Make It Hypothetical

A variation on letting them know what you want is to express what you want hypothetically. This is no more (or less) likely to achieve the aim. The point is that it’s a direct, straightforward, and honest way of asking, which you might find easier than actually asking. It comes across as being far less pushy—because it doesn’t require the other person to give you a yes or no answer—so if you are remotely under-assertive, it may appeal to you. Here’s how it goes:

• “If ever you were thinking of selling that piece of land, I might be interested.”

• “If a job came up in the PR department, I’d really love the opportunity to apply for it.”

• “If you need another trustee on the board in future, I’d love to be more involved.”

If you’re feeling brave you can turn it around and request a hypothetical answer:

• “If I could find an evening class to learn another language, do you think you might babysit one night a week?”

• “If we find the perfect house and it’s just a bit over our budget, is there any chance you and mom might help us meet the difference?”

• “If Sarah does transfer to the Manchester branch, could I be considered as her replacement?”

This version does require some kind of response, but you’re sounding the other person out rather than asking directly. And it can give you a lot of useful information to help toward getting what you want.