When you're a business owner operating in the world of agencies and freelancers, it's easy to look at the world in black and white. Some designers are great, the others suck, and there's a little wiggle room in there for the 'average' crew too.
You might think that freelancers think much the same way you do; that there are good clients and bad clients. However, when a designer has been working with different clients for a long time they learn that there's a little more nuance to this dynamic than meets the eye. You see, everyone has different expectations and everyone communicates in different ways. What might be true for one client may not be the same for the next. What one client loves the next one might hate.
Perhaps a good analogy (just in time for Valentine's day!) is that of a relationship. Everyone has different needs and expresses those needs in different ways. If you're simply a terrible person, nobody will ever want to date you. If, on the other hand, you have a moderate level of self-awareness and know vaguely what you're looking for, you'll eventually find somebody else that you can connect with and make things work. When you meet them, it will feel like you just ‘click’.
Then, of course, there are those people. The ones that seem to make their relationships look like a daydream to you and I. The reality is that they face the same challenges as everybody else, but they have the self-awareness, emotional health, and confidence to communicate their needs without fear of being judged. They hold up their end of the arrangement and have the decency to admit when they've made a mistake. For them, it’s not a question of ‘clicking’ because they accept that the long-term health of the relationship is as much their responsibility as anyone else’s.
Step one: Listen
It's the first rule in the book. When you hire somebody for their expertise you should pay them the respect of treating them like an expert. That means taking their advice seriously and paying attention when they have requirements of their own. You may also have to read between the lines a little to be really effective. For example, if a freelancer says they're very busy then it means their availability is limited. Rather than being critical, see this is a chance to understand your contractors better.
Step two: Be confident in what you know...
It's ok to think critically about other people's work, as long as you're thinking critically about your own first. Nobody knows your product, your audience, or your vision as well as you, so take this chance to really understand what it is you're looking for. Being ready to answer questions like "what are your brand values?", "how do you want customers to feel?", and "what's the most important thing for your customer to know about you?".
Step three: ...and what you don't
Never lose sight of the fact that you're paying somebody to do a professional job. If you're not sure exactly what you want they are there to help you figure it out. Be upfront about the fact that it could take several iterations to get the finished product right. Don't be afraid to tell them that you know nothing about design. As long as you set these expectations clearly they will be ready to meet them.
Step four: Give mindful feedback
I'll never forget one piece of feedback I got on a particular section of work. Scrawled lightly in the comment section it simply read, "needs more here". This is so particularly useless that I find it hard to believe the writer wasn't intoxicated whilst writing it. Don't ever do this to your freelancer. Open communication is the key to every healthy relationship, so be as specific as you can. If you can't be specific, explain why. Your freelancer can help you get there as long as they understand what the challenges are for you.
Keep these four golden rules in mind and you'll be well on your way to a healthy working relationship with every designer you know.