How to Turn a Bossy Toddler into an Assertive Playmate - "-Encourage the toddler’s fighting spirit without encouraging obnoxious behaviors likely to do social damage down the line. -Normalize sharing. Structured scenarios can help kids grow comfortable with sharing and help them see there’s no need to be paranoid. -Supervised play in a safe place with a sibling, cousin or familiar friend gives a toddler opportunities to stretch those sharing muscles.