Working with creative individuals can be a challenge at times. Especially if you’re more analytical. But that’s ok. Creative people just think differently, and that’s a good thing. It’s why you hired them.
One of the best pieces of advice I can give is to set clear deadlines. Let them know when you need to see a first draft, second draft and final. Doing this helps the project stay on track.
The second bit of advice I give everyone is to be respectful. When a creative person presents you with something, they take what they’ve created very personally. It’s a representation of their self and the time and energy they’ve spent in the creative process. If what they present it’s what you need and want, that’s fine – tell them. Just keep it objective and explain as clearly as possible what it is that you feel needs to be different. It’s never a bad idea to sit down with them and have them do some sketching with you. This allows the creative person to check with you on direction in real time and get a good idea of what you want.
Lastly, it’s important to remember they’re the expert, not you. You’ll still want to make sure they’re actually an expert, so ask them to explain their though process about the design and justify it if you’re not convinced.