Sweating the Small Stuff: How to Ask for What You Need (and Want) at Work

How many times have you talked yourself out of asking for something at work because it didn’t seem “important enough?”

Whether it was a “mental health day,” a learning stipend, a laptop, WFH flexibility, or even a few “DNS” hours on your calendar – no matter the scale of the request, if you’ve thought it over enough to consider asking, it is likely worth asking for.

Even if you don’t get your ask (and that’s okay), the more you practice advocating for yourself and prioritizing your growth and health at work, the easier it becomes to take the stand and make the case for more big league “asks” (like raises and promotions).

It’s a matter of exercising your “self-advocacy muscle.” If you never use it when the stakes are low, it might not pack the same punch when there is more money on the table (literally and figuratively).

Convince Yourself Before You Plea to the Jury

Oftentimes, we hold ourselves back from asking for things because in the process of considering that thing’s importance, we overwhelm ourselves with potential rebuttals, and ultimately convince ourselves that it isn’t worth debating.

This is natural. Humans are inherently prone to weighing negative outcomes more seriously than positive or even neutral ones. It is a defense mechanism that dates back to our primitive instinct to avoid threats to our lives.

In a non-caveman, work setting, it plays out as such:

Identify a need (EX: more flexible “online” hours to balance your caregiving schedule).

→ Predict rejection (your boss assumes you’re not “committed to your job,” your reputation is damaged, etc…).

→ The perceived initial value of your request goes down in comparison with the effects of a possible negative outcome.

→ You begin re-rationalizing for non-action, and ultimately decide to play it “safe.”

This downward spiral happens most frequently with women, as we are not only going up against our own personal insecurities and fear of disappointing others, but very real and widespread cultural biases that frequently penalize women for appearing “needy” or attempting to balance their careers with outside priorities.

Bottom line: those biases are very real, but shying away from facing them will do little to change the tide. You are allowed to ask for things that you know will serve you and help you thrive (…men do it all the time).

If you find yourself dwelling on whether or not that “little thing” is worth mentioning, odds are it might be you who needs to be convinced of its value. Stop yourself from spiraling into the land of “what ifs” that may or may not happen if your manager says no, and dive into the nitty gritty of all of the good things that could happen if she says yes. 

Root Your Request in Research

In the process of convincing yourself to pop that question (and in preparation to actually pop it), it helps to get down to brass tacks.

First, answer this question: what would be the ROI for the company if they said yes to your request?

Would having a laptop (in lieu of your stationary desktop) provide you with more “workplace” flexibility? How would that mobility affect your productivity and focus? Further: how deep does “lost productivity” cut into an org’s finances?

Having those numbers in your back pocket will not only make you feel more confident about the validity of the conversation, but will undoubtedly increase your chances of “winning” against all of those imagined rebuttals (should they materialize).

Pro-tip: if it seems like doing a little bit of “napkin math” to sort out the numbers is overkill for the scale of the request, we promise – the amount of time it takes to round up a few self-assuring stats is well worth the alternative energy drain of “wondering” whether or not your request is worth mentioning.

Don’t Overdramatize It

At the end of the day, if you think [whatever “it” is] is not that big of a deal, then it shouldn’t be a bigger deal to just ask for it.

The more we make the act of asking seem more monumental than the request itself, the more taboo self-advocacy starts to feel. And guess what? If you aren’t comfortable self-advocating (especially as a woman), you are going to have a pretty hard time advancing your career. 

If it would better your life/work balance, your performance, your health, your finances, your relationships with your colleagues (the list goes on)…bring it up to your manager. As long as you have a valid reason (which I’m sure you do), trust: you won’t sound needy, and the likelihood of that one thing unraveling your career is very low.

Besides: if you’re not doing your best, that means your company isn’t doing its best, and that’s something they want to know about.

(P.S. If asking for a few DNS hours per week to optimize a project does end in a blowout with your manager…that says more about them than you.)