how to talk to your boss

How to talk to your boss: 10 tips to help you

How to talk to your boss about…leaving the company. That you deserve a promotion. That the stress level you are under is unbearable. You are pregnant. You want to take a leave of absence. You need a day off for something you can’t justify.

Knowing how to talk to your boss about something is hardly ever easy. Some bosses are indeed very approachable, understanding, and accessible. Communication with them is easy, and although this does not make all your fears or uneasiness disappear, you know that your chances of success on how to talk to your boss are relatively high. On other occasions, too many, the moment of bringing up situations that may pose a problem for the company or your career within it becomes an actual conflict

To deal with this situation, which can be a significant obstacle to your emotional well-being at work, here are ten things to consider when you aren’t sure how to talk to your boss about something.

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How to talk to your boss

1. Think carefully about what part of the information you want to disclose

Think carefully about what part is best to keep to yourself. You don’t need to be too honest or give irrelevant information to the case that could make you look bad, or that could be used against you in the future. Synthesize so that your request is more straightforward and you are not left more exposed than you already are.

how to talk to your boss

When you’re worried about how to tell your boss you need something, simplify it so that your request is more precise and you’re not more exposed than you already are. If what you are going to give is simply information (for example, that you are pregnant or that you have to take a compulsory sick leave), do not feel obliged to provide unnecessary explanations about your private life. To do this, it is best to anticipate possible indiscreet questions and prepare standard answers. 

2. Choose the right moment

There are issues where the timing is never right, or you can’t tell if an occasion to bring up what you want is the right one. However, do not act impulsively and think about your recipient’s needs so that they do not feel invaded, harassed, or interrupted. Make sure that if what you are going to ask for is essential, your boss is available to listen to you. 

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Knowing how to talk to your boss requires you to prepare your speech, anticipate their objections, and maintain a professional attitude.

3. Prepare your reasoning

When it comes to thinking about how to talk to your boss about something important, think carefully about how you will justify what you are asking for. Any self-respecting project has a section on identification and justification of needs. Not always, but often you will be asked for reasons for what you are asking for, and they will surely expect these to have a certain weight or a certain sense. Prepare them in advance.

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4. Do your homework

Ensure all your tasks and responsibilities are well covered before asking for anything. One of the best ways to be forgiven for an excessive request or show merit is simply having them. Go to the meeting with your homework done, your duties fulfilled, and your areas of responsibility under control. Explain to your listener how you will ensure that, in your absence, these areas of management remain in this state without your request being prejudicial. It is often beneficial to have given something in return before, not just afterward, asking for something and getting it. 

5. Address it as a win-win

Think about how to talk to your boss about your request in a way that benefits the company. Or at least in a way that does not cause excessive organizational or economic damage. Show that you are on top of things and anticipate future developments. Investigate ways to make what you’re asking for interesting to others, a learning experience, and a benchmark to build on for future challenges. If you aren’t sure how to talk to your boss about it, make them see that even when you ask, you are working. 

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6. Get advice and inspiration from others

Seek advice from people you trust on how to talk to your boss. Discuss the topic with people you trust who have experience working in companies or faced situations similar to yours. They will help you see potential blind spots in your plan and find solutions in advance. It is also vital that you feel the support and motivation of people you trust if you have to communicate something very conflicting for you

7. Show confidence and planning in your request

Don’t beg, be professional. If you don’t know how to talk to your boss, remember the key is to communicate in an orderly manner, demonstrating that what you are asking for is not the result of a whim but of a circumstance that arose against your will or a need that you feel comfortable sharing with your superiors.

If you want a good answer to how to talk to your boss that you want a raise, a change in your duties or schedule, or simply that you are leaving, think carefully about how you will start the conversation. What key phrases are you going to use, and how will you close the conversation and say goodbye, whether you leave the office successfully or not, or with doubts. 

8. Offer a possible compensation

Think about how you will compensate the company if it does you a favor. In addition to reassuring the bosses that the company will not be affected by what you are requesting, it may be useful to offer compensation for any inconvenience your request may cause.

Think carefully about what that would be because you will then have to commit and deliver on it so that they can continue to trust you. Think about it and keep your ears open in case you are counter-offered. 

9. Flee from victimhood

Do not prioritize blame or abuse the comparative aggravation. It will be hard if you do not achieve your goal or achieve it but unpleasantly and “as if they were doing you a favor or sparing your life,” but you should not collapse or use an aggressive style.

Whatever happens, you have to show professionalism and not fight back in the heat of the moment. Take some time to rethink your strategy and, in the future, from a clear perspective. You will be able to use what has happened from a more advantageous position than the one you are in now. 

10. Communicate with assertiveness

Sometimes we ask for things, sometimes we try to impose them by force, and periodically we simply report an inevitable fact. Whatever the case may be, no one wants bossy people, but no one likes those who are too soft either. If you’re going to request rather than impose, assertiveness is the best way to safeguard your position.

Think that you will most likely have to continue in a working relationship with that person, who is also your superior, and who knows how life will turn out. Protect your relationship with that person, even if they have not given you what you want or have given you a hard time. The time will come when the elegance you show now will continue to play in your favor.

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Test: How well do I communicate with my managers?

Answer the following questions honestly and without overthinking. Trust your intuition. 

1. Every time I ask my boss for something, my voice trembles. YES/NO

2. We have to go on a rampage if we want to be granted anything in my job. YES/NO

3. It often happens to me that I am not sure if I can ask for something or not, so I prefer not to ask anything at all. YES/NO

4. I’m never sure which way my boss will go, so I try it out and figure out as I go along how to explain what I want. YES/NO

5. I always have the feeling that I’m the one doing favors for the company instead of the other way around. I guess that’s how jobs work. YES/NO

6. I once wanted to raise a significant change in my terms and conditions, but when the meeting came around, I realized I was caught on many grounds that I didn’t know how to argue. YES/NO

7. It often happens to me that I want to ask for things I am entitled to, but I never know how to stand up for it and end up compromising more than I should. YES/NO

8. I am likely to have to take leave soon, and I dread the thought of bringing it up with my boss. YES/NO

9. There is a lot of unpaid overtime in my company, and I am getting tired of it, but I don’t know how to explain it to my boss when everyone else is doing it. YES/NO

10. I thought it was my turn in the last promotion, and they chose another coworker. I would like to know why but I’d rather not raise the issue. YES/NO 

If you answered YES to half or more of the questions, there is no need to panic, but take good note: your level of assertiveness must start to grow from now on so that claiming your role in the company does not cause you suffering or unnecessary strain. Think about it, and if you are up for it, an excellent option is to work on these aspects with a psychologist in the context of therapy. It can be a big step forward in your health and work. 

Emotional well-being for companies

At ifeel, we want to help companies with the process of building a healthy corporate culture where all members of the workforce can develop professionally. To achieve this, our team of psychologists specializing in well-being at work has created an emotional well-being program for companies.

Through this collaboration, HR managers can receive personalized, data-driven advice on how to improve their team’s psychological well-being. In addition, this program offers employees a comprehensive mental health care service structured at different levels according to their needs. Try our program today to see all its benefits.

Be sure to visit our Resources section. We have a variety of content that could be of interest: podcasts, guides for Human Resources, or Interviews with important HR managers. In addition, we have a Psychosocial Risk Factors Template and use it to comply with the requirements of the Labor Inspection.

We hope this post about how to talk to your boss has been interesting. If you want more information about our emotional well-being program for companies, simply request it and we will contact your team as soon as possible.

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