Is there a more exciting time than when an entrepreneur decides to sign a contract with a freelance virtual assistant or get a retainer with a graphic designer? You put the word out to friends and associates, and you get lucky. You find a freelancer you like! Hurray!

You look over their contract, pay the first invoice and celebrate because things are finally going to get easier!

The first week goes well, but the work isn’t quite on the mark. You want to be reasonable, so you wait to give feedback and try not to pounce on your new virtual team member’s mistakes.

And yet, after the first month, you’re left wondering:

“Is this more work than just working on my own?!”
“Did I decide to work with the wrong person?”
“Why are they asking so many questions?”
“I hate emailing them everything – I need to get them on a Skype call stat so we can get to the bottom of this!”

I get it. Powerful delegation – that makes other people independent – is tough and nerve-wracking. In my previous business, I managed over a dozen freelancers at one time. I was always their primary contact point, and it wasn’t always pretty!

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15 questions that will make you better at managing freelancers

I’ve come to believe that how well a freelancer performs tells you about how skilled their clients are at supporting and training them.

During 2009 and 2010 I went through five virtual assistants for my web design business inside two years. It was brutal. The web design business I co-owned was booked out over six months in advance, our inbox was constantly flooded with inquiries, and we needed help as of yesterday! So we contracted virtual assistants to ease the pressure.

I thought working with freelancers and contracting was different from hiring. People would self-manage, I would give them money and get results out. I would do basic training, and we’d be up and running in no time! My job wasn’t managing freelancers!

Or so I thought.

What happened was that I was both inexperienced and wrong. I spent a lot of time being upset over work that wasn’t getting done to my liking or wires that got crossed between my business partner and myself. I communicated that frustration to my contractors, often without much else for them to act on.

I was a hot managerial mess, you guys! I did the best I could, and my best  sucked. Thankfully, that was a long time ago and I eventually saw what was going on. I apologized to all my contractors – even the ones I wasn’t working anymore – and took responsibility for being the kind of leader I would be proud to work for.

I trust that you’re doing your best but just add money pressure to high-performance demands, and we’re all at risk of becoming that terrible boss.

You know the one, right? The one who’s always behind, gets lukewarm results from anyone reporting to them, and never asks themselves: “How can I create a supportive, training-rich environment for people who work with me?”

This isn’t just the responsibility of employers, it’s also the responsibility of entrepreneurs who work with freelancers. Taking responsibility for managing freelancers makes a huge difference in the results you get from your collaborations.

Does it take an effort? Of course. Can small teams and entrepreneurs afford to make this happen? Absolutely!

Stepping up to actively collaborate with and manage freelancers is less time-consuming and expensive than serial hiring that gives you a reputation for being demanding and difficult.

Because, as in any industry, you know that freelancers talk to each other about who to avoid.

So I stepped up and became the supportive, well-prepared manager they needed to do their job right. And you can too! But first, you need to consider what behavior to avoid when you’re managing freelancers.

Consider these common scenarios that entrepreneurs create to solve problems with freelancers that end up creating roadblocks to success:

Do you ask your freelancers attend regular meetings with you?

Why this doesn’t work:
Freelancers aren’t your employees. They have limited billable hours every week, and other clients. Freelancers complete their assigned responsibilities at a time that works for them – that’s when they do their best work, and that’s what you want them to do. If you ask multiple freelancers to attend project meetings, while it may feel good for you, most of the meeting content will not apply to them.

Unless you’re meeting about a substantial project or have agreed that regular meetings work best for both of you, this is a potential red flag that your project management systems need strengthening. Adding tools and systems instead of relying on meetings can build trust and foster healthy independence.

Remember, if you start asking your freelancers to act like employees, they can come back at you and ask for all the employee benefits that go along with that role.

How to make it work:
Be clear on what you expect your freelancers to do, what you need from them, and give them step-by-step training that they need to do their best work. If you’re not sure what that is, ask them. After each project, ask “What could we do differently next time to make that more seamless?”. Give feedback on their work, and set clear deadlines and targets for your projects together. Ensure you both meet these goals. Open, and clear communication is essential here.


Do you ask for work to be completed in under ten days without expecting to pay rush fees?

Why this doesn’t work:
Your freelancers have other clients, and they likely need to plan their time weeks in advance. Respect their time as you want them to respect yours. Just because you didn’t plan ahead, doesn’t mean they should drop everything for you.

How to make it work:
Set deadlines before you start working together, create a workflow that you can both agree on and works for the project. Keep in mind factors such as holidays, time zones and other moments that may arise worked out too. Be sure to deliver your part of the agreement in time and to be polite, suggest that you can pay rush fees if you do have a last-minute emergency. Nothing will endear you to your freelancers more than valuing their time.


These situations are only the tip of the iceberg, so consider the questions below can help you get started on deciding how to handle your team. At the end of the day, you’ll need to reflect on the type of manager you want to be and work at this every day. Just remember: Managing others is a learned skill and a muscle. It’s hard at first, but

15 questions that will make you better at managing freelancers

Are you helping your freelancers work with skill and confidence, or are you turning into the client they’d rather avoid? These questions will help you support your contractors and freelancers to do their best work for you! Journal your responses and then make decisions about how you’ll act in advance.

  1. How productive and self-motivated do you want your freelancers to be?
    Note: The higher this is, the more ownership of the process you need to give them. You need to ask them what they need, and how you can support them.
  2. What training or resources would your freelancers need to be able to work at that level?
  3. How do you want your team to feel about your business?
  4. What are the most common mistakes you see? How do you want to handle them?
  5. How can you make sure freelancers get the information they need without having to attend unnecessary meetings?
  6. What systems would you need to have in place to make that happen? How could your freelancers let you know about progress, so you don’t have to ask them about it?
  7. How can you casually check in on a freelancer’s progress and celebrate wins, so you don’t over emphasize mistakes in your communication?
  8. Think back to the worst manager you had. Describe an unpleasant situation with them in vivid detail.
  9. Think back to one of the best managers you had and describe a highlight of your work with them vivid detail.
  10. How did each manager motivate you to work precisely? How often did they check in with you?
  11. How did each manager let you know your contribution mattered?
  12. What made you like or dislike each manager?
  13. How would you want someone else to act toward you when you make a mistake? How would you want subsequent warnings handled?
  14. What kind of manager will you strive to be? List 3 – 5 actions that kind of manager would take, to try them out yourself.
  15. What kind of manager will you refuse to be? List 3 – 5 actions that kind of manager would take, to be on the lookout for them.

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