How to Effectively Talk to Your Boss: 25 Dos and Don’ts

Need to have a talk with your boss? Here’s how to go about it.

Reviewed by Hayley Ramsey

How to talk to boss

Talking to your boss can be difficult; especially when it comes to sensitive topics like bonuses or quitting your job. Your career is ultimately in your manager’s hands, and you need to make sure you can build a stable relationship with them, while still staying true to your values and opinions.

Telling your boss what you really think can be a slippery slope, depending on their disposition (and ego). Disagree with them, and you could wind up on the unemployment line. But being a yes man or woman and blindly supporting all their ideas probably won’t do much for your career either.

To turn this nerve-wracking topic into a stress-free one, read our list of dos and don’ts when communicating with your boss effectively.

Alternatively, you can watch the best techniques and tips in our video:

The dos

These are the things you should make a point to do:

1. Clearly state what you need

Your manager is probably busy and doesn’t have the time to sit there and listen to you, giving them tons of background information that is irrelevant to what you are asking. Whether you’re just giving them a heads up or asking approval for something; clearly state what it is that you are hoping for so he can decide the outcome in a timely manner.

2. Pay attention to your boss’s communication preferences

Everyone’s communication preferences differ; some bosses keep their door open and don’t mind being interrupted for a quick chat. Others prefer a heads up by an IM chat or a calendar invite. Timing is also key; pay attention to find a window when your boss is less stressed so you can contact them then. Taking all of this into consideration will give you a good indication of the best time to talk to your boss.

3. Show value

You were hired for a reason; this will be due to your qualifications, experience and personality, so don’t be afraid of adding value to the organization - you know what you’re talking about, so don’t be shy of voicing your opinion. According to Teri Hockett, Chief executive of What’s for Work, “bosses want employees not only to agree with them but also be willing to speak up about the realities and challenges in the business that need to be addressed. Be the person that speaks with facts, confidence and reasonable suggestions that produce results. This builds your boss’s confidence in you.”

4. Establish a line of open communication

Most employees work themselves up about speaking to their boss because they don’t have an open line of communication with them. If you can’t anticipate how they are going to react, you can’t deliver your question or opinion with confidence. To combat this feeling, you will need to build transparency and trust in the relationship; you can schedule bi-weekly meetings to discuss any issues, build a rapport and seek advice. If this is unnecessary in your role, try to socialize with your boss as much as possible, in the kitchen or during team lunches (without coming off as a suck-up).

5. Be aware of your body language

When you are talking to your boss, make sure you give off confident body language. Hold a tall posture and avoid fidgeting or slouching in your seat. Always keep eye-contact and lean into the conversation. There’s nothing worse than having an employee that is looking everywhere else in the room apart from the person they are having a conversation with. If you struggle with any of these points, practice before you have to approach your manager.

6. Plan your time off

Of course, you’re allowed an allotted time off per year and are encouraged to take it. But when planning your annual leave be considerate to your employers. Give them enough time to approve your request and plan for your leave of absence. If you’re covering for a colleague during their time off, you’d like to know in advance to plan your schedule too.

7. Empower your boss

If your boss looks good, you do too, and if you make them look bad, you’re essentially making yourself look bad too! Get my drift? Think about ways to make your boss look great and you can bet that your name will be on the next promotion.

8. Be loyal

Try not to keep work-related secrets from your boss. If you’ve made a mistake, own up to it and explain how you will rectify it - you’ll get a lot more respect for your honesty. A strong bond with a manager is vital; even if you or he moves on to another company, you’ll still value the bond and will have made a good contact that will support you throughout your career.

9. Offer to take on more tasks

If you have spare time on your hands, try to make your employer’s job easier by offering to take responsibility for those tasks that they may dislike doing. It will not only help your boss, but you will learn other aspects of the company and will be in a better position to move up the career ladder.

10. Get your facts straight

If you go into a discussion about your job with all guns blazing and no factual evidence, you can kiss your promotion and credibility goodbye. Management has enough opinions of their own and won’t want yours unless asked. If you disagree with an opinion or angle of a new project, back up your counter-argument with objective evidence.

11. Be solution-oriented

If you go to your manager with a problem, be sure to also have a solution. This shows that you’re proactive and can be trusted to get on with your work. You’re bringing the issue to their attention and saying that you’ve got it under control – proving that you have the skills needed to progress within the company, too.

12. Ask for advice

Your manager will value you more when you ask for their advice. If you are faced with a problem or just need some feedback, be open about it and ask for your boss’s thoughts. They will respect that you’ve gone to them directly.

13. Be confident in your skills

It’s important to be confident about your skills and what value you bring to the company. When you’re speaking with your boss reiterate your achievements, outline your trajectory and share your knowledge and ability. By doing so, you will respectfully remind your boss of your competencies and strengths allowing them to see what they will lose if you left the company.

