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Difficult workplace conversations are discussions that feel uncomfortable because the subject is sensitive, the outcome matters or emotions may be involved. They can include conversations about performance, behaviour, missed expectations, conflict, attendance, boundaries, workload or a breakdown in a working relationship.
Avoiding the conversation can feel easier in the short term, but unresolved issues often become more difficult over time. The aim is not to make every conversation comfortable. It is to make it clear, fair, respectful and constructive.
What makes a workplace conversation difficult?
A conversation can feel difficult when:
- you expect the other person to disagree
- the issue affects their performance or reputation
- you are worried about upsetting someone
- you are personally frustrated or angry
- there is a power difference between the people involved
- the facts are disputed
- the relationship has already become strained
- the subject involves sensitive personal information
- you are unsure what response you will receive
Managers can also delay conversations because they hope the problem will resolve itself. Sometimes it does. Often it does not.
Why should difficult conversations be addressed early?
Small issues are usually easier to discuss before they become established patterns.
An employee who has missed one deadline can be asked what happened and what support is needed. After six months of repeated missed deadlines and growing resentment among colleagues, the same conversation is likely to be much harder.
Early discussion can help:
- clarify misunderstandings
- identify underlying problems
- reset expectations
- prevent conflict from escalating
- give someone an opportunity to improve
- protect working relationships
Acas advises that many workplace problems can be resolved early when people are encouraged to raise issues and discuss solutions.
Step 1: Be clear about the purpose
Before arranging the meeting, ask yourself:
- What issue actually needs to be discussed?
- What evidence do I have?
- What outcome am I hoping for?
- What does the other person need to understand?
- What might I need to learn from them?
A vague objective such as “sort out their attitude” is not useful.
A clearer purpose might be:
Discuss three recent occasions where customer calls were not returned within the agreed service standard, understand what is causing the problem and agree what needs to happen next.
Specificity makes the conversation easier to manage and fairer for the other person.
Step 2: Separate facts from assumptions
People often enter difficult conversations with a mixture of evidence and interpretation.
Compare:
You do not care about the team.
with:
You arrived after the agreed start time on three occasions this month and did not let the team leader know in advance.
The first statement assigns a motive. The second describes observable behaviour.
Where possible, prepare:
- dates
- specific examples
- agreed standards
- relevant records
- previous conversations or commitments
This does not mean going into the meeting like a prosecutor. It means being able to explain the concern accurately.
Step 3: Consider your own emotional state
If you are angry, embarrassed or defensive, that emotion can shape the conversation.
Before the meeting, identify what you are feeling and why. Ask:
- Am I still reacting to what happened?
- Am I making this personal?
- Am I expecting the worst?
- Am I ready to listen to an explanation I may not agree with?
If the conversation is genuinely urgent, you may not have much time to prepare. If it is not urgent, a short delay to regain composure can be better than starting while emotions are running high.
Step 4: Choose the right setting
Sensitive conversations should normally take place privately and without unnecessary interruption.
Think about:
- confidentiality
- enough time to avoid rushing
- whether the conversation should be online or face to face
- whether another person should be present under organisational policy
- any accessibility or communication needs
A performance concern should not be raised casually in front of colleagues or squeezed into the last two minutes of another meeting.
Step 5: Open the conversation clearly
A good opening establishes the subject without unnecessary drama.
For example:
I want to talk about the delays in completing the weekly reports. There have been three occasions this month when they were submitted after the agreed deadline. I would like to understand what has been happening and agree how we can address it.
This is clearer than beginning with several minutes of small talk while the other person tries to guess why they are there.
Step 6: Describe behaviour and impact
A useful structure is:
- Describe the specific behaviour or situation.
- Explain the impact.
- Invite the other person's perspective.
For example:
During yesterday's meeting, you interrupted Alex several times while they were presenting. They stopped before completing their explanation and the discussion became tense. What was happening from your point of view?
This keeps the discussion grounded in observable events rather than character judgements.
Step 7: Listen properly
Difficult conversations are not simply opportunities to deliver a message. They are also opportunities to learn information that may change your understanding.
Use active listening by:
- allowing the person to finish
- asking open questions
- checking your understanding
- summarising key points
- not preparing your next argument while they are speaking
Useful questions include:
- What happened from your perspective?
- What has made this difficult?
- What do you think is contributing to the problem?
- What support would help?
- What could you do differently next time?
What if you disagree with their explanation?
Listening does not require agreement.
You can acknowledge that you have heard someone's perspective while still explaining that a standard has not been met.
For example:
I understand that the team has been particularly busy and that you have been covering additional work. We still need customer complaints to be acknowledged within the agreed timescale, so we need to agree how that will happen.
What if the person becomes defensive?
Defensiveness is common when people feel criticised or threatened.
