This is definitely a grey area. CIC really needs to provide more details explaining the question. The Travel History form for India and Pakistan Country Specific forms clearly asks for Entry/Exit for each travel which makes it clear. BUT Question 8 of IMM5669 does not explicitly ask for this. I mean what if a business executive travels frequently out of the country for meetings? He is still employed but travelling at the same time. You would have some drastic overlaps. Same thing goes if you are a student and travelled for a student project or internship term. You are still a student at that time but was travelling for that purpose.
Also, the form only allows you to only enter Year and Month. So you could potentially have parallel events occur during the same month in a situation where you are working and travelling within the same month. Also, note that in the last column it asks Name of Company, Employer, School, Facility, as applicable. This implies to me that the intent is to capture work history, unemployment, education, and long term travel etc. For example you travelled to another country for volunteer work..then yes this should be put down but short vacation's would be questionable.
Unfortunately, this question is subject to personal interpretation. If Question 8 of IMM5669 actually required you to enter Entry/Exit for overlapping time periods then why in the world would they even create the Country Specific Entry/Exit Travel History form since this information would have to be provided in Question 8. If they wanted such specific information they would include a day field as well.
The two questions serve different purposes in my opinion.