Most positioning failures aren’t intelligence failures — they’re context failures. Consultants, AI chatbots, and internal teams all produce generic output when they’re asked generic questions by people who never gave them the context to be specific.
The Messy Middle is a daily comic strip about a New York marketing team navigating the chaos of AI adoption. New strips every week.
What is the Messy Middle? It’s that awkward phase between “we should use AI” and “we actually use AI well.” The part nobody talks about at conferences. The part where tools don’t integrate, prompts don’t work, and the intern somehow figures it out first.