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Strategies For Approaching a Manager and Asking For More Paid Time Off

Americans work hard and often don’t get as much time off as our European counterparts. However, the need for adequate paid time off (PTO) has become increasingly significant for many since the return to the workplace. Many employees, still in roles they began many years ago, find their personal circumstances evolving. Starting a family, caring for relatives, or simply seeking a well-deserved break, especially in demanding sectors like technology, underscores the need for more flexible leave policies. If you’re ready to have that difficult talk with your boss or supervisor about more time off, here are our strategic tips for negotiating for additional PTO.

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Leverage Company Values

If your company or its leadership publicly endorses family values or work-life balance, use this to strengthen your case. This aligns your request with the organization’s professed principles.

Pose Questions, Not Ultimatums

When facing resistance, adopt a questioning approach. Inquire about the feasibility of your PTO request in different scenarios. This strategy fosters a collaborative problem-solving atmosphere rather than a confrontational one.

Be Proactive with Your Manager

Blind-siding your manager with a sudden request for increased leave is ill-advised. Liane Davey, an expert in organizational psychology and author of “The Good Fight,” suggests easing into the conversation, perhaps at the end of a meeting. It’s better to prepare your manager for the discussion than to catch them off-guard, leading to an immediate rejection.

Timing is Key

The Bureau of Labor Statistics reports that most American workers receive just ten days of paid leave annually, excluding sick days and holidays. The optimal moment to negotiate for more PTO is ideally before job acceptance or during annual performance reviews, where one can leverage one’s contributions and discuss compensation beyond salary.

Present a Constructed Argument

When discussing PTO with your manager, emphasize your dedication and achievements, then explain the personal changes necessitating more leave. Prepare to discuss how the additional time off would impact your work and the team. Avoid making your request seem like a reward for performance alone, as family needs and personal well-being should not be contingent on work achievements, according to psychologist Lindsay B. Jernigan.

A Rejection Could Signal a Bigger Issue

If your request for additional leave is denied, or if the prospect of making such a request is daunting, it might be an indicator of an unsupportive work environment. Jernigan suggests that this could be a sign to explore opportunities elsewhere, where your need for family time and self-care is more valued.

Carefully negotiating for more paid leave is a delicate yet vital process for employees seeking to balance their professional and personal lives in a manner that reflects their evolving circumstances.

Josh Dudick

Josh is a financial expert with over 15 years of experience on Wall Street as a senior market strategist and trader. His career has spanned from working on the New York Stock Exchange floor to investment management and portfolio trading at Citibank, Chicago Trading Company, and Flow Traders.

Josh graduated from Cornell University with a degree from the Dyson School of Applied Economics & Management at the SC Johnson College of Business. He has held multiple professional licenses during his career, including FINRA Series 3, 7, 24, 55, Nasdaq OMX, Xetra & Eurex (German), and SIX (Swiss) trading licenses. Josh served as a senior trader and strategist, business partner, and head of futures in his former roles on Wall Street.

Josh's work and authoritative advice have appeared in major publications like Nasdaq, Forbes, The Sun, Yahoo! Finance, CBS News, Fortune, The Street, MSN Money, and Go Banking Rates. Josh currently holds areas of expertise in investing, wealth management, capital markets, taxes, real estate, cryptocurrencies, and personal finance.

Josh currently runs a wealth management business and investment firm. Additionally, he is the founder and CEO of Top Dollar, where he teaches others how to build 6-figure passive income with smart money strategies that he uses professionally.