach the conversation as a mutual exploration rather than a verdict delivery, you reduce defensiveness and increase the likelihood of productive dialogue. Your opening words might be: “I’ve noticed some challenges with the recent project deliverables, and I’d like to understand what’s been happening and work together on getting things back on track” rather than “Your performance has been unacceptable.”
Preparation: The Foundation of Effectiveness
Spontaneous difficult conversations rarely go well. Emotion hijacks reason, important points get forgotten, and you risk saying something you’ll regret. Thorough preparation transforms difficult conversations from volatile encounters into structured discussions.
Begin by clarifying the specific performance gap. Vague concerns like “poor attitude” or “not meeting expectations” provide no foothold for improvement. Instead, identify concrete, observable behaviours and outcomes. “The client report was submitted three days late, contained multiple factual errors, and omitted the market analysis section we discussed” provides clarity that “sloppy work” never could.
Document examples with dates, contexts, and impacts. This isn’t about building a legal case; it’s about replacing subjective impressions with objective evidence. When you can reference three specific instances of late submissions rather than a general feeling that deadlines are being missed, you ground the conversation in reality rather than perception.
Consider also what you don’t know. What circumstances might explain the performance issue? Has anything changed in the employee’s role, team structure, or personal situation? What barriers might exist that you haven’t noticed? Approaching the conversation with curiosity about these unknowns prevents premature conclusions and demonstrates genuine interest in understanding rather than condemning.
Finally, clarify your desired outcome. What specific improvements do you need to see? By what timeline? What support can you offer? Having clear answers to these questions before the conversation begins ensures you can provide direction rather than just criticism.
Timing and Environment
When and where you hold difficult conversations significantly affects their outcome. Ambushing someone as they’re leaving for the day or pulling them aside in a crowded office creates unnecessary stress and signals that you haven’t given the matter serious thought.
Schedule conversations with adequate notice—enough time for the employee to prepare but not so much that they spend days in anxious speculation. “I’d like to meet tomorrow at two o’clock to discuss the recent project outcomes and how we can work together to address some concerns” provides clarity without excessive drama.
Choose a private, neutral space where interruptions are unlikely. Difficult conversations require concentration and emotional safety. Having the discussion in your office can feel intimidating, whilst meeting rooms offer neutrality. Ensure you have sufficient time; rushing through a difficult conversation because you have another meeting scheduled telegraphs that the issue—and the person—isn’t a priority.
Consider also the broader context. Avoid having difficult conversations on Fridays, when employees will stew over the weekend, or immediately before major deadlines when stress is already elevated. Timing demonstrates respect and maximises the chances of a productive discussion.
Opening With Clarity and Care
The first thirty seconds of a difficult conversation establishes its trajectory. Begin with clarity about why you’ve scheduled the meeting, but frame the issue as something you’re committed to resolving together rather than a judgement you’ve rendered.
Avoid small talk that feels incongruent with the seriousness of the meeting. Asking about someone’s weekend before delivering critical feedback creates cognitive dissonance and can feel manipulative. Instead, acknowledge the nature of the conversation directly: “I’ve asked to meet because I’ve noticed some concerns with recent work, and I want to discuss this openly with you.”
State the performance issue clearly and specifically, referencing your documented examples. Use objective language focused on observable behaviours and outcomes rather than character assessments. “The last three client deliverables were submitted after their deadlines” differs fundamentally from “You’re unreliable.”
Crucially, after stating the issue, pause. Create space for the employee to respond before you continue speaking. This pause serves multiple functions: it prevents you from verbal overflow driven by anxiety, it signals that this is a dialogue rather than a lecture, and it allows you to hear the employee’s perspective before you’ve committed to your full narrative.
Active Listening: The Conversation’s Engine
Many difficult conversations fail not because managers can’t articulate problems, but because they can’t genuinely listen to responses. Yet listening is where understanding emerges and solutions become possible.
