At what point would you decide that you need to fire a creative? We have a designer who is talented and I liked the work that they had on their site but they're really not able to come up with what we're looking for. I'm not good at feedback on creative in terms of actually helping someone to pick up what I'm putting down, so I'm not sure where to go from here.

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I think this is more so of a learning lesson for you. You have identified your weaknesses. In order to be a manger, you will have to learn how to give out feedback or you will find yourself replacing creatives a lot.

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Open and honest feedback first and foremost so they can at least try to improve. If it’s not working after trying to get them to improve, best to move on. Are they in their probation period? Sometimes it takes a while for someone to ramp up and understand what the bar is at the company.

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I would ask yourself if you can find ways of improving your feedback. As you stated, the designer is talented and has a great portfolio. Have you approached them about the issues? Sometimes, all it takes is a meeting to create a better understanding. Feedback given should be specific to goals. Not so much on a color or font choice unless it is specific to the goal of the project. Give the designer the ability to think about the problem you present as they can come up with a solution that may work better than the one you had in mind.

You need help. If you fire this person while admitting you are not a good manager when it comes to feedback, you will feel bad. But more importantly you open yourself up to a legal action. I’m a creative who consults with people on the brand side who need to know how to work with creative people. I teach evaluation and feedback techniques. If you want to jump on a call to explore your options I’m happy to take some time. If you need more than a free consult call, I’ll give you a fair one page proposal.

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