I have a several years experience doing visual identity design. I primarily do them for companies from small startups to mid-size businesses.
I have been paid by a friend who used my services for their business. Now he wants a personal logo for his brand as an influencer/thought leader.
I found this to be abstract and challenging so I asked for a few keywords they'd use to describe himself which he provided. I was also given a Pinterest mood board which consisted of dark imagery. Primarily B&W photos of lions, lightbulbs and trees. The first round I got some feedback and I improved some of logos they seemed potentially interested in and provided 2-3 new ideas.
They followed up they "weren't feeling it" and it's not what they want. I'm a bit embarrassed I don't know where to go from here. I'm good at understanding a companies concept and brand direction and designing around that. Based on feedback (or one of my award winning designs - no feedback!) I can resolve a logo that compliments the brand's messaging.
I've done research on influencers logos as well as logos for some of the things he wants to be a thought leader in and I feel I'm not missing the mark by any sizable margin. I've provided different types of logos from logomark + type that felt a bit more corporate, to a graphic mark with type, a hand-drawn tree inspired logotype and even a heavy metal custom lettered logo since they identified with this "hard rock bad-ass persona" just to elicit a response.
I don't know how to extract their expectations at this stage. I will admit this is a side project (and priced as such!) and perhaps these could be improved (but that's the point of iterating in 3 rounds). Unfortunately I don't know where to go from here. I thought about creating a questionnaire he could fill out but I don't even know what to ask anymore. I thought about "check which of these logos closely resemble your vision" or something along those lines.
I could use some ideas you've used in the past to get more information from your clients, I'd really appreciate it.