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There’s Only One Good Way to Email Your Boss

Photo: Tarik Kizilkaya/Getty Images

My boss gets 500 emails a day. I try not to email her but sometimes I have to, and the one way to get her to reply quickly is simple: I start every email to her with a question. And then if needed, I explain the context to my question in one or two more sentences in the fewest possible words.

Starting with a question is important because if your boss scrolls through emails on her phone, like most of us do, her screen allows her to see only the first few words of an email before she chooses to reply, delete, or ignore it. Words like “Do you think…” or “Could we…” or “Will you confirm…” are quick shorthand phrases that tell her THIS IS AN EASY EMAIL. All she has to do is reply yes or no. And she’ll email you back faster.

Another great touch you can add while emailing your boss, co-workers, and especially people who don’t work at your company is changing every “can” and “will” to “could you please” and “would you.” At first you will worry you sound ridiculously formal: “Could you please tell me if…?” and “Would you consider…?” But then people will start being SO NICE TO YOU and MOVE MOUNTAINS to help you only because you SOUND like a very nice refined person with poise — even if you’re falling apart at your desk, even if they’ve never met you. Big-name fashion publicists do this, and I think it’s one of the reasons they’re at the top.

Here are some examples of how to rephrase messages to your boss as questions, either in emails or DM:

Would you please tell me if this sounds okay? [Explain how you want to solve a problem]

Could we please pay X freelancer the usual $Y to complete Z task? [Tell her what the task is, and why this freelancer is the best person for the job]

Is it correct that you’re no longer working on the X project? [Tell her why you’re asking or who wants to know]

Will you please approve this deck by end of day if possible? [Tell her when exactly the presentation is, in case end of day doesn’t work for her]

I learned this strategy from my very corporate consultant friends, whose soul-sucking companies demand and encourage this streamlined way of communicating and even gave it a name: “High-Level Summaries.” Their emails are expected to contain only the most important information their bosses need to know (none of the minutiae we all survive on a daily basis), purposefully written to require only a one-word answer, if at all: Yes. No. Okay.

If something really important has come up, I front-load urgency in messages rather than starting with a question, like this: Something urgent has come up that I need to discuss with you before Friday. Could we talk tomorrow after 2pm?

If I don’t suggest a possible time like that upfront, doing the legwork and checking my boss’s Gcal to see when she’s free, her answer will be delayed. Which isn’t her fault: There are too many emails and Slacks to keep track of, and I’ve learned that my poorly phrased messages make both of our jobs harder. Phrasing them well helps her, but more importantly (selfishly) it helps me get my own work done faster.

This strategy is also effective if you’re responding to something your boss asks you to do. Remember, in the interstitial space between when your boss messages her request and she’s waiting for you to confirm yes, you can do it, you have her full attention. But you get only one “ask.” So ask all of your questions upfront with the strategies listed above, while she’s still thinking about it (and, to save time later, make sure you’re actually doing the task correctly).

Usually the things I stress about when replying to these kinds of e-mails are: 1) When does she need this? and 2) How exactly does she want me to do it? So I frame my response to her accordingly. For example, say your boss messages you: “Will you write up a summary of X?” In a single message, I’d say: “Of course. I can email it to you by 3 p.m.: a single page focusing on X, Y, and Z. Does that sound right?”

By describing HOW you’re already thinking you will do it (“focusing on X, Y, and Z”), and what time you’ll finish, all your boss has to say is “Yes” or “Actually, Slack it to me” or “No, I think you should focus on A, B, and C.” Plus, she sees you’re an independent thinker and able to execute tasks well on your own.

In the book Women in Clothes, a very wise executive-type woman said back when she was an assistant, she learned from her very important boss to always respond “Of course” when you’re asked to do something, rather than “No problem” or “Sure,” because it makes you sound as if you were already planning to do it.

Happy emailing!


There’s Only One Good Way to Email Your Boss