In this paper, we introduce usability workarounds that take place in system design during IT tendering, and usability evaluation around work that characterizes an iterative IT product development. We claim that highly formal and detailed verification criteria and procedures in tendering cause usability workarounds by the IT vendors. To avoid workarounds and to bring usability activities more around work during IT tendering, we suggest applying open-ended usability test tasks for system validation and usability problem qualifiers as criteria.