When the employee responds—whether with explanation, defensiveness, agreement, or confusion—resist the urge to immediately counter their points. Instead, listen to understand their perspective, even if you ultimately disagree with it. What do they believe has been happening? What factors do they see as contributing to the situation? What barriers or challenges are they experiencing?
Demonstrate active listening through both verbal and non-verbal cues. Maintain appropriate eye contact, lean slightly forward, and use minimal encouragers like “I see” or “Go on.” Paraphrase what you’ve heard to confirm understanding: “So what you’re saying is that the project scope changed midstream and you didn’t feel you could push back on the new deadline?” This paraphrasing accomplishes two things: it ensures you’ve understood correctly, and it signals to the employee that you’re genuinely trying to comprehend their perspective.
Listening doesn’t mean accepting excuses uncritically. Rather, it means understanding the full context before determining how to move forward. Sometimes what initially appears as a performance issue reveals itself through dialogue to be a communication breakdown, resource constraint, or systems problem that requires a different intervention entirely.
Collaborative Problem-Solving
Once you’ve established shared understanding of the performance gap and any contributing factors, shift explicitly into problem-solving mode. This transition point is critical: it’s where the conversation moves from examining problems to creating solutions.
Ask open-ended questions that invite the employee into solution creation: “What do you think would help you meet these deadlines consistently?” or “What support would be most valuable in improving the quality of these reports?” When employees generate their own solutions, they’re more committed to implementing them.
However, collaboration doesn’t mean abdication. If the employee proposes solutions that seem inadequate or unrealistic, explore those concerns directly. “I appreciate that suggestion, though I’m uncertain how it addresses the quality concerns. Can you help me understand how that would work?” This maintains collaboration whilst ensuring rigour.
Be prepared to offer your own suggestions, particularly regarding resources, training, or process changes within your control. The goal is co-creation: building an action plan that draws on both your perspectives and commits both parties to specific steps.
Document this action plan clearly. What specific actions will the employee take? What support will you provide? What are the timelines for improvement? What does success look like? This documentation isn’t punitive—it’s practical. Both parties need clarity about commitments made during an emotionally charged conversation.
Setting Clear Expectations and Consequences
Compassion and clarity aren’t opposites; they’re complements. Being clear about expectations and potential consequences demonstrates respect and fairness, whilst vagueness creates anxiety and sets employees up for failure.
If the performance issue is serious enough to warrant formal consequences if unresolved, communicate this directly: “I need to be clear that if we don’t see improvement in these areas within the next month, we’ll need to move to a formal performance improvement plan.” This isn’t a threat; it’s transparency about the stakes and the seriousness of the situation.
Equally important is defining what improvement looks like. “Better quality work” provides no guidance; “Client deliverables that are proofread, contain all requested components, and are submitted by the agreed deadline” creates a clear target.
Following Through: Where Conversations Become Change
The difficult conversation itself is merely the beginning. Follow-through determines whether the discussion produces genuine improvement or simply becomes another uncomfortable memory that changes nothing.
Schedule follow-up conversations at intervals specified in your action plan. These check-ins serve multiple purposes: they demonstrate your continued investment in the employee’s success, they allow for course corrections if initial approaches aren’t working, and they hold both parties accountable to commitments made.
When you see improvement, acknowledge it specifically and genuinely. Recognition reinforces positive change and demonstrates that your feedback wasn’t just criticism but part of a genuine developmental process. Conversely, if improvement doesn’t materialise, address this promptly rather than hoping things will eventually change.
Difficult conversations that improve performance share common elements: thorough preparation, genuine curiosity about the employee’s perspective, collaborative problem-solving, clear expectations, and consistent follow-through. They’re challenging not because they involve conflict but because they require emotional intelligence, courage, and the discipline to address problems directly rather than hoping they’ll resolve themselves.
When you develop competence in these conversations, something remarkable happens: they become less difficult. Employees learn that feedback is delivered constructively and followed by support. Trust deepens. Performance improves. The dreaded difficult conversation transforms into simply another tool in your leadership repertoire—one that, skilfully deployed, creates the clarity and accountability that allow both individuals and teams to flourish.
