The Hard Conversation (you know you need to have)


The Hard Conversation (you know you need to have)

November 29, 2021

The holidays always present us with many interesting relational dynamics.  Most of them are good.  It’s great to reconnect with family and friends and share in the all warm-fuzzies surrounding the holidays. 

But, if we are going to be completely candid, there will also be situations that will be seriously uncomfortable – perhaps even scenarios we would just as soon avoid.  Relational conflicts are always difficult, but around the holidays they can be especially unsettling.  Part of what makes them so frustrating is that some of these conflicts have long and complicated histories, and in those moments when we around those people all we want to do is leave unscathed.  Because we have tried being nice – and all we heard in return was, “Yeah, well if you hadn’t….”

So, every holiday, it’s just easier to say, “I am not going to do that again!  If they want to sort this out, they can come back our way.”

I get it.  Been there and done that.  It’s really hard to be the one who is always trying to mend the fences only to be rebuffed for those efforts.  That said, I know there are also situations where we feel led to make another attempt.  Each year where something remains unresolved, we see it effecting more people.  The wounds go deeper.  The resentment becomes more intrenched.  And then the conviction of the Spirit of God hits.  We hear him speak (lovingly but persistently), “I want you to try again!” 

Once that prompting comes our way, it helps to put together a strategy for that conversation.  As one who has navigated that conversation more than a few times (sometimes successfully, sometimes less so), let me share a few lessons that might helpful in developing a more effective approach.


Sometimes prayer can seem perfunctory, and often (even as believers) we can be half-hearted in our prayer efforts, because of our disappointments over those times when prayer didn’t seem to make a difference.  Why bother?  Consider this, let’s admit that God knows more than we do.  Every situation is we enter is multi-layered, and just because something didn’t go according to our prayer plan, that doesn’t mean God wasn’t working.  Besides, in these difficult conversations we want every positive vibe working in our favor.  Even if prayer only helps a little bit – that little bit may be extremely valuable.  It’s also quite possible that by quieting our hearts in prayer, we create the internal space for the Lord to graciously impart an idea that will enhance the likelihood of our being heard.  There might even be some wisdom in inviting a few people to join the prayer effort.

Sample prayer

God, would you help me do this well!  I confess, I’m nervous about this conversation.  I’d rather not have it.  I am afraid I could make things worse.  My emotions may also get the best of me and I hate it when that happens. But I want this relationship to be better. I’m tired of the tension, the avoidance, and the talking behind each-other’s back.  Would you do a work by your Spirit to prepare their heart and my heart.  Open this situation up for a reconciliation – even if this is but a first step.  I’m willing Lord.  I pray they are too.  May they be open to me.  May I open to them.  Take what was meant for destruction in this family/friendship and turn it to good.  In Jesus name I ask.


Once we decide we need to have the hard conversation, figuring out how to start it is one of the most complicated parts of the process.  In the book, Crucial Conversations, the authors talk about the “Hazardous Half Minute” referring to the first 30 seconds of a difficult conversation. It’s a big deal!  If we fumble the start, we probably won’t see a positive outcome.  One of the things I have found helpful is to begin by owning and admitting to my own nervousness and insecurity, acknowledging- that this could go poorly.  That is not what we want to see happen, but given the history and heartache, its understandable that this would be difficult for everyone.  That simple act of humility often has a way of defusing the tension at the front of the conversation.  Those who know “something’s coming” (especially after long-standing conflict), half expect that we’ll come in powered up with our finger pointed.  But, interestingly, if we are willing to express our own misgivings and anxiety, it allows us to side-step the defensiveness that might otherwise be a hurdle to the process of making things better.

Sample prequalifier

I have been looking forward to trying to make things better between us, but I also need to admit, I’m nervous about this.  I’m not always great with words, and I don’t want to make things worse.  I have prayed a lot about our conversation, and even though there is a good bit of history and hurt, which makes this even more complicated, I’d rather try and do this poorly, then let what has happened between us to keep us apart any longer.

