How to Have Difficult Conversations With Employees
Having difficult conversations with employees in the workplace can be intimidating, especially for leaders who have recently stepped into a senior role.
A Sydney psychologist can provide support with managing these types of discussions as a natural part of leadership.
Difficult conversations need to feel safe enough for honesty, clear enough for accountability, and constructive enough for learning and growth.
Whether you're addressing conduct, or checking in on an employee's wellbeing, the same underlying discipline applies.
Prepare deliberately, communicate clearly, and stay adaptable once the conversation is underway.
Throughout this guide, our psychologically-informed executive coaches look at difficult conversations through three connected pillars: emotional regulation, communication skillsets, and the organisational context around the issue.
Conversations tend to go better when all three are considered together, rather than relying on a script alone.
What are Difficult Conversations?
A difficult workplace conversation is one where emotion, identity, disagreement or potential consequences make ordinary communication more challenging.
Common examples include underperformance, inappropriate behaviour, interpersonal conflict, attendance concerns, or decisions that affect an employee's role.
What makes these conversations hard is rarely the subject matter alone.
A manager must communicate an uncomfortable reality while regulating their own emotions, understanding the employee's perspective, maintaining a workable relationship, and upholding organisational standards.
All at the same time.
Managers may know exactly what they want to say but struggle the moment an employee becomes defensive, distressed or angry.
Sometimes, this can lead to avoiding the issue, over-accommodating, or becoming unnecessarily confrontational.
Effective communication in these moments requires meta-communication capability: recognising what the interaction needs at a given moment, selecting the right technique, and adapting as the conversation unfolds.
An upset employee may need reflective listening first, someone who doesn't understand the problem may benefit from exploratory questioning.
The real skill isn't knowing techniques in isolation, it's knowing when and how to apply them under pressure.
How to Prepare for Having Difficult Conversations
Effective preparation happens on three levels: your emotional state, your communication approach, and the organisational context around the issue.
Professional executive coaching can teach you strategies for preparation that ultimately lead to a beneficial outcome for both you and your employee.
Identify the purpose of the conversation
Start by clarifying the issue itself.
Define the specific behaviour or performance concern, separate observations from interpretations, gather recent examples, and establish what standard was expected.
Then examine your own reaction: are you anxious about confrontation, frustrated, or have you already decided the employee is deliberately behaving badly?
Noticing these patterns in advance helps preserve your judgement once the conversation starts.
A useful frame is to ask yourself: What do I need to communicate? What do I need to understand? What could trigger me? What would help me stay effective if the conversation changes direction?
Choose the right time and place
Choose a private, interruption-free setting appropriate to the seriousness of the matter.
Managers should avoid public areas or timing these interactions immediately before important client meetings.
Give notice for formal discussions so the employee has time to prepare and, where relevant, arrange a support person.
Timing also requires judgement.
A manager who is highly frustrated may need to regulate themselves first if the issue isn't urgent, and an employee experiencing acute distress may need a more carefully timed conversation (subject to any necessary immediate safety or conduct action).
That said, searching for a "perfect moment" can itself become a form of avoidance.
Good timing creates reasonable conditions for a fair conversation without delaying necessary feedback indefinitely.
Plan what you want to say
Managers should choose their tools before choosing their words.
Behavioural feedback can state the concern clearly, reflective listening can help you understand the employee's response, and exploratory questioning can surface contributing factors you don't yet know about.
Don't plan a rigid interrogation, plan a structure flexible enough to adapt.
It also helps to prepare for adaptation.
You should think through how to respond if the employee challenges the facts.
Perhaps they become distressed, or reveal information that changes your understanding of the issue.
Ensuring you’re adaptable during these conversations prepares you for unexpected changes to what you initially prepared.
In Summary
Each part of preparation draws on a different pillar of Sentient Professional Wellbeing’s approach to support.
Clarifying your purpose and noticing your own reactions is the psychological side.
Choosing the right time, place and people is the systemic side.
Planning your tools and how you’ll adapt is the skills side.
Preparing across all three gives you a steadier foundation than focusing on any one in isolation.
How to Start Challenging Conversations
Begin by establishing the purpose, stating the concern clearly, and inviting the employee's perspective.
