During the fighting of the Overland Campaign of 1864, Ulysses S. Grant is reported to have said to President Lincoln that he proposed to fight it out along that line all summer if necessary to defeat rebel armies led by Robert E. Lee. Depending on how one views that statement, it could have been an understatement or an exaggeration. It would take longer than the summer of 1864 to defeat Lee’s army and conquer Richmond. A lengthy siege of the city of Petersburg was followed by a daring but ultimately futile attempt to escape, leading to the famous surrender at Appomattox . Yet in one line of view, Grant did not fight it out along that line all summer. Instead, after suffering a bloody reverse at Cold Harbor, he shifted his direction and sought to move on Petersburg rather than continuing to try to find some way of attacking Richmond directly. He fought all summer, but not on the same line he had fought in the first four weeks of the war, in the eyes of many historians.
I have a great deal of empathy and compassion for people as awkward as I am. Being a person of great awkwardness, shyness, and a deep native reserve and timidity, it is immensely difficult for me to set the stage for difficult conversations. I may fret over what I want to say for weeks or months, lose large amounts of sleep, pray and fast and reflect, and often find that all of the concern has been for naught because the message I am trying to send simply does not get across. At least in my observation, this does not appear to be an uncommon experience. As I have been the initiator of many an awkward conversation or interaction, so too others have blindsided me with equal awkwardness, and likely they too have spent a great deal of time and effort and concern and care preparing and laying ground for a difficult conversation only to find it go awry because it triggered some kind of panic or alarm in me.
The timing of when one plans difficult conversations matters a great deal. One of the most crucial steps is ensuring that something is a good time for both parties. It is easy for us, when we are concerned about something and want to get it off of our minds and release the burden on our hearts, to think about when it is most convenient for us to engage in these conversations at the time of our convenience. Often this does not prove to be convenient for others–more than a few times I have found my own sleep harmed by people who felt it was absolutely necessary at 11:30PM to have a serious conversation I was entirely unprepared for, which is not conducive to having conversations that are enjoyed by all parties with mutual pleasure. No doubt my own efforts at having difficult conversations have been equally inconvenient or unwelcome to those I was conversing with. Before we have difficult conversations, then, we need to have a talk before the talk, one that sets the stage, finds some common ground, and makes the conversation less difficult. We need an agenda, and some kind of mutual consent to agree on a conversation, because where there is coercion there will never be the sort of meeting of minds, much less hearts, which people desire from their communication with others.
Like Ulysses Grant, we may pride ourselves on or even be praised by others for having a bulldog-like tenacity. Before we become carried away, though, by this sort of self-congratulatory attitude, we need to examine to what ends and by what means we are being tenacious. Are stubborn for our own self-interest alone, or is our tenacity a strong sense of loyalty to our commitments? If it is merely the first, then all of our stubbornness merely leads us to run over others and deny them their own freedom to make decisions. If it is the second, we may well be unsuccessful, but there is at least nobility in what we are about. It may take all night to resolve problems with someone, it may talk all summer, and sometimes, if we are wrestling with ourselves as we ought to do, it may take our entire lives to wrestle with and overcome the burdens that we have been given. Be that as it may, much depends on how we wrestle with those issues, in the realization that other people are not simply the problem, but are people who even at their most frustrating and difficult are worthy of respect and honor and even love.
 See, for example: