The above questions are negatively framed, and if you take the question literally you might get negative too.  You might go into gory detail about how dysfunctional your last work environment was.  Or you might take the difficult boss question as an invitation to vent.  Or you might answer the weakness question by offering a laundry list of what you hope to improve about yourself.  As a former recruiter, I often knew where my candidates had issues based on where their answers would linger.  The guilty can’t help but confess, and when candidates would go on and on about something I took that as a sign to probe further. 

Instead of emphasizing where you are uncomfortable, prepare truthful but concise responses to these tough job search questions and move forward quickly.  Go back to your talking points that answer positive questions:  what are your strengths, what are your biggest achievements, how are you a fit for this job.  Negative questions look to the past but the job is in the here and now.  Negative questions answered literally are disempowering because they focus on what went wrong.  You must resist the temptation to expand on these negative questions and instead weight your interview towards positive answers.