This study investigated perceptions of and engagement with the concepts of planning and problem-solving, within a weight management sample. A total of 53 participants (62% female, 20–74 years old) completed a semi-structured interview and quantitative measures after a 16-week weight maintenance period. Preliminary weight maintainers (who had maintained losses of, at least 10% of their original weight) were compared with heavier-than-baseline participants (who had re-gained more weight than was originally lost). The maintainers exhibited stronger problem-solving skills (p < .05). The heavier-than-baseline participants tended towards non-rational problem-solving styles. Qualitatively, the maintainers described more planning events and were more accepting of mistakes than the heavier-than-baseline participants. Implications are discussed.