One of the most obvious—and yet frequently overlooked—ways we can support our contacts in following their dreams is to pay them for their work. As Forbes contributor Natalie Zfat explained in an article entitled Here's What To Say When Someone Asks To 'Pick Your Brain' About Social Media Over Coffee:

For me, social media is a business. I earn a living (as do my employees) by providing social media expertise to other businesses. These businesses are happy to pay for our time—a very limited resource—as I’m sure it is for you and your colleagues. Just as your job pays your bills, social media consulting is how I pay mine.

Would you offer to pay for any other service with a drink?

I shared this piece with my network, many of whom—as writers, as career coaches, and as creatives, whose acquaintances ask them to “just glance at” something or “share some thoughts” for free—responded along the lines of “Yes!” Because as the title of this article states: Smart People Don't Let People “Pick Their Brain”—They Call it Consulting and Charge Accordingly.

However, by so vocally sharing this (important) viewpoint, I realized I might be alienating the people I’d be happy to help. Of course I said yes when my sister-in-law asked if I could review her resume—and no, I didn’t expect her to offer to pay me! The same goes for that half-hour career brainstorm session with a close friend: We talk through most major life transitions together (and money only comes into the equation when we’re splitting a check).

So, how can you know if your request is completely appropriate, or if you’re making the other person feel taken advantage of?

Remember that it’s less about where you’re coming from (“I’m a good person, and it would really help me out if someone talented could lend a hand for free! Oh wait, I know someone who does that…”), and consider how your request will come off.

Here’s a two-question guide to thinking through it:

1. How Close Are You—Really?

Social media is great for getting back in touch with old contacts. But it can also give people a false sense of connectivity. Sure, I’ll accept your request if we went to the same summer camp, but that doesn’t mean you can dive in and ask me to help you the same way I’d help my brother. Zfat shares how these requests translate: “ ‘It’s Erica from 11th grade chem, btw.’ (It’s an especially gutsy ask if you also have to remind me that we went to high school together.)”

So, be honest about with yourself about the relationship. Do you guys spend holidays together? Is asking for (and sharing) advice—outside of her area of expertise—part of your relationship? Do you talk on the phone? Would you help him move? Yes, you really should be this close before you ask someone to work for free.

Oh, and there’s a caveat: You should still offer to pay the other person if his business is new and fledging—particularly if you have the resources. Sure, this makes it less “a favor” and more you “supporting his new endeavor,” but isn’t that what family and close friends are for?

2. How Big Is the Ask?

This question may be controversial for some. Because I understand the person on the receiving end who’ll thinks: Sure it only takes me 15 minutes to look something over, but that doesn’t mean I think it’s appropriate for people to ask me to do it for free. (And that’s totally valid.)

However, this question is instructive as far as whether you, the asker, should opt in to pay the other person, even if he says he’s 100% happy to help you out. Because you shouldn’t let your cousin the web designer overhaul your entire site in exchange for a lasagna.

Whatever you’re asking for, do some comparison shopping online. If you see that other professionals expect large sums of time or money to complete similar work, you have two options. One is to consider paying your close contact! The other is to moderate your request by giving her true options and an actual out.

Instead of just asking your cousin to redesign your site (or plan your event or design a logo or help update all of your application materials), ask if she can assist in a way that makes sense for her. Could she respond over email by pointing you to a particularly instructive resource or sharing one piece of general advice?

Limiting the amount of time the other person would have to spend to fulfill your request is one way to be respectful—and still get pointed in the right direction.

Related: 3 Email Templates That'll Make Asking for a Favor Feel Less Awkward for Both People

Some may misunderstand the spirit of this advice and think I’m telling children to charge their parents and BFFs to set an hourly rate for phone calls that dive into one person’s area of expertise. I’m not. But I am trying to save someone from asking a relative stranger to work for free, or a close contact to complete a massive pro-bono undertaking, because that approach usually fails. The other person will likely decline (perhaps uncomfortably), and you’ll have offended him or her along the way.

So, remember this: You can inquire about rates, and if the other person would rather help you out for free (or barter or sign up for a lifetime supply of free lasagna because she can’t imagine charging her dear aunt or childhood confidante), she’ll tell you!

A lot of people who are hustling or side-giging or chasing their dream job, while we need the money, also have a strong desire to pay it forward and put our talents to good use for those we love. We just want to be respected enough to be able to choose for ourselves when we’d like to be magnanimous, and not have it be assumed.

Photo of two people talking courtesy of Hero Images/Getty Images.

Updated 6/19/2020