Inside a make target you can compare the timestamps of two different files and determine a course of action based on this:
compare:
FILE1=$$(stat -f "%Sm" -t "%m%d%H%M%y" file1.yml);\
FILE2=$$(stat -f "%Sm" -t "%m%d%H%M%y" file2.yml);\
echo "FILE1 timestamp is $$FILE1"
echo "FILE2 timestamp is $$FILE2"
if [ $$FILE1 -gt $$FILE2 ];\
then\
echo FILE1 has been modified more recently than FILE2;\
else\
echo FILE2 has been modified more recently than FILE1;\
fi;