Do you find yourself spending too much time re-reading emails you've already finished writing? Worried if you sound too harsh? Concerned about being rude? Wondering if your point is getting across? Whether it's a critique, a reminder, or a rejection, the heavier the subject, the longer you hesitate before hitting the send button.
Let me tell you upfront: this isn't a problem with your writing skills. It's a problem of not having someone to read it before you send it. When we were new, seniors would check our important emails. But as you move up in rank, there's no one left to look them over.
Outlook's Copilot has a button that acts as that "person who reads before you send." It's called "Coaching by Copilot." It reads the email you wrote and provides suggestions for improvement based on three perspectives: Tone, Clarity, and Reader Sentiment. Instead of writing the whole thing for you, it improves your own writing while keeping your own voice. This is the key difference from simple draft generation.
In this article, I will explain how to use this button, the conditions for it to work, and even the specific prompts to use when you have a clear goal. By the time you finish reading, you can try it out with your very first email today.
This is for those using a paid Microsoft 365 Copilot license at work. It is especially effective for managers who frequently give feedback to subordinates, sales staff who repeat requests and rejections, and anyone who needs to be careful about the "temperature" of their customer correspondence.
I am an AI Promotion Manager at a major Japanese company. Due to my position, I often have to communicate difficult things via email, and this is the feature I personally rely on the most.
No programming is required at all.
Let's begin.
Chapter 1: Why Your Hand Stops Before the Send Button
To jump straight to the conclusion, there are three reasons:
1. Because there is no one to read it before you send it
Writing only reveals its flaws when viewed by someone other than the author. Reports to executives, requests to other departments, apologies to customers—the more important the text, the more it needs a third-party check. However, it's unrealistic to ask someone every time, "Does this sound too harsh?" Since there's no one to ask, you have no choice but to re-read it yourself. If you spend 10 minutes re-reading one email and send three heavy emails a week, that's 120 minutes a month.
2. Because you cannot objectively view your own writing
Immediately after writing, your brain fills in the gaps with your own intentions. A sentence that looks normal to you might look like an interrogation to the recipient. This gap is impossible for the author to find, no matter how many times they re-read it.
3. Because harshness is determined by phrasing, not content
The content itself cannot be changed. A deadline is a deadline, and a rejection is a rejection. The only thing you can adjust is the phrasing. And adjusting phrasing is the most time-consuming task, requiring a deep vocabulary.
Just to be clear, hesitating before sending isn't about being oversensitive or indecisive. The more you care about the recipient, the more you hesitate. What you lack isn't courage; it's a dressing mirror for your emails.
You look in a mirror before leaving the house because you can't see your own back. Emails are the same; the author cannot see how they appear to the recipient. Think of Coaching as the dressing mirror for your emails.
So, here is the core of this article:
Write the email yourself. But let Copilot read it before you send.
Chapter 2: What is "Coaching by Copilot"?
It's easy to use. Write your email as usual, and before sending, select "Coaching by Copilot" from the Copilot icon in the compose window. That's it. Copilot will read your text and provide feedback on Tone, Clarity, and Reader Sentiment. If you like the suggestions, you can apply them all at once with "Apply all suggestions," or you can manually incorporate only the good ones.
There is one condition for it to work: It must be at least 100 characters long. It won't appear for one-line replies. Conversely, it's designed specifically for "proper emails" that exceed 100 characters.
It works in many places: the new Outlook, classic Outlook, the web version, and even the Outlook mobile app. This means you can use the "mirror" even for heavy emails you send from your phone while on the go. Communication accidents often happen when sending while tired. Its value shines late at night or during travel.
For managers, there's another use: tell your subordinates, "Run your external emails through Coaching once before sending." This reduces the number of draft checks sent to you, and subordinates can fix things themselves before being pointed out. As email education for newcomers, it's easier to sustain than human feedback because the AI's critiques don't feel like personal attacks.
Chapter 3: How a Reminder Email Changes
It's hard to convey with just words, so I'll use a scenario I often encounter: a reminder to a subordinate.