For example:
“I wanted to speak with you about some concerns regarding the last few project deadlines. My intention is to understand what's happening and work out how we can improve things. I'd like to explain what I've noticed, hear your perspective, and then agree on the next steps.”
This kind of opening communicates both care and accountability. It combines a clear statement of concern, a respectful intention, and an invitation to respond.
Avoid lengthy small talk purely because the topic makes you uncomfortable. This often makes the employee more apprehensive, not less.
And remember that psychological safety doesn't mean promising the conversation will have no consequences.
In formal performance or disciplinary matters, explain the process and possible outcomes accurately.
The goal isn't a consequence-free conversation, it's a fair, respectful one where both parties can speak honestly.
Managing Difficult Conversations in the Workplace
To begin with, there's no ideal length for a difficult conversation.
A straightforward feedback discussion might take 15 to 30 minutes, while complex performance, conduct or health-related conversations may need more time or more than one meeting.
Managers need to recognise when continuing is no longer productive.
If the employee is too distressed to process information, a pause or a follow-up meeting is often more effective than repeating the same point.
When an employee becomes upset, defensive or angry, regulate your own response first.
Slow your pace and acknowledge their experience without assuming their account is accurate:
“I can see this has been difficult to hear. I'd like to understand what's upsetting you most about what I've raised.”
Reflective listening can help demonstrate your understanding of the employees scenario and lower their panic.
Once intensity falls, a question like “What would need to change so this doesn't happen again?” can help shift the focus towards a solution.
It’s important to recognise that distress is not the same as threatening behaviour.
Set clear boundaries around abuse or intimidation, and end the meeting if safety requires it, following your organisation's incident and HR procedures.
When HR Should be Involved
Not every difficult conversation needs HR or a witness present.
Routine feedback is often best handled directly, while HR becomes more relevant for serious misconduct, potential disciplinary action, discrimination or harassment allegations, safety concerns, or a relationship strained enough that impartiality is difficult.
As best practice, Fair Work recommends telling employees the purpose of an underperformance meeting in advance and letting them know they may bring a support person.
However, this isn't a blanket statutory obligation for every meeting.
It's also worth considering alternatives to a fully confrontational conversation, including informal feedback, coaching, training, workload redesign, or written expectations.
The key skill is correctly diagnosing the problem.
An employee who doesn't know the standard requires clarity, someone who lacks a skill needs training.
Recognising the needs of the individual and the concern being addressed can streamline challenging conversations into more manageable interactions.
Tools & Frameworks for Structured Feedback to Employees
Frameworks serve different functions.
The strongest managers use them as a repertoire, not as a single universal script.
Framework | Main Function | Typical Application and Caution |
Sandwich Method | Places corrective feedback alongside genuine positive observations | Balance recognition and correction & avoid disguising the concern |
Crucial Conversations | Supports respectful, honest dialogue when stakes and emotion are high | Helps restore dialogue (not a substitute for fair processes) |
Socratic Questioning | Examines assumptions and supports insight through guided questions | Use genuine curiosity, not a disguised interrogation |
Columbo-style Questioning | Gently explores unclear details or discrepancies | Be transparent and avoid catching people out |
Reflective Listening | Checks meaning and acknowledges the employee's experience | Understanding does not mean agreement |
SBI (Situation → Behaviour → Impact) | Offers specific, structured feedback | May need further exploration |
DESC (Describe → Express → Specify → Consequences) | Structures assertive requests and boundary-setting | Useful for assertive requests and boundaries |
Feedforward | Focuses on desired future behaviour | Supports development but cannot replace addressing serious past conduct |
For example, SBI may identify the concern, reflective listening may clarify the employee's perspective, socratic questions may explore causes, and feedforward may establish the next steps.
The Sandwich Method can be helpful when praise is genuine but may sound manipulative if used mechanically.
Meta-communication is also a very helpful skill when addressing difficult topics in the workplace.
This refers to the ability to diagnose what the conversation needs, select and sequence tools, monitor the response, recognise one's own emotional influence and adapt.
The goal is flexible judgement rather than script delivery.
Examples of Hard Conversation at Work
Difficult conversations take different shapes depending on the situation:
Giving feedback to a friend: When a direct report is also a friend, name the role conflict rather than ignoring it → “I value our relationship, which is one reason I don't want to let this issue sit unresolved. I need to speak with you in my management role about the expectations of the position.”
