From A Pay Rise To A Promotion: Here’s How To Get Your Boss To Say Yes To Anything

When was the last time you asked your boss for something? Chances are, it wasn’t that long ago – from a flexible lunchtime to accommodate an appointment; an extra unpaid holiday day; or a risky business venture that you just know will pay off, we frequently find ourselves negotiating with our bosses for something that we want.

But when what you’re asking for involves a certain level of risk – or the riskiest factor of all, money – figuring out how to ask for it, and when, can be no mean feat. We’ve got the ultimate crib sheet – here’s how to get your boss to say yes to… just about anything. No, really!

…to a meeting

“Timing is really important when you’re asking to talk to your boss,” says Ella de Guzman, owner of the Siopaella chain of consignment shops in Temple Bar. “Be someone who sets aside a time to say, ‘can we have a meeting?’ And don’t ask in the middle of a busy day – we work in retail so, no, we’re not going to have a meeting on a Saturday morning. And when someone asks at the wrong time, it just makes me feel like they haven’t really thought it through, or considered my time.”

…to a pay rise

“You have to put yourself forward,” says Ellen Kavanagh, co-founder of Waxperts. “If you feel like you’re going above and beyond, and you can back it up by saying, ‘here are my examples’, and you know that it’s within the parameters of the operation, you’ll have a better chance.” She cautions that it’s worth bearing in mind what’s going on with the business, and whether cashflow is tight. However, just because there’s no extra cash to flash doesn’t mean you’ll come away empty handed. “If you know the business and you know there isn’t extra money, you could be pushing it – but you might get something else. Maybe it’s hours, maybe it’s parking… It might be something else that’s of value to you.”

…to a risky idea

Ella’s old-school when it comes to brilliant ideas: “Write them down! People don’t write things down on paper any more. For some reason, when you commit it to paper, it means more – you put more thought behind it,” she posits. “Write down the pros and cons. Don’t say to your boss, ‘there are just pros!’ Show that you’ve thought it through by listing the cons, and that it’s still beneficial because of A, B, C and D. Every project will have pluses and minuses, but a lot of people make the mistake of thinking something’s foolproof. Nothing’s guaranteed.”

…to a promotion

“We don’t hire people who think they’re too good to do a job,” says Siopaella’s Ella. “In fashion, everyone thinks it’s all glam – but it’s really not. If you’re asking for a promotion, make sure you’re not the person who’s going, ‘I’m too good to be steaming clothes.’ We’re looking for leaders, yes, but you have to be a team player, too. Everyone chips in.”

…to a flexible working week

In Ellen’s experience, a flexible working week isn’t always an advantageous move – and can end up backfiring. “Sometimes, people can end up doing five days’ work in three days,” she warns. “It’s about communicating all the time. You need to be able to blow your own trumpet, and go, ‘I can do this in x amount of time, but I’m at capacity then.’ Make sure you’re not landed with other people’s work – there’s always somebody who goes above and beyond, but in order for a team to work well, it has to be fair.”

..to extra responsibility

“Remind your boss of times you’ve excelled,” Ella recommends. “Sometimes we forget – you’re so busy, that you forget that so-and-so managed this project really well. Remind me, so I can think, oh yeah, you are really good at that! Be able to prove that you can walk the walk, with evidence, showing that you should be the one to lead this project.”

…to anything

“A really basic thing is, be a nice, friendly person,” says Ellen. “Be somebody other people want around. Don’t put up challenges – be part of the solution. That way, if people know you’re already on board, and you do as much as you can in work, and you’re doing your job really well, but also helping the rest of the team, you’re going to get, basically, whatever you want. It’s really hard to say no to nice people.”

This article first appeared in STELLAR’s January issue. Our October issue is on shelves now! 

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• career