How to Communicate Effectively With Your Boss: 16 Do’s & Don’ts

Everyone should practice good communication habits at work to be effective and to demonstrate your capability in every interaction. However, your relationship with your boss is unique in both the closeness and the power dynamic. You want your boss to empower you with additional decision making authority and responsibility – to truly see you as a peer – but not feel that you are challenging their authority or trying to knock them off and take their job.

Effective communication at work requires you to be aware of your bosses feelings and motivations as well as your own. Strike the right balance of assertiveness and respect by following these 21 do’s and don’ts for effective communication at work with your boss.

Do Lead With Your Main Point Early in the Conversation

Your boss is busy and wants to understand how they can help so you also need to respect their time. Instead of giving all the backstory that leads up to the main issue, describe the current challenge you are facing and then support with additional details as necessary.

Notice how the example below is only two sentences but you’ve already framed your request and provided the needed context. Only add details when they are relevant to the decisions at hand, then engage in the discussion and answer any questions your boss may have.

Expert Employee: Hey boss, I need some advice on how to get Purchasing to prioritize this item correctly. I’ve met with them twice already to explain our impact from the delay but it is still not being expedited.

Strive to deliver a clear and understandable message. Take time to organize your thoughts so you know the main points and what type of outcome you are working toward. Stay on topic, don’t wander with inconsequential details, and don’t talk just to fill the silence.

Don’t Continue To Debate After a Decision Is Made

You won’t agree with every decision made, get comfortable with that fact. If there was any doubt before, the global pandemic reinforced how speed is vital to business survival. When conditions change overnight the business must respond and not delay decisions until uncontested agreement is achieved.

Apply the concept of disagree and commit – vigorously question the pros and cons of each option in order to make the best informed decision possible. Once the decision is made everyone must commit 100% to driving success even when it was not the option you supported.

Do Be Assertive and Clear About What You Want

Many employees make the mistake of assuming that bosses will bring opportunities to their attention, as if they are at a buffet and can pick and choose which ones they want. In today’s business environment, bosses are stretched thin just like every other employee.

Good bosses will act on what they know – when a new project comes up they are going to give it to the person that has expressed interest. By the time you find out about the opportunity it may already be gone.

Do be concise but don’t confuse direct and clear with being short. Present the facts and don’t be shy. When you are confident in your actions it causes others to have more confidence in you.

Don’t close your body language. Just like your tone when speaking, your body language shows others how you are receiving communication. If you are not making eye contact, have your arms crossed, or turn your body away from your boss then they will perceive that you are not truly listening or are responding negatively.

Always address your issues directly with the people involved before bringing them to your boss as a problem. Whenever you bring up a problem expect your boss to ask you “what did they say on this matter?” If you don’t have an answer because you haven’t spoken with them then you are not doing your job.

Expert Tip: Be clear in your language – there is a difference between taking a problem to your boss for help and informing them of a potential issue while giving a status update. To get input from your boss say “I want your…” and when informing them say “You should be aware…”

Don’t Correct Your Boss in Public

Whenever possible pull your boss aside for a private conversation and get clarity on the issue. Even when you are absolutely certain you are correct, carefully consider if the correction is truly needed. If you are motivated by an opportunity to make your boss look bad it is best to just be quiet. Another approach is to make a suggestion that points in the right direction without directly contradicting your boss.

When you do identify a concern that needs to be resolved in the moment, focus on the issue and not on who is right or wrong.

Boss: We need to prepare our proposal for the ABC Company meeting on Friday.

Expert Employee: I thought the email yesterday postponed the meeting until Monday, was there another change?

Bosses will usually have higher connections and better information flow than their staff, but not in every circumstance. By focusing on the question it is clear that you are trying to be constructive and not simply calling out their error.

