10 Questions to Ask the Freelancer in Your Life

How to “catch up” when you don’t understand what they actually do for a living


Talking to myself isn’t very fun. Photo by Yasmina Shields

Recently, I caught up with some friends I hadn’t seen in a while. I asked them all about their jobs: responsibilities, bosses, coworkers, office drama… And they had lots to say. But then, when the conversation shifted to my work life, they didn’t seem to have any idea what to ask about.


As a freelancer, I don’t have any of those “normal job” things. (Well, I have responsibilities, but they aren’t handed down to me from a supervisor.) So I think my friends were at a loss for how to approach the topic of my employment. No water cooler? No one to give me a raise or promotion? Maybe my work life is just a boring status quo of chugging through project after project with nothing very interesting happening along the way.


I’ve got news for you: that couldn’t be further from the truth! So if you don’t know how to talk to the freelancer in your life about their work, here are ten suggestions for what to ask them:


1. What did you work on today?

Always ask this question, because you’ll get a different answer every time. And you might be surprised at the unusual or nitty-gritty tasks that your friend has to do—either for their clients, or as a part of running their own business. Bonus: this question works great for people with “regular jobs” too!


2. Where do you do your work?

Possible answers include but are not limited to: at home, at a coffee shop, at a co-working space, at the local library, in bed, on the roof, at the park, in a friend’s apartment, at the local bar, on the plane to Europe, and at Mom’s house. And ask your friend why they work where they do, too.


3. What project are you most excited about right now?

Most freelancers are juggling multiple clients at any one time. But not all projects (or clients!) are created equal, so your friend definitely has one project that they would rather work on than all the others. Ask them why it’s so much better than the rest!


4. Who’s your favorite/least favorite client?

I guarantee your friend has a client they love and a client they hate (often correlated with their answer to #3). There are usually some interesting stories there! Make sure you give your friend a chance to complain a little, no matter how small their grievances—they have no one else to vent to!


5. What clients or projects are you pursuing right now?

Freelancers never stop thinking about the next project, because if they do, they’ll run out of money. So your friend will jump at the chance to tell you their master plan for pitching a big project or approaching a lucrative client.


6. What do you think is the next step for your business?

Just as freelancers are always thinking about what’s next in their work, they’re also always thinking about what’s next for their business overall. Maybe your friend wants to learn a new skill. Maybe they want to redesign their website. Your friend will love you for giving them a space to verbalize some of their business plans.


7. Do you feel like your rates are high enough?

Ah… money. Depending on your relationship, this topic may be uncomfortable. But your friend thinks about finances a lot, because figuring out how to set your rates when you’re in charge of your own health insurance, retirement accounts, and vacation days is a real struggle. Pro move: no matter what your friend is currently charging, encourage them to raise it!


8. How’s your work–life balance these days?

This question will make your friend feel like you really understand their life. Many freelancers, especially those who bill hourly, struggle to “clock out,” because all non-work time in some ways represents lost wages. Don’t tell your friend how you think they should be using their time—you can’t understand their mindset until you’ve lived it. Instead, ask them about their goals. What do they want to spend more or less time on?


9. I read [such and so] about freelancing—does that apply to you?

Not only will this show your friend that you pay attention to headlines or stories relevant to their lifestyle, it may lead to an interesting conversation about how they either align with or or defy stereotypes. Freelancing is by no means a monolithic field.


10. Is there anything I could help you with?

This is just a nice question to ask in general. But your freelancer friend might have a very specific thing you could help them by doing. Maybe they want to see how their website loads on your phone. Maybe they’d like your opinion on a pitch email they’ve written. Maybe you could endorse them for a skill or write them a recommendation on LinkedIn. Keep in mind that lots of freelancers get most of their business through word of mouth, so the absolute best thing you can offer is an introduction or referral.


There you have it: a cheat sheet for having an interesting and fulfilling conversation with the freelancer in your life. Now, go forth, and make your freelancer feel understood!

©2020 Eric Dale Creative

freelance designer • freelance photographer • freelance writer • career coach