#026: A Hiring Manager Explains What He Looks for in a Freelancer

Summary: Craig has hired dozens of freelancers over the years. He works with them every day. And in this candid interview he explains what he looks for...

We spend a lot of time on this show talking about how find and land better-paying clients, how to work smarter and how to develop the mindset you need to succeed in this business.

You've heard from me and from fellow freelancers. You've heard from industry experts, well-known speakers and authors.

But I've yet to bring on someone who hires freelancers. Someone who can speak to what it's like evaluating freelance talent and working with us.

That's what this episode is about. In today's show, you'll hear from Craig Chappelow from the Center for Creative Leadership (CCL), a non-profit leadership and training organization headquartered in the U.S.

Craig has hired—and continually works with—dozens of freelancers in multiple disciplines. And in this candid interview, you'll get his perspective as a client on what it's like to find, hire and fire solo professionals.

The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe in iTunes or Stitcher to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

Tell us about what you do

Craig works for the Center for Creative Leadership (CCL), a non-profit leadership and training organization headquartered in the U.S.

The Center has about 500 full time employees. It also works with about 500 freelancers.

How do you work with freelancers?

Craig is a portfolio manager for some of the open enrollment leadership programs.

Generally, he works with three kinds of freelancers:

1. Trainers. Craig hires trainers on a program-by-program basis. About 30 percent of CCL trainers are freelance.

2. Executive coaches. Most of the executive coaches work for CCL on a freelance basis.

3. Miscellaneous. Craig also hires other kinds of freelancers, such as writers, researchers and designers.

What do you look for in a freelancer?

Craig looks for freelancers who are:

1. Low maintenance. Craig and his team are busy. They don’t have time to deal with drama.

clicktotweetAnticipate the demands of a gig. If you have a problem, don’t wait. Let the client know immediately.

If you’re high maintenance, you probably won’t get feedback to that effect. You just won’t get rehired.

Follow the rules. Craig doesn’t want to have to follow up with you if you’ve violated the company’s travel policy, etc.

2. Professional and ethical. Craig’s freelancers work directly with his clients. He expects his freelancers to dress professionally and act appropriately at all times, including meals and cocktail events.

If you’re instructing a class, think about the stories you’ll use in advance. Make sure they’re professional and appropriate.

Don’t approach Craig’s clients for your own consulting practice. It’s a major betrayal of trust.

3. Generous with their time. Craig looks for freelancers who are willing to do more than what they’ve been asked to do.

Look for opportunities to help out. Even little things, like arriving early to help set up, are appreciated. Make the effort to mentor new hires. Help create a positive environment.

clicktotweetAs a freelancer, treat your client as a partner. Take a long-term view of the relationship.

Craig expects his freelancers to socialize with program participants and other trainers. While socializing isn’t in the job description, it shows up in feedback forms.

4. Knowledgeable about the client. Craig expects his freelancers to show up knowing something about his clients.

Do your research. Who is the CEO? Has the company been in the news lately? Learn about the company’s products and services. Don’t come with basic questions that you could have answered with a little research. Having some understanding of the client’s world adds to your credibility.

How often do freelancers approach you for business?

Often. CCL has a formal system to deal with these kinds of inquiries. Craig’s best source of freelancers is other freelancers—so it’s important to use and maintain your network.

What intangibles do you look for when hiring a freelancer?

Travel is a big part of the job. Craig asks himself, “Is this someone I would enjoy traveling with? Could they remain positive and low maintenance in the face of unexpected layovers, bad food and boring airports?”

Any parting thoughts?

We all want to hire people we enjoy being around. Sometimes freelancers are so eager to close the deal and show their expertise, they forget about this aspect of the job—and it’s especially important in long-term projects.

Where can listeners learn more about you and your organization?

Visit the CCL website: http://www.ccl.org/

You can reach Craig Chappelow through LinkedIn.


  • cloudlancer

    Mr. Chappelow makes an excellent point about doing due diigence on the client. I work with clients who fit into one of two general categories, i.e. what I call the tool buyers (looking for a specific skillset or deliverable) or the support seekers (looking more for a coach/friend than a tangible product) and getting a feel for their personality is critical to providing the best service for them.

    • edgandia

      That's brilliant! Few people realize they should make that distinction. Very smart of you to do that.

  • Great advice and ideas! Don't have my first client, yet, but will keep all of this in mind to be the perfect freelancer and team player.

    • edgandia

      Cool! Thanks for checking out the show, Lisa.