Whether a family member is facing a health issue where they require your assistance, you want to go back to school, or you need to step back from work for another personal reason, lots of people negotiate leaves. Asking for leave can be daunting, especially when there is no clear process in place at your organization. How will your boss respond? What is company policy? Can you ask for only a few weeks or a month off, or is it possible to take a year? How will this affect your career in the organization?

Extended leaves are part and parcel of what are known in academia as idiosyncratic deals (i-deals, for short), special conditions of employment granted to an individual employee that differ from what their coworkers have. Having researched special deals like extended leaves for 20 years, I know it’s possible to reach an agreement for extended leave — and make it work for you, your company, and even for your boss and coworkers.

There are two primary types of leave requests: extended leaves you can anticipate and plan for and unplanned requests in response to sudden family demands. The biggest difference between the two is whether you have time to prepare to negotiate.

Two important features of negotiating a leave are what you can learn about your company and its policies and culture before you ask, and what your company and, especially your boss, knows about you and your contributions. Putting this information together forms the building blocks of a negotiation process.

When There’s Time to Plan Your Leave Request: Three Phases of the Negotiation

Let’s talk about the three phases of extended leave negotiations — preparation, negotiation, and implementation.

Prepare

The critical first step of leave negotiation is prep. Get yourself ready by reflecting on your goals and gathering information.

  • What are your goals? What do you want to achieve? For example, do you need to recover from stress, have more time for family, or create concentrated time for studying or a passion project? What arrangements can help you do so? Talk with friends, family, and trusted colleagues about possible arrangements that could realize your goals. Is a month enough or do you need a year? Is there some middle ground? Think about where you need to be firm and where you might be flexible in your negotiation.
  • What precedents exist? The onus is on you to gather information about company policy and precedents. Have other leaves been granted before? Tap your network to identify and talk with people who were granted leaves. Ask your contacts for details on how they made the deal and what they did to manage it. How well did it work out? A boss who is reluctant to be the first to grant extended leave can take cover and comfort from hearing about prior successful arrangements. But your boss may not know what deals others have made, so you’ll need to scope out the kinds of leaves and flexibility others in the company have been granted. If there is no precedent, look at organizational policies that could be tweaked to address your request. A classic example of this is the engineer who wanted to take a year off to do underwater photography of coral reefs — so his boss gave him “educational leave.” If the concept of “leave” already exists in your organization, it opens the door for yours.
  • What can be done to reduce the burdens on your coworkers and boss? Given your current responsibilities, think about how your duties can be covered in your absence. What can you finish now? What can be postponed until later? What else can be done to pick up the slack? Talk with your close coworkers to brainstorm ideas and problem solve. The timing of your request matters. Leaves are often easier to request soon after you have completed a big project or delivered an important outcome. Your contributions are more visible then — and your boss may feel he or she owes you. Try to avoid making your request in the busy season or when your boss and your department is working at capacity.

Negotiate

With a clear goal and information on policies and precedents, you’re ready to talk to your boss. When your relationship is good and the trust between you is high, the negotiation process is easier and can be more of a conversation framed around solving a problem. If your relationship with your boss isn’t great, it’s not uncommon to shop around for internal opportunities that would allow you to report to a manager you think would be more supportive.

  • Adopt a problem-solving approach. Frame the conversation with your boss around your desire to remain with the organization while needing to deal with your family or personal concerns. Provide enough information regarding the challenge you’re facing so the reality of your needs is clear, but don’t say more than you are comfortable with. Convey your commitment to the organization in the long term, and explain how granting a leave will make your future with the company possible.
  • Seek win-win or win-no lose solutions. If possible, provide advance notice of your need for leave. Creating a window of opportunity for planning and adjusting helps to make problem solving easier, allows you to consider the impact of your leave on your team, reduces burdens for others, and shows your organizational commitment and sense of responsibility. Win-win solutions often involve discussions with coworkers about timing and possible arrangements to help the organization manage without you. Your goal is an arrangement that leads your employer to agree to your request and brings you the flexibility you need.
  • Check for differences in assumptions. Clarify boundaries and time limits associated with the deal you negotiate with your boss. Confirm the time frame involved, whether you will have contact with the organization in the interim, and your availability to support colleagues if need be.
  • Manage the message. Work with your manager on a communication plan. Figure out what you and your boss are going to say to others regarding your leave and who needs to know what when. If the time frame is clear, say so. If you have agreed to remain accessible to coworkers in need of your support while you are away, explain how this should happen (such as preferred communication channel, hours of day you anticipate being more available, and so on).
  • Keep a written record. Because memories are fallible, take the initiative to write an email to your boss summarizing what you both have agreed to. To check for understanding, ask them to indicate if they have any corrections or clarifications.

