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My assistant consistently writes emails to our customers that contain basic mistakes like confusing "you're" and "your", and "there", "they're" and "their". She's a great assistant and I don't want to offend her, but I feel that this reflects poorly on me and my company. How should I go about approaching her on this?

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    Do you have a proofing tools installed and a workflow/policy in place for using them (e.g. required for customer emails) ? Another possibility is to create a policy whereby she sends you the draft email for review whenever it's customer-facing.
    – Brandin
    Commented Aug 20, 2015 at 13:40

3 Answers 3

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Basically the approach should be the same with any criticism of someone else's work (no matter whether it's a peer or not):

  • Be direct, but respectful. Don't accuse the person or attack them personally.
  • Never criticise in front of others (do it in private, by email or similar).
  • Be clear and precise about what you see as a mistake/problem, and about what change you expect.
  • Depending on the answer, be prepared to accept that you may have made a mistake, and that the person is actually right :-).

In your case, since it is a rather minor problem, I'd probably just try an email at first. Something like this, when replying to an email:

Thank you for [whatever is the main content of the mail].

One more thing: In your mail, it looks like you mixed up "you're and your" and "there, they're and their". While this is no big deal in internal communication, please take care about correct use when communicating with customers - after all, we want to present the best image possible.

The exact wording will depend on the details, your style, your respective positions etc.

You could also address the problem in person (privately). The advantage is that social cues are easier to transmit in person, this may reduce the risk of the assistant feeling insulted or belittled. On the other hand, scheduling a private meeting may make it feel like the issue is being blown out of proportion - you'll have to make a call what is more appropriate in this case.

For example, if you have regular private discussions / one-on-ones, it is probably better to address it during such a meeting rather than by email. If you don't have them, scheduling a meeting just for this issue may seem overblown...

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    I would strongly recommend against doing this by email as it's almost impossible to accurately convey tone in writing and this sort of criticism is very quickly taken personally. Just ask the person in question if they have a minute and if they do, take them off to the side somewhere and say something along the lines of "Don't get me wrong, I love the work that you do, but you've been making mistakes with your/you're and they're/their/there and I'm concerned about how that will look in external communication". The goal is to convince them to change, not to "be right" and have proof of that
    – Cronax
    Commented Aug 20, 2015 at 8:32
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    @Cronax: Yes, conveying subtle cues is easier in person - on the other hand, making this a formal private meeting also makes it seem like a big deal, which you might want to avoid. So it's a tradeoff...
    – sleske
    Commented Aug 20, 2015 at 9:04
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    @Cronax: Also, I'd avoid general statements like "you've been making mistakes...". You wait for one email with the mistake, and address that specific mistake. At that point, there's no need to point out it's not the first time. If the problem persists after that first reminder, you can ratchet things up a notch and have a talk in person. . Anyway, thanks for the note. I added a paragraph to my answer.
    – sleske
    Commented Aug 20, 2015 at 9:06
  • @JoeStrazzere: Yes, if you already have regular private discussions with someone, addressing this in person is probably better. However, if you usually don't hold private discussions, scheduling something just for this may be disproportionate (and set a problematic mood). That's what I wanted to address; anwer edited again.
    – sleske
    Commented Aug 20, 2015 at 12:44
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    I agree with this and most of the comments stating that it might be better to have an in person discussion. That, however, depends on management style. If you're extremely busy or in a different location where that's difficult obviously e-mail is the way to go. The only advice I can give is that when you point out this issue(or any issue) try not to point blame in a blunt way. There's a difference between "I noticed some of our correspondence had minor grammar mistakes." and "I noticed your correspondence had grammar mistakes." It's subtle, but it prevents defensiveness.
    – zfrisch
    Commented Aug 21, 2015 at 19:21
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Does she not know proper grammar or is she just careless? You need to establish that in a non-confrontational way.

I suggest you meet with the assistant privately and focus on a specific email that was effective, but had improper grammar. For example, *You're order shipped on 01/01/2015 and the tracking number is 12345." You could complement her on her research and providing the proper information, but note that the grammar is incorrect.

Poor grammar does reflect negatively on the company.

You need to establish that your assistant understands the problem. If it is a training issue, then provide training. If she is not being careful, then tell her that she needs to take care to use proper grammar, even if it means not getting that email out as quickly.

Explain that something like a status update on shipping to an individual is not that big a deal. While, an invite to event sent to many people is a big deal, and have her send a draft to you prior to mailing it. Don't just fix the draft; talk to her and explain what was wrong.

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  • Come on down vote. What is the problem?
    – paparazzo
    Commented Aug 20, 2015 at 19:10
  • Not the downvoter but I'm assuming it's because your answer is a bit rambling in nature and could use some copy editing which makes it come across as somewhat hypocritical.
    – Lilienthal
    Commented Aug 20, 2015 at 19:41
  • @Lilienthal I don't get hypocritical? You can understand the value of grammar with having perfect grammar. I am a pure techy.
    – paparazzo
    Commented Aug 20, 2015 at 19:48
  • Some techies love grammar. Commented Aug 20, 2015 at 20:55
  • @CarlSmith I like it I am just not good it
    – paparazzo
    Commented Aug 20, 2015 at 20:58
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It will be difficult to correct this. People get set in their ways and have certain abilities. You cannot change such things just by complaining about them.

There are various options for trying to solve the problem. Here are a few:

(1) Require that all customer communications be drafted as a letter in Microsoft Word first before being emailed. Then, make sure all such letters are spell-checked and grammar checked.

(2) Route all customer communications through yourself and correct them yourself.

(3) You make the customer communications.

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