10 Questions to Ask When Hiring Your First Team Member

bottom half of woman in jeans and floral top holding a woven hat at her side

You’re growing in some big ways over the last few months (years) and you’ve got your workflow down. Now it's time to hire some help. But there’s dozens of social media assistants, copywriters, graphic designers, and strategists out there... how the heck do you find someone who’s a good fit for your creative business? 

I know you’re probably tired of workflows (which is why you’re looking to hire someone else to take care of it for you), but you really need a system in place to find the right people for your team. (Or you're probably going to end up in a really giant pickle when you sign a contract because you're desperate and it turns out to be the wrong fit entirely.)

10 Questions to Ask a Freelancer Before You Sign a Contract

Before we get to the questions, I want you to start with a job description of the tasks you want someone else to handle. (Don't have one yet? Just download this handy Planning for a New Hire guide to get started.)

After you have a job description ready to go, you can start to put together your application (or at least plan to ask these questions on a video call). 

1. What are you good at, and what do you love to do?

Spend some time looking through their website (they have a website, right?) to checkmark their list of services against your job description. When you connect, ask which areas they excel in and enjoy. You don’t want someone who hates managing her inbox in charge of yours. 

Pro Tip: Look for someone who you vibe well with, even if their background isn’t a great fit. When I was looking for someone to manage my business operations, I found someone who didn’t have the project management background I thought I’d need for that role. She has turned out to be fantastic because she’s ambitious and organized and her personality was a great fit.

2. Can you show me a portfolio/examples of your work?

This is pretty much a given for graphic designers, but it’s equally as important for other skill sets, too. You say you’re good at Facebook Ads? Show me an example and tell me how it performed.

Pro Tip: If they’re just starting out, they may cost less, and still do a great job. The lack of a portfolio or profile isn’t a deal-breaker, but it can save you time while you’re looking for leads. 

3. Do you have relatable experience?

The creative industry is relatively new, which means many of us didn’t start our careers in this world. Ask them to explain how they can meet your needs with examples from their prior endeavors (which don’t necessarily have to be from an official salaried position, either). 

Pro Tip: If they’re lacking specific experience, ask if they have the energy, drive, and motivation to learn and grow in new ways. Make them show this to you by giving them a project with relatively little to no instruction and see how they do. 

what to ask when hiring contractors



4. How many clients do you currently have? How many do you work with at once?

Independent contractors typically work for a few clients at the same time. You don’t want to invite yourself into a stressful, bottleneck situation if they already have TOO many clients. Ask them how they prioritize their work, how they allocate their hours, and if they know their breaking point (aka how many clients are too many). 

Pro Tip: You shouldn’t expect to be their first priority all the time. Set realistic deadlines and don’t wait ‘til the last minute to give them their assignments... they’ll love you so much for it that they’ll make you their first priority anyway.  

5. Who are your other clients?

While I can’t make them, I indicate it’s not really cool if my contractors are working directly with my competitors. If you want exclusivity (you’re a wedding photographer and you don’t want your team members working with another wedding photographer in your area), it’s important to make this clear, but know that until they are employees, they may do as they please. 

Pro Tip: My team members sign a Non-Disclosure Agreement (NDA) before we start working together to protect my project ideas from drifting elsewhere between development and launch day.

6. Can you send me a few references?

You could take someone at their word, but it’s helpful to have some backup to make it more credible. A good contractor will be able to give you a list of former/current clients right away.

Pro Tip: Set up calls with each reference, and be prepared to ask them what they did and did not like about working with your potential hire.

7. Do you have any competing demands?

As a creative business owner, you know that your schedule isn’t the traditional 9-5, and it’s very likely that your future team member operates the same way. You need to know how committed they are to the role. Is their business full-time or a side hustle? Do they have kids that require flexibility (if yes, do they stay home or go to school/daycare?) 

Pro Tip: Their answers to these questions shouldn’t exclude them from the top of your list, but they should complement their other answers… if someone tells you that they work with 5 clients, work full time, and have 3 kids at home, it’s OK to wonder how they’d fit you into their schedule.

8. What’s your desired rate?

Some contractors charge hourly while others charge by the project. Some require upfront payment by retainer, and others send an invoice at the end of the month. You don’t want to be caught by surprise, so ask. 

Pro Tip: For hourly hires, ask them how they track and report their time. Do they log in 15 minute increments? Do they send you a warning when you’re close to your limit? 

9. How many hours can you work for me per month?

You may need more help than they’re willing or able to give. Decide how their timing works for your current needs, maybe you start small and add hours later, or hire multiple contractors for the same projects. 

Pro Tip: Everything always take at least 30% more time than you plan for. Always.

10. Who’s your favorite boyband?

Ok, it doesn’t necessarily have to be this exact question, but you’ll want to ask them something fun and unexpected to get a sense of their personality. I like to ask them a question I genuinely am curious about!

Whether you're ready to hire or you're not quite there yet, it's always good to have a plan ready to go, so that you aren't left scrambling at the last minute searching for help.

How to hire contractors

Click Here for Our FREE "Planning For Your First Hire" Guide!

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