How to Ask Your Boss Tough Questions

How to Ask Your Boss Tough Questions

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How to Ask to Keep Working Remotely

As this article was originally published pre-pandemic, this wasn't a template we "needed"—yet. If you're looking to keep your work remote or flexible, you should have a discussion with your boss. They should be receptive and listen to you. The entire workforce did incredible things to "make it work" during the wild ride that was

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How to Ask to Keep Working Remotely

2020-2022. None of that should be forgotten. If you feel like you "found your groove" and that going back to work in person would destroy it, communicate that. We know that everyone's situation is vastly different, so here is a starting point.

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How to Ask Your Boss for a Raise

G: Give Background Info I: Introduce Why You’re Awesome M: Make Your (Researched-Based) Case M: Make the Ask E: End with a Bang

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How to Tell Your Boss You're Leaving

If you're looking to tell your boss that your last days are rapidly approaching, we have another article called "How to Tell Your Boss Anything." In this article, we unpack everything from resigning to disclosing sensitive information to a trustworthy and understanding boss. For a quick refresher on how to tell your boss about your 

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How to Tell Your Boss You're Leaving

departure without revealing too much, we have a quick and easy guide. Let's make this a smooth transition and keep all professional relationships intact. 1. Request a Meeting Pen an email to request a general meeting with your manager or supervisor. 2. Pen a Formal Letter of Resignation

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How to Tell Your Boss You're Leaving

Prepare a resignation letter to hand to your boss after your meeting. Include relevant information like your last day (hopefully + two weeks out), any transition plan you might have, and a section to express gratitude. – Resignation Letter Templates Your notice letter does not need to mention any information about your new job. You'll also 

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How to Tell Your Boss You're Leaving

want to avoid sharing any negativity about the circumstances of your departure. We know, it's tempting to slam the door behind you in a rage fit, but try to leave on good terms. 3. Keep the Transition Smooth + Expect the Unexpected To maintain a positive relationship, have an open dialogue with your current employer. 

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How to Tell Your Boss You're Leaving

Be open to an exit interview, where you can constructively share what worked for you—and what could be improved within the organization. If asked, you can also share any suggestions of coworkers to fill your position. If you're feeling really generous, you can even share a letter of recommendation. Finally, expect the unexpected. Some 

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How to Tell Your Boss You're Leaving

employees prepare a transition period and two-weeks' notice when they give their notice of resignation. Be prepared for your boss to tell you that today will be your last day of work. To that end, make sure you clear your work computer and gather any personal belongings and records you need to take with you.

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How to Ask Your Boss for a Promotion

Asking for a promotion in title only might be a little less intimidating than asking for a monetary raise. What is our deal with talking about money, society? However, before asking for a promotion in title, make sure that your increase in responsibilities and duties doesn't also warrant a pay raise. If it does, then address this as well.

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How to Ask Your Boss for a Day Off

If you're sick, stay home. We have plenty of sick day email templates for you to use so that you can focus on your own recovery. And yes, mental health days count, too! Why should it be so scary to ask for a day off?  Alas, it can be! If you have a close relationship with your boss, you might ask for a day off in a face-to-face 

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How to Ask Your Boss for a Day Off

conversation. However, it never hurts to write a follow-up email or ask in writing. This also makes it easier for your boss to track your PTO or vacation days. If your company requires advanced notice for requests, make sure to follow these guidelines. That might mean pre-planning your day off a few weeks in advance. However, if 

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How to Ask Your Boss for a Day Off

there is a medical reason, family emergency, or another factor that requires you to make the request later than suggested, simply communicate that in written form.

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How to Ask Your Boss for More Work

If you find yourself nodding off at your desk by 2:00 every day, it might mean that you’re uninspired and actually underworked. Nothing makes a workday go by faster than...well, actual work. If you feel uninspired or like you’re suffering from under-challenged burnout at work, consider asking your boss for more work and responsibility.

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How to Ask Your Boss for More Work

This sort of initiative shows your boss that you’re not the type of employee looking to show up, clock hours, and collect a paycheck. Here’s how to ask for more work. A little advice here—don’t make your boss do the work. Do a little legwork to identify areas in which you would like to work. Have you noticed the marketing team struggling with 

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How to Ask Your Boss for More Work

some data management? Maybe that’s a place to help. Also, be sure to keep your language positive. Don’t come to your boss from a place of frustration and discontentment. Rather, frame your ask in a positive light by highlighting all the work you’d be excited to do.

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How to Ask Your Boss for a Performance Evaluation

Not all workplaces are created equal. As such, not all organizations offer performance reviews, at least not on a scheduled basis.  If you want a performance appraisal in a work environment like this, you'll need to ask. This is also a great way to test the waters for the possibility of a promotion or an increase in compensation down the line.

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How to Ask Your Boss for a Performance Evaluation

Before asking, make sure to put together a summary of your achievements, highlights, and your overall track record. Have thoughtful questions planned around recommendations for future success.  Find out what insights your boss has in regards to your work so far and get ready to make an action plan to achieve more.  The best part is that a  

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How to Ask Your Boss for a Performance Evaluation

few months from now, you can come back and ask for a raise. At that time you can cite all of the recommendations your boss made—and how you went the extra mile to achieve them.

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