This paper offers an explanation of how collaboration leads to abstract and flexible problem solving. We asked the individual and paired subjects to indicate 3/4 of 2/3 of the area of a square sheet of paper and found that (1) they primarily folded or partitioned the paper rather than algorithmically calculating the answer, (2) they strongly tendened to backtrack and confirm their proto‐plans on externalized traces such as creases on the paper, and (3) only the paired subjects shifted to the (...) mathematical strategy in their second trials. Based on these results, we propose that two factors, individuals' activeness in choosing and confirming the initial strategies and the frequent role exchange between task‐doing and monitoring in collaborative situations, interact in collaboration to generate various solutions differing in the degree of abstraction, which are then reflected upon by the participants to lead them to abstraction. (shrink)