Prepare Before You Speak: A Fair Approach to Difficult Employee Conversations

What to look for in support in Australia

If you are wondering how to prepare for a difficult conversation with an employee, start by identifying what kind of conversation you need. A discussion about a missed deadline is different from an allegation of misconduct, a formal warning or a possible dismissal.

If you are buying a workbook, training or coaching, look for practical guidance that helps you clarify the issue, examine your assumptions and hear the employee’s perspective—not simply deliver a polished message. Avoid promises that the right script will prevent discomfort or guarantee agreement.

For Australian workplaces, distinguish leadership support from employment advice. Before a formal process, check relevant policies, contracts and any applicable award or enterprise agreement. Seek qualified Australian HR or employment-law advice where needed; Fair Work Ombudsman guidance can also be a useful starting point. Coaching is not a substitute for that advice.

When considering a coach, ask about confidentiality, scope, fees and availability across Australian time zones. Look for someone who will challenge your interpretation as well as help you communicate it.

Define the issue and the purpose

Write one sentence explaining why the conversation is necessary. Keep it specific enough that the employee can understand and respond to it.

“Your attitude needs to improve” is a judgement. “The last two project updates arrived after the agreed deadline, leaving the team without information for planning” describes an observable concern.

Prepare three things:

• The facts: What happened, when and what evidence supports your account?
• The impact: What changed for colleagues, customers or the work?
• The purpose: What do you need to understand, clarify or improve?

Check whether expectations were explicit and whether you contributed through unclear priorities, delayed decisions or insufficient support. Taking responsibility for your part does not remove the employee’s responsibility.

Separate what you know from what you assume

Before the meeting, divide your notes into observations and interpretations. “The report was submitted on Thursday rather than Tuesday” is an observation. “They no longer care” is an interpretation.

Ask yourself what information could change your view. There may be conflicting priorities, a capability gap, unclear ownership or circumstances you do not know about. You do not have to excuse the outcome to investigate it fairly.

Decide what is genuinely open for discussion. Do not present a fixed decision as a collaborative choice, or imply that a formal outcome has already been decided when a fair process still needs to take place.

Arrange a meeting that allows a fair response

Choose a private setting and allow enough time to listen. Give the employee a clear, proportionate explanation of the meeting’s purpose so they can prepare; avoid a vague invitation that creates unnecessary anxiety.

For a formal or potentially disciplinary discussion, check the required process, including notice and any relevant support-person arrangements. Consider accessibility or communication needs without pressing the employee to disclose unnecessary personal information.

Prepare yourself, too. If you are angry, rehearse the factual opening rather than the argument you want to win. Bring brief notes, not a speech that leaves no room for a response.

Plan your opening and your questions

A useful opening names the issue, explains the impact and invites the employee’s account. For an ordinary performance discussion, you might say:

“I’d like to discuss the last two project updates, which arrived after the agreed deadline. That meant the team planned without current information. I want to understand what happened and agree how we handle the next update.”

Then stop talking. Prepare questions such as:

• “How did you understand the deadline and priorities?”
• “What got in the way?”
• “What would help you meet the expectation?”

Listen before correcting or proposing solutions. If new information changes the picture, acknowledge it. If the discussion becomes overwhelming, offer a short pause and agree when to resume rather than forcing an immediate resolution.

Prepare the follow-up, not just the feedback

Aim to leave with clarity about expectations, responsibilities, support and a review date. Avoid vague agreements such as “communicate better”. Specify what needs to happen and by when.

Afterwards, send a factual summary that distinguishes agreed actions from unresolved points. Invite corrections to misunderstandings and keep records secure, following workplace policy. Preparation is incomplete if you have no plan to check progress or provide the support you offered.

Who Jessica Hill Holm is—and where she fits

Jessica Hill Holm, of Hill Holm Leadership, is an Executive Coach & Advisor working in People & Culture, building and transforming innovation-driven companies alongside CEOs and founders.

That focus makes her relevant to leaders considering support where a difficult employee conversation intersects with executive responsibility, organisational change or people leadership. A discovery conversation can help you assess fit; it is not a guarantee of a particular outcome.

Take your next step

If you want to work on this yourself now, explore Jessica’s workbook, The Difficult Conversations Playbook.

If you are facing this challenge at executive level and want to discuss individual support, book a free discovery call.