Background: Planners will engage with people with cognitive disability and complex support needs in the Australian National Disability Insurance Scheme, but the specific skills needed to build sustainable plans with this group are not yet known. Method: A qualitative study was conducted to explore the barriers and facilitators to planning with people with cognitive disability and complex support needs. Focus groups were held with 99 planning practitioners across metropolitan and regional locations in New South Wales, Australia. Results: Thematic analysis showed planners need to build a partnership based on mutual trust and respect with a person with complex support needs and harness a range of skills to respond to individual support needs, learning capacity, systemic hurdles and life challenges. Conclusions: Planner skills can be used to address barriers to planning for people with cognitive disability and complex support needs. Gaining skills took professional support and personal commitment.