Personal Responsibility

Every long-standing relational conflict has many chapters and multiple characters, and we are typically most aware of those times and places where we (or those we care about) have been hurt.  Once those offenses become layered, it’s extremely difficult to recognize our own part in the breakdown.  We tend to evaluate our actions through the grid of best intentions, but we judge other people’s action through the grid of evil intentions.  We say things like, “I know why they did that!  They knew if they went there, things would blow up!  I was just defending myself!”  The truth is, depending on the day, we can all be rightly /wrongly motivated.  No one is purely one or the other.  Taking personal responsibility for the ways we have contributed to the misunderstanding and relational chaos opens the door to real dialogue and forgiveness.  Be specific and genuinely apologetic.

Sample statement of personal responsibility

I want to begin by talking responsibility for the ways I have contributed to this challenging situation between us. If you’d allow me, I’d like to make a couple specific apologies.  I did not give you the benefit of the doubt when this happened ___________.  I allowed myself to believe the worst.  I didn’t ask you about it.  I should have.  I’m sorry about my failure to do so.  I also feel badly about the way I responded to our last communication ____________.  I was angry and upset, and because of that I said things I regret, and again I am truly sorry.  Might you be able to forgive me?

Pose Questions

One of the biggest mistakes I have made in processing relational hurt and misunderstandings is that I thought I knew what was “really” going on.  More often than not, I didn’t.  I read the situation wrongly or I only had one piece of the story and there were some important elements missing.  The best antidote to making poor assumptions is to ask sincere questions.  A great intro line is, could you please help me understand?  Questions accomplish two things.  First (and this is critical), our questions illustrate our desire to understand.  It shows we are no longer interested in rehearsing the same arguments and excuses that have been revisited time and again.  We want to move past them and try and understand what was really taking place – at least in the mind of this other person.  Second, if we are genuinely open to hear, and the person is willing to tell the truth, then we have an opportunity to correct their misinterpretations as well.  Our interest in understanding their perspective opens the door for them to do the same with us.

Sample questions

I know there are a lot of things we could talk about and I think one of my bigger mistakes was that I assumed I knew what you were thinking/intending when this happened _____________.  Can you help me gain a better picture of what was actually transpiring from your perspective?  Can you help me understand _____________?

Practice Tone of Voice

We are all familiar with the statistics regarding non-verbal communication.  Depending on the research, 80% of our communication happens non-verbally.  But what is being studied more widely now and is particularly relevant for this topic is that non-verbal cues are significant contextually and are most important when there are discrepancies between what is said and how it said.  In other words, in casual conversations we take people’s words at face value, but in emotional charged interactions we are highly sensitive to non-verbal cues – especially when the words and tone don’t match.  We all get this instinctively!  How many times have we thought (in the middle of an argument), “I don’t believe a word they are saying!!”?  Why do we draw that conclusion?  Typically, its because something doesn’t match – words, posture, eye contact, tone of voice.  One is betrayed by the others.  So, if we are the one trying to move a relationship in a new direction, it seems wise to ensure that we are not inadvertently sending mixed messages.  Practice can help ensure congruency!

Prospects for success?

I can imagine, after reading all this, some of us might feel less confident about the prospects for change.  And yes, there is a lot to sort through.  It is as hard as it sounds.  And maybe too hard for some.  But, one of the things I have often had to tell myself (in these moments of hesitation), is that the only real choice we have is which ‘hard’ we prefer to perpetuate?  We don’t have the option of opting out of the hard altogether.  The only choice we have is what kind of hard do we want to endure? 

Do I want the continued hard of broken relationships that get worse with every passing year, effecting more and more people, becoming a relational curse that every new generation must revisit and invariably repeat?  OR, do I want to be courageous and embrace the hardship of making an attempt at reversing the curse and setting up the next generation with a little less heartache and a little more freedom than what I got to experience?

Do all that you can to live in peace with everyone. 
~Romans 12:18

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