How to Have Honest Conversations with Your Boss

How to Have Honest Conversations with Your Boss

The thought of having a conversation with your boss alone is enough to make us anxious. Whether it’s about correcting your boss or the raise and promotion request email you sent yesterday, having a open conversation with your boss can be nerve-wracking. Especially if you don’t have a particularly warm relationship.

However, honesty in the workplace is very important because it’s an essential ingredient to create a healthy and productive work environment. As an employee, getting into the habit of asking for feedback and sharing your ideas openly on a regular basis can definitely improve your performance at work. By showing your willingness to learn and be receptive to feedback, you shouldn’t have anything to worry about during the year-end performance review. Plus, you’ll get a better understanding of your boss’s expectations and know exactly which are the areas you can improve further.

Therefore, brace yourself for the awkward conversation, but it will be totally worth it for your career growth.

Here are some tips for communicating effectively with your boss:

1. Take baby steps

If you aren’t particularly close to your boss (like many of us, unfortunately), you’ll want to take baby steps by initiating simple conversations first. You can utilize questions like, “What do you think about the presentation earlier?” or “Would you mind to review the Powerpoint slides before the client meeting? I’d appreciate some honest feedback.” to get the conversation going without being to invasive. Meanwhile, it helps to build your confidence over time so you can approach your boss about bigger issues next time.

2. Speak the language you are comfortable using

The bottom-line here is—be as professional as possible. Never use foul and obscene language. Speaking the language you are comfortable with is a must. Although English is the business language in the Philippines, but if it would work best to speak in Filipino if you are not comfortable with speaking English. Asking to speak the native language is a valid request if it makes the conversation less awkward.

3. Keep your facts straight

Most bosses won’t have the patience to listen to you beating around the bush. Hence, keeping your facts straight and organized helps to keep the conversation concise. It allows your boss to understand what you’re trying to say easily. If you keep your thoughts clear, the discussion would more likely to go smoothly.

4. Do not jump into conclusions

Keeping your facts straight and organized helps you to think objectively and most importantly, not jumping into any conclusions during the conversation. A good way to avoid that is to analyze the information and think critically before making any judgment about what your boss has said.

It’s common for bosses to have high expectations of their subordinates and their honest feedback might be hard to take sometimes. Remember, having a one-to-one dialogue with your boss is never easy. But, it’s a good learning opportunity to speak your mind and take constructive criticism to improve yourself.

5. Have a mental outline

You might have taken writing classes back in your basic and secondary schooling. Can you recall any key points that your teacher constantly asks you to remember? Have an outline, so your writing is organized and easy to be read. Same goes for speaking, having a mental outline helps as you can easily articulate your thoughts in a clear, organized, and concise way.

6. Don’t spill unnecessary beans

Set a clear boundary and make sure you don’t tattle. Keep the pantry gossip and personal stories to yourself, your boss is definitely not the right person to share those information with. Spilling unnecessary beans to your boss will only make you look unprofessional and petty. Make sure you’re clear with the intention of why your want to have the conversation. If spilling irrelevant information isn’t going to facilitate the discussion, there is no reason to overshare and cause any unnecessary disputes.

7. Don’t be too emotional

For people who are more in touch with their feelings, setting away your emotions can be quite challenging. This is because they tend to feel strongly about things and people around them. However, it doesn’t mean that they are any less logical than others.

For such situation, try not to take things too personally and be less emotional might help you to get through the conversation easier. Always remember, work is work. Don’t let your emotions get the best of you especially when in a workplace setting. No point getting worked up over something at work, always remember that life isn’t and shouldn’t be only about work.


Having a candid conversation with your boss can be nerve-wrecking especially if he or she isn’t exactly the kind-boss type. However, being able to hold honest and transparent conversations with your boss and other colleagues is crucial for your career growth and personal development. Remember that effective communication won’t happen overnight. It takes consistent effort and practice to be able to have genuine, productive chats with your boss.

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