5 Ways To Keep Your Boss Happy With Better Communication

I am sharing 5 ways to keep your boss happy with better communication. Before we dive in, ask yourself “How happy is my boss with me right now?” What score would you give your boss against the scale showing below.
Keeping your boss happy with you and involved in what you are working on is one of the most important things you can do, whatever your role.
The 5 Ways To Keep Your Boss Happy With Better Communication
- Use their communication style
- Proactively overcommunicate
- Be clear, concise and progress focused
- Question, understand and respond
- Commit to no surprises

Zero is very unhappy with you, has no clue about your work, doesn’t know your strengths or anything much about you and doesn’t demonstrate they care much or are interested in who you are.
Ten is where your boss is very happy with you, knows exactly what you are up to without being a micromanager, fully utilises your strengths and plays to your interests wherever possible and demonstrates they care and are interested in you.
What score would you give your current boss?
If you are scoring below a 7, I am sharing 5 ways to move your boss’s happiness and interest in you towards the 10 score through how you communicate. You don’t have to work harder. You don’t need to suck up or pander to your boss. You just need to change how you communicate with your boss and how often.
For each approach, I am giving you practical actions you can start doing today. This is not theory. This is tried and tested actions I have used very successfully for decades. 13 promotions in as many years prove these work.
I coach senior managers and leaders on how to improve relationships with their boss and other leaders to win promotion. Improving how they communicate is one of the most important factors. Anyone can use these actions no matter where you are in your career from just starting out to board level.
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The first way to communicate to make your boss happier is to use their communication style
To make your boss happier, learn what communication style works best for them. This might be quite different to your preferences.
Think about when and with what method to communicate to your boss. Do they prefer:
- Email updates
- You popping round to their desk to give a quick verbal update
- You, booking in weekly one-on-one meetings
- Getting updates before 9am or after 5pm
- Daily updates, or weekly or ad hoc or a combination
Find out by observing what other team members do, particularly the ones your boss likes. Ask your boss what they want. Experiment to find out what combination works best.
Style Matters Too
As well as the method and frequency, think about the style of communication. For example, here are 4 different styles you could use:
- Concise and direct communication of results and process for busy bosses. Keep it short, snappy and factual.
- Detailed and analytical communication to prove to your boss the points you are presenting. Show your boss the data so they can see for themselves.
- Visual – using graphs, charts, dashboards and similar to show progress and results. This is great for very visual learners to get updates fast.
- Collaborative – where you are chatting with your boss and asking for input and validation, so they feel part of the process.
You are likely to use a combination of different styles and approaches. Most bosses want you to be solution focused when communicating and be supportive of their goals and workloads.
Always experiment and find out what style or combination works best with your boss.

proactively overcommunicate – The second way to communicate to make your boss happier
I learnt the hard way early in my career that not keeping your boss informed about what you are up to is dangerous to your job security. If your boss doesn’t know what you are up to each day AND doesn’t have an opportunity to input into decisions, actions and solutions you are considering before you take them, you are probably not communicating enough.
If in doubt over-communicate rather than under-communicate. I always preferred face to face communication – usually by popping round to their desk. Then I would use the phone. Lastly, I would use email or chat methods. The reason being is that face to face is the best way of build relationships and email and chat is the worst. Good relationships matter to you personally much more than your boss.
Put in the effort to make sure your boss knows exactly what you are doing and working on at all times. Don’t wait for them to ask. Proactively and assertively seek them out and tell them.

3 – be clear, concise and progress focused
Nearly all the bosses I have had were much more time poor than I was. The more senior, the more time poor your boss is as a general rule. Most bosses I had wanted to know what was happening quickly, without being confused or having to ask a ton of questions to draw it out.
Before speaking to your boss, work out exactly what you want to say in terms of updates. Always be progress focused so you can quickly explain where you are against goals and targets. Put what you want to say into 2-5 bullet points. If it is longer than that, cut it down to a few bullet points. Then go to speak to your boss.
Keep working on making your communications clear and concise, and you will have a very happy boss and valuable communication skills too.
Question, understand and respond – The fourth way to communicate
Questioning, listening and understanding is the other half of communication. If you don’t know what your boss’s goals are, what their pressures are and what they are working on, you won’t be able to support them very well. The more you can support your boss to achieve their objectives, the happier that boss will be with you.
So ask your boss questions about what they are working on, about what goals they need to achieve and about what challenges are taking up their thinking time. Listen carefully to what they tell you and understand their position. Then take action to help solve some of their problems. Start small and work upwards. Take actions that will reduce their pressures, reduce their need to solve specific problems, reduce the communication they need to do to team members and reduce their involvement while still getting the team results needed.
Ask questions, listen and understand your boss and their needs, then take action to help them reach their goals. Lots of little helping actions are every bit as important as the bigger more visible actions.

The fifth way to communicate to make your boss happier is to commit to no surprises
Every boss hates surprises, even the good surprises. You can remove surprises for your boss by thinking ahead and communicating what is happening. Be realistic and be honest. If something is going badly or is really late, tell your boss as soon as possible. If you are well ahead on certain deadlines, tell you boss so they know you might be free earlier.
When your boss gets very few surprises from you because you are communicating a lot and in a way that your boss likes, you are likely to have a boss who is very happy with you.
Commit to no surprises for your boss.
in summary
Work at your communications with your boss. Keep your boss informed and involved in your work and you will get a ton of benefits including:
- A better relationship with your boss
- Greater job security
- Probably a bigger bonus and pay rise
- Better promotion prospects and
- Great influence over your work and opportunities
These are all very useful professionally to you and they make actually turning up for work a lot more enjoyable.
Don’t forget to go to resources and take a look at our guides on keeping your boss super happy with you and how to improve your communications with peers and stakeholders within the workplace.
If you have any questions on “5 Ways To Keep Your Boss Happy With Better Communication, please email me at support@enhance.training and I will get back to you.
Keeping your boss happy, informed and involved in your work is one of most important activities you can undertake, no matter what job you do. I learnt the hard way – I didn’t proactively communicate with my boss. I paid the price, not him. Since then, I always worked hard to keep my boss informed, even when they fully trusted me to get on and complete the work.
There are a ton of actions you can take to improve the communication levels with you boss. Take the actions in this article and visit our resources sections for more detail on how to keep your boss super happy with you.
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