Email might be a convenient way to communicate in the office, but that doesn’t mean all grammar and etiquette rules go out the window when shooting off a note.

Not being careful when crafting emails at work can easily tarnish your professional reputation and even lead to getting fired, warn workplace experts. “The biggest thing you need to remember with email in the professional setting is that your reputation is always on the line,” says Richie Frieman, author of Reply All and Other Ways to Tank Your Career. “When people read your email, they are hearing your voice so be as profound as you like and say what you mean. Don’t let them poke holes in your message for their own interpretation.”

One of the biggest mistakes people make when sending an office email is not taking into consideration how the message might come across to the recipient. Often people will use their speaking voice in an email, but what they forget is that the reader can’t pick up inclination and tone, says Mark Jaffe, president of executive search firm Wyatt & Jaffe. “Being clever, witty, factious, sarcastic, playful or perky in an email can be easily missed or misconstrued,” he says. “The tone of the email is one of the most widely misinterpreted things.” Instead of trying to be clever, Jaffe recommends writers stick to the facts in a note with short sentences and to always re-read their messages to fix any ambiguities before hitting send.

Frieman adds that people often get in to trouble with office email because they think they can get away with ranting or flexing their “keyboard muscles” by using all caps or filling the message with emoticons or multiple exclamation points. He says senders think these moves make them sound more official or passionate, when it reality, they come off as bratty or less intelligible.

Another mistake: getting too cozy with someone through email. “Familiarity on email happens quickly, since it’s so instant,” says Frieman. “A couple emails back and forth and next thing you know you’re best friends with someone who was a stranger a half hour ago.” Even if you hit it off with the person through email, always maintain a veil of professionalism in your correspondence. “It’s never proper to assume people are prepared to have 10 emails about their favorite 90’s movies when they just want to find out the agenda for the 2:00 meeting,” he says.

Because of the ease of sending an email, many people multi task while crafting and email and get distracted and end up sending off emails full of typos and misspellings. “Don’t text while you are driving and don’t email while you are doing something else,” warns Jaffe.

Always proofread a note before hitting send to check for grammatical errors and to make sure the message is clear and concise. After all, you don’t want to have sender’s remorse “What you say and even what you do will be forgotten quickly. But when you put it in writing, it’s forever,” says Jaffe. 

When it comes to email, a good way to annoy your co-workers is to hit “reply all” when you only meant to send the message to one person. Even if it’s an innocent email, it can quickly irritate co-workers, bosses and anyone else getting the note. “Reply all is the best way to describe putting your foot in your mouth in the digital age,” says Frieman.

Email is a common way for co-workers to share documents and other data, but if a file is large, career experts suggest having the courtesy to warn recipients of a message’s size before sending it. That large file could lock up an inbox, which can not only be annoying but a productivity killer. If you and your team are on a deadline, the last thing you want is a hold up in collaboration.

Because email messages can be easily be misconstrued, Frieman recommends never leaving open questions when sending an email as they can quickly cause confusion and foster anger or resentment. “Some people tend to leave very gray spots in with their answers and the recipient is left thinking, ‘Did they really understand what I needed?’ or ‘I’m pretty sure I made myself clear on this,’” says Frieman. “Make sure an email sends a complete message, not creates more questions.”