Word 2016 Crashes when trying to insert new citation

I would first determine if the issue is document specfic.

Open a new Word document and try inserting a citation.

If a new document does not crash then you will want to try the following steps on the document that does crash:

 http://endnote.com/kb/81143

If the new document crashes as well then please try the following steps:

http://endnote.com/kb/81003

If that fails to resolve the issue please contact Technical Support

Technical support

For help using EndNote

Monday – Friday, 9 a.m. – 8 p.m. Eastern (GMT -5)

+1-800-336-4474, press 4

Submit a technical support request

http://ip-science.thomsonreuters.com/techsupport/