How to Ask Your Boss for Anything (+ the Templates You'll Need to Ask)

There’s a ton of fear around asking for what you want or—gasp!—what you feel you deserve in the workplace. Even in 2020, salary and money are still seen as very taboo topics (sidenote: that’s why we created The Salary Project™, so check it out.) 

If you want to skip ahead to the asks, you can go ahead:

Asking for anything can be uncomfortable, but let's dive into why it's that way in the first place.

First, Identify Your Fears 

To begin to tackle your fear behind asking for what you want, you’ll need to first identify where your fear is rooted. Four common fears in asking for a pay bump or other changes are:

Fear that you don’t deserve it 

This is pretty common and can come up at any time, for any ask. This is classic impostor syndrome—and it’s important to be able to recognize it and shut it down. Here’s the deal. If you’re asking for a raise, we trust you’ve done your research and crunched the numbers. If impostor syndrome is still garbling in your ear, shut them out. 

Fear of rejection

If you don’t ask for what you want, you don’t ever expose yourself to the chance that someone will say no. That’s how rejection-based fear works. But, as any old inspirational basketball poster will tell you, “You miss 100 percent of the shots you don’t take.” Take the shot. 

Fear of negotiation

Negotiation can be scary, especially when it involves money. We’re not here to tell you that negotiation is easy and can be learned overnight. However, we are here to tell you that knowledge is power. Come to any negotiation prepared with research, results, data, and numbers whenever you can. 

Fear of job loss

This is a legitimate fear for many. Surely your less-than-satisfactory employment is better than no employment at all, right? Well, not really. Negotiation, career exploration, or job adjustments should not get you fired. Rather, when done right, asking your boss for a change should show a real investment in your position—and in your future with the company.

Using Science-Backed Methods to Ask for Anything 

So, by now you’ve identified your fears and you might be thinking, “yeah, so what?” If your fear is still looming large, you'll need an additional weapon to yield when asking. That’s right, we’re bringing in science to help you get what you want at work. 

Anchoring Effect

The anchoring effect is a cognitive bias that describes the human tendency to rely too heavily on the first piece of information offered to them—otherwise known as “the anchor.” Once the anchor is presented, all judgments are made around the anchor. 

The anchoring effect is commonly used in car sales, where an initial sticker price is set and the two parties negotiate from there. Similarly, the anchoring effect can be used in a salary negotiation. Be thoughtful when offering your anchor. 

In our own GIMME Script, we advise that you set your salary expectations higher than the number you’d be comfortable landing on, assuming negotiations will happen between the initial ask and the agreed amount. 

Use the Rule of Reciprocity

The rule of reciprocity depends on the assumption that humans are more likely to return good deeds. In many social situations, we pay back what we receive from others.

When using the rule of reciprocity in a negotiation setting, you don’t want to present by saying, “I’ll give you X if you give me Z.” Rather, come to your negotiation with all the accomplishments you have already achieved—as well as your plans for future projects and improvements. 

For example, if you’re looking for a flexible work situation, you might lead by detailing all of the distraction-free work and strategy you can achieve while working from home or a remote location. If you are looking for a title promotion, you may present the skills you have learned or optimized in the past year—as well as how you plan on using them in your new role. 

Opportunity Cost 

In investment terms, an opportunity cost is the benefit an individual, investor, or business misses out on when choosing another alternative. While we all know you are much more than an investment to your boss (or at least you should be!) it doesn’t hurt to bring this bargaining tactic to the table. 

We’re not suggesting that you affix cold, hard numbers to your presence at your company (you're always worth more than a dollar amount.) Rather, it’s affixing your value both to-date and going forward. Present this to your boss when making a specific ask. While collecting and analyzing your own KPIs, we bet you’ll be surprised at just how valuable you are—and that’s great motivation and inspiration for how much more valuable you can be. 

Let's Get To Asking

Without further ado, let’s get to asking our bosses for what we want (and what we deserve!) Here are a few templates to get your asks into writing—or to use as a guideline script to ask face-to-face. 

How to Ask Your Boss for a Raise

If you’re familiar with Career Contessa, you’re probably familiar with our Gimme Script—which is our signature method for asking for a raise. It goes like this: 

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

For more on using the Gimme Script, download the entire script here. 

The best thing about the Gimme Script is that you can apply elements of it to most asks. Whether you’re looking for an increased salary, a title change, or more support, use the Gimme Script to build and explain your reasoning. 

to Ask Your Boss for a Promotion

Asking for a promotion in title only might be a little less intimidating that asking for a monetary raise. However. before asking for a promotion in title, make sure that your increase in responsibilities and duties don't also warrant a pay raise. If it does, then address this, as well. 

Subject: Following Up on Our Promotion Discussion 


Greetings [NAME], 


Thank you for taking the time to meet with me on [DATE and TIME.] I appreciate that your time is valuable and I appreciate you carving out the space to hear me out. 


As we discussed, I would like to be considered for a promotion to [JOB TITLE.] I believe that in my [TIME] here at [COMPANY] I have contributed am ample amount of accomplishments with extremely positive outcomes:


[EXAMPLE ONE] + [POSITIVE OUTCOME]

[EXAMPLE TWO] + [POSITIVE OUTCOME]

[EXAMPLE THREE] + [POSITIVE OUTCOME]


I also believe I have proven that I am a valuable team player. Here is some feedback I have recently received from coworkers and clients. 


[POSITIVE FEEDBACK] 


In addition, I have great ideas that I believe I can implement going forward, including [EXAMPLE OF IDEA AND HOW TO IMPLEMENT.]


I believe that my accomplishments, proven positive feedback, and thoughtful vision for my future here at [COMPANY] show that I am ready for this promotion and the responsibility that comes along with it. 


