Working With Creatives Doesn't Have to Be Hard

Hardwon wisdom on how to streamline workflows to manage smoother and more successful creative projects.

I have an agency buddy that uses a particular term when he needs to be upfront about something.

He calls it his “Come-to-Jesus moment”: the moment where frank, honest, upfront conversations have to go down, in order to “get saved”.

We’re going to have a “Come-to-Jesus moment” around project management, and getting the work you need completed, well, completed.

All too often people talk to me about their flaky freelancers, or their unreasonable clients.

The problem with projects seems to be people, in their eyes.

But that’s not the whole story.

I want to go over what the real challenges are with getting projects completed, and how to avoid a project meltdown.

Let's begin.

Before you put together a brief for a freelancer or agency, inventory what you really need done.

Think about the “why’s”, “what’s”, and “how’s”.

If you find yourself in need of some creative work done, you have to ask yourself why you need it in the first place.

If you want your website redone for example, why, exactly?

Is it oceans slower than the DMV?

Do users bounce the minute they enter because it looks like a 90s-era Geocities disaster?

Is your UX copy all flavors of WTF?

Why do you need it, and what is the end result you’re looking for?

If you don’t know why you need something, and what you personally think the end result should be (even just an idea!), a freelancer is going to have a hard time delivering.

That’s like walking into Starbucks and ordering “The Best Coffee”, then getting mad when it’s not the type of coffee you never said you actually wanted.

Nobody wins in this scenario, and the project will most likely fail unless your freelancer (or agency) is a miracle worker.

Or you hire them to help you figure out the "big answers" to the "big questions".

When you’ve decided on what you need done, think about what you need to have prepared.

Do the leg-work to get your talent the assets required.

If you don’t have a brand style guide, best practices for your logos, fonts readily available to be downloaded, use-case examples, or messaging architecture examples, be prepared to be let down.

Nobody will do this for you, unless they are contracted to craft your brand style guide.

This also includes photography and video assets. If you can't hand off these assets in a timely fashion, in the format requested, this means trouble.

This destroys creative projects, because talent has to put in the work to orient what it is you’ve even made (or haven’t made), when that might not even be on scope.

You, as the client, must prepare this unless you’re willing to pay someone to help you orient all of this.

Because if you do not prepare it, your talent / freelancer is going to be guessing at a lot of stuff.

And we know what happens when people start guessing:

Disaster.

Be aware of a budget’s limitations.

And prepare for moments where asking for ‘one small change’ adds up to a crippled budget.

As I tend to be the person other people call when shit hits the fan, I’ve seen this mistake repeated over and over again.

Something went wrong, the budget is straining, and I’m called in to perform miracles.

Avoiding “deux ex machina” solutions is really simple: freelancers like me will tell you when a project’s budget is apt to explode.

Please heed their words when they tell you this, and be aware that if you come with multiple lists of things to fix, the costs will expand.

Chances are, if you end up with a laundry list of fixes on the first draft, you didn’t do the above few points listed in this article to protect your project.

You have to be aware of what a cut-off point is — for yourself — because you need to be aware of your budget, when you ideally want things completed, and have a rough idea of what success looks like.

Project managers can only go so far with this.

If your expectations are not clearly communicated to your point person, this is an obstacle.

Good talent will apprise clients. They will judge, with a keen eye, if a project is going to explode.

Listen to them.

Be aware that not all project managers are created equal.

A lukewarm project manager is worse than not having one at all.

Say you are primed for a big project, and you’re considering hiring a project manager to help you orient your talent around goals.

What exactly do you look for in a project manager, though?

You should find a project manager who is able to tell you something won't work, and offer the best solution possible to meet your needs.

Here’s a very firm “come to Jesus” moment: project managers who say “yes” to everything, without a critical eye to project challenges, are not managing your project.

They’re just passing on requests.

Good project managers will tell you that a project is zigging when it should be zagging, if the source of the zig isn't the talent in question.

If project managers won't let you know blockers and how they’ll be solved, this should be your loudest warning siren that the person you took on to help you manage work isn’t managing.

Tough love: if you, as a client, can't rely on talent for their expertise, or you don't want to hear their advice, you might as well just go take some courses and do it yourself.

When a project is big enough to need a project manager, or has a very tight budget, you can’t really afford someone who will tell you only what you want to hear.

