  AI technologies continue to advance from digital assistants to assisted
decision-making. However, designing AI remains a challenge given its unknown
outcomes and uses. One way to expand AI design is by centering stakeholders in
the design process. We conduct co-design sessions with gig workers to explore
the design of gig worker-centered tools as informed by their driving patterns,
decisions, and personal contexts. Using workers' own data as well as city-level
data, we create probes -- interactive data visuals -- that participants explore
to surface the well-being and positionalities that shape their work strategies.
We describe participant insights and corresponding AI design considerations
surfaced from data probes about: 1) workers' well-being trade-offs and
positionality constraints, 2) factors that impact well-being beyond those in
the data probes, and 3) instances of unfair algorithmic management. We discuss
the implications for designing data probes and using them to elevate
worker-centered AI design as well as for worker advocacy.
