Create A Plan A And A Plan B When Requesting Holiday Leave

Create A Plan A And A Plan B When Requesting Holiday Leave

In many offices, making a holiday leave request isn’t as simple as stating the dates you want. For those situations, Harvard Business Review suggests offering up a couple of different options.

Photo by Julien Bell

If your office culture balks at holiday requests, it’s tough to broach the subject. To make that conversation easier, offering two plans gives your boss an option to choose, which makes the whole tone of the conversation better:

If it works for your family or others participating in your vacation, create an A plan and a B plan with a difference, for example, between length of vacation and particular dates, in order to give your manager some options. You might say, “My family is looking at two options to coordinate at my spouse’s firm and here in our company.”

You’re entitled to leave and shouldn’t be bullied out of it — but flexibility also helps.

Make It Easier for Your Boss to Say Yes to a Vacation Request [Harvard Business Review]


  • You: “Hey boss, I’d like to request a week off in September.”
    Boss: “No. Can’t afford to have you off then.”
    You: “Let me rephrase that. I’m taking a week off in September. Whether or not I come in on the Nth is your call.”

    Don’t accept bullying.

    • Get over yourself. There’s this little thing called responsibility. It’s not bullying to refuse a non-emergency request for leave if it there is a legitimate and important reason for you to be at work on a particular day(s).

      • Sorry, I was probably commenting based on a raw nerve in an apparently unhealed wound. 🙂

        I guess it’s all a matter of perspective. Responsibility as a good employee includes having your role well documented so the business can function without you. It also does include giving your boss enough time to plan around your leave.

        Responsibility from a boss’ perspective though… well, that includes making sure your people get sufficient leave that you never have to state before an inquest, “We didn’t see this coming, but in hindsight the signs were there.”

        I’ve referred to my vacation time as Stab Minimisation Absences with my current boss. He gets it.

        • I think responsibility is not just documenting your job so that someone else can do it. It’s also knowing when is and isn’t a good time to ask others to take up your slack when you’re away.

          In a lot of industries, there are certain times of year where it is far busier than others. An accountant could schedule a holiday at the end of financial year and there are probably others who can take up their work. It is their busy season though so it’s not the most responsible thing to do given that everyone else is probably stretched just keeping up with their own stuff around that time.

          Or, if several other people are taking leave at the same time and you’re the last to apply for it – it’s pretty reasonable for the boss to say no.

          Sometimes a boss has valid reasons to refuse leave approval without it being called bullying.

  • My solution was always to book leave almost a year in advance. Always approved, never considered properly.

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