15 Emails You Should Never, Ever, Send Your Boss

Be sure to think twice before you hit the send button.
Updated May 14, 2024
Fact checked
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Email has become a primary mode of communication in the workplace, but some should be kept out of your boss's inbox. 

In the fast-paced world of work, it's crucial to know what not to send to your supervisor to maintain professionalism and keep you boosting your bank account.

Here are 15 types of emails you should steer clear of when corresponding with your boss.

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Complaining without a solution

Nadia L/peopleimages.com/Adobe employee struggling on a deadline

Sending emails solely to complain about issues without offering potential solutions can come across as unproductive and negative. 

Instead, consider proposing constructive solutions or addressing concerns in person to demonstrate proactive problem-solving skills. This approach shows initiative and a willingness to collaborate on resolving issues effectively.

Personal matters

Chanelle Malambo/peopleimages.com/Adobe businesswoman reading email while scratching her head

Avoid discussing personal issues or sharing personal details via email with your boss. Keep professional correspondence focused on work-related topics to maintain appropriate boundaries and professionalism in your interactions.

Sharing personal matters through email can blur the lines between professional and personal relationships, potentially causing discomfort or awkwardness.

Inappropriate jokes or humor

nicoletaionescu/Adobe stressed businesswoman receiving bad news

Humor is subjective, and what may seem funny to you could be offensive or inappropriate to your boss. Avoid sending emails containing jokes, memes, or humor that may be perceived as unprofessional or offensive in a work context.

Remember that humor can be interpreted differently by individuals, so it's best to err on the side of caution in professional communication.

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Confidential information

Reese/peopleimages.com/Adobe business man reading email

Never share sensitive or confidential information via email unless it's necessary and secure. 

Confidential information, such as proprietary company data or employee-related matters, should be communicated through secure channels or in-person to prevent unauthorized access or breaches.

Protecting confidential information is essential for maintaining trust and upholding professional standards within the workplace.

Unnecessary flattery

BullRun/Adobe businessman thinking sitting in office

While it's essential to show appreciation for your boss's guidance or support, excessive flattery in emails can come across as insincere or disingenuous. Keep praise genuine and relevant to maintain professionalism and credibility in your communication.

Authentic expressions of appreciation demonstrate sincerity and respect for your boss's contributions without appearing overly flattering.

Requests for special treatment

wichayada/Adobe businesswoman dealing with smartphone problem

Avoid sending emails requesting special treatment or privileges that are not standard practice within the organization. 

Making unreasonable or inappropriate requests can reflect poorly on your professionalism and may strain your relationship with your boss. Instead, adhere to established policies and procedures to ensure fairness and equity in the workplace.

Negative feedback without context

Srdjan/Adobe businesswoman on a lunch break

Providing constructive feedback is essential for growth and improvement, but delivering negative feedback via email without context or clarification can be counterproductive.

Instead, opt for face-to-face or virtual meetings to discuss feedback in a more nuanced and empathetic manner. Providing context allows your boss to better understand the feedback and address any concerns or issues effectively.

Emails with spelling and grammar errors

nicoletaionescu/Adobe reading a wired text message

Sending emails riddled with spelling and grammar errors reflects poorly on your attention to detail. Always proofread your emails before sending them to ensure clarity, accuracy, and professionalism in your communication.

Attention to detail in written communication demonstrates respect for your boss's time and attention to ensure clear and effective communication.

Rambling or lengthy emails

pathdoc/Adobe man confused with laptop software

Long-winded or rambling emails can be overwhelming and difficult for your boss to digest, especially if they're busy or have a high volume of emails to manage. Keep your emails concise, focused, and to the point.

Concise communication allows your boss to quickly grasp the key points and take appropriate action without unnecessary distractions.

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Overusing urgent or high-priority flags

stockbusters/Adobe nervous executive send reply

Reserve urgent or high-priority flags for genuinely time-sensitive matters that require immediate attention from your boss.

Overusing these flags for non-urgent or routine matters can dilute their effectiveness and undermine your credibility in prioritizing tasks. Misusing these flags may cause your boss to overlook genuinely urgent matters due to the inundation of notifications.

Excessive follow-up emails

Graphicroyalty/Adobe businesswoman annoyed by online problem

While it's essential to follow up on important matters, bombarding your boss with excessive follow-up emails can be perceived as pestering or impatient. 

Instead, practice patience and discretion when following up, and consider alternative communication channels if necessary. Sending too many follow-up emails may create the impression that you lack trust in your boss's ability to prioritize tasks or that you're micromanaging.

Sending emails outside of work hours

alauli/Adobe walking while looking at smartphone

Respect your boss's boundaries and avoid sending emails outside of standard work hours unless it's genuinely urgent or agreed upon in advance.

Sending emails during evenings, weekends, or holidays can disrupt your boss's work-life balance and create unnecessary stress. To respect your boss's downtime, consider using email scheduling tools to send emails during work hours, even if you compose them outside of those times.

Unverified information or rumors

fizkes/Adobe serious puzzled businessman

Refrain from forwarding or sharing unverified information, rumors, or gossip via email with your boss. The spread of misinformation can damage trust, credibility, and professional relationships within the workplace.

Verify information from credible sources before sharing it with others. Your boss is relying on accurate and reliable information to make informed decisions.

Personal opinions on sensitive topics

Studio Romantic/Adobe businesswoman stress while reading news

Keep personal opinions on sensitive topics such as politics, religion, or controversial issues out of professional email correspondence with your boss. 

Expressing personal opinions on such matters can lead to misunderstandings, conflicts, or discomfort in the workplace. Focus on discussing work-related matters professionally and objectively to maintain a positive and respectful work environment.

Overly emotional or confrontational language

fizkes/Adobe businesswoman annoyed by online problem

Avoid using overly emotional or confrontational language in emails, especially when discussing disagreements or conflicts with your boss. 

Maintain a professional and respectful tone in your communication to foster constructive dialogue and maintain positive working relationships.

Remember that written communication lacks the nuances of face-to-face interaction, so choose your words carefully to avoid misinterpretation or escalation of conflicts.

Bottom line

goodluz/Adobe senior man working on laptop

Effective communication with your boss via email is essential for maintaining professionalism and fostering positive working relationships. By avoiding these 15 types of emails, you can ensure that your correspondence is respectful, productive, and conducive to a healthy work environment.

Before hitting send, always consider whether your email aligns with professional standards and contributes positively to your professional reputation and relationships. Your career goals and financial fitness will thank you.

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Author Details

Adam Palasciano Adam Palasciano is a personal finance-obsessed and money-savvy individual who loves to hash out content on all things saving money. He specializes in writing millennial-friendly personal finance content, covering topics ranging from trending financial news, debt, credit cards, cryptocurrency, and more.

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