Asking for a long holiday can feel daunting, especially when the calendar is busy and workloads are high. Whether it’s a long-awaited trip abroad, or a pause from routine, approaching the conversation with clarity and transparency can set the tone for a productive conversation.

With a clear understanding of leave entitlements and a well-prepared plan, securing an extended holiday is often more feasible than many realise.

Understand Your Leave Options

Ahead of discussing your plans, ensure you’ve reviewed your leave entitlements under Australian workplace laws.

• Annual Leave

Full-time employees typically accrue four weeks of paid annual leave each year, part-time employees accrue a pro-rata amount, and casual employees are paid a loading in lieu of annual leave, so do not accrue anything. This leave is designed to provide time away from work for rest, travel, personal commitments or anything an employee wishes to use it for. For most extended holidays, annual leave will be the primary option.

• Leave Without Pay

When paid leave has been exhausted or an employee requires a longer break than their entitlements allow, leave without pay may be requested. As this type of leave is unpaid and subject to approval, it is best suited to situations where a longer absence is necessary but annual leave is insufficient. Keep in mind that your employer does not have to approve any leave without pay.

Prepare for the Conversation

When asking for time off, an organised approach sets a positive tone and leads to more constructive discussion.

• Do not book your holiday, till you have spoken to your employer

It is always best to speak to your employer first before you book your holiday. The earlier you do this the more chance of success, as you are able to negotiate and work together with your employer around your plans. Presenting a non-negotiable date and travel plan is never the way to go.

• Start the conversation well in advance

Most important is to start talking to your employer well in advance of any proposed leave, and definitely well before you have booked any travel. Businesses need to plan for absences and it is in your interest to give them plenty of warning and options. If your travel dates are non-negotiable, due to a family event for instance, talking to your employer well in advance, will give time to plan.

• Find the Right Moment

Timing influences how smoothly the conversation unfolds. If workloads are lighter or major tasks have been finalised, that can be an ideal time to begin the conversation. Try not to chose a time when your boss or manager is under pressure!

• Share the Purpose of Your Request

Transparency is important when requesting an extended break. Offering an upfront explanation, such as travel plans, family needs, or the need for additional rest, provides clarity and helps managers to prepare for any operational adjustments.

• Be Open to Flexible Solutions

A flexible approach and a willingness to support team continuity shows reliability consideration for the broader workload. Offering to complete key responsibilities beforehand or preparing handover notes can reassure managers that essential tasks will continue to be managed smoothly.

Consider Alternative Arrangements

In situations where approving a long overseas holiday is difficult to accommodate, exploring other working arrangements can create solutions that support both your travel plans and the organisation’s needs.

• Remote Work From Holidays

Working remotely during part of the trip can support an an overseas break while keeping connected to essential tasks. Clear expectations around availability and boundaries are important to ensure this arrangement works smoothly.         

• Organising temp staff or in-organisational cover

Talk to your employer about arrangements that can ease the workload while you are away. Suggest training a temp a week or two before you leave or starting now to hand over work to colleagues.

Reassure Your Ongoing Commitment

Reaffirm your commitment to your role and the organisation. A brief reminder of your reliability and future plans can strengthen the request and support its approval. Once the leave has been approved, confirming your return date and demonstrating readiness to resume responsibilities, helps ensure a smooth transition back into the role.

Set Yourself Up For Success

Taking an overseas holiday can be both refreshing and incredibly valuable for long-term wellbeing. With thoughtful preparation and a clear plan in place, extended leave is often more achievable than many expect. Returning refreshed benefits both the employee and the workplace, setting the foundation for success.

Need Support?

If you’re looking to step back for a while, knowing how to approach the discussion can make securing leave much easier. If you want to suggest temporary staffing options call CIRCLE Recruitment & HR Temp Desk on 1300 923 000

Important Note: These articles have been prepared for general circulation and are circulated for general informational purposes only; these articles should not be regarded as business or investment advice. The articles represent the views of the writers and are subject to change without notice. Additionally, while every care has been taken in the preparation of the articles no representation or warranty as to accuracy or completeness of any statement is given. An individual or organisation should, before any business or investment decision is made, consider the appropriateness of the information in this document, and seek professional advice, having regard to objectives, situation and needs. This document is solely for the use of the party to whom it is provided.