7 Tough Conversations You Should Have at Work Sooner Versus Later

Women Talking at Work


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AnnaMarie Houlis4.87k
Journalist & travel blogger
May 24, 2024 at 10:26PM UTC

Tough conversations can be intimidating and awkward and uncomfortable — and we don't blame you for not wanting to have them. But the fact of the matter is that, at some point, you're going to need to have them. And it's sometimes better that you get the conversation out of the way sooner rather than later.

Here are seven difficult asks and requests you should get off your chest ASAP.

1. You need to ask your boss for a raise for doing everyone else's work.

If you find that you're always doing everyone else's work, it's probably time to ask for a raise. While this can be a nerve-wracking conversation, it's best to do it sooner rather than later because you don't want to spend anymore of your time being underpaid for the work you're doing. You deserve to be compensated fairly, and you should ask for that.

2. You need to ask your boss for time off to take care of your mental health.

Sometimes you just need a day or two or even more off to take care of your mental health. It may feel easier to ask for the day or two days off when you're physically sick, since you wouldn't want to contaminate the office. But asking for a day off to take care of your mental health might not feel as warranted. Your mental health is equally if not more important than your physical health — and you need it to be in good shape in order to do your job well. 
You're better off asking for a mental health day sooner rather than later, as you don't want your mental health state to deteriorate.

3. You need to report discrimination in the workplace to the human resources department.

If you're experiencing or witnessing some form of discrimination in the workplace — whether it's sexism, racism, homophobia, ageism or something else — it's best to report it as soon as possible. The longer you allow it to go on, the worse the situation can get. The sooner someone in HR knows about the situation, the sooner they can take action to resolve the situation or involve legal authorities to take care of it.

4. You need to ask your boss for a promotion because you deserve it.

If a promotion opportunity arrises, and you feel that you genuinely deserve the promotion, you need to express your interest in it immediately. You want to be on your boss' radar when they start thinking about potential promotion candidates — and you want them to be aware that you're interested if they were to choose you. You also want them to start considering exactly why they should choose you.

5. You need to tell your gossipy coworker that you don't have time.

Everyone has that one coworker who comes to the office every morning to chit chat with everyone about their crazy weekend or gossip about how so-and-so did such-and-such. You've probably spent way too much of your valuable time allowing this coworker to chew your ear off when you could have been spending your morning productively. So it's about time you tell your coworker that, frankly, you don't have  the time to talk. You can start closing your door if you have one, popping in headphones or simply telling them that you're not interested in gossiping — despite how awkward that confrontation might feel.

6. You need to tell your mansplaining colleague that you don't need his two cents.

Your mansplaining colleague is the man in the office who is always condescending you and other women, telling you how to do your job — you know, the job in which you're trained and he is not. While you might not want to start any drama or cause any conflict in the office, it's better to have a conversation with this colleague sooner rather than later so that you don't set the precedent that his behavior is OK. While it's certainly not your burden to bear, and you shouldn't be blamed for setting any precedent (that's victim blaming at its finest), you'd be doing yourself a disservice by not confronting this coworker.

7. You need to tell your boss that you're quitting.

If you're planning on quitting your job, you might be nervous to tell your boss. But it's best to give at least two weeks of notice before quitting so you can give your boss ample time to start finding your replacement. The sooner you can tell your boss, the more respectful it is. You don't want to burn bridges, after all.

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AnnaMarie Houlis is a feminist, a freelance journalist and an adventure aficionado with an affinity for impulsive solo travel. She spends her days writing about women’s empowerment from around the world. You can follow her work on her blog, HerReport.org, and follow her journeys on Instagram @her_report, Twitter @herreport and Facebook.

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