How to Manage Freelancers For Mutual Long-term Success

If you’re visiting LocalSolo, you probably already know that jobs in general are becoming more distributed and project-based and that more businesses are relying on the growing independent contractor workforce to tackle those projects.

These trends make “talent management” for external resources a critical issue for modern businesses. How you work with designers, web developers, engineers, consultants, content strategists and writers will matter in the emerging gig economy as much as all the attention companies now give to managing employees.

I made my living as a freelance writer for 15 years, and now I run my own content marketing agency where I’m still in the role of outside contractor for my clients. But I also built my business with a network of freelance talent — writers, editors, designers, social media specialists, etc. — who can reliably deliver for me and for my clients. My experience as an independent contractor informs a lot of my approach to working with my growing team.

I say team, even though they are all freelance and I’ve met few of them in person, because I’ve found that a team-building and workforce development mindset is critical for my success. I can’t treat these resources like a commodity and expect that I will deliver a premium service to my clients on the other end.

If you don’t manage them, you’re leaving value on the table

I’ve written elsewhere about everyday practices that an agency, Fortune 500 company or any other business can use with their contractors to shift to a team-building mindset. For example, you can:

  • Budget for some training.
  • Go out of your way to give recommendations and career advice.
  • Set up processes to connect them with and learn from one another.
  • Celebrate their success.

But the main thing you must do is give independent contractors clear instructions for a job and ongoing guidance. Clients and employers are going to have to think through their processes for “supervision” of their independent workforce.

As this model grows, it won’t be good enough to take the position that once a consultant signs a scope of work you sit back to let them do their thing. The value you get will be determined largely by how you manage them. And “hands off” will rarely be the right approach.

The management process will be different for every company, department and role, but you can check yours by reflecting on two big categories — onboarding and supporting.

1. Onboarding your independent contractors

When you hire a new full-time employee, you onboard them, right? Whether they are an entry-level associate or a new VP, you still want everyone to understand the strategy, the market, the value proposition and the customer. So you show them orientation videos, you give them a stack of background reading and you take them around and introduce them to everyone else.

The first time I had a client contract with me for a months-long project, I was amazed at how slow they were to share key information and connect me to key stakeholders. Now I’m pushy about it with my clients, essentially saying this will only work if they onboard me.

Working in the other directions, my business has the equivalent of an employee manual for our mission-critical freelancers. First, it has everything they need to know about workflow and processes. It’s the remote freelancer parallel to giving them the parking pass and introducing them to payroll. I don’t want anything bottlenecked because we forgot to give someone the login credentials they need for our project management software or don’t have our house style guide.

Then my assistant editor and I give them the big picture, both for my business and for each of the clients they will be working with. We capture and synthesize all this in a creative brief document that serves as a content strategy roadmap. This is an essential part of our onboarding process, along with a standard checklist of everything we need to cover with each new freelancer who joins us. And we take time to get on the phone and go over it.

In short, we onboard them as if the business depends on it. And in the gig economy, it increasingly will.

I think some companies may be worried about sharing proprietary information, which is understandable. But don’t reflexively default to a mode of no sharing and therefore no onboarding. The rule of thumb should be that if there’s a slide deck you want new employees seeing in their first day on the job, then you should want your external talent seeing it also. Otherwise you are squandering some of the value they could provide you.

2. Supporting your independent contractors

The next generation of smart businesses will have a process for supporting the success of external talent on particular assignments.

Picture a workplace team that is heads down on an important project. Where is the boss? Hopefully, they are checking in, troubleshooting problems and finding resources that they didn’t anticipate needing at the start. They probably even roll up their sleeves to pitch in where it makes sense. Or they’re ordering the pizza the team needs to keep going.

It sounds like “management by walking around,” right? Except now they may “walk around” via Skype, Hangouts, Slack and the comment threads on Trello.

But few companies work with gig economy professionals in that way. The usual approach is to get them started and wait for the deliverable. Especially if you are paying a premium for consulting services, you understandably expect them to manage themselves. After all, one benefit of hiring consultants is that they show up ready to provide value right away.

But it’s counterproductive not to monitor them so that you can support and adjust. While holding high standards on the value I expect from freelancers, I find that I get even more value from them if I’m aware of their progress.

For example, writers commonly have responsibility for finding their own sources to interview. I like to hire experienced journalists for marketing roles, because they know how to track down authoritative sources. But even experienced reporters have assignments where, no matter who they contact, they can’t get a call back.

What good does it do me to let them flounder? Or to not be aware of the problem at all? I let my team know I’m here to help, and I check in unprompted. When there is a problem, I can usually make an adjustment to get the project going again.

Sometimes it makes sense for me to pitch in even for work I’m paying them to do, because it may mean a more productive route to a good outcome overall. For example, if I can look over interview questions in advance to see and give guidance, so much the better. I could leave it all to the writer, but an interview has a huge opportunity cost, so our collective efforts there ensure we get the most out of it.

I can also target resources strategically. Traditionally, writers have responsibility for transcribing their own interviews. But if I unbundle everything a writer does and examine the value of each thread, it turns out that transcription is something I can pay to have done for them, freeing up their time to provide me higher value.

Your business may hire very different professionals for very different projects, but the same principle applies. Make sure your management process has a bias toward supporting independent contractors. Trello, Google docs, Slack and and platforms like LocalSolo shouldn’t just be a dashboard by which we monitor freelance teams from afar. They should be strategic tools that we use to support their success on individual assignments.

Look to your employee development for a model

In conclusion, you can check that you’re managing your freelance team well just by comparing it to how you manage internal employees. There shouldn’t be a lot of daylight between how you work with each group.

Consider whatever you do for the people in the cubicles nearest your desk and then think about what the equivalent is for a remote and temporary professional. Obviously, you can’t buy all your freelancers pizza to fuel them through a project, but whatever the impulse is behind that, you should try to direct it toward freelance also.

You should always be asking, “How can I get you what you need?” Start with onboarding and ongoing supervision and management. Strive to make those as thorough and effective for your external team as you do for employees.

Author Robert McGuire operates McGuire Editorial, a content marketing agency specializing in B2B and SaaS companies. And he’s so passionate about the gig economy that he launched Nation1099, an online magazine for independent contractors who want to grow their businesses.

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