Starting a new job or looking to sweeten your current one? Learn how to make the ask from people who’ve done it (and succeeded).

By Kathleen M. Harris
Updated March 15, 2018
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Woman Working on Computer
Credit: Christin Hume/Unsplash
Woman Working on Computer
Credit: Christin Hume/Unsplash

A Change of Scenery

Sick of being in a cube with no natural light? “An intra-office location change could make you much happier,” says Marjie Terry, a professional-growth coach based in New York City. Mark Cheng, who works at Nickelodeon, agreed to a much farther-away office move for one of his employees: “I couldn’t match the salary requirements for someone I wanted to hire in New York City, so we negotiated that he could work out of the Los Angeles office for two weeks in the winter,” says Cheng. Before you ask, predict what your boss’s concerns may be—that you won’t be around for a last-minute client meeting, say, or that it will be harder for her to pop by if you’re on a different floor. “Have a specific plan as to how you’re going to address any issues,” says Linda Babcock, PhD, professor of economics at Carnegie Mellon University and coauthor of Women Don’t Ask: The High Cost of Avoiding Negotiation—and Positive Strategies for Change.

Extra Personal Days

Try for more vacation time, or ask for a routine personal day—like the first Monday of the month—to get a chance to recharge. Tell your boss you want to work together to figure out how you can have some additional time off. “Don’t come at it like, ‘Here’s what I want and why,’” says Babcock. “What you say should reflect that it’s a problem-solving conversation.” Emily Hill, who works in investor relations in New Jersey, asked for six months of paid maternity leave instead of the company’s standard three. “Having extra time with my newborn, without stressing out that I wasn’t going to get paid, was worth more than any salary bump,” says Hill. If your company says no, don’t get discouraged. “It doesn’t mean no forever; it means no at this moment,” says Terry. “You may be in a much better position three months from now to negotiate for the same thing you desire.”

More Assistance at Work—or Home

Buried in paperwork? Ask for help if it will improve your productivity. “A former employee of mine could never make time for expenses, so we arranged for him to work with an assistant,” says Dorothy Kalins, a publishing consultant in New York City. Your manager will be more inclined to take your request seriously if you explain the benefits to the company (like more time for you to engage in big-picture work). Extra hands can come in many forms: a virtual assistant via a service like Prialto or Belay, a shared assistant, or even childcare. Melissa Dowling, who works in public relations in Stanford, Connecticut, negotiated a stipend to help cover babysitting costs during her late nights at the office.

Flexible Hours

Even if you don’t punch a clock, your coworkers probably all keep similar hours. Don’t view this as law. “If there’s a 6 p.m. exercise class you really want to take, ask to shift your schedule by 45 minutes once a week,” says Terry. Los Angeles–based television writer Liz Cackowski negotiated a 5 p.m. departure on Fridays so she could make it home in time for movie night with her kids. “In TV rooms, you do not leave early on Fridays, so this was a very big deal,” she says. Be flexible: Maybe it’s one day a week or two days a month. Let your boss propose a schedule first.

Working From Home

Depending on your company, this may or may not be a big ask, so research precedents. “Does anyone else work from home? What’s the arrangement? If you don’t know, ask administrative personnel who have been there forever,” says Babcock. When you ask, lead with work-related reasons: You need a quiet place to read; you’ll free up time for calls by avoiding a long commute. “Paint a vivid picture of what this would look like,” says Terry. “Say, ‘I see myself getting x, y, and z tasks done on those days.’” If your boss is hesitant, propose a trial period. Say, “Maybe we could try this for two months, then regroup to talk about what did and didn’t work.”

Conferences and Continuing Education

If there’s an event you’ve always wanted to attend, put it on your ask list. Or consider other professional-development opportunities. Emily Law O’Donnell, a teacher in Winchester, Massachusetts, negotiated graduate school tuition assistance into her contract. “Schools have a tough time paying teachers competitive salaries, as everyone knows, but they often have pockets of money set aside for things like professional development,” she says.

Commuting Costs

Joe Maggio, a technology-storage sales specialist in Hoboken, New Jersey, doesn’t drive. So when his new company offered him a car, he asked for a commuting stipend instead. Calculate travel costs and request a membership to a bike-share system, a parking space, or even a prepaid gas card. “Have a ranked list of asks,” says Terry. “If you get dinged on your first ask, you can then propose a second and possibly a third.”