Hiring and Keeping the Best Freelancers for Your Startup

Three things to start us off…

  1. The good freelancers are out there. Don’t give up.
  2. You can find the right freelancers, if you know where to search and how to woo them.
  3. The right freelancer can become a long-term, essential member of your team, if you treat him right.

Scrolling through the list of profiles on oDesk or Freelancer.com can get old, fast. Maybe you find one you like, with just the right experience at a great price, and for some reason she’s not the least bit interested in your project. So you move on to the next freelancer on your list, and this one won’t even return your messages. It’s not fun.

Even worse, you hire a good one, and start working together. The price per hour is phenomenal, and the work is outstanding. Then at the end of the first task, just when you’re ready to hire the guy for another three months of work, he says, “See ya later,” and moves on. Now you’re back on the profile list, scrolling again.

I’ve never been on the hiring side of things. But I spent the past year on the freelancer side. Recently an entrepreneur I know sent me an SOS. He was trying to hire a developer for his startup, and finding it much harder than he expected. He wanted an insider peek into the mysteries of why freelancers say yes, no, and bye. While I can’t speak for all the freelance workers in the world, I can say for certain what has worked for me. Maybe you’ll find it helpful on your next big talent search.

Characteristics of job offers I accept:

  • I’m invited to interview. Established contractors with a healthy client base aren’t trolling the job feed, because they’re busy working. They have to be invited to look at your job description, or they won’t see it at all. On the other hand, those who do troll the job feed are often new or underemployed. That could mean an inexpensive, lucky find for you.
  • No flashy, gimmicky titles or overly hyped descriptions. Just the facts, and a pleasant tone.
  • A good fit for what I already do for other clients.
  • Starts small, with the potential to go big. I’m just as unsure about a new client as they are about me, so a small intro project (paid) is more inviting than committing to a year-long job.
  • A clear description of the job, the expectations and the deadline, and maybe a bit about your company.
  • Carefully chosen candidate list. I can see whether the client invited 200 people to interview, or just ten. I’m not even going to look at a job posting that invited more than 50 people, because they don’t seem to be looking at the profiles all that closely, and it’s probably spam or a pyramid scheme.
  • A willingness to adjust the pay rate, in light of experience and results. Most offers that come in are too low, because clients assume you need more work. Some of them will try to use that to justify a rock bottom pay rate: “Come on. More work is more money.” Contractors who are in steady demand usually work up, not down. If they’re very busy they won’t even accept any new clients, unless the work pays more and starts small. (Good reason to hire someone new to freelancing, but experienced in the field.) So be prepared to offer a little more, if you want a spot on a great freelancer’s client list.
  • Takes all of my time into account, including research time. An hour on your project is an hour that could have been spent on someone else’s project. This is true whether the time is spent actively writing, or simply preparing and researching. If it’s going to benefit your company, it’s okay to pay for it.

Things that send me running from a job offer:

  • Unpaid test projects. Everyone’s time is valuable. It’s a bright red flag if a potential client asks for a free hour of work before she’s even met me.
  • Clients with a pattern of giving overly critical reviews to others. One or two bad experiences is perfectly reasonable, but if I look at a client’s history and see complaint after complaint, I’m not going anywhere near that negativity.
  • Clients who consistently get bad reviews from other freelancers. I’m not cocky enough to believe I’ll fare any better than they did.
  • Anyone who low-balls an offer and acts like he’s doing me a favor.
  • Sounds unfriendly or demanding.
  • Talks about how past freelancers screwed him over.

Things that keep me happy with a project:

  • Clear communication about what’s working and what’s not, with the person who actually makes the publishing/branding decisions. Or someone who can communicate in detail what the final decision maker needs. Startups usually manage this much better than large corporations.
  • Clear, frequent communication about project changes, deadlines, and outcomes.
  • Clarifying what’s urgent and what can be spaced out.
  • Valuing my time for extras like meetings and long phone calls.
  • Giving raises at appropriate times. (After first project, after a few better than expected outcomes, as demand increases, as you realize you need to keep this person around.)
  • Creative clients who love excellence, provide a challenge, believe in my abilities, and work together to create something perfect.
  • Clients who give increasing leeway for creativity, as trust develops.
  • After a few successes… Clients who bring me into the discussion to develop their projects/brands together. I want to know what we’re working toward, and feel like part of the team.
  • Longtime clients who just hand me something they’re working on and say, “Here, make this awesome.”
  • Favorites: Clients who play on my best strengths, let me run wild and do what I do, and let me have a hand in developing their face/voice. Those are almost all startups/entrepreneurs. It’s fun to watch them grow.

Things that make me look forward to the end of a project:

  • Subcontracting, playing Telephone, with no access to direct feedback. I need to hear from the person who makes the publishing decisions, not their well-meaning assistant. Otherwise, requests, complaints and comments tend to get lost in translation, and soon I have no idea what’s working or what we’re aiming for.
  • Sarcastic or condescending messages and feedback.
  • Expecting a lot of unpaid meetings/phone call time.
  • Tacking on extra service demands (i.e. “Could you hunt down some images and format those into the piece?”), or revisions that have nothing to do with the original intent of the project (i.e. “I changed my mind. Let’s write about this instead.”), without raising the project price.
  • Come and go clients who assume they’re the only client and demand immediate attention when they resurface.
  • Or come and go clients who show up months later and expect the same rate as last time. Rates can go up fast, if the freelancer is in demand. But I’ll often take a new job from an old client, close to their old rate, if it’s someone I love working with.

A few extra tips:

  • Get samples as closely related to your project as you can. Samples are their best best best work, in most cases, so if it’s not quite good enough, run away.
  • Reviews are very important in online hiring. Don’t mark someone down, unless you really have an issue with their work. Future contractors won’t want to work with you if they see you leaving consistently bad reviews.
  • Read reviews for signs of communication issues and quitting early. But there is always that one client who is just impossible to work with, so use discretion.
  • Hire people who are new to the freelance world, but proven in their field, for the best combination of cost-effectiveness and skill.
  • Give raises to the ones you want to keep, because as demand for their service increases, so will the money offered by others. If you like them, someone else likes them, too. Contractors are free to move on at will.
  • Give them a goal and a project to believe in, and let them know how they contribute to your success. Two of the jobs I stick with don’t pay as well as some of my other clients, but I’m okay with it because I love what they’re doing, and I know why they need me.
  • Say thank you as often as possible.
  • Remember to value the freelancer’s time like you value your own.
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