The Questions I Wish I Would Have Asked Independent Contractors

Mmmm, solopreneurship. We get to work our own hours, be our own boss, and focus on whatever we want.

Well, sometimes.

At least until we realize running our own business comes with a lot of to-dos that we don’t actually have time for (or dislike doing).

Rather than hiring an employee (kind of defeats the purpose of being a solopreneur, no?) we often turn to independent contractors and virtual assistants for help.

This is a fantastic choice, but the hunt to find the right candidate can be a tough one, especially if you’ve never done this before and don’t know the right questions to ask to find the person that is right for you.

In my experience, I’ve found that the generic questions aren’t always that telling of how well your experience will go. There are many more intriguing things you can ask contractors that rarely make it to the interview.

Interviewing An Independent Contractor

There are only 24 hours in the day, and spending time vetting numerous contractors may not be how you want to spend them. Once you’ve narrowed down your candidates and are ready for the interview, have a set list of questions ready to go to be as efficient with your time as possible.

For first-timers, the types of questions to ask in an interview can easily be found with a simple Google search:

• What’s your experience with this type of work and in this industry?
• What do you charge? 
• Do you have references?
• Do you have insurance?

Blah, blah, blah.

To be fair, these types of questions should certainly be asked, but their are other things you can ask contractors that will give you quick insights as to whether contracting them will be a good fit, or will cost you more time than if you just do everything on your own.

After polling a number of solopreneurs, I’ve narrowed down some of my favorite questions that don’t always get asked in the interview process, but totally should.  

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The Work-Style Questions to Ask Independent Contractors

Since the people you are speaking with are independent entities, not your employees, you need to remember that you are technically their client, not their boss. You must be comfortable giving them their desired autonomy. They are simply working on a project for you and likely have other clients and projects to work on as well, so it is imperative that you understand the desired work-style and working relationship from the get-go.

What is your ideal client relationship?

This cuts right to the chase. With one quick question, you can get an understanding of what to expect working with this person. Do they like to be micro-managed? Do they like autonomy? Do they even know what type of relationship they want? Make sure whatever their answer is matches your preference as well.

What is your current capacity?

If a person has very limited hours, this may be a red flag depending on your needs. Alternatively, if they don’t have any other commitments, you may want to question why that is. 

If you had multiple projects and limited time, how do you manage priorities?

Remember, contractors likely have other clients they’re working for, so be sure to ask them what they do if they have numerous deadlines set for the same time frame. How do they pick one project or another if need be?

Do you have the right tools and equipment to get the job done?

This question may fall under the “standard questions to ask a contractor” category, but the reality is, not many people ask this because they assume the contractor has everything they need to get the job done. That simply isn’t true. 

Will they need their own Zoom account? Do they expect you to provide the software they need to get the job done or do they already have it? Are you able to provide what they need or is that a hard pass? Get these questions answered.

The Tough Questions to Ask Independent Contractors

You are bringing on a contractor to help with your workload, give you hours back in your day, and make your business better as a whole. Don’t feel guilty asking the tough questions. Some solopreneurs feel uncomfortable asking direct questions, but the answers you receive will truly ensure you’re making the right choice once a candidate is selected.

Has a client ever ended a working relationship with you before a contract was up?

If the answer is “no”, great (provided they’re telling the truth), but if it’s “yes,” you can get an understanding of the circumstances and how the contractor handled it, but you can also see how they talk about previous businesses. The last thing you want if something goes wrong with your contract is for them to talk poorly about you or your business to others. For solopreneurs, this can be especially detrimental since you and your business are one in the same.

How do you choose what companies and roles you apply to?

Are they just contracting with you for a paycheck or do they genuinely care about what you do? The answer may dictate how good the work is that they create for you.

Describe this project to a kindergartener.

Anybody can read a project description, but does everybody truly understand what is required? Make sure the candidate understands what you are asking by breaking it down as simply as possible. 

The Icebreaker Questions to Ask Independent Contractors

Here’s the thing, yes, you want people to be experienced, but you also want to make sure you have a good working relationship with them. You may find the most experienced, award-winning person, but if they are a drag to work with and make your life miserable, it isn’t always worth it. So, in my opinion, fun, get-to-know-you questions should absolutely be a part of the interview process. Here are a few questions to consider asking.

Tell me a fun fact about yourself.

This is one of my favorite ice-breakers. It’s silly and helps you get to know more about a person quickly. It’s also a great way to build rapport. Fun fact, when I was an independent contractor, I got a handful of projects because of my answer to this question alone.

If you could have one superpower, what would it be?

There really isn’t a right answer to this question, but the reasoning behind this superpower can be very telling. For example, if they wish they had a superpower to sleep anywhere, they may not be the most driven person (this may seem like a random example, but it’s one I’ve actually gotten in the past).

If you could have dinner with one person, dead or alive, who would it be?

I like this question because the answer can actually reveal a lot more about a person than you’d think. It can show their core values, the type of people they admire and aspire to be, their personality, as well as critical thinking as to how they land on their answer.

The Trial Question To Ask Independent Contractors

Here is my problem, how can you fix it?

Seems easy enough to ask, right? But it’s rarely asked! You are seeking to bring on a contractor to help you solve a problem, so in the interview figure out what their solution is! Additionally, don’t be afraid to ask them to show you an example of how they would go about whatever it is you’re hiring them to do.

Leave out hypotheticals, let them know what you need, and see if their expertise can shine.

This may be controversial, but I personally think it’s important to pay the contractor for the work done during the trial. It doesn’t have to be a lot, but they are actually doing the work for you, whether it’s what you want moving forward or not, so make sure you compensate them for their time.

I’ve done this a lot when trying to find writers. Sure, I can review past samples of work, but I want to see how they would write about a topic that is relevant to my company. If I have them write a 1000-word blog post, I’m going to pay them for it, even if that’s as far as the relationship goes.

Of course, the questions above are just a few of the many types of questions you can ask potential candidates. Remember, you want to ask direct questions, but never ask questions that you think will make a candidate uncomfortable. Asking inappropriate, private, or discriminatory questions are major no-nos. That’s interviewing 101 but you’d be surprised at the number of people who don’t follow proper etiquette during the interview process.

Good luck with your contractor search! If you’re curious how other solopreneurs bring contractors on board and work with them, I encourage you to join The Solopreneur Community, a Facebook group made up of savvy one-person business owners who are looking to learn a thing or two, get questions answered, share knowledge with others, and build their networks.