From the testimony this is what I read about the Flynn thing:

“I hope you can see your way clear to letting this go, to letting Flynn go. He is a good guy. I hope you can let this go.”    This was when the two men supposedly discussed about the job.

Many GOP Senators jumped on that one word "hope" and concurred that it was not an order.   Then came Senator Kamala Harris from CA.    She put this out to the FBI Director:

In my experience as a prosecutor, when a robber held a gun to somebody's head & said "I hope you will give me your wallet," "hope" wasn't the operative word.

What do you think folks?

END OF MESSAGE

1.   Your boss says "I hope you finish that widget order this afternoon".

2.  You are a teenager and ask to borrow the car.  Dad says,  I would like you to bring it back by 6:00 without any damage.  

3.  Your hooker tells you she would like to use a condom.  

Are you going to do as they say or are you going to ignore them and do the opposite?

“Most obstruction of justice cases, the person involved doesn’t come out and say, ‘Oh, I’m going to obstruct the investigation!'” he said. “If they do, it’s a wink, it’s a nod, it’s a hint.”

1)  You will finish the job in the afternoon if you want to make your boss happy.  BUT if he really absolutely  needs it done that afternoon he should be clear about that and say something else like "I need it done this afternoon".
2)  It is your dad's car so he gets some say, but in any case for this example the dad should be saying "I hope you bring it back by 6:00 without any damage."  The damage parts seems obvious, but again if the time is important dad should say "I need it...."
3) Again you choose bad words.  If your hooker says "I hope you will use a condom" you will either do it, OR perhaps respond with "I'd rather not" and then she can decide whether to be clear and say non condom, no play.

I think the context of kicking everyone else out of the room causes the potential problem, not the words.  But I think the words give him wiggle room.

Once again, words matter.

Here is the results of you answers.

1.  The boss is Donald Trump.  You didn't get the job done - you're fired.
2.  Dad is Donald Trump.  You got the car back at 6:30.  You give up car privileges Until you buy your own car.
3.  The hooker is Ivana.  You end up with Donald Trump, Jr, as your son.

You got that right.

In every case you did a lousy job not getting done what was "hoped for" so the punishment is justifiable.  It is not disobeying an order, but rather not meeting expectations.