If you employ or manage employees, or hire artists or arts workers as independent contractors, knowing how to have difficult conversations is important.
Whether you are addressing a workplace conflict, discussing concerns about job expectations or work quality, responding to inappropriate behaviour, setting personal and work boundaries, or letting people down about an unsuccessful promotion or quote, having conversations early can help prevent issues from becoming larger problems.
Approaching difficult conversations respectfully, fairly and constructively can help maintain positive working relationships while also addressing workplace issues.
Addressing issues early by having a conversation can also help:
- clarify job expectations
- improve working relationships
- support worker development
- resolve misunderstandings
- prevent small concerns from escalating
- contribute to a positive workplace culture.
Learning to have a difficult conversation with care can support good working relationships with your employees.
Preparing for a difficult conversation
Preparing well for a difficult conversation can make the experience more productive and less stressful for both people in the conversation.
Before meeting with person, take some time to properly identify:
- what issue needs to be discussed
- what might be causing the issue
- the specific facts or behaviours involved
- the outcome you would like to achieve
- what support or resources may help resolve the issue
- whether there are any individual circumstances you should consider.
It is important to focus on observable behaviour, actions or incidents rather than assumptions about a person’s intentions, attitude or character.
In practice:
| Instead of saying: | Try: |
|---|---|
| “This is unprofessional.” | “The design was provided after the agreed deadline.” |
| “You don’t seem to consider the other people who work here.” | “Some team members have told me that they were unable to access important information from you that they needed in order to open the exhibition on time.” |
| “Your attitude is inappropriate.” | “I noticed you interrupted others several times yesterday during sound check.” |
Be fair and equitable in your approach
It is important to approach difficult conversations fairly and equitably.
- Being fair — Where similar situations arise, employees should generally be treated consistently.
- Being equitable — The way a conversation is conducted should take into account individual circumstances, including cultural considerations, disability, mental health, communication preferences, or other factors that may affect how a person participates in the discussion.
Depending on the issue, telling the person in advance that you want to speak with them about a particular issue can lead to a better conversation with more considered input. Taking somebody by surprise when raising an issue (particularly a serious one) can sometimes trigger stress responses or defensiveness, rather than constructive dialogue. Think about whether requesting a conversation in advance is likely to support what you want from the conversation.
Choose an appropriate setting
Choosing the right setting for a difficult conversation is essential. Think about both the place and the time. An inappropriate setting can derail a conversation or lead to unnecessary harm and stress for the people involved.
Wherever possible, find a place where you can:
- speak privately
- make sure you allow enough time
- minimise or avoid interruptions.
Put yourself in the shoes of the person who will be on the receiving end of the conversation. Would they be comfortable in that conversation environment? You are more likely to have a constructive conversation where the other person feels comfortable and can speak openly and honestly.
In practice:
Giving a worker advanced notice
Anh works remotely from a home office and has access to online technology for meetings.
Anh’s manager wants to discuss some sensitive issues regarding Anh’s contribution to a recent project.
Rather than invite Anh to meet in the open studio where other workers move about, Anh’s manager sends him a meeting invitation to a confidential online meeting. In the invitation, she includes that she would like to discuss the recent project Anh was involved in.
Having the conversation
Difficult conversations can be more beneficial when they are direct, respectful and focused on resolution options.
Try this simple approach to a conversation:
- Describe the issue — Explain the concern clearly and factually.
- Explain the impact — Help the person understand why the issue matters.
- Listen — Invite the person to explain their perspective.
- Discuss solutions — Identify practical steps to move forward and try and do this together.
- Confirm expectations — Agree on any actions, support or next steps.
When leading or taking part in a difficult conversation, it can be helpful to:
- Ask open questions — You may be more likely to get the information you need and understand more about the issue.
- Actively listen — Avoid interrupting the person, use clarifying questions to understand the other person’s perspective and what they are sharing with you.
- Seek their perspective on a way forward or a solution — Depending on the issue, imposing a solution or attributing blame may not resolve the issue in the long term. It is important to take their perspective into account when deciding on a way forward.
- Adjust your approach if needed — Pay attention to how the other person is reacting. If they appear confused or unsure, try rephrasing the issue. If they appear distressed or are finding it difficult to provide a response, you can take a break or make another time to continue the conversation later. Learn more about managing difficult responses.
In practice:
A difficult conversation about a person’s reported behaviour
Malik is the production manager for a performing arts organisation. He has been receiving complaints about one of the stage technicians, Tessa. Several members of the crew have described her as ‘abrupt’, ‘rude’, ‘aggressive’ and ‘disrespectful’ when responding to questions. Malik has witnessed this himself, He has also noticed that other technicians and crew are becoming reluctant to approach her for help.
Malik arranges a private meeting with Tessa. He explains that he wants to discuss some observations about communication within the production team.
