How to Communicate With Your Boss

Have you had a brief go horribly wrong? Disasters like this happen to most professionals in the workplace.

I once had a brief go so poorly that my Army boss called me by my full rank and full name (second lieutenant is a long rank to say) and scolded me for the duration of the brief. It was not good.

Some briefs are beyond saving from the start. However, learning to recognize these moments before they happen is one of the best prevention techniques to learn.

Here are four tips to consider for better communication.

Bottom Line Up Front (BLUF)

Start with the purpose of your brief, discussion, or meeting. Make your BLUF one sentence. The boss wants to understand why you’re taking his/her time.

Remember, they have many demands on their time, and you need to respect their decision to listen to you over their other competing priorities.

Having a BLUF eliminates confusion. Moreover, anyone in the meeting-especially your boss-should know precisely the reason for a meeting.

If someone doesn’t understand why they’re there, then it’s time to rearrange your BLUF or change your target audience. Regardless, your boss is the prime audience, and everyone else is there to listen in.

I have attended several status meetings that went very poorly because there was no BLUF. Usually, these are recurring meetings, but each session is different.

Still, the purpose changes depending on the focus of the meeting. Here’s a hint: the focus is usually on the boss’s most pressing issues. Make your BLUF centered on the boss’s priorities, and status meetings will go better.

Have An Outline

I highly recommend you put your BLUF at the top of the outline. Refer to it often. To avoid being too wordy, set time expectations for each agenda item.

For example, in John Wooden’s book Wooden: On Leadership, he planned his basketball practices down to the minute and did not deviate. Do this in your meetings with your supervisors.

Inevitably, mystery items creep into the meeting’s agenda. Although that item may be important, try to stick to your agenda. Your boss will appreciate that you’re organized and will cater to the company’s priorities.

Briefing Your Boss In Meetings

To avoid looking inflexible, address the new topic, write it down, and talk about it next time. Remember, the only exception should be if the boss wants to talk about it immediately. He/she is ultimately responsible. You’re just chairing the meeting.

Having an outline keeps the meeting on time and on schedule. I may sound rigid here, but your boss’s time is precious, and so is yours.

I have yet to meet someone that praised a meeting for going over an hour when it should have been only 30 minutes. It creates a time expectation for everyone involved as well.

Additionally, send out invites for more formal meetings. Attach the necessary documentation for your invite. If you have PowerPoint slides for the session, attach those to the invite along with your agenda.

Adhering to pre-set expectations is a great way to build credibility amongst your peers. And it helps people stay on track with their day.

If you’re informally talking with the boss, be upfront and brief. For example, Joseph McCormack’s book Brief: Make A Bigger Impact By Saying Less advocates for brevity while allowing for clear communication. However, being brief doesn’t always mean being clear. You must portray the right details in the correct context.

Most importantly, never hide a problem. Problems are like leftovers; they only get worse over time.

Anticipate The Boss’s Needs

As a staff officer in the Army, I needed to know my job and know what information my boss needed to know. For instance, if you’re getting bombarded with questions in meetings and closed-door discussions, then that should be a red flag for you that you’re not giving your boss what they need.

Jocko Willink and Leif Babin emphasize this concept in their book Extreme Ownership. When you don’t understand your boss’s priorities, then you can’t know what they need. Even if you disagree on the priorities, fulfill your boss’s requirements, then get to the rest. It may be difficult, but it’s also necessary for team cohesion.

What if you have a demanding boss? Watch your boss closely. It’s not about what they say that’s most important. It’s about what they do.

Actions will show priorities, so pay attention.

If you’re stuck between competing priorities, then ask your boss. For instance, request information that will support your job. Your question might open your boss to their real issue that you can solve.

Be persistent about getting feedback from your boss. For instance, I’ll usually ask my boss once per quarter about things I can improve on. The better you know your boss, the more capable you are of answering their needs and questions.

Set Your Boss Up For Success

Your whole job is to make sure your boss doesn’t get in trouble. That objective may seem shallow, but your supervisor has competing demands that require prioritization. If you’re able to tap into that prioritization process, then you will have met your boss’s goals.

Additionally, it’s not a bad idea to get to know the company’s structure. When you make your boss look good, then you’ve met their expectations.

You’re on a team. The team effort is more important than any individual accomplishment. If one person on the team is doing well but not helping their peers, then the team has failed the boss. Have a sense of ownership over your job and that you can help the team make an impact.


There’s a lot of preparation you need to do to brief your boss. Moreover, they’ll have lots of questions for you. However, if you answer those questions before the boss asks them, then you’ll be better able to articulate your message.

How do you communicate with your boss? Let me know in the comment below. Thanks for reading!

Books Mentioned

Wooden: On Leadership by John Wooden

Extreme Ownership by Jocko Willink and Leif Babin. Read a review here.

Brief: Make A Bigger Impact By Saying Less by Joseph McCormack. Read a review here.

Photo Credit

Featured Image: August de Richelieu

1: Mikael Blomkvist

2: Christina Morillo

3: ThisIsEngineering

4: Sora Shimazaki


4 thoughts on “How to Communicate With Your Boss”

  1. I’m an architecture student, so my boss is my critic or professor. Getting advice and feedback from my superiors is often an uphill battle. We agree to meet at a certain time to discuss the project. I start presenting, they start asking questions. I know I have to leave for my next class, and we’re nowhere near getting through what I wanted to cover. More often than not, the critic ends up getting stuck on an aspect of the project that I didn’t even have any questions about.

    While I’ve gotten better at anticipating possible questions and speed bumps, the tips that you’ve outlined here will be invaluable in my future career in architecture where it’s all presentations and meetings. There’s so much talking involved in our process that anything less than 100% efficiency in discussions is a burden on everyone involved. I think the main things I could improve on after reading your article are arriving with a list or even providing one to the superior in advance and making it very clear that I understand that there are other issues but for time’s sake would like to only focus on the ones listed and address the others if time permits. I believe that this could vastly improve my success and productivity in the future. Thank you so much for this great advice!

    1. Maria,

      I appreciate you sharing your personal experience. Being an architecture student seems like a difficult and rewarding career path. One part I could add about anticipating questions is using a technique called action, reaction, counteraction. Anticipate a question that your professor/boss might ask (action), develop your answer (reaction), and then determine their reaction based on your answer (counteraction). It can help with anticipating needs and how the conversation might go. Let me know how things go! 


  2. Hi, thanks for the great article. I think you have hit the nail on how to communicate with your boss: BLUF,  prepare an outline and anticipating the boss and its need for success. I’m working in a place where the movement of persons is very high (2-3 years for each position) so I also meet a lot of bosses. In my case, it is also a challenge to understand what each boss needs and wants, and each boss will have a different approach. In your view, what is the best way to anticipate different bosses?

    1. David,

      That’s a great question! I find it helpful to ask your new boss to sit down with you to review the expectations of your job. Job descriptions change when a new boss arrives because each boss has different styles and priorities. So, within the first week, get that sit down with them and let them know what you’re doing and if they have additional insight. Also, ask for feedback. The boss will give it to you. If they’re good, they’ll mold you to better fit the overall team. This way, you’ll be able to better assess your boss’s priorities. 

      I found the book Extreme Ownership to be incredibly useful here. The authors, Jocko Willink and Leif Babin talked about how they knew when they weren’t meeting their boss’s expectations when their boss consistently asked for information, reports, or other items. That shows that there was a mismanagement of expectations. It’s pretty military-heavy but they apply their experiences to corporate as well. Here’s a link to a review I wrote:

      I would love to hear more from you! How have you worked with your bosses to anticipate their needs? Thanks for your thoughtful comment!


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