The project matters; ego-trippers and "yes" people need not apply.

Falling prey to this will cost you more money out of the gate, every single time, without fail.

You get what you pay for, each and every single time.

If talent isn’t delivering, consider how skilled they are, then consider if you’re paying accordingly.

I’m a pretty flexible freelancer. If I really like you as a person, your work is fun, you’re easy to work with, and/or you’re promising long-term work, my rates will drop for you.

But know that this isn’t always, or even often, the case with hiring talent.

Like all freelancers, I also have an asshole tax. If I know you’re going to fight me every step of the way, rates rise. If you’ve been misusing my flexibility and kindness, work reconfigures and rates rise.

That’s just how it is, with all of us (or it should be).

To avoid problems where the above is concerned, please research industry standard rates for the work you want done, and complete the tasks listed in this article.

Furthermore, if someone is low-balling you, they might not have the necessary skills you need to get work done. Think on it a bit.

If someone seems to be high-balling you, that could honestly mean the same thing — you’d be surprised.

A good rule of thumb is to check out their testimonials, but with a keen eye.

Pay attention to the how they are written to gauge if the testimonials are fake or not.

Pay attention if they discuss work in other spaces, like articles. It doesn’t matter how it’s written — it matters that they're knowledgeable.

Don't fall prey to sales tactics. Investigate for understanding, not pizzazz.

The most important thing about getting the most bang for your buck is realizing your buck doesn’t go as far as you think it does.

Also consider that disengaged — but experienced and skilled — talent means something deeper is going on. Something that you need to address.

More often than not, it’s that a project is failing despite their best efforts, and they’re demoralized.

Gig workers, by their very nature, have other projects than your’s to work on.

Be aware of the limited time given, and maximize it.

Fundamentally, freelancers (and agencies) are not employees, which means they aren’t required to be available at all hours. They often have other work obligations they need to attend to.

If you spend a lot of time trying to warm up to a project, chances are you won’t get the optimal work done you need.

Unless you pay for that deep-knowledge-work, like snagging an expert consultation.

If you spend a lot of time getting back to people, chances are you won't get the optimal work done you need.

If you pounce on small time-frame deadlines willy-nilly, chances are you won't get the optimal work done you need.

Consider the example of the financial advisor:

You take on a financial advisor to help get your business / your own finances back to tip-top condition.

They are charging a very high fee to do this work, so what’s the best way to maximize their time?

It’s to realize the time they’ve set aside needs to be “maximized time”.

Get your documents in order. Get the necessary paperwork ready. Prepare your tax information.

The financial advisor in question might very well prepare all of this for you, and more. But they’re also going to charge you for it.

Which could mean you’ll be paying them an exorbitant sum of money to do the thing you’re trying to fix: financials.

This also goes for freelance talent, for really any project under the sun.

If your freelancer has other obligations, your “come to Jesus” moment should include being aware that you aren’t the only client they’re working with.

Their boundaries, and agency turnaround time too, are important to keep in mind. Good talent communicates this as best they can. Be aware!

You may want to feel like you’re their only client bae, and people may be expected to treat you like you are, but you aren’t.

The smartest way to maximize a project is to maximize the time of the talent you’ve contracted.

When you do not do this, projects fail.

If your projects never run smoothly, take a breather.

Reaffirm your goals, prepare your materials, work on communication, and hire people who can help you.

Technology projects and creative projects are a challenge, for everyone. Each project is a bit different than the last, and there are always new things to consider.

But that doesn’t mean all of them need to be helter-skelter, root-canal levels of difficult.

In fact, most projects really can run smoothly.

If you’re finding yourself struggling with managing a project, or you’re finding your projects always fail, consider reaching out to me.

I earnestly want to help your stuff succeed, or I wouldn't have bothered to write this huge article about project success.

It doesn’t really matter to me where you get the help you need.

It matters that you set up your projects for success, and you do that important “pre-work” to make it so.

Because it means that tech is a brighter, happier, less stressful place, and by extension, all our work is simpler and easier.

It doesn’t have to be hard to make the magic happen. 😃

Kira Leigh is a snarky marketing nerd, writer, and artist. See her work here and send her a message if you want to work together.

Special thanks to Renato P. dos Santos for his continued support.