Redesigning an established website like Craigslist comes with a number of challenges, working with a small team on a design sprint format makes the challenge pool bigger with the time constraint. Given the limited time frame, we needed to prioritize which aspects of Craigslist to focus on for redesign. Determining the key pain points or areas for improvement requires careful consideration and collaboration with stakeholders to ensure the most impactful changes are addressed.

The team was well aware of the challenges from the beginning of the project, we knew the time constraints will present issues like limited user research, limited data availability, less time for iteration and testing, and many more.

Craigslist had a unique challenge of visual overhaul vs familiarity, redesigning Craigslist would involve finding a balance between modernizing the visual aesthetics and maintaining the familiarity that users associate with the platform. Users might be resistant to drastic changes that deviate too much from their accustomed experience.

To address these challenges, it was essential for the team to establish clear project goals, align priorities, and leverage the team's cross-functional expertise to maximize efficiency and collaboration. Regular communication, setting realistic expectations, and maintaining a focus on the most critical improvements would help overcome time limitations and deliver a meaningful redesign within the given week.