Raising a hygiene or grooming issue: Meet privately, avoid jokes or unnecessary detail, and keep the focus on what's relevant to work → understand that medical, cultural or personal circumstances may need a more considered response.
Talking about mental health and performance: Lead with observable concerns rather than assumptions → “I've noticed several deadlines have been missed recently. I wanted to check how you're going.” Never attempt to diagnose an employee, instead, discuss relevant support, EAP options or reasonable adjustments instead.
Meetings involving a union representative: Clarify roles, address the employee directly where appropriate, and stay focused on fairness and the issue rather than treating the meeting as a contest of authority.
Across all of these, the same discipline applies: describe behaviour rather than character, invite the employee's perspective, and keep sight of what a fair outcome actually requires.
Common Mistakes to Avoid When Having Difficult Conversations With Employees
The most damaging mistakes in difficult conversations are predictable, and can largely be prevented with preparation and self-awareness:
Delaying until frustration builds: raise small, specific concerns promptly rather than waiting for a major incident.
Attacking personality instead of describing behaviour: replace “You're unreliable” with a dated example and its impact.
Assuming you know the employee's motives: separate what you observed from what you've inferred, and ask before concluding.
Using questioning as disguised interrogation: ask one question at a time, allow silence, and be transparent about why you're exploring something.
Hiding the real message inside a feedback sandwich: state the concern directly rather than burying it in praise.
Trying to suppress or immediately fix emotion: acknowledge it, pause, and return to the issue once the person can engage.
Becoming defensive when challenged: notice your own signs (speeding up, interrupting) and slow down instead.
Raising every historical grievance at once: decide in advance which one or two current issues matter most.
Confusing empathy with removing accountability: validate difficulty while still restating the requirement.
Treating it as only a person-level problem: check whether skills, capacity or system issues are contributing.
Ending with vague intentions: replace “Please improve” with an observable standard, agreed actions and a review date.
Failing to follow up: document what was agreed and check progress, or the conversation loses its value.
One recurring pattern worth watching for is avoidance leading to accumulated frustration, as this will often result in an overreaction and an unproductive resolution pathway.
Early, proportionate conversations interrupt that cycle before the emotional stakes and stress become unnecessarily high.
If a meeting is already going badly, it can still be repaired:
“I think I've started to sound more confrontational than I intended. Let me restate the concern clearly, then I'd like to hear your perspective.”
Legal Risks in Australia: Understanding Fair Work Regulations
Employers are entitled to address legitimate performance or conduct concerns, but the process matters as much as the outcome.
Risks include failing to comply with an award, enterprise agreement, contract or policy.
For underperformance specifically, Fair Work guidance recommends setting out concerns with examples, giving advance notice, inviting a support person as best practice, listening to the employee, agreeing reasonable improvement steps, and documenting outcomes.
Termination-related decisions require additional procedural care, and the precise legal requirements depend on the circumstances.
Communication skill does not replace legal process, and a manager can deliver an empathetic message but still act unfairly if the outcome was predetermined.
Recording laws also differ across Australian states and territories.
In NSW, for example, the Surveillance Devices Act 2007 generally restricts recording private conversations (including ones the recorder is a party to) subject to statutory exceptions.
Hence, participating in a conversation does not automatically permit secretly recording it.
For most routine discussions, accurate contemporaneous written notes are the more proportionate approach.
Documentation: Handling Difficult Conversations
After any difficult workplace conversation, keep a factual, secure record covering:
Date, time, attendees and purpose of the meeting
The specific concerns raised, with examples and supporting material
The employee's explanation and any factual disagreements
Required standards, agreed actions and responsibilities
Training, support or workplace adjustments offered
Timeframes, review dates, and any warnings or consequences communicated
Follow-up correspondence and outcomes
Fair Work recommends keeping notes of performance discussions and a written record of improvement plans and follow-up.
Separate observation from interpretation: “The employee disputed the feedback and explained why” is more reliable than “The employee was uncooperative.”
Avoid putting speculative diagnoses or untested psychological explanations in personnel notes.
Good documentation records what happened and what needs to happen next, not assumptions about someone's character.
How Does this Vary for Remote Workers?
Remote meetings can reduce access to non-verbal cues and introduce privacy or technical issues.
