How to ask for a leave of absence from Work:

In 6 easy Steps!

Asking for a leave from your Boss is a fight to finish, where both the parties try to defeat the other in most respectful manner as possible.

Let me re-write the sentence, you don’t ask for leave, you actually request for it. And how you request a leave from work can make or break your relationship with your employer.

Since, in either way we want absence from work and to win this battle a strategic planning is required.  It may sound funny but you better prepare yourself against any possible responses from your boss. Imagine, stating certain organizational reason he/she said NO! or said YES! with T&C applied. What could possibly be your reaction to it?

Yes, you are smart, but we never know whether we can make it at 11th hour or not. Therefore, in order to ask or request your boss for leave, one should know –

– How to approach for leave of absence,
– When to approach to ask for leave from boss and
– What to say while asking or requesting for leave of absence from work.

Read the following passages that will help to answer above mentioned queries:-

1. Rules and Regulations – Company Handbook

Every Organisation including start-ups have certain written or verbal rules and regulations for various actions and key roles associated with the workers / employees. So before you plan your leave and before executing the request, learn the related laws and company policies.

You should first check your eligibility to take time off from work. Determine, whether your case can be addressed under the policy.

Depending upon your situation, you do have the right to take leave from the work. Urgent situations like; Pregnancy, Military Service, Illness, death in the family, etc, in such cases employers are obliged to grant work off.

Also, unless and until your reason for leave is valid, avoid making any kind of work off excuses and requests that may lead to stress for your manager / employer and co-workers.

2. Advance Time –

Make sure you avail your request well ahead of time. An advance notice makes it easy for managers as well as co-workers to manage the workload or find any replacement to fill the void. This also helps you by making them more likely to accept your request.

3. Preparation –

Before approaching to your employer for leave you should be prepare with certain responses. If your request is more likely to be accepted you should act in favour with your employer. Try and be flexible with your decisions. Even if your request will be denied, get ready with well-practiced explanation, explore available options like reducing working hours, partial leave, part time work off, temporary work from home, etc.
In case of denial whether you are going to continue your work or leave the place, plan your next step. Also, planning including finances can be a smart decision, either you take paid leave or unpaid, you should take it in consideration.

4. Final Presentation:-

Before you ask your boss for leave, analyse the preferable time to approach him/her. When he/she is less stressed or overworked, and things seems to be smoothly functioning, a leave request have better chances to get approved.

You can also schedule this appointment when your employer is feeling positive about you and your performance. Also, choose the time of your leave to minimize the impact of workflow.

Be willing to listen to your employer’s reasons, in case he denies.

Once you know the process for requesting for leave, ask your boss for few moments of his/her time. Start with informing your immediate supervisor about the leave, do not share with your colleagues until you clarify terms with your employer.


5. Final Approach:-

This may vary as per different workplaces, casual or formal. In casual environment, you can just simply state to your Boss that you would like to have a day or more leave from work, and ask whether it will be feasible or not. In formal environment, you are suppose to request in writing and may involve taking appointment in order to approach for discussion.


For example:

Me – “Sir, I won’t be able to come on 20th July – Monday. I would like to have a day off, because ….”

Remember, adding ‘because’ to your statement is effective, as asking for work off is an imbalanced situation for your employer, providing a valid reason to your request not just forces your Boss hard to not to say “No” but will also provide an impression that he/she is updated about his/her employee’s situations and establishes a frank relation.

Another case would be when you ask for more than a day off, in that situation indicate your end date of leave. This makes the request specific and clear and your Boss has the comfort of knowing when you’ll return. Even if you are not able to provide exact date, it’s better to provide a general time frame of your leave period.

Just to remind you, even after all these efforts there will be or could be lots of reasons for your Boss to say ‘No’. But you want to make this negotiation as favourable as possible, so frame this properly and positively. Try to understand his/her objectives, hesitations, etc.

With this, here comes the major question:

What to do and how to handle when your Boss said “No” for Leave of absence from work?

Like I said earlier, try to understand his/her objective for denial. Consider the reason and if even then you want to avail leave:

5.A. Talk with Boss –  

Sit down and discuss with him/her about your leave, why it is important and why you cannot afford missing this opportunity. Get yourself prepared for proper negotiable conversation, how can this be beneficial for the organisation. Come up with explanation of achieving new ideas, skills and even if you need any break, elaborate why you believe it can improve your performance when you return.  Bring multiple options and explanation for how it can work.

5.B. Legal Terms –

It is preferable not to use these legal rights conversation in the beginning. Once your offer have been denied then you can let your manager know that you are aware about your company policies and time off from work and you would like to proceed. Again explain the reason and apologize for inconvenience. 

5.C. Consequences of Leave –

Let your Boss know that you are concerned with the affect on productivity because of your absence and would like to discuss any plan or convenient time for leave and to find someone suitable to fill in for your place. Complete projects, tasks. If possible work from home, time off from work in phases. Any alternative idea/(s) that can work for organisation’s benefit.

You can even suggest training your replacement or co-workers. Explain your workload and duties to them, as no-one would like to come from a vacation and then handle the messed up and piled up work. And do inform your manager that your work will get covered up.

5.D. The Announcement –


Inform every person who need to know, colleagues, clients, customers etc related to your work.
In case of colleagues share your plan and ask them to help you in covering up your task in your absence and offer them to help whenever they need.
In case of clients or customers you handle, let them know who will accommodate their needs in your absence.

5.E. The Meringue Concept –

‘Meringue’ as you are aware is a sweet that mostly acts as a final garnish over dessert, in similar form you have to give your plan a final touch up.
Get yourself caught in the eyes of your Boss before leaving. If possible give some extra working hours as well as productive hours, complete your major task and try giving as much as possible less burden to your colleague.

Remember planning well for your absence, its consequences and making sure everything is and will get covered up will not just make it easier for you but will also create a good impression in front of your Boss as well as your colleague for you being in favour of them by making them feel comfortable with as much as possible less work.

6. Wrap up with your Final Action:-

After discussing with your Boss and getting the approval for the same if your company policies says to request the same in writing then do follow it. Most of the companies have a form to be filled out to apply for leave, then indicate the type of leave and mention the return date.
If they ask you to write an absence letter then include the information you discussed with your Boss.


In any case make sure to send a follow – up email to confirm the details of your leave that you discussed with your Boss.

With this I hope every aspect is covered and clear. Although it’s not easy enough handling your Boss even if you are very smart handling clients, customers, etc, especially if it is about you being not productive for the organisation.

But as said by Rousseau, “I find that more people are more successful when they frame the unpaid leave as developmental, because it’s seen as something that could actually bring value back to the employer.” 

Adding to the message, Vacation, Work off improves potential of an employee, and it is also one of the legal rights of them.

In the end Best of luck from my side!

Plan your actions and conversation about how to ask leave of absence from your Boss, and do share your views.

I will be more than happy to know your experience! 🙂