Dealflow.eu · Web Summit 2026← All side events

Challenger Safety: The Missing Link in AI Adoption

by Carolina Palombini

WhenTuesday 10 November, 19:00–20:00
WherePortugal Tech Week Palace
AccessFree registration
WhoFounders, team leaders and AI adoption managers
Going24 registered on Luma
FreeAIStartup
Register ↗☆ Save to my planGoogle CalendarCalendar file (.ics)

About this event

AI creates enormous possibilities for innovation. But capturing them requires people who feel safe enough to experiment, challenge how things are done, and propose new ways of working.

Challenger Safety is the highest level of psychological safety. It opens organizations to new ideas while also protecting them from their own enthusiasm, creating space to question assumptions, raise concerns, and make better decisions about AI.

In this interactive masterclass, we’ll explore how leadership behaviours can either encourage constructive challenge or create quiet compliance. Through storytelling, reflection, and practical exercises, you’ll learn how to build a culture where people feel safe to challenge, experiment, and turn AI possibilities into meaningful innovation.

What You’ll Learn

Why Challenger Safety matters for AI innovation — and how it creates the conditions for people to experiment, challenge existing ways of working, and propose new solutions.

How to spot quiet compliance — recognise signs that your team may be withholding ideas, concerns, or alternative perspectives.

How leadership behaviour shapes constructive challenge — identify subtle behaviours that can encourage or unintentionally shut down questioning and experimentation.

How to balance experimentation with better judgment — create space to explore AI possibilities while questioning assumptions, risks, and unintended consequences.

How to strengthen Challenger Safety in your team — leave with practical leadership behaviours you can apply to encourage constructive dissent, smart experimentation, and better AI decisions.

By registering for this event, you agree to the PTW Palace Visitor Terms & Conditions. Your registration data will be processed and shared between Portugal Tech Week and its partners under GDPR for event coordination and community updates.

Description from the organiser’s page.

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