Do Keep Your Boss Informed of Significant Events

Even when you have the situation under control, your boss needs to be informed of what is going on with their team. When your boss is in the loop they have the opportunity to bring additional resources to the issue, remove obstacles, share information, or add their support to your response plan. Demonstrate a connector mindset and welcome the expertise that other members can bring to bear on the

Make it clear when you communicate with your boss that you are not handing the problem off for them to solve. Follow the CAR format to quickly get your boss up speed – state the Challenge, your Action plan, and the target Results. During the exchange keep an open mind to input from your boss and let them steer when they have input.

When your boss gets blindsided at work they lose credibility with their boss. Where highly hierarchical organizations control the flow of information on a need-to-know basis, the digital workplace has democratized information flow. The new currency of leadership is emphasizing collaborative relationships (MIT Sloan).

Don’t Be Distracted by Your Phone or Computer

The most important part of communicating is that the other person believes they have been heard. Research shows that supervisor – employee interactions interrupted by a supervisor’s smartphone use are negatively associated with supervisory trust.

Remember how you feel when your significant other is looking at their phone while you are trying to discuss something important, don’t do the same thing to your boss while they are communicating.

Give the conversation your full attention. Keep your phone out of sight and lock your computer to reduce the temptation from email and IMs. Many people report feeling overloaded by their email demands at work.

The effect of smartphones and dopamine levels is getting increased attention from the publicity of films like The Social Dilemma. However, you can gain back control using systems like the Pomodoro method that provide effective techniques to stay focused amid all the distractions.

Do Offer Suggestions for How To Handle Issues

Do provide a path forward with what you can do and when you can get it done. A partial solution is better than no solution. When you away part of the challenge the parts remaining become smaller and easier to manage. Good bosses want input from their staff on issues because they value a different perspective that is frequently better informed.

Always work to be constructive and helpful in every work exchange. Demonstrate an employee owner mindset even when you are not the responsible person and provide a path forward that helps the business succeed.

Average Employee: I don’t know, that’s not my job.

Expert Employee: I think Jessica owns that item, let me introduce you.

When you focus on the blockers or what you can’t do, the cost of pessimism spreads beyond the issue at hand. Instead do your best to think ahead, anticipate problems, and deal with them constructively.

Don’t fall into the trope of “don’t bring me a problem without a solution” because it is meaningless in today’s business operations. When you obscure problems until you know how to solve them you only waste time that is better spent mitigating or unraveling the issue.

Do ask direct questions when you need a clear answer. Particularly in urgent situations open-ended questions can lead to overthinking – also known as analysis paralysis. Instead, present options to limit the perceived choices:

Average Employee: I’m not sure, what do you think we should do?

Expert Employee: We can proceed with Option A or Option B, or do you have an Option C?

Options A and B establish anchoring bias that determine the general framework for the discussion. Your boss still has unlimited flexibility because Option C could be anything, but narrowing to three options helps everyone to focus their thought process.

Don’t Assume Your Boss Can Read Your Mind

According to Gallup, 74% of American workers believe they are missing information necessary to do their jobs and this feeling stems from poor communication with their manager. Employees always list poor communication as one of their top complaints about their bosses, and usually it takes the #1 spot.

Yet when the situation is reversed, employees frequently display the same patterns and thinking that undermine effective communication.

A Closed Mouth Doesn’t Get Fed

Urban Dictionary

If you don’t open your mouth you won’t get what you want. If you want to leave work early because it’s your birthday, dropping hints around the office probably won’t work. Simply go to your boss and ask directly. Your boss will appreciate the directness rather than passive-aggressive suggestions and you are more likely to get approval.

Average Employee: (thinks to themselves) my boss signed the birthday card, I sure hope they are nice and let me leave early…

Expert Employee: Hey boss, today is my birthday and we have plans, do you think I can leave an hour early?

Do Be Civil and Professional at All Times

Follow the golden rule and always treat others the way you want to be treated. There is no justification in the workplace to belittle others, to be disrespectful, or to be condescending. Even when rudeness is tolerated by leadership, your actions will damage your relationship with coworkers and cause you to be less effective. Always be polite.

