Many managers dread difficult conversations with employees. Whether it’s addressing a brilliant scientist who dismisses colleagues’ ideas, confronting persistent lateness, or tackling a technical expert who responds to feedback with hostility, these discussions trigger anxiety even in experienced leaders. The problem gets worse in technical environments where you’re managing people who may know more about their domain than you do.
The good news? With the right preparation and approach, you can navigate these discussions whilst maintaining positive working relationships and your calm professionalism. Here’s what actually works.
Don’t Put the Conversation Off
It’s natural to feel nervous about confronting unsatisfactory behaviour, especially when the other person might get upset. Yet delaying only increases tension for both parties. Your team member probably senses there’s a problem, making them tense too.
Address issues promptly. Minor problems prevented early don’t become major crises that damage team morale and productivity.
Stop Storing Things Up
One of the biggest mistakes managers make is accumulating grievances for performance reviews. If someone is habitually late or consistently misses deadlines, address it when you first notice the pattern.
When faced with a lengthy tally of failures during an annual review, employees feel ambushed. They wonder why you didn’t mention these issues when they occurred. This damages trust and makes the conversation far more difficult than necessary.
Nip issues in the bud as they arise. You’ll have fewer formal disciplinary conversations because you’ve addressed concerns before they escalate.
Know Your Policies Inside Out
Before initiating these conversations, understand your company’s procedures and policies. Whether you’re addressing timekeeping, social media use during work hours, or bullying allegations, know the official policy backwards.
Inform your line manager or HR contact beforehand. While you might prefer to sort things independently, this can backfire if your team member makes a complaint. Documentation and transparency protect everyone.
Be crystal clear about your desired outcomes. What specific changes do you want to see? Focusing on positive outcomes creates a calmer, more constructive atmosphere.
Create the Right Environment
Physical setting matters when handling these conversations. Book a meeting room. Conversations with disciplinary or coaching elements should always take place in private.
Even analytical employees can have emotional responses to feedback. Choose a neutral space where both parties feel comfortable. Your office might create a power imbalance, so opt for a meeting room where interruptions are unlikely.
Schedule morning meetings when possible. Tension builds throughout the day, making afternoon conversations harder.
For remote team members, use video calls rather than phone conversations. Facial expressions and body language show how your message is being received.
Be Honest with Yourself First
Before initiating the conversation, examine your own motivations and potential biases. Personal dynamics complicate workplace relationships, particularly under tight deadlines and high pressure.
In technical environments, managing highly skilled specialists requires separating technical brilliance from professional conduct. Both matter, but expertise doesn’t excuse poor behaviour.
Consider whether this is an ingrained pattern or recent development. Recent changes often signal personal issues affecting performance, whilst long-standing patterns need different interventions.
Consistency is non-negotiable. If you’re addressing one person’s behaviour, address it with everyone who exhibits the same conduct. Unfair treatment is toxic in any workplace.
Stick to the Facts
When it’s time for the meeting, remember you can only control yourself, not the employee’s reaction. A calm disposition goes a long way towards controlling the conversation’s direction.
We all make errors of judgement. When this happens, keep facts firmly in mind. Focus on observed behaviours rather than assumed impacts or intentions. Managers often make sweeping statements that fuel defensiveness:
“David, you’re always late and never at your desk when I call you!”
This triggers defensiveness because it uses absolute terms and lacks specificity. Compare it to this factual approach:
“Last week, David, you arrived after 10am on Tuesday, Thursday and Friday. On Monday and Wednesday, we had video calls booked for 11am. I rang both times and you weren’t there.”
For technical professionals, be equally specific: Instead of “You’re not collaborative,” say “In Tuesday’s project review, you described Sarah’s methodology as ‘fundamentally flawed’ without asking questions about her approach first.”
Facts are harder to dispute and create less emotional resistance. They also demonstrate you’re paying attention without making the employee feel unfairly targeted.
