Yes Man / Warner Bros. Pictures
Maybe you chat about the possibility of hiring someone in the elevator. Maybe you Slack a request for vacation days among a sea of links and cat GIFs. Maybe you make a conference request in person, while waiting for the crush around the coffee machine to ease.
Or, maybe you email.
Jocelyn Glei, author of "Unsubscribe: How to Kill Email Anxiety, Avoid Distractions, and Get Real Work Done," writes that an effective emailed request frames the question in terms of the value provided to your boss rather than the value it provides you. You also want to convey that you've been thoughtful about "any eventualities stemming from the request and have them covered" in that initial note.
"If you're asking a question, propose a solution," she writes. "Email is not a good venue for debate. Thus, messages that offer nothing but a question like - What do you think about X? - are generally ineffectual. Busy people don't want to figure out your problems for you, and they don't want to write you a lengthy response."
For that reason, she says, you'll want to provide all the information your boss requires to make a decision upfront. Sure, you can take the discussion offline (for instance, a single email probably won't be the only mention of hiring a new team member), but your boss will be equipped with the basic info needed to give the matter some thought before speaking further.
Glei provides the below scripts for three common requests:
For a new hire:
"Hi Karen - I know you're about to set budgets for the coming year, and I wanted to ask if we could discuss the possibility of hiring a new salesperson? I've looked at the numbers, and adding someone should allow us to double the new accounts we bring in each year, which means it should only take about three months for the for the new hire to pay for his salary in value added to the company."
For time off:
"Hi Karen - I wanted to request your approval on taking some vacation in October: Mon 10/6 thru Mon 10/13. We'll have just wrapped the big web relaunch, so it'll be a slow period and Mark has agreed to step in and handle all my clients during my absence. Then I can come back rested and refreshed for the big holiday sales push!"
To attend a conference:
"Hi Tina - I've been thinking about ways to enrich my work skill set, and it looks like there are some speakers and workshops at SXSW next year that would be very helpful. I can also put together a report to share what I've learned with the team after I return. I've estimated the cost, and it looks like a ticket, hotel, and airfare would run the company about $2,500. Do you think the company could sponsor me to attend?"