How not to piss off your boss

It’s all about email etiquette


Email is there for times it’s too scary to ask for something in person.

Email is there for when it’s too frightening to tell your boss something they don’t want to hear. Email is there for asking for time off, or a pay rise, or permission to leave the office early without sounds like an idiot. But the timing is everything.

There is the Friday rule. Everyone is in a better mood on the last day of the week – including your superior. Catch them in that sweet spot between finishing up some small Friday tasks and going out, then your plaintive request will likely hold more sway. Then, follow up in person on Monday morning.

“Hi Martin, did you have a good weekend? Just wanted to check if you saw my email on Saturday?” If they say they don’t remember, remind them – firmly, though likely without making eye contact – that they said yes.

Mornings are generally a bad idea: the last person they want to hear from is anyone. Try to pick a point when you can point to a visible success. Something in the region of bringing in a new client, making the company look good and just nailing a presentation are ideal. If that doesn’t work, right after you’ve made tea for everyone can work too. Everybody is in a better mood right after lunch or having some tea.

There’s a weird self-imposed rule people seem to stick by. If it’s a new job, we seem to dictate our own “probation period” – taking one day off for every month we’ve worked. If this seems like a big deal to you, it most likely isn’t one to your boss unless you’re trying to book a big holiday in your first week.

Don’t go overboard in the email and try to avoid giving them a sob story about how you have to leave for a made-up funeral. There’s only so many times in a year a grandparent can die so it’s probably worth keeping track of how many times you’ve asked. You could make it seem like a chore to be taking time off and you’d obviously rather be at your desk. This could look a bit transparent though.

How do you end the email which could make or break your career? Maybe you should go super personal so you seem like friends. You could get away with “Thanks”, “Cheers”, “Ta’, “Appreciate it mate”. Or maybe you should go super formal so they think you’re always professional round the office and that is how you speak to clients. Happy holidays!