To Top

The Most Effective and Clever Way to Ask Your Boss for an Unpaid Leave for Traveling, Studying etc…

You’re feeling like you need some much needed time away from work to hang-out with friends and family and go on a trip far away from home.

How would you approach your boss and Human Resource in order to be granted an unpaid leave? What would you do to figure out if your colleagues have ever asked for leave that way? Must you base your request for a leave on work? What elements of your case would make it more convincing to your manager?

Expert Advice

In many organizations, asking for more than a few days off requires a careful approach. According to Jeff Weiss, who authored HBR Guide to Negotiating and is also the president of Lesley University, this is an intricate arrangement, that needs more efforts put into it than even salary-related negotiations. You must be particularly tactful and creative in your request else it may be considered non-beneficial to your boss as per your company policies. However, being strange doesn’t imply that your request is impossible. Many individuals are known for negotiating for unpaid leaves, says Denise Rousseau, author of I-Deals and Carnegie Mellons Tepper School of Business professor. Workers at Idiosyncratic Deals handle bargaining by themselves successfully. Below are some of the best ways to effectively request for unpaid leave.

Know Your Worth and Risks

Before making the request, understand your worth in the company. It would be much easier to convince your employer if they think you are important. Also, if you are irreplaceable, they might hesitate to grant you the leave. Think of the long-term objectives of the company and how your extended absence will affect them both positively and negatively. Besides, consider the individual risks you may encounter, such as missing a promotion. If you conclude that your position is good enough to risk opportunities, go ahead.

Define Your Goals

It’s essential to envisage the accomplishment you’re planning to make while away, says Weiss. Do you have plans to acquire a specific skill? Do you want some time off away from burning out? Rousseau says more employees succeed in their leave requests by simply framing it as developmental. If you know exactly what to make out of your time away, more people will likely support your goals.

Look for Preference

Handsome Office Man with Eyeglasses Listening to his Female Co- Worker Talking to him at his Worktable with Computer.

Find out if someone else has done a similar thing in your company. Rousseau says that one element of your preparation should be to answer questions such as; has someone done this before? What approach made it successful? What didn’t succeed? Contact colleagues in your industry to help brief you on certain specifics regarding arrangements you might be aware of but are inflating the benefits. You can as well ask the HR about company policies that allow for requested unpaid leave. Weiss says that when you are aware of what’s happening at your own firm, it helps you raise the case of legitimacy and the uniqueness of your situation. However, you don’t have to be discouraged if there is no precedent. You can be the first to get an unpaid absence.

Consider Potential Objections

Decision-makers will probably fine many reasons to reject your request. Your only strength is to be as convincing as possible says, Weiss. Think tactfully about the mindset and concerns of whoever you shall be negotiating with. What will make them hesitate? Will they be afraid that your case will set a bad precedent? Will your boss think that you might not return? Now, think of how you will defend your request against these objections provided they are raised. Prepare for them as if they are positive opportunities for you and the company.

Make it Beneficial to the Company

Explain to your boss what the company will benefit from the leave. Be prepared to lay-out a negotiable plan which convinces the boss that you’ll come back stronger and more beneficial to the organization. To concretize your case, prepare to outline some ideas and new skills as well as professional connections you’re hoping to make while away. Give a convincing argument on why being fresh will help improve your performance when you come back. There are managers who understand how well arrangements like this can be of assistance to employees and companies alike, in terms of performance and other advantages, Rousseau says. Prepare well for all these with numbers, multiple options and everything that makes sense to that effect. Your time off can also happen in phases.

Pick the Correct Time But be Flexible

Be smart and start this conversation when you know that your manager feels great about your performance as per the glowing reviews. Also, make sure the timing for your leave minimizes the impact on the flow of work in your company. You want to make it much easier for the industry and less burdensome for clients as well as coworkers. Be positive and flexible enough to postpone it if the manager concludes it that way. They might be a big order the company has to handle, a new project you don’t know about or a shift in personnel, explains Weiss.

Prepared to Say No or Yes

The negotiation can go both ways and therefore, you have to be ready for both a positive or negative response. It’s but natural that your company’s decision-makers may push back. Have you reached a point where you may have to quit your job if the leave is not granted? Whatever the case, open up and don’t be scared to ask.

Do and Don’t Principles to Remember:


Remember that your unpaid absence won’t be rejected simply because maybe no one in your company has taken one yet.

Carefully build your thoughts around the goal you want to achieve while away and blend them in your request such that they also favor the company. Ensure that your leave maximizes its impact on clients and coworkers.


Come prepared with convincing reasons and be tactful against any objections from your manager.

Ignore any prospect of objections. Be ready to address them when the time comes.

Make sure you’re as flexible as possible, to improve your chances of negotiating your leave successfully.

Case study #1: Be Passionate and Flexible

The Chief Marketing Officer of Shoe Review website, Paul Ronto, has a passion for river rafting. In the previous years, he planned to travel to Grand Canyons Colorado River when he was working for a nonprofit organization assisting injured veterans, at-risk and disabled young people to experience life outdoors. Though given a generous vacation package, Paul’s time off wasn’t well paid.

Previously, he passed on the leave due to work obligations though this was the time he actually wanted to go. So after analyzing his worth as well as the risk involved, he made the case. Besides, the trip was so important to him that quitting the company was a possibility provided they said no.

When he sat down with the HR, Manager and Executive Director, he concentrated more on his excitement since according to him, they were a passion-driven Company.

Besides, his plan was smart and concrete. He proposed to volunteer to work for the company for additional days during the two weeks Christmas holiday of the organization which involved taking in phone donations, process checks, and collecting the mail. He also suggested consulting with the HR to also grant him unpaid days.

Paul’s bosses accepted his proposal. According to him, “they understood that my trip came from my true passion and would benefit them if they let me go in order to come back more motivated.”

In fact, the trip was wonderful, and as Paul put it, “it changed my life.”

Now Paul works in a company that offers unlimited time for vacations, and he will be returning to the Grand Canyon in five months. His CEO even encouraged him to go.

Case Study# 2: Count on Your Worth

The approach of Matthew Ross, who co-owns and manages RIZKNOWS & the Slumber Yard which runs many internet properties is worth exploring. Last year when faced with an eight-week off leave proposal, Matt hesitated initially.

He says he wasn’t giving employees any extended leave periods, but this particular employee’s strategy was well defined and convincing.

He began by saying that he was among the company’s top-notch employees for years in terms of performance and experience. That made Matt more flexible listening to him.

When the employee tabled his objectives for the trip, he explained that his trip was on behalf of a humanitarian organization which works in various African villages. Matt and his business partner liked the idea and offered to support with a donation.

Most notably to Matt, this employee also volunteered to offer training to other employees to handle his duties in his absence. Ensuring that no critical work will be left undone in his absence gave Matt positive feelings about the trip.

No wonder Matt and his business partner granted him the extended leave which included a stipulation. Matt said the employee would have to work extra hard when he returns from the trip in order to catch-up. He accepted and did exactly as he promised when he returned.

More in Business