Trust your freelancers to be experts in their work; but know you're an expert in your organization.

How to work with freelancers when their work is a mystery

The first time I worked on a website redesign, it was not pretty. Not the design of the site but the process. I had copy and pictures and figured we’d need to review layouts. So the button that leads to the donation page should be — wait. Who is making sure the donation page will work and be connected to all the right accounts after we change web hosts? Does the vendor do this? Will the project still be on time? What on earth is a merchant account or payment processor and why do we need two?!

To this day, I remember what it felt like to ask a question, anticipate getting some super expensive or horribly complicated answer, and get laughed at by the web developer.

Thankfully, I’ve worked with many more freelance developers (graphic designers, printers, consultants) who listened to my fumbling questions and said, “I hear that you’re concerned about or interested in X, and I can answer that, but I think the question you really want to be asking is Z.”

These were professionals who asked me questions to understand the context within which my organization was working, dug deeper into what success looked like, and held up a mirror to help us recognize our blind spots — rather than trying to skate by within them.

Own what you know. Also, own what you don’t know.

You don’t need to know anything to ask someone, “What else should I be thinking about? What have I missed? What questions would you have that I have not asked?”

If you’re a mission-driven organization, you know your organization best. You know your mission, your theory of change, and your objectives. Maybe you know what needs to be done, and maybe you don’t. In any case, a collaborative team who is well versed in their skillset and/or the nonprofit world can guide you.

But you will know your why best — own that. It’s what should drive every question you ask and every decision you make. And you need to share it with anyone you are working with who is outside of the organization and not a part of those conversations and meetings. Vision is not something that should only be shared with donors.

If you’re a freelancer, nonprofit organizations need your ability to provide the right techniques, strategies, tools or content, based on how well you understand their needs, goals, and capacity. If your client isn’t forthcoming, ask. In addition to informing your work, you demonstrate that you respect the organization’s work and want to understand how you can best support that. Besides, sometimes people aren’t actually ready to bring you in on a project and wouldn’t you rather know that upfront?

Yes, there will always be people who are convinced they already know the right answer.

They are not always wrong. But even if someone ends up reaffirming what you had in mind, it is worth it to be open to the chance that they may not. For one, it’s a much more pleasant work experience when everyone respects what the others bring to the table. Maybe that is or isn’t what your nonprofit needs or has the capacity for at this time, but it should be an active choice rather than a passive choice based on assumptions.

Focus on the outcome

Yes, you could ask for the lowest priced solution and you would get that. That’s what we tend to ask for when we are worried about budget. And if that’s the question, then the answer might be an open source platform that is technically free but costly to use because your organization doesn’t have the in-house capacity to update it. It might be worth paying more upfront for a system that will cost you less to maintain.

We ask about price when what we are worried about is controlling costs.
We ask about videos because everyone else has them when what we truly want is to get your audience to register to vote. Maybe you need a video, and maybe you don’t.

Still, let’s be real.

Call out your constraints and concerns

If you work with a freelance graphic designer, for example, they will probably spell out how many changes are included, whether a print or digital proof will be provided, deadlines to get a project to print by a certain date, etc.

Even if we hire the best freelance grantwriter, we still need to empower them with the right information (and supporting documentation)!

Let’s not waste anyone’s time. And let’s respect other professionals in their ability to be professionals.

Say you’re worried about deadlines and getting approval from various decision makers.

Ask about certain changes and how they might affect the turnaround time. That way, when you get non-minor changes instead of final approval, you can be informed enough to ask, “Is this change important enough that we can push the print date back?” before you have a panic attack.

Or if you know that you will need 16 people to approve something, ask your freelancer to adjust the timeline accordingly.

If you’re worried about costs spiraling out of control, state that. Ask what different options will cost over the lifetime of a project. Describe current staff capacity.

If you want to ensure your marketing respects people’s dignity, state that. Describe what respectful looks like and explain why it matters. Share the narrative you’d like to shift.

Remember that the purpose of language is communication, not perfection.
Forget jargon. Ask the question, call out the constraints. Ask what other questions you should be asking. If your collaborator can’t communicate clearly, you may question whether to keep working with them. It’s when we let our fears prevent us from having open conversations that we run aground instead of accomplishing our missions.

This article originally appeared on the Wethos blog.

Janice Chan
Janice Chan never was able to pick one thing to be when she grew up. While grown up status could be debated, what she currently does is consult (, teach data management in NTEN’s Nonprofit Technology Professional Certificate Program, and co-organize NTEN’s Nonprofits and Data online community group. She is also is working towards a Master of Information Management at the University of Maryland. Originally from New York, Janice arrived south of the Mason-Dixon Line via St. Mary’s College of Maryland. Post-graduation, Janice served as an AmeriCorps*VISTA before officially joining the nonprofit sector. She has worn hats in data management, volunteer management, marketing and communications, grant writing, curriculum development, program management, technical training, change management, and project management. In short, Janice has spent 11+ years organizing and restructuring information so that teams can work together more effectively and focus on their missions. She also enjoys editing, making playlists, and figuring out how we could do this better. You can find her on Twitter @curiositybone.