14. Rehearse the conversation

If you’re typically an anxious person, why not rehearse the conversation before you speak to your boss? It will help you feel calm, focused and prepared for what is going to come. Of course, you can’t predict what your manager will say. But you will have practiced the points that you’d like to get across without getting distracted.

15. Be appreciative

Regardless of the outcome, you should show your appreciation for the time taken to discuss your issue. Be polite and sincere (even if you don’t like what your manager had to say). It’s important to show that you value their opinion also. If you have had an in-person meeting, you can always follow up with a ‘thank you’ via email or Slack (or whatever your normal method of communication is).

The don’ts

And this is what you should avoid doing when talking to your boss:

16. Beat around the bush

If you have something important to say, don’t spend 10 minutes creating a build-up to the cliff-hanger. Start with the upshot and then fill in the details once you’ve laid the idea on the table. This way, your manager will be able to process the details, which means you’ll receive a more useful answer.

17. Correct your boss in front of others

Everyone hates being corrected in front of an audience. Imagine that you’re the boss and you are trying to deliver important information in the weekly meeting when an employee comes along and corrects you in front of everyone – cringe alert! If it’s a serious mistake that really needs to be addressed, mention it after the rest of the team have left the room.

18. Hide your mistakes and challenges

It’s disloyal and unethical to hide your mistakes in the workplace. If you’re experiencing challenges, communicate those with your boss. Their duty is to guide you and teach you how to progress, if you keep your manager informed, you can tackle the small issues before a big one arises.

19. Go to your boss when you’re emotional

You might be super angry that your colleague is handling the new account that you worked so hard to get and want to go and give your boss a good piece of your mind. Whatever you do, give yourself a cool-off period to get your emotions in check. Speaking to your boss erratically will not solve anything, other than drive a wedge between you.

20. Let your boss’s mood affect you

Does your boss have a Jekyll and Hyde personality? If so, don’t let it bother you. You can’t change who someone is, but you can control the way you act. Be aware of your boss’s mood and only talk to them when they are in a good one.

21. Go over someone’s head

Even if your supervisor doesn’t have the power to affect the change you’re proposing, you must still discuss it with them first. It’s important to follow the organizational hierarchy. This could also foster a more fruitful discussion when pitching your idea to your boss.

22. Wait for praise

You don’t need a pat on the back for doing your job. You need to be confident in the work you’re putting into the world as you wouldn’t have got that position if you weren’t capable of doing it. Your boss isn’t a mind-reader so if you are really unsure of your work, simply ask how you did on your last project.

23. Take criticism as a personal attack

Many employees take criticism personally and believe that their boss has a vendetta against them. This just seems completely unreasonable to me. Your boss has more on their plate than to sit there and plot against you. Criticism is given so you can learn and improve, embrace it, move on and do better next time.

24. Get involved in office gossip

Even if you think your work wife will never rat you out, it’s best to never engage in gossip about your boss or fellow co-workers. Word always tends to get out, which can weaken your reputation and your relationship with your manager.

25. Interrupt

Even if you think you know better than your boss on a specific topic, never interrupt him while he’s speaking. Always be patient and wait until he has finished so you can offer your opinion in a constructive way.

26. Throw others under the bus

Telling on your colleagues to make yourself seem more capable isn’t a good look! In fact, it proves that you’re not a team player and can’t be trusted. It’s always best to sort out any issues at work with the person directly, rather than running to your boss.

25. Be too humble

While you shouldn’t throw your co-workers under the bus, you should also accept credit when it’s due. It’s fine to sing your own praises from time to time and stand up to prove your worth!

28. Diminish boss’s position

Regardless of whether your boss is good at what they do or not, you should always be respectful when you talk to them. Don’t go into the conversation with an attitude and an air that your manager isn’t qualified for their position and therefore dismiss whatever they have to say. Not only is it rude, but it shows a lack of respect – things that you should always maintain in a professional environment.

29. Refuse to complete your work

You don’t agree with what your boss has said, so your solution is to refuse to do the work. While you think that this is a clever move, it’s actually offering the company a reason to let you go. If you refuse to do a task, you’re not fulfilling your duties as an employee. So, whether you like it or not, you’re going to have to contribute to whatever you’ve been tasked to do.

30. Threaten to leave

Another scenario when the conversation hasn’t gone in your favor is to threaten to leave. While you may think that it’s a great tactic to get your own way, it’s actually making you look bad to the management team. They won’t be likely to consider you for a promotion in the future after pulling a stunt like that. So, if it’s more money you’re after, why not have an open discussion about it before threatening to pack up and walk out of the door?

Final thoughts

With all this in mind, regardless of the goal of the conversation, you should be fully equipped on how to talk to your boss and build a lasting relationship. Remember that any conversation is a two-way-street, so you have to listen and be as understanding as you’d expect in return.

Have you got any other useful tips on how to talk to your boss? Share them with us in the comments section below!


Originally published December 2, 2020.