Against a backdrop of private sector investment in developing countries, companies and local communities typically face difficult land rights and land use contexts. It is therefore critical that communities, companies, and development practitioners develop and use constructive tools to help manage challenging relationships and circumstances. This Advisory Paper summarizes some insights that the Compliance Advisor Ombudsman (CAO) has gained from its experiences with communities and companies in the arena of land, private sector development, and conflict. Specifically, this Advisory Paper highlights recurring challenges faced by the communities and companies CAO has worked with—including competing community perspectives on private sector projects; competing national and local land tenure systems and development priorities; histories of land conflict; and information imbalances between companies and local communities—as well as competing development perspectives. It then focuses on some of the tools CAO has used to help address these challenges, including the use of third-party neutrals; participatory monitoring and project evaluation; company/community collaboration and land management; and strengthening grievance and redress systems. This paper was originally prepared as a submission for the 2014 World Bank Group Land and Poverty Conference. It has been revised as an Advisory Paper to articulate the issues and challenges raised by complainants related to land, and to highlight some of the practical tools CAO has used to assist communities and companies in managing these challenges