Build people up instead of tearing them down and point out the good aspects rather than the negatives. When you have feedback to deliver, be direct and sincere in your statement.

Avoid sarcasm with your boss and at work in general. Saying the opposite of what you really mean requires high levels of familiarity and trust that are only present in well established teams. Bosses are more likely to use sarcastic irony but don’t follow their example.

Sarcasm can create higher levels of perceived conflict, in particular when trust is low between the people involved. Sarcasm can be disastrous when the recipient does not pick up on your humorous intent and takes a sarcastic comment literally.

Pay attention to your tone when speaking – remember its not so much what you say but how you say it. Tone is even more difficult to manage in written communication. Emails and text messages get interpreted based on the mood of the recipient, not based on your intent as the sender.

Do be credible and transparent. Trust is vital to your reputation and difficult to recover once it has been damaged. Speak the truth and don’t engage in rumors or gossip. Don’t say yes to a request when you don’t mean to deliver.

Don’t React Emotionally When Your Boss Has Unwelcome News

Take a moment to calm yourself before responding and ask to continue the conversation at a later time if necessary. When you have an emotional reaction you are more likely to say or do something you later regret. Demonstrate self-control and keep your reputation intact.

You won’t always have advance notice, but whenever possible prepare for difficult conversations by thinking through the issue. Write down your main points so you don’t forget them during the moment. Try to avoid volleying back and forth and focus on practical steps to move forwards on the matter.

Do Engage in Active Listening With Your Boss

Paraphrase and restate the message after someone else speaks. In complicated communication the message may not be easily understood, even when both parties are actively engaged. Acknowledgement words like “OK” and “Yeah” or head nodding are not good indicators of comprehension, they may simply indicate the other person has already tuned out and is ready to move on. Paraphrasing demonstrates that you have heard their message and understand, not by telling them but rather by showing them.

Active listening is critical to your comprehension, but it takes practice. Instead of waiting your turn to talk, listen to understand the full message.

Don’t Assume Text Messages and Emails Are Send It and Forget It

Do not assume that your message was received and understood until the owner acknowledges receipt and confirms their understanding. All too often communication is misunderstood as a simple status update when the sender intended the recipient to take action.

Expert Tip: A face-to-face request is 34 times more effective than an email. When you need something done always go talk to them in person.

For situations handled by email, don’t leave your request vague and open-ended. Deliver a specific request that requires a response. For example, at the end of your email a phrase like “Please respond with your commit date for the deliverable.” makes it very clear that the recipient is expected to take action.

As the sender you can follow-up with confidence without fear of being annoying if you don’t receive a reply in a reasonable amount of time. Email deferral happens to 37% of business emails, even important messages that need a reply. Emails that contain attachments, require an in-depth response, or that are read on mobile devices are more likely to be deferred as part of the recipient’s task management system.

Do Change Your Communication Method To Fit the Subject Matter

When you have an information dense topic it is best to use email. Make it easy for your boss to follow along with the conversation. Give them the details they need to reference to understand the situation – provide the numbers, figures, schedule dates, etc…

When the topic is urgent, send the message and then go to your boss for the discussion. They will appreciate having the details in front of them as you decide how to proceed. You can avoid the back and forth confusion of “what was that data point again?”

Face to face communication should be your go-to method for the following topics:

  • controversial topics that need explanation and discussion
  • confidential topics that require discretion
  • sensitive topics that may get emotional

All of these subjects benefit from two-way conversation in real time. Give your boss the opportunity to break down the situation with clarifying questions and give their input. Complex issues need your strongest communication methods that utilize your words as well as body language and vocal features to deliver a clear message.

Don’t Use Email To Avoid Difficult Topics

Difficult conversations are best held face to face or over the phone because both sides need the opportunity to immediately ask and answer questions. Sometimes it helps to write down and organize your thoughts in advance, but if the thought of having the discussion with your boss fills you with dread then imagine the self-induced torture of waiting for them to reply.

