How To Communicate Effectively With Your Boss

Kim & Roy
5 min readMay 17, 2020

Every company is different, but almost everyone in the corporate world is required to report to someone else. Learning to communicate with your boss more effectively will lead to more success in your career.

People are quick to share all sorts of best practices for team leadership, or in other words, managing . But an equally important but less frequent topic of conversation is how to manage .

When we enter the working world for the first time, too few people talk about the best ways to build a productive relationship wit h a manager. Like with any other relationship, what you talk about, and how, when, and why you talk about it is a pretty big piece of the puzzle.

Here are 6 strategies to help you communicate with your boss in a valuable and meaningful way:

Take time to get to know them.

The best relationships form when both people take the right amount of time to get to know each other. Professional relationships are no different. Knowing your boss means understanding what makes him or her tick. What gives them anxiety at work? Are they good over email, or do they prefer in person communication? Do they give better answers to questions when you ask them in a certain way?

Rather than bombarding them with these sorts of questions upfront, first pay attention to their actions and reactions and if you still can’t figure out their preference, then you should ask. If you’re able to figure out your manager’s professional personality, you’ll understand their expectations of you much more clearly.

Engage in proactive communication.

All managers appreciate unprompted, proactive updates, good or bad. This doesn’t mean that you need to fill your boss in on every last detail, but they will want to know about meaningful events, findings, and data sooner rather than later. Doing this successfully means being able to anticipate something before it happens.

Let’s say they’ve assigned you to a high priority project, and you know they’ll be anxious to hear about progress and results. For whatever reason, you’re having a hard time making headway. Send them an email or talk to them in person about the issues you’re encountering before they ask you about the lack of progress. Be clear on what you’re doing and why it’s not working, and anything they can do to help move things along. Again, don’t give meaningless updates, but do keep them in the loop when you know they will inevitably wonder about the status of something.

Admit when you need help.

Something is worth asking about once you’ve determined that you can’t figure it out on your own. Know-it-alls may attract attention initially, but they typically don’t do well over time. Contrary to popular belief, you shouldn’t have an answer to everything, especially while you’re still on the upswing of your career.

If it feels like you’re in over your head trying to figure things out, there’s a good chance your boss doesn’t know you need help. Of course there are exceptions and some managers won’t or can’t be of assistance. Even if this is the case, you can only control your actions. Be direct about what you need from them and most of the time, they will be happy to help you.

When you do ask for help, it won’t be productive to rattle off tons of questions. Even if they are good questions, bombarding anyone with too many disparate thoughts all at once will overwhelm them. Instead, narrow down your ideas, get to your point quickly, and ask the most meaningful questions in as few words as possible.

Be yourself and don’t suck up.

Some people do things at work for the sole purpose of being noticed. Similar to know-it-alls, these folks don’t tend to do well over time in the corporate setting. But even if you’re not a classic brown noser, it can be easy to fall into the habit of doing and saying only the things you’re sure your boss will like.

The goal is to be likable and yourself at the same time. Inauthenticity sets you up for failure from the start. You risk remaining at a job for longer than you should, or working for a manager who isn’t right for you from a career development standpoint. Remember that no two people are the same. Focus on being self-aware, getting to know your boss, and communicating in a genuine way that brings out the best in both people.

Remember that they report to someone too.

In the corporate world, even people in top positions report to someone else. CEOs report to the board of directors and partners in professional services firms report to clients.

Your boss is no different. They too are required to prepare for calls, meetings, and presentations with clients or upper management. The more effectively you communicate with your boss, the more prepared they will be for these interactions.

Typically, the more senior someone is in an organization, the less immersed they are in the most granular details. So, your boss likely reports to someone who is less in the weeds than you are. Learn to synthesize details and simplify them in a way that is digestible for others above you. This will streamline communication as it moves through the hierarchy.

Understand not just the what, but also the why.

The why provides information about the present, but the what sheds light on past events and helps inform future decisions. Let’s go back to the example of the high priority project assigned to you by your boss. If you’re not making the right amount of progress, it’s not good enough to simply provide an update on the current situation. To communicate with your boss effectively, you’ll need to understand and articulate the reasons for the holdup. This additional layer of information will give them a fuller picture of the situation, which will help you both determine the path forward.

If you are able to demonstrate a consistent understanding of the why through effective communication, your boss will have more confidence in your ability to take on increasing levels of responsibility over time. This is because each subsequent promotion requires a deeper familiarity with why and how things happen in an organization. The what will always be important, but being able to communicate the why will help take you to the next level.

Related Article: 5 Ways To Be Successful At Work

Originally published at https://www.kimandroy.com on May 17, 2020.

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Kim & Roy

We’re Kim and Roy. We created this as a way to inspire couples and individuals to achieve greater mental, physical, and financial health.