Recently I was asked to design a logo for a non-profit organization, and the challenge at this point is to define the problem, more than it is to create the solution.
The project is still ongoing (it's pro-bono, so ostensibly I can take the time I need, rather than meet a short deadline). But identifying visual symbols that will relate to the concepts that the organization wants to portray has been quite difficult.
To this point, I've shown two concepts, and neither were what the client is looking for (The first was, but once they saw it, decided against it). It's a classic "I'll know it when I see it scenario." I call it skeet shooting in the dark.
As a designer, it's critical that we are able to deal with ambiguity. We need to be able to invent meaningful symbolism merely than create surface decoration.
Over 20 years ago I formulated my General Theory of Design: "Design consists of creating things for clients who may not know what they want, until they see what you've done, then they know exactly what they want, but it's not what you did."
Thankfully in my experience, the antithesis of the Theory has been true in most instances: "Clients who know what they want will provide a design brief, and evaluate all designs based upon that brief."
Regardless, (and this is where leadership meets design) those for whom we work expect us to lead them. That's why they hire us!
The solution to the ambiguity problem seems to be time and concentration. Once I find that the assignment has turned into a skeet shoot, it's time to think about it in a completely different way.
Maybe I do need to assign it a deadline. There's nothing like a deadline to inspire!