Listen More Than You Talk
Always begin by asking the employee their perspective. Is there anything bothering them? Are personal issues affecting their work? Then listen. Really listen.
Opening scripts that work:
- “I’d like to understand your perspective on [specific situation]. Can you walk me through what happened from your viewpoint?”
- “Before I share my concerns, I want to hear your take on how the project deadline was missed.”
- “Help me understand what’s been going on. I’ve noticed [specific behaviour] and I’m concerned.”
You may disagree completely with what they’re saying, but you owe them the courtesy of being heard. The meeting will continue on a more productive basis when they feel their side has been acknowledged.
Active listening doesn’t mean agreeing with inappropriate behaviour. It means understanding the motivations behind it. Often, difficult behaviour is symptomatic of broader issues: workload problems, unclear expectations, personal circumstances, or workplace changes affecting performance.
Once you’ve given them space to speak, steer the conversation towards outcomes. Don’t continue rehashing mistakes. Move forward so they feel there are solutions and you’re giving them the chance to improve.
Prepare for Emotional Responses
Hopefully you’ll have some sense of how your team member will react, but prepare for anything. Whilst we’re all intelligent professionals, we also have instinctive responses to being challenged. Be ready for shouting, swearing, statements not backed by facts, and yes, tears.
Stay calm. If you’re sticking to facts and speaking collaboratively, their emotional response is about them processing difficult information, not about you personally.
What if they get defensive? Don’t argue. Try: “I hear you disagreeing. Help me understand your perspective on what happened.” This acknowledges their reaction without abandoning your concerns.
What if they cry? Offer a tissue, pause briefly, then continue calmly. Don’t rush to comfort or abandon the conversation. Most people appreciate being treated professionally even when emotional.
What if they deny it completely? Return to specific facts: “I have the meeting notes here showing the deadline was agreed as Friday. Can you help me understand the disconnect?”
If emotions escalate beyond productive dialogue, take a timeout. Often this release of energy puts the meeting back on track. The key is remaining steady and professional regardless of their reaction.
Set Clear Expectations and Follow Through
Make sure that when the meeting concludes, there’s absolute clarity about next steps. What specific changes are expected? What’s the timeline? What support is available? What are the consequences if improvements don’t occur?
Get the employee to acknowledge these expectations, ideally in writing. This creates ownership of the improvement process and eliminates ambiguity about performance standards.
Schedule follow-up meetings to review progress. It’s tempting to tick the situation off as ‘solved’ once you’ve had the conversation, but it’s not over until your expectations have been consistently met.
Approach follow-up positively, with the assumption they will succeed. Most people respond better to belief in their capability than to scepticism about their commitment.
Model the Standards You Expect
If you’re asking team members to be punctual, you need to model that behaviour yourself. Employees facing challenging conversations will seize on any inconsistency between your words and actions.
Your team watches how you handle these situations. Consistency demonstrates your commitment to fair leadership and maintains respect across the board. When you hold everyone to the same standards whilst treating individuals with dignity, you build a culture where these conversations become less frequent because expectations are clear and consistently reinforced.
Frequently Asked Questions About Having Difficult Conversations
Building Confidence Through Practice
Difficult conversations with employees are a fundamental part of effective leadership, yet they don’t have to be dreaded. With proper preparation, a calm disposition, and a focus on facts rather than emotions, managers can navigate these discussions whilst maintaining positive working relationships.
The key is addressing issues promptly rather than letting them fester, approaching each conversation with fairness and consistency, and focusing on future improvements rather than past failures. When handled skilfully, these challenging moments become opportunities to strengthen trust, clarify expectations, and support employees in their professional development.
For science and technology leaders managing team dynamics and building psychological safety across entire teams, our guide on leading difficult conversations with confidence provides additional frameworks for navigating complex group discussions.
Every difficult conversation you handle well builds your confidence for the next one. Over time, what once felt daunting becomes simply another aspect of competent leadership.