Schedule a dedicated conversation, explain its purpose in advance, ensure privacy on both ends, use video where appropriate, avoid multitasking, and allow slightly longer pauses than you would in person.
Check understanding explicitly rather than assuming it: “I want to make sure I've understood correctly, is the main issue the changing priorities rather than the amount of work itself?”
Don't equate silence with agreement, and be cautious about recording calls by default. Consider accessibility, policy and applicable law first.
Summarise outcomes in writing and agree on follow-up afterwards.
If technology is getting in the way of a productive conversation, adapt.
A phone call or a rescheduled meeting can be more constructive than pushing through repeated disconnections.
The underlying interpersonal skills don't change; what changes is how a manager establishes connection and monitors understanding without being in the same room.
When Cultural Differences & Language Barriers Apply
Cultural responsiveness requires curiosity and acceptance without stereotyping.
Communication norms can vary around hierarchy, directness, eye contact, silence, disagreement and emotional expression.
However, background alone doesn't explain any individual employee's behaviour.
Use plain language, avoid unnecessary idioms, and explain expectations explicitly.
Consider a professional interpreter or appropriate communication support where language proficiency materially affects understanding, and use reflective listening to check meaning:
“I'd like to check that I've explained this clearly: how do you understand the expectation we've discussed?” A pause may simply mean someone is thinking or translating, not refusing to engage.
The goal is to preserve legitimate standards while making sure everyone has a genuinely fair opportunity to understand, respond, and contribute to the solution.
Measuring the Success of Tough Conversations
Success doesn't require an employee to agree immediately or leave the room feeling happy.
Instead, look for understanding, a fair opportunity to respond, clear expectations, and a workable path forward.
This can be tracked across three horizons:
Short term: the concern is understood, perspectives and disputed facts are recorded, and actions, owners and support are clear.
Medium term: target behaviour changes, milestones are met, the manager follows through on their own commitments, and the relationship stays workable.
Long term: improvement is sustained, the employee builds capability, the manager addresses future issues earlier, and any underlying systems issues are corrected.
It's also worth assessing the manager's own performance in the conversation: did they notice when an approach stopped working, shift technique, stay regulated, and listen to unexpected information?
The real measure of success isn't whether the meeting felt comfortable, it's whether it produced understanding, meaningful change, and more sustainable performance.
How to Have a Difficult Conversation: Big vs Small Companies
The interpersonal task is similar regardless of company size, but the surrounding system differs.
Larger organisations typically have formal HR support, documented procedures, and more separation between personal relationships and authority.
Smaller organisations often have fewer specialist resources and closer owner-manager-employee relationships.
In a small business, personal familiarity can make feedback feel awkward and encourage avoidance.
In a large organisation, formal procedure can become so dominant that genuine dialogue gets lost.
Different dismissal rules can also apply depending on size.
The Fair Work Commission's Small Business Fair Dismissal Code applies to national-system employers with fewer than 15 employees, counted according to the statutory rules, including certain regular casual employees and associated entities.
Whatever the size of the organisation, good management combines clear relationships, clear expectations and appropriate processes.
Structure alone isn't enough, and neither is good intent without process.
When to Speak to a Psychologically-Informed Executive Coach
Practice and structured training build confidence for most managers. But sometimes, short regulation strategies aren't enough.
A capable manager may still feel intensely anxious or overly accommodating around certain conversations, especially with authority figures or during criticism, and longstanding patterns around rejection or authority don't shift with a single workshop.
If a manager already knows what a difficult conversation requires but consistently can’t carry it out under pressure, the gap is rarely just one thing.
It’s usually a mix of mindset, skills and context. Sentient Professional Wellbeing’s psychologically-informed executive coaches work across all three:
Psychological: understanding the patterns behind anxiety, over-accommodating or defensiveness, and building emotional regulation so you can stay steady when a conversation becomes tense.
Skills: practising the techniques in this guide, including meta-communication, so you can choose the right approach at the right moment, including under pressure.
Systemic: thinking through the organisational side, such as timing, setting, who should be involved and whether HR should be there, so the process is fair and well considered.
Because these areas influence one another, working on them together can provide a fuller picture than addressing any one in isolation.
Get in touch with Sentient Professional Wellbeing to talk through what support might suit you and your team.