Do utilize direct conversation for complex topics that could easily be misunderstood. Face to face or phone calls are invaluable when you expect a lot of questions or you don’t want your meaning to be misunderstood.

Assume the best of others until they prove that your trust is misplaced.

Do Collaborate During the Conversation

Use “we” language to show your boss that you are on the same team with common goals. Frequent use of “I” and “you” language sets an opposing tone that implies competition rather than collaboration.

Ask direct and probing questions to learn more when there is something you are unclear about. Which version below do you think will get a better response from your boss?

Average Employee: Why did you change this?

Expert Employee: Tell us more about the reasons for this change.

Both statements are asking for more information, but the ‘typical’ question is phrased as an accusation that will immediately put your boss on the defensive. When you show that your intent is to genuinely learn more information the request leads to an open exchange.

Keep an open mind and truly listen to what your boss is saying. Look for the meaning behind the words – what are they trying to communicate and what is it that they want to accomplish?

Don’t make assumptions before you hear the entire message. You might know that the other person will say, but then again you might be wrong. Jumping in with an interruption is always dismissive, and disrespectful to boot if you do it after an eye roll.

Don’t interrupt or be rude. The only message received when you interrupt is that you think what you have to say is more important. This affects others in the conversation just as much as the speaker you interrupt. When you do accidentally interrupt someone always acknowledge your bad manners and apologize. A quick “I’m sorry, please continue” is respectful and makes up for the occasional gaffe.

Don’t Set Traps in the Conversation

Don’t put your boss on the spot and don’t ask loaded questions. Whether you ask pointed “all-or-nothing” questions or are just fishing for compliments, your boss will not appreciate the manipulation (and neither does anyone else).

Avoid these common conversation traps that are immature and contrived – not only with your boss but with everyone at work.

  • All-or-Nothing Statements: This binary way of thinking doesn’t allow for the shades of gray that always exist. Its true that someone arriving one minute late is still late, but it is not the same as 15 minutes late. Improvement projects will never be 100% successful the first iteration, there will always be growing pains. Small hiccups do not mean the project is a failure or even that it was poorly implemented. Don’t throw out the baby with the bathwater.
  • Passive-Aggressive Statements: Sometimes they come across as accusation “Why do you think we are in this situation” or threats “I knew I should have taken that job offer last week” but as a rule rhetorical statements have a darker implied meaning.
  • Fishing for Compliments: Fishing for compliments conveys insecurity. “I was here until midnight but I got it done” – yes Bob, we know you work hard – good job.
  • Shifting Responsibility: Everyone has heard statements like “we wouldn’t be working this weekend if so-and-so had just done their job” but complaining doesn’t help move forward from the current conditions.

Do Share Facts (Not Conclusions) for Controversial Topics

Different situations require different types of thinking to address the challenge at hand. Aristotle outlined the three realms 2,000 years ago: craft knowledge from hands on experience, scientific knowledge from the laws of nature, and ethical wisdom when competing values are in play.

Many situations combine aspects from all three. For example, when an automotive company discovers a flaw in one of their products there is the technical aspects of how and why the problem happened, the practical side of managing the recall, and the principles of protecting consumers without unnecessary expense to the business.

In the heat of the moment it is easy to slip into the mode of trying to solve the problem immediately without full understanding. Worse yet is the common response of assigning blame and pointing fingers before the situation is under control.

Don’t add stress to a problem by making provocative statements before you are certain of the facts. Don’t assign blame or ‘throw people under the bus’, focus on the issue. When your company has an established after-action review process the root cause and responsible owners will become clear.

Dan Sawyer

Founding editor and head writer of Dan is a job interview and career expert, with more than 20 years of experience in senior roles at high tech leaders Space Exploration Technologies and Samsung Austin Semiconductor.

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