  Software startups develop innovative, software-intensive product and
services. This context leads to uncertainty regarding the software they are
building. Experimentation, a process of testing hypotheses about the product,
helps these companies to reduce uncertainty through different evidence-based
approaches. The first step in experimentation is to identify the hypotheses to
be tested. HyMap is a technique where a facilitator helps a software startup
founder to draw a cognitive map representing her understanding of the context
and, based on that, create hypotheses about the software to be built. In this
paper, we present the Digital Mentor, an working-in-progress conversational bot
to help creating a HyMap without the need of a human facilitator. We report the
proposed solution consisting of a web application with the backend of a natural
language understanding system, the current state of development, the challenges
we faced so far and the next steps we plan to move forward.