Take Your Leave

How your leave is actually implemented and the relationships you maintain during it will shape whether it realizes the goals you had for it. Implementation also shapes the leave’s benefits and costs for you in the long term.

  • Manage your relationship with your coworkers. Stay in regular contact with your coworkers while on leave, if possible. By remaining accessible, you provide support to help your coworkers through your absence. This contact also reinforces your personal relationships with colleagues and helps you appreciate the organizational situation to which you will ultimately return.
  • Manage your relationships with your boss. Staying in touch with your manager while you are on leave signals that you plan to return and are committed to the organization. Maintaining contact can reduce the likelihood you’ll be discounted in future decisions regarding training or assignments and smooth your return to work.
  • Prepare for reentry. Coworkers can come to occupy different roles while you’re out, making it less likely the job you return to is the one you left. Organizations will differ regarding whether your old job has been “saved” or whether you’ll reenter in a new position. Sometimes there are changes to leadership, and your immediate manager may no longer be your boss. So, when you return, do the things you would do if you were new to the organization: Talk to as many different coworkers as you can to get up to speed. Reorient yourself to the organization; take the initiative to learn how your boss and colleagues understand your (new) role and what they might need from you.

When Your Need for Leave Is a Surprise — Even to You

What if you are blindsided by a family need? Let’s say a grandparent comes down with a serious illness and needs full-time care or your child’s daycare closes suddenly. In the case of an unanticipated need for extended leave, the request process will be shorter — you will make your request using the information you have in hand. But even without a ton of notice or prep, you can make a request that clearly states your need and why your organization should support it.

  • Frame the request around your need and future commitment to the organization. Tell your boss or company contact person what your needs are and the likely duration of the leave — a week or two (for example, until your daycare reopens) or a month or more (such as when you’re dealing with the uncertainty of a family member’s illness). Convey the urgency of your need (giving only the details you feel comfortable providing). Offer assurances of your commitment to the organization and your colleagues, but don’t overpromise.
  • Indicate how you might manage the leave’s duration. Given your leave’s suddenness, your hands may be tied regarding the help you can give to reduce disruptions. Being realistic about how much time you need will help avoid mixed signals. Setting a specific point — say, two weeks or a month — when you’ll purposefully check in with your boss about the status of your emergency may help allay concerns about lack of certainty of the length of your leave. And if the leave must be indefinite, as in the case of serious family illness, it is better to say so.
  • Check in — but respect the real constraints you face. Your personal bandwidth in dealing with an urgent family need is probably more limited than if you’d had advance time to prepare. So be it. You may need to disengage from work more completely. If you’re able to check in with your boss and colleagues, even briefly, it eases your return.

What If the Answer Is No?

What is your best alternative if you are not granted a leave of absence? Recall the goal of your leave and consider how you might still meet it in some way. Do you need to quit? Shortchange your home responsibilities? Shelve your novel project for a better, later time? Or burn yourself out working extra hours in every arena of your life to meet your personal and professional commitments?

If your leave request is not granted and reduced hours won’t help you meet your goal, pivot and lobby for the flexibility you need — “no” can sometimes mean “maybe.” You can also escalate to look for support elsewhere — from HR or senior leaders. The latter option has some political risks, so be savvy about who to talk with and how your request can be a win-win.

Last, you can offer to quit. This is a card you probably can only play once a job, but if getting an extended leave really is important to you, this can give you leverage — or provide evidence that this isn’t the best employer for you. Consider how you frame quitting. “I am sorry to say this, but I might have to quit this job” is very different from “If I don’t get leave, I am out of here!” If this is your last resort, try to introduce this last, most dire option in a way that will preserve your reputation and your relationship with your boss, coworkers, and the organization.

Everyone Needs a Leave Sometime

Asking for what you need is a life skill — on the job, at home, in any realm of your life. Negotiating and joint problem solving is the best way forward to realizing your goals. It is normal to craft your work situation much as you do in your home life: to meet your needs and build good relationships. In your daily interactions at work, you are gathering intelligence about how the organization functions, what others care about, and your own goals and concerns. You can put that intelligence to use — whether you anticipate needing a leave or the need for leave finds you.