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This report of the 14th Virtual Dialogue by the UN Women Training Centre’s Community of Practice (CoP) summarizes discussions on why privilege and power matter for training for gender equality, and how they can be addressed through, and within, training. Training prompts questions, reflection and dialogue, thereby offering a critical entry point into the examination of the structures and systems of privilege and power that underlie gender inequality. By thinking about privilege and power in more complex ways – and considering different dimensions of empowerment – training for gender equality can disrupt some of the privileges that we take for granted, and help us consider how we can each use our power and privilege to advance equality.