I'd be happy to field that.
At this stage it's very simply conversations with those who have a deeper understanding of brand, brand architecture, and brand development. You raise probably the most important point of discussion (which has been around for a long time, I'm sure) - How do the brands of the Foundation and the projects, especially WP, interlock and affect each other.
Of course we have lots of hunches, and I certainly spend a lot of time talking about this internally and with outside people. By engaging with people who have managed this kind of situation with hundreds of other organizations - especially non-profit, web/online properties, and (broadly) higher-education organizations, we're hoping to get some preliminary advice around what our brand means and how to strategically plan with brand in mind.
Initially that's conversations, but if we do proceed with someone (hopefully pro-bono, but we're considering options) it would initially include lots of outside analysis of the Wikimedia brands, who else is here, what it all means. In fact the first phase, which is classically the biggest part of the work, is just helping the client understand their situation. In this case it's essential that we have input and advice from many sources, not the least of which would be the community of volunteers. I would suggest we have a pretty fascinating, complex situation :) Many interwoven project brands and a lesser-known WMF brand. And on top of that we one of the most successful global brands on the web.
After research/analysis it may or may not include advice or changes to the brand, improvements - or maybe nothing at all. It's worth mentioning as well that brand does not necessarily include the 'visual' aspects of trademark or look and feel of the visual identity. More importantly it's about building a notional understanding of brand - words and ideas that best represent the mission, the projects, the people, the ideas - a simple approach. From there we would hope to significantly streamline our communications work, improve the simplicity of the fundraising work, and hopefully just make it easier for the outside world to understand what the foundation is and what we're up to.
Still just conversations at this point, but I look forward to keeping you posted on how this work proceeds.
Thanks for your questions...