I look forward to hearing back from you and thanks again for your valuable time. 


[SIGN OFF]

How to Ask Your Boss for a Day Off

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 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 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. 

When making a last-minute request for time off, supply your boss with a back-up plan. If there is a coworker who can handle your workload for the day or if you are going to frontload your work for that week, communicate these plans. By leaving as little room as possible for questions, you will increase the chances that your PTO is approved. 

Subject Line: Request for PTO [DATE] 


Greetings [NAME,]


I hope this email reaches you well. I would like to request [DATE] off from work to attend [EVENT, DOCTOR’S APPOINTMENT, ETC.]


Let me know if this works for the team and if you need any additional information from me. 


Best, 

[NAME] 

How to Ask Your Boss for a Meeting 

Sometimes, you'll want to save your specific ask for a face-to-face discussion. To do so, you'll first want to set up a meeting with your boss in the first place. Here's an email template to carve out time to meet with your boss in order to have an in-person meeting. 

 You may also choose to use this email to hint as to the subject matter of your meeting. If it's about a salary increase or promotion, you might include a line like, "I'd love to discuss my future at [COMPANY]" or "I'd love to discuss some ideas I'd love to implement over the coming months, as well as my future at [COMPANY.]" 

Subject Line: Time to Meet This Week?


Greetings [NAME,]


I hope this email reaches you well. I was hoping to get some time in the coming days to discuss a few things with you. I checked on your public calendar and noticed that [DATE and TIME] and [DATE and TIME] were open. I was hoping one of those slots would work well for your schedule! 


Thanks for your time + I look forward to speaking with you. 


Best, 

[NAME] 

How to Ask Your Boss to Work From Home 

Work flexibility is increasingly important to the modern workforce. Whether you're looking to work from home permanently, a few days a week, or for a certain period of time, it's going to be crucial to do most of the legwork, to explain the benefits, and to develop systems that make keep lines of communication open. 

For these purposes, we created a template for the middle-of-the-road, asking for a work from home day every Friday. 

Subject Line: Request for WFH Fridays 


Greetings [NAME,]


I hope this email reaches you well. I wanted to discuss with you the possibility of instituting Fridays as a WFH day for me going forward. As you may know, most of my Friday work involves heads-down writing and data analysis. For this reason, I think my productivity would soar if I am afforded a solitary environment in which to complete this work. 


Let me know if this works for the team and if you need any additional information from me. 


Best, 

[NAME] 

How to Ask Your Boss for More Work

If you find yourself nodding off at your desk by 2 pm 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. 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 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. 

Subject Line: My Responsibilities at [COMPANY]


Greetings [NAME,]


I hope this email reaches you well! 


As you know, I am pretty settled into my role as [POSITION] and I enjoy my work immensely. However, I do believe I have the time, talents, and energy to contribute even more to the team. 


I’ve taken some time to identify some needs and I’d love to add the following responsibilities to my current workload in order to round out my weekly duties:


[RESPONSIBILITY + WHAT IT ENTAILS]

[RESPONSIBILITY + WHAT IT ENTAILS]

[RESPONSIBILITY + WHAT IT ENTAILS]


I’m really excited about my future here at [COMPANY] and I am completely open to discussing these responsibilities—as well as how they fit into my current role—with you, at your own convenience. 


Thank you for your time, 


Best, 

[NAME]  

How to Ask Your Boss for Support 

And sometimes, the last thing you need is more work. In fact, sometimes you need less work and more support in order to avoid total workplace burnout. 

There’s a reason that burnout is recognized as a serious clinical diagnosis by the World Health Organization. It’s because, for some workers, it’s very very real—and it bleeds into their relationships, physical well-being, and mental well-being. Here’s how to ask your boss for more support in your role. 

Subject Line: Discussion About My Role 


Greetings [NAME,]


I hope this email reaches you well. Before getting into it, I want to reiterate that I love my job and I feel privileged to contribute as a [POSITION] at [COMPANY.] 


However, I am becoming concerned that my personal workload is becoming a little daunting–and I wanted to run a few ideas for some support by you. 


My current workload includes these responsibilities:


[RESPONSIBILITY + TIME SPEND]

[RESPONSIBILITY + TIME SPEND]

[RESPONSIBILITY + TIME SPEND]

[RESPONSIBILITY + TIME SPEND]


As you can see, with these responsibilities, along with weekly incidentals, I am left with little to no time to [MANAGE CLIENTS, MOVE FORWARD, COLLECT DATA, ETC.] I believe that, with the help of an assistant or an additional [POSITION], I can move this department forward successfully. 


I would love the opportunity to speak with you more at length about my ideas and how I think hiring some additional support would greatly benefit myself and [COMPANY] as a whole. 


Thank you for your time 


Best,

[NAME]

How to Ask For Learning Resource Reimbursement  

Sometimes, there are perfect opportunities for you to upskill on your own time in order to improve your competencies at your current job (and your future positions, too!) 

Here's a template to ask your boss for resource-related reimbursements. 

Subject Line: Learning Resource Reimbursement Possibility 


Greetings [NAME,]


I hope this email reaches you well. 


As you know, I've settled into my role as [POSITION] and I enjoy my work immensely. However, I do believe I have the time, talents, and energy to contribute even more to my team here at [COMPANY.]


I recently discovered a great [LEARNING RESOURCE] via [PROVIDER (ie, Career Contessa, Skillshare, Master Class]—and I would love to enroll in order to further develop my [SKILLS.] 


I would love the opportunity to speak with you more at length about the [RESOURCE] and how I believe it would improve my overall skill set and allow me to contribute even more to my team. 


Thank you for your time 


Best,

[NAME]