Avoid escalating by:
- keeping your tone calm
- returning to specific facts
- allowing reasonable time to respond
- acknowledging emotion without abandoning the issue
- asking questions instead of arguing
If someone says, “Everyone else does it too,” you might respond:
We can look separately at any wider team issue you think needs attention. In this conversation, I need to understand what happened in these specific situations and what needs to change.
What if emotions become strong?
People may become upset, angry or frustrated.
Do not assume emotion means the conversation has failed. Sensitive topics can produce emotional responses even when they are handled appropriately.
You can:
- pause briefly
- acknowledge the emotion
- offer a short break if appropriate
- keep your own tone steady
- avoid filling every silence
If behaviour becomes abusive, threatening or unsafe, the conversation may need to stop and be handled under the organisation's procedures.
How to use assertive communication
Assertiveness means expressing a concern clearly while respecting the other person's rights and perspective.
It sits between passive communication, where important concerns are avoided, and aggressive communication, where the speaker disregards the other person.
See Assertive vs Aggressive vs Passive Communication.
Focus on the future as well as the problem
Once the issue is understood, move towards what needs to happen next.
Agree:
- the expected standard
- specific actions
- who is responsible
- support or resources required
- timescales
- when progress will be reviewed
A conversation that ends with “please do better” leaves too much room for different interpretations.
Document important agreements
Depending on the seriousness and organisational process, it may be appropriate to record:
- what was discussed
- the agreed actions
- support offered
- review dates
Records should be factual, proportionate and handled according to organisational policy and data-protection requirements.
Informal vs formal conversations
Many issues can be addressed informally, especially when they are raised early.
However, serious conduct, safeguarding, discrimination, harassment, grievance or disciplinary matters may need formal procedures.
Managers should follow their organisation's policies and seek appropriate HR or professional advice where necessary. A communication technique does not replace employment procedures or legal obligations.
Examples of difficult workplace conversations
Underperformance
Keep the conversation focused on expected standards, evidence, possible causes, support and improvement.
Inappropriate behaviour
Describe the behaviour and its impact. Avoid broad labels such as “unprofessional” without explaining what actually happened.
Poor attendance or punctuality
Use accurate records and allow the employee to explain circumstances. Follow relevant attendance policies and consider whether additional support or formal advice is needed.
Conflict between colleagues
Explore the underlying issue rather than simply deciding who is “right”. Where appropriate, informal resolution or mediation may help.
Saying no to a request
Explain the decision clearly and respectfully. Avoid creating false hope through vague language if the answer is genuinely no.
Common mistakes to avoid
- Waiting too long. The issue becomes larger and evidence becomes harder to discuss.
- Making it personal. Character judgements create defensiveness.
- Going in with a fixed conclusion. Important context can be missed.
- Talking too much. The other person's perspective is never properly explored.
- Softening the message until it becomes unclear. The employee leaves without understanding the concern.
- Becoming aggressive. A difficult subject does not justify disrespectful communication.
- Failing to agree next steps. Nothing changes after the meeting.
- Ignoring policy. Serious matters need the correct organisational process.
A difficult-conversation checklist
- Define the issue clearly.
- Gather relevant facts and examples.
- Check your assumptions.
- Decide what outcome is needed.
- Choose an appropriate time and setting.
- Explain the issue directly and respectfully.
- Ask for the other person's perspective.
- Listen and clarify.
- Agree actions and support.
- Follow up.
Frequently asked questions
Should difficult conversations always be face to face?
No. A private video meeting may be appropriate for remote teams. The important factors are privacy, clarity, enough time and the seriousness of the issue.
How do I start a difficult conversation?
State the issue calmly, provide specific evidence and explain that you want to understand the other person's perspective before agreeing what happens next.
What if the employee refuses to engage?
Explain why the conversation is necessary and follow organisational procedures. Managers may need HR advice where an employee repeatedly refuses to participate in a required process.
Should I use a feedback model?
A simple model can help structure the conversation, but it should not make the discussion sound scripted. Specific behaviour, impact and future expectations are more important than memorising an acronym.
Can difficult conversations improve relationships?
Yes. When issues are addressed fairly and respectfully, people can gain clearer expectations and greater trust. Poorly handled conversations can have the opposite effect.
What if the issue might involve discrimination or harassment?
Follow organisational policy and seek appropriate HR or professional guidance. Serious allegations should not be treated as an ordinary informal communication problem.
Develop your skills with ExperTrain
ExperTrain's Handling Difficult Conversations course provides practical techniques for preparing for challenging discussions, listening effectively, remaining composed, giving feedback, communicating assertively and working towards constructive outcomes.
The half-day course is part of our wider Professional Development training portfolio and is available as scheduled live online training or for private groups.
You may also find our Conflict Resolution, Increasing Assertiveness and Communication Skills courses useful.
Further reading
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