I often write to my boss (Director) to report the changes that I make to the software. These changes could be new functionality or enhancing the existing features. My problem is, I make spelling mistakes quite often. Sometime just a couple and sometimes the sentence is a bit wrong because while proof reading/editing, I left old text in as well while adding new text.

Nowadays, I report to the CEO, so it is even more important for me to address this. My question is: Should I take the extra time out to print the email and proof read it every time I write a major email that goes to a couple of top executives? Or are some minor spelling/sentence mistakes acceptable and understandable and I do not need to worry about it? We are a financial company of about 50 employees.

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    Do you have access to spell-checking software? Commented Jul 20, 2012 at 14:52
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    spelling may be right for example a was required when an was used. In some technical terms like referring to database fields, we don't run it through spell checker, like RepID etc. I use outlook which has speller checker.
    – TheTechGuy
    Commented Jul 20, 2012 at 14:56
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    My boss can't spell or punctuate. (And always types to as ot when he's in a hurry.)
    – TRiG
    Commented Jul 20, 2012 at 20:37
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    "BLUNDEREROUS" is misspelled. The word is "blunderous". Good grief!!!
    – Xavier J
    Commented Apr 8, 2022 at 2:48
  • Reading the original version of this question, I'd guess you're not a native English speaker - is this correct? And if so, are you communicating with your boss in English and is English your boss' native language? All of this might change how they view your messages. Commented Apr 8, 2022 at 9:24

7 Answers 7


At a glance, I count 7 spelling or grammatical errors in this question (prior to all the edits). I think that, when composing an email, people are generally forgiving about an occasional typo. Obviously, there are some people who couldn't care less as long as the point is adequately conveyed and, for others, it's a deal breaker.

I find typos and errors in grammar distract me from the message being delivered. The more there are, the more distracting it is. All types of communications are basically additional or alternative presentations of yourself. If you can't take the time or effort to ensure that you're sending me a message that is not laden with errors, then it makes me automatically question how that translates to the work that you are doing.

My suggestion would be to double and triple check your memos/emails when sending them to executives. You can only lose if you don't.


It's important to try to correct these mistakes, as it looks more professional. Depending on how bad your mistakes are, correcting them will improve communication by improving other people's understanding of your messages.

If the mistakes are very bad (or the readers are extremely fussy about such things) then it could impact you negatively - you might be passed over for promotions to more senior roles if they don't feel your communication skills can handle it.

Do you have access to spell-checking software? If so, it's probably not necessary to print your emails and correct them by hand. Spell-check and grammar-check software aren't perfect, but they can catch many problems. Have you considered having a co-worker proof-read and make corrections, if there is no spell-checking software available?

Also, I've noticed that people generally are more forgiving of spelling and grammar mistakes when they come from someone who is not communicating in their native language. That doesn't give you an excuse not to try, but it looks much worse when you send an email with obvious mistakes in your native language rather than in a language you've only spoken for a few years.


Executive Responsibility

When a company gets bigger than a few people, there is no way one person can review everything that goes on. The bigger the company gets, the more you have to trust tasks to other people. The more people you depend on to get the job done, the more important trust becomes.

If you are the CEO of the company and something goes wrong, you will ultimately be held responsible. That's your job. There is no way you can check everything yourself, so your job is to create an organization that you can trust to do the job right.

Trust is Fleeting

If you are in a company of 50 people, your CEO probably knows you well, and can trust you personally. Depending on his/her personality, he/she may not care if you don't proofread your e-mail, because the CEO knows he/she can trust the content of your work (even though the presentation may have room for improvement).

For bigger companies, the CEO doesn't have this luxury. If he/she gets sent an e-mail from manager X of division Y, and manager X has 200 people below him/her who actually did the work, the CEO likely has no hope of objectively judging the quality work of manager X. So the CEO takes a shortcut and looks for reasons to be wary with the limited information he/she has.

Careless Mistakes are Endemic

That is one of the real reasons that many people put such a high value on good proofreading, spelling, grammar, etc. This is the reason that many people will throw out a CV if it has even one mistake on it. The ability to check a document for careless mistakes thoroughly says that the person is taking responsibility for something under their control. That's a good sign.

