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Ryan Standil is a former lawyer and the owner of Write To Excite. He leads workshops for businesses and governments about effective writing in the workplace.

When it comes to e-mail etiquette, there are well-established dos and don’ts. Experts from Bryan Garner to Mignon Fogarty (aka Grammar Girl) agree on matters such as the following:

Dos:

  • Use a subject line that accurately describes your main point.
  • Be as brief as possible, without being impolite.
  • Proofread for grammar and typos. Sloppy mistakes diminish a writer’s persuasiveness.
  • Make it clear to your recipients as to how they should take action.
  • When copying a new recipient into an existing chain, remember to delete confidential information.

Don’ts:

  • Don’t assume someone goes by a shorter name. If a person’s e-mail address says Frederick, don’t call him Fred unless he has signed off that way.
  • Don’t use ALL CAPITAL LETTERS. It is perceived as shouting.
  • Don’t write an overwhelming wall of text. Use headings, white space or lists if you have a lot of information to convey.
  • Don’t forget your attachments. If your e-mail software has the attachment warning feature, remember that this feature will only activate if you have written a word like “attached,” and it won’t activate if you have already attached one file but forgotten a second one.
  • Don’t mark every e-mail with “High importance.”

I have led approximately 100 workshops on e-mail etiquette, and attendees across Canada widely agree on these matters. But things become harder to navigate when the proper etiquette is dependent on the situation. For example:

  • What is considered appropriate response time?
  • Should you greet someone with Hi, Hello, or Dear?
  • Are greetings and sign-offs still required for your second or third message?
  • Should you include a pleasantry, such as, “I hope all is well?”
  • What is the appropriate degree of formality? How do readers react toward contractions, exclamation marks and emojis?

Having both taught and learned from thousands of participants in my course, I have noticed consensus about one thing: When facing these questions, the safest strategy is to mirror your recipient.

I am thinking of two lawyers whom I correspond with, named Leanne and Daniel. Leanne’s e-mails begin with, “Hi Ryan!” Daniel’s begin with, “Ryan:”

My point is that neither writer thinks their etiquette is wrong. Therefore, if I respond in kind, I will likely avoid the reactions that we fear when we send an e-mail, such as sounding rude or seeming unprofessional.

Having said that, you should still do what makes you feel comfortable. Personally, I would respond to Leanne without the exclamation mark (“Hi Leanne,”) and I might add the word “Hello” when responding to Daniel (“Hello Daniel”). But in each case, I would maintain a similar level of formality.

I want to outline two examples that may frustrate certain readers, but can help advance your career.

Let’s pretend you have a supervisor who has an ultra-friendly tone and always includes pleasantries, such as, “I hope you had a great weekend.” That would be a good situation in which to echo the supervisor’s tone by including pleasantries of your own – even if you detest the idea of using a pleasantry. I am not arguing that including a pleasantry is right or wrong. My only point is that if your supervisor will be determining whether you receive a promotion, it could benefit you to communicate in a way that they do not find off-putting.

The same idea holds true for sending e-mails late at night or on weekends. Again, I am not arguing this is right or wrong. I am merely suggesting that if you have a client who never e-mails you outside of business hours, it may be a signal that, similarly, they don’t enjoy receiving e-mails outside of these hours. If you wish for the client to buy your products or services, this would be a situation in which it would be wise to copy their behaviour.

Exceptions will always exist. For instance, people who live in different time zones can ignore the concept of e-mailing during business hours, and when a matter is urgent, writers should dispense with pleasantries and cut to the chase.

I interviewed Justice David Stratas about tailoring your communication to the preferences of your reader. He serves on the Federal Court of Appeal and is one of Canada’s most respected voices in the field of writing. He described to me a golden rule: “Always write for your audience. It’s not about you.”

This column is part of Globe Careers’ Leadership Lab series, where executives and experts share their views and advice about the world of work. Find all Leadership Lab stories at tgam.ca/leadershiplab and guidelines for how to contribute to the column here.