Stalemates frequently obstruct disaster risk management related initiatives, including related to risk financing. They can arise from misaligned stakeholder objectives and a cognitive effort to avoid decision-making under uncertainty. Participatory action research techniques can be useful for overcoming stalemates but have not been examined in the context of disaster risk management. To fill this gap, we explored how participatory techniques could overcome one disaster risk financing related stalemate: the case of landslide insurance in a highly landslide-prone location, Sitka, Alaska. Landslide insurance in Sitka is a classic stalemate, as diverse stakeholders see the value of offering a landslide insurance policy, but their respective concerns and information gaps stymie their ability to feel confident in decision-making making landslide insurance generally unavailable. Utilizing a series of inclusive interviews and workshops as our participatory techniques, respondents describe how the workshop engendered confidence in the prospect of landslide insurance, specifically by brokering new relationships and serving as a catalyst for new public-private partnerships while effectively reframing the landslide risk financing conundrum. However, they also note that a new market for landslide insurance requires sufficient state or Federal funding support, improved probabilistic landslide models, and sustained consumer demand. This suggests that participatory techniques can play an enabling role in overcoming stalemates, but only if certain conditions are in place. These findings may have relevance to policymakers facing stalemate-related obstacles in disaster risk management.