Malik says, 'I wanted to talk to you about your communication style. We try really hard here to be respectful to each other, and I’ve noticed several occasions this week where your responses to team members have been quite abrupt. A couple of the crew have let me know that they find it hard to raise things with you because of the way that you talk to them. They’ve said it can feel aggressive, and that’s something that worries me.'
Tessa explains that she has been working long hours to manage several technical issues and has been feeling overwhelmed by competing demands.
Malik acknowledges the pressure Tessa is under. He explains that, even when things are busy, respectful communication remains important. Tessa acknowledges this.
They set up a time later in the day to discuss strategies to reduce workload pressure and agree on expectations for future interactions. Malik also schedules a follow-up discussion after the production concludes to check in about how Tessa has been communicating with others.
A difficult conversation about job expectations
Elena supervises front-of-house staff at a regional performing arts venue. She notices that a recent employee, Sam, has not been completing post-event incident reports following several patron complaints.
Elena arranges a private conversation and asks why incident reports have not been submitted on several occasions when issues occurred during events. She outlines why the reports are important for organisational records and the organisation’s risk management decisions.
Sam appears surprised. They explain that they thought incident reports were only required is a serious injury or security incident had occurred.
Sam started working for the performing arts centre during a busy period and Elena appreciates that she may not have clearly communicated the different situations when incident reports are needed.
Elena takes the time now to properly explain the reporting process, provides examples of situations that should be documented, and directs Sam to the relevant procedure.
They agree that this is the expectation moving forward. Elena schedules a brief follow-up after the next event so that Sam can ask any further questions and Elena can check that their understanding.
The issue is resolved through clarification and additional guidance by Elena.
Managing difficult responses
Not everyone will respond positively when concerns are raised. An employee may be surprised, upset, defensive, frustrated or disagree with your perspective. Try hard to remain calm and steady.
It can help to:
- slow the conversation down
- acknowledge the person’s perspective
- ask questions to better understand the situation
- return to the facts if the discussion becomes emotional our unclear
- take a break if necessary and come back to it later.
Sometimes a workplace issue may be influenced by circumstances you didn’t know about, such as illness, caring responsibilities, workload pressures or other personal circumstances.
Consider whether additional workplace support could help address the issue. For example:
- Support from an Employee Assistance Program (EAP) — If your organisation doesn’t have one, Support Act offers a free EAP-style service to small and medium-sized creative organisations without a formal EAP of their own. Learn more about Support Act as an EAP.
- Support from another organisation — There are lots of organisations that offer information, advice and pathways for resolving different workplace issues, including artform-specific organisations that understand your kind of art. Find out where to get help.
In practice:
A challenging response in a difficult conversation with a contractor
Aisha manages a community arts festival. Staff members have reported to you that the festival’s lighting contractor, Bryce, has missed coordination meetings and has been slow to respond to schedule updates.
Aisha arranges a private discussion and explains the specific concerns and their impact on event planning.
Bryce responds defensively, saying, 'I’m not sure what the issue is here. As far as I’m concerned, I’m completing the work and shouldn’t need to be available every time somebody wants to meet.'
Rather than arguing, Aisha remains calm and acknowledges his perspective. She says, 'I appreciate the work you’ve delivered. My concern is that when key updates aren’t shared, it creates challenges for other teams and increases risks during the event.'
Aisha keeps the conversation focused on project outcomes rather than personal criticism. She asks Bryce what communication approach would work best while still ensuring he receives important information.
Together they agree that Ben will attend critical coordination meetings and receive written updates when attendance is not required.
Aisha makes a note to remember for next year’s festival to talk about and agree on these kinds of expectations as part of her process for hiring contractors. This way, she knows they will both be on the same page before work begins.
Tip: We think having a written agreement essential for hiring independent contractors.
Having clear, straightforward written agreement can help everyone know what is expected of them. They set out what you and the independent contractor have agreed about the work and payment arrangements, and can include other things too, like how you will deal with a dispute.
A written agreement does not have to be a formal written contract. For example, it could be an exchange of emails. Learn more about written agreements and contracts.
Following up after the conversation
A difficult conversation may only be the first step in seeking a resolution.
It can be a good idea to follow up with the person after the conversation as part of supporting them to improve and to reiterate your expectations.
Depending on the issue, follow-ups may include:
- checking their progress regularly
- providing them with additional coaching or training
- documenting the actions you have both agreed on
- reviewing any workplace adjustments or support measures you have agreed to put in place.
If they have improved, recognising their positive improvement and effort.
Positive reinforcement can strengthen confidence, motivation and ongoing work performance.
If concerns continue despite support and feedback, you may need to consider more formal responses in accordance with your workplace policies and legal obligations.
Keep learning:
Difficult conversations in the workplace — free online course for employers and managers
Fair work Ombudsman
Learn more