If Manager X in the above example can't even check an e-mail, how can a CEO trust that they can properly control the quality of the 200 people working below them? If the manager makes careless mistakes, what message does that send to subordinates? What does that say about that department's attitude toward checking work or quality control? It raises a bunch of red flags that say, "Caution!"

Does This Mean Good Spelling = Good Manager?

At the end of the day what matters to the CEO is that the job is done properly. And that is what is ultimately important to you and your company. If the CEO trusts that you have done the job properly with typos, then don't worry about it. If the CEO has ever pointed them our or you've received comments from upper management about that aspect, it's probably worth your time to proofread.

While the job being done properly is the most important, losing the trust of anyone who can give you a headache will ultimately force you to spend more time building trust, and less time actually doing the work well. That's counterproductive and should be avoided. An ounce of prevention is worth a pound of cure in this case.

For Safety's Sake

If an e-mail is around 250 words, you can probably read through it in a minute or two. Correct obvious mistakes, read it again, and within 5 minutes you'll likely have corrected 99.5% of all mistakes. That 5 minute investment always seems worth it to me.

As a bare minimum, I would always proofread the following:

  • Proofread any e-mail that will get forwarded around (people who don't know you will read it and judge you based on the content, including spelling)
  • Proofread anything that will go outside your company (customers will make judgment calls of their own, and good luck explaining why 5 minutes of proofreading wasn't worth it)
  • Proofread anything that will go to your boss' boss or higher (you don't want to make your boss look like he condones carelessness)
  • Proofread any numbers in any document ever (triple-check numbers, always, always always)
  • Proofread any official reports or regulatory documents that will get filed away (again, judgments will be made on the little information that you provide)

Anything other than this is up to you.


When your position requires reporting changes to management then it is a sign of professionalism to have proper grammar and spelling in a memo. The more formal the report the more important it is. If the document you are creating will be both distributed and retained for records then it is even more important. You can get away with more mistypes when writing an informal note to your boss than in a release for wider distribution. But do realize if you are constantly sending him emails with mistakes and errors it could undermines their confidence in you.

I find that writing these types of documents in Word and using its Spelling, grammar, and readability tools is very effective for this. I know that my first draft of documents tends to be error prone. But with the help of word, and revisions until I can get the document as succinct and readable as possible.

If it is the very rare circumstance then sure, it is understandable and you do not need to worry about it. But if you find you are allowing mistakes through regularly then I suggest adding a proof reader to help reduce these.


Two simple things to do with emails:

  1. Run spell checker.
  2. If you have problems being clear with your message read it (aloud if possible -- it really helps).

If there still are mistakes once you're past these steps and you are afraid how the top execs perceive them, go and ask what they think . You don't work for a heartless corporation where it's all about how others look at you -- the company is still small enough that you should be able to talk directly to either of execs easily.

So you either learn that the effort you already make is enough or that they expect perfectly polished emails and you know you need to work more on this. Anyway, don't assume it is one way or the other.


Nothing beats a second pair of eyes (other than the intended recipient) for picking up these types of mistakes. Proofreading by yourself works well the first time, but becomes less effective the more times you do it. And relying on just one method doesn't work as well as combining several different tools/processes.


It varies, a lot.

My father was a senior management guy, from Harvard, and he hated it when people wasted time on spell checking. As long as the numbers are right, it's fine. However, he had severe dyslexia and English is a second language in the country, so spelling errors were acceptable.

In my wife's company (construction), you'd get yelled at for wasting time spell checking a memo. In my own company, English is not the native language, and people are very accepting if it is difficult to write in proper English, and welcome the thought processes more.

On the other hand, there are plenty of management people who think that poor attention to detail to spelling means poor attention to detail in work. That is, even if you're in math or finance, they'd expect you to make mistakes more often than someone with proper spelling. If you work with a person who values good English (or whatever language you're using), it may even harm chances of raises and promotions.

The key would be to see what language they are using, and imitate it. If the orders and memos that come down from management are grammatically perfect, follow the same level. If your boss is making a lot of spelling and grammar mistakes, don't worry about it.

  • I guess you could ask your boss if spending a few more minutes per email for spellchecking is priritized.
    – lijat
    Commented Apr 8, 2022 at 4:55

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