Cross-expertise technical communication (i.e., communicating about computing topics across levels of computing expertise) is important for workplace collaboration. However, students are underprepared because computing education rarely explicitly teaches communication, and available practice tends to occur among peers with similar expertise. We take a learner-centered design approach to inform technologies for developing these skills. We interviewed 12 industry professionals and conducted focus group and co-design sessions with 14 college students preparing for computing-related roles. Professionals emphasized adapting communication, negotiating expectations, building shared understanding, and using multiple modalities and artifacts. Students anticipated challenges adapting communication, navigating unfamiliar workplace dynamics, and communicating under fear of judgment, and valued rich, realistic practice environments that preserved their psychological safety. Synthesizing professional and learner perspectives with educational theory, we conclude that building self-efficacy through authentic mastery experiences and changing attitudes related to help-seeking are critical elements for educational technology design in this context.

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