[Draft I wrote myself]
"Regarding the materials I requested the other day, are they ready yet? Please hurry."
There's nothing wrong with the content. But when you let Coaching read it, it returns feedback like this: The deadline "hurry" is vague. Because there's no reason given, it might be perceived as just being pushy. There's no word asking about the recipient's situation. By the way, this feature is designed to mention the good points of the text first before suggesting fixes, so it doesn't discourage you. It's a much easier partner to work with than a senior who starts with criticism every time.
[After reflecting suggestions]
"Regarding the materials I requested the other day, I would appreciate it if you could get them to me by Thursday noon so I can use them for Friday's meeting. If there are any difficulties, please let me know."
The content is the same. The request for a deadline hasn't changed. Only the phrasing changed. And this adjustment of phrasing is exactly the task you were agonizing over for 10 minutes before hitting send. Now it takes 1 minute.
Same business, same writing. The only difference is whether you let it be read once before sending.
Chapter 4: 3 Steps Starting Today
STEP 1: Write as usual, then press Coaching
First, finish writing it yourself. If you start worrying about phrasing halfway through, the trick is to just write to the end without worrying. Use the time you would spend worrying for writing, and leave the polishing to the mirror. This division of labor makes the writing itself faster. Once it exceeds 100 characters, select "Coaching by Copilot" from the Copilot icon. It's a button you press after writing, not before.
STEP 2: Don't "Apply All," just pick the good ones
Pressing "Apply all suggestions" regenerates the text, which is convenient but can dilute your voice. For everyday emails, applying all is fine, but for important ones, read the suggestions and manually fix only what you want to adopt. Take the advice, but don't surrender control of the writing. This is the best way to use this feature.
STEP 3: When the goal is clear, ask via Chat
Coaching looks at the whole thing, but if you've already decided "I want to fix it in this direction," it's faster to paste the draft into Copilot Chat and ask like this:
1I am sending this email draft to (Recipient, e.g., a Manager at a client). Please revise it so that the (Purpose, e.g., request for deadline extension) is clear, but the recipient doesn't feel blamed. Also, tell me what you changed and why.
The phrase "tell me what you changed and why" is the secret sauce. By reading the reasons, you build up your own library of phrasing. For those whose emails tend to get long, this is also useful:
1Reorganize this draft so the conclusion comes first and keep it within (Character count, e.g., 300) characters.
The final etiquette remains the same. Always check the recipient's name, your name, dates, and numbers with your own eyes before sending. Delegate the editing, but don't delegate the responsibility for sending. You are the one who pushes the send button until the end.
Chapter 5: Two Things You Must Not Do
1. Don't handle heavy emails like apologies with one click
For apologies or condolences, the fact that it's written in your own words, even if slightly awkward, has meaning. An apology made too smooth by "Apply All" will feel suspiciously slick. For heavy emails, use suggestions only as a reference and keep your own words.
2. Don't use "The AI said it was good" as a reason to send
Copilot only sees the text. It doesn't see the context of your relationship—what happened with that person last week or their current situation. An email can be perfect as a text but still be something you shouldn't send right now. The judgment of timing is a human job until the end. Text editing and the decision to send are separate processes; you can only hand off the former to the machine. People who can maintain this boundary are the ones who can use AI safely.
Summary: Graduate from the 10-Minute Pre-Send Wait
Finally, the core of this article once more:
Write the email yourself. But let Copilot read it before you send. That alone turns the 10 minutes before the send button into a 1-minute check.
That said, you don't need to do it for every email. Just do one thing:
Today, take just one email that you hesitated to send and run it through Coaching. The emails you hesitate over are where the mirror effect is most visible.
Once you know the peace of mind that comes from a third-party check, you'll never go back to re-reading drafts alone at night.
Copilot is evolving so fast. It's much faster to learn from those practicing it than to try to keep up with the latest news alone.
Thank you for reading to the end.
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