How To Handle Difficult Discussions When They Get Off Track

How To Handle Difficult Conversations

We all want to become more effective at having difficult conversations.

We plan. We strategize. We even play out in our minds how the conversation will go—one idea, comment, or question at time. Why? We do this in the hope that understanding and agreement can and will happen on both sides of the table.

But even with our preparation, our conversations don’t always go according to plan. They run off the rails, take a swift direction we rarely see coming, and people leave feeling demoralized or belittled. We all know what it’s like to walk away from a conversation that we are still carrying hours, days, or even years later.

It doesn’t have to be this way.

We recently wrote about Six Simple Steps to Having Effective Difficult Conversations and provided a practical guide to help you navigate those hard, often unexpected exchanges with your boss, co-workers, or others in your life.

Tools are great, but what if the other party isn’t willing to use them? What do you do when your boss blows up or your co-worker turns helpful dialogue into a judgment-filled rant?

Of course, it’s a huge advantage to have all parties involved in the conversation, working towards a win-win conclusion—but sadly that won’t always happen.

Regardless of how well you prepare, difficult conversations will and do go off track.

The good news is that even when the conversation derails, there are some tried and true methods to ultimately keep the train moving forward.

Here are a few common ways that difficult conversations go awry, and what to do about them.

The “Ambush” Scenario

The first step in having successful conversations is to recognize the tell-tale signs of a difficult one. Look for a change of tone, shift in body language, or simply an all-around awkwardness that sets in on the environment.

Recognizing that a conversation is shifting into difficult terrain can often help you plan for a continuing conversation that’s coming—however more often than not, the conversation can’t wait. It begins and gains momentum the minute you recognize it’s happening!

Unplanned difficult conversations can feel like an ambush. Often it will seem like the other party is dumping all their thoughts and emotions onto your shoulders without warning.

When this happens—take a deep breath.  As soon as the other party is finished speaking, use tentative language to try to re-frame the conversation.

How do you do that?

Try saying something along these lines. “I can tell you are upset, and I’d like to work through each of these issues. Can we schedule a time to address the points you are presenting? I want to honor your feelings, and give them the attention they deserve.”

You don’t have to use those exact words, but make sure the other person understands that you don’t want to avoid the conversation. You are just making room for it in a healthy way that will be more likely to lead to a win-win conclusion.

It’s okay to set boundaries and agree to hold the discussion for later. If the other party presses to have it now, start to give them the soonest available times you have for working through the issue appropriately.

For an effective outcome, both parties need time to dig, process, and be able to relate their “puzzle pieces” of perspective and emotions. This is essential to filling out the picture of what happened, what is happening, and what needs to happen to work towards a healthier conclusion for all involved.

Without both parties even recognizing they are in a difficult conversation, what’s appropriate will immediately go out the window—leaving the dialogue off the rails right from the start. Take time to find what’s appropriate!

The “Bad Frame” Scenario

Imagine yourself late Friday afternoon, sitting in your boss’ corner office while trying to work through a difficult conversation. The walls are closing in and the weekend can’t arrive quickly enough for either of you. Odds are long that a win-win conclusion will emerge from that exchange!

A difficult conversation moves forward when both parties are given room to bring their puzzle pieces to the table, share tentatively, and listen to the other party with the goal to understand—not interject or punish.

If one party feels that the other is clearly favored by the environment (boss’ office), or the participants (three against one), the conversation will quickly get off track.

Even worse, one party may completely dominate—feeling that they’ve shared what needed to be shared, the other person has “heard them,” and that’s all that matters. This is an all too common disaster!

Without the appropriate frame on the conversation—both in the environment around the conversation AND the environment within the conversation—it is likely doomed from the get-go.

Once a proper environment is agreed upon, and the number of participants (third-party facilitator, if necessary) invited, an appropriate “frame” needs to be placed on the conversation.

What ARE we talking about and what are we NOT talking about in this meeting?

Establish the boundaries for where the conversation is going, and you’re less likely to be derailed into other conversations that will only muddy the waters of the clear picture you are trying to find together.

To give an example, if in attempting to discuss last month’s budget shortfall someone brings up the fact that the company spent too much money on last year’s retreat—pursuing that line of thought will only derail the conversation.

Keeping the main thing the main thing is crucial. If in the process of collecting puzzle pieces some legitimate questions are brought up that both parties agree need to be explored, write them down and set them aside to discuss at a future time.

Nothing derails a conversation like trying to run down multiple tracks at the same time. Well, almost nothing…

The “Blow-Up” Scenario

Inevitably we’ve all been in this scenario—tempers flare, a ‘sensitive-spot’ is pressed, and all the sudden verbal rockets are flying. If the conversation turns destructive—STOP it immediately!

Do whatever it takes to get all parties to cease and desist from the conversational warfare. Take a break. Go outside. Coffee. Tea. Anything to give everyone at least five minutes to clear their head.

When the conversation turns destructive, absolutely nothing positive can come out of it. It will only dig the hole everyone is trying to get out of even deeper—making the future difficult conversations more time consuming and emotionally draining.

I was once facilitating for a practice where the environment was so charged that I had to establish a ground rule—every time I wanted the conversation to stop, I would throw a white hand towel on the table. It was their cue to surrender before the war continued in the wrong direction!

That hand towel was tossed more than a few times (signaling a five-minute break), but the conversation moved forward. In fact, we got to a powerful conclusion much quicker, even with the pauses, than we would have if I would have let the verbal rockets continue to fly.

If the conversation gets nasty, with words like “you always …” or “you never…” being thrown around, take a break and re-frame the conversation. Remind everyone what the goal of the conversation is.

If both parties can’t agree on the frame and goal of the conversation, then it needs to stop until they are found. The goal cannot be, “I want to give them a piece of my mind” or “make sure they never hurt me again.”

A better goal would be to share how and what was hurt, understanding different perspectives, and find better processes that will limit the particular behavior in the future. It’s okay to be emotional and share what’s hurt—it is not okay to get revenge, or take any anger out on the other party.

We are in the business of collecting puzzle pieces—not creating more wounds. When we have a bigger picture of the puzzle we are trying to solve, often we will realize that the other party did not mean to cause the pain that seemed to be intended.

Over the last 20 years I’ve been brought in on countless occasions to consult in businesses that were at supposedly impossible relational impasses. And almost every single time, the chasm that seemed too wide to cross was bridged by gathering the right pieces of information and perspective that were lost before.

I’ve seen top executives shed lots of tears and use words that many people thought would never grace their lips— words like, “sorry” and “please forgive me.” