How to Communicate With Your Boss

Have you briefed your boss, and it went poorly? The boss asked a ton of questions. Your message didn’t get out how you wanted. And it was just an overall disaster. Disasters like this happen to most people. I once had a brief go so poorly that my 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. Learning to recognize these moments before they happen is one of the best traits a leader can learn when briefing a boss or even subordinates. A leader should always look for ways to improve communication.

I have learned a lot since my early Army days. I’ll share some things I have learned.

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. Everyone knows what the meeting is about and why they are there. 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. The purpose changes depending on the focus of the meeting. Here’s a hint: The focus is usually about 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. In John Wooden’s book Wooden: On Leadership, he planned his basketball practices down to the minute and did not deviate. Do this with your meetings.

But what if something else comes up? That item is for another time or an email. To avoid looking inflexible, address the new topic, write it down, and mention that you’ll talk about it next time. The only exception to that should be if the boss wants to talk about it. 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.

On a similar vein, send out invites for more formal meetings. Use those features that the company gives you to invite people. Attach the necessary documentation for your invite. If you have PowerPoint slides for the session, attach those to the invite along with your agenda. Creating expectations and keeping them is one 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. Explain details in written memos or when the boss asks questions. 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. 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 in their book Extreme Ownership. When you don’t understand your boss’s priorities, then you can’t know what they need to be successful. Even if you disagree on the priorities, fulfill the requirements for your boss, 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. Take their actions as their priorities, and that’s how you can anticipate their needs. Sometimes, that’s necessary for a good relationship.

I value my bosses, and as a result, have not had too many poor experiences with most of my leaders. I have had disagreements with my leaders, but we have always worked things out. It has been beneficial.

If you don’t know, ask. Ask your boss what their expectations are if they haven’t told you already. Be persistent about getting feedback from your boss. 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 for 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. It’s not a bad idea to get to know your boss’s boss as well. 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. 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!

If you want to read a book review on Extreme Ownership by Jocko Willink and Leif Babin, click here.

4 thoughts on “How to Communicate With Your Boss”

  1. Maria says:

    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. Robert says:


      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. David Pratama says:

    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. Robert says:


      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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