How to ask your boss for things

If you want to maximize the influence with your boss, you need to be strategic with when, and how you ask for things.

Designers can’t ask for everything and get everything. It’s important you “spend” your “boss bucks” on what matters.

Just like cash, if you keep spending your boss bucks fast enough you start running low on boss bucks to spend. Blow it all on little frivolous things and you’ll wish you had saved up for the big ask when it really counted.

This approach is one of the reasons that I have my bosses full attention when I have something important to ask for. He’s not thinking “uh, I heard you on the coffee thing last month, and we changed your desk location to avoid display glair the month before, so…”.

That doesn’t mean I’ll always get what I’m asking for, but it does mean that he’ll be more receptive because I haven’t been hammering him on the small stuff.

While your performance and adding value to the company should be your primary concern, your relationship with your boss really matters. 

It is important to be strategic with your requests.

What to ask for

Save for the big stuff beyond your control.

I don’t ask for the small stuff. I’ve never asked my boss for better coffee at work or snacks in the break room. It is worth it for me to solve minor stuff like that on my own, in favor of saving my boss bucks for bigger things beyond my control that really matter to me. If it is within my control to solve, I probably don’t need to bother my boss with it. I wanted better coffee at work, so I buy myself better beans and grind them at home, without bothering my boss.

How to ask

Build a relationships with your boss that is more than just you asking for stuff.

It is important to build a relationship with your boss that involves more than you just asking them for things. You don’t want them to feel like you view them as your personal Santa Claus where the majority of the interactions initiated by you is you asking them for stuff. 

Ask in a way that it communicates the benefit to your boss or the company.

You must keep your request honest and accurate. Don’t try to twist the purchase of better coffee beans into higher productivity. Your boss will see through that. But if you are asking for a faster computer because your machine is slowing your work down, that has an honest and clear link to benefiting the company. Any way you can authentically demonstrate real value to the company, then frame it in that way.

When to ask or not ask

Consider the timing

How recently have you asked for something? Did you ask for something small last week? Something big the month prior? Or has it been awhile since you asked your for anything? Consider these factors when you are considering if you should ask your boss for something. Also, if your boss seams stressed out this week, could your request be made next week instead?

Be conservative if you are new to a company

How long have you worked at the company? If you’ve only been there a week and you’re already asking for things that team members who have worked there for years have never asked for, think twice. You don’t want to be the new person who brought a long list of demands with them when they walked through the door. 

Recent screw something up?

Recently drop the ball on a project or receive a bad review? This is simply not the best time to bring requests to your boss. Instead focus all of your effort on on going above and beyond with adding value to your boss and the company until you can get back on-track.

Don’t put yourself in a situation where you owe your boss

The last position you want to find yourself in is one where you’ve asked for so much that you actually kinda owe your boss. You don’t want to be calling down favors only to find yourself owing him or her for the favors. That’s like like running up a boss bucks credit card.

Be strategic about when and how you approach leadership, and how and when you ask for things. Save up your boss bucks and spend wisely. The relationship you have built with your boss, the length of time working for a company, and the value you present to the company all factor in to your invisible boss bucks account. Handle the little niggles on your own. Solve the problems you can solve that are within your control. Save up the asks for the stuff that really matters, and your leadership will be more likely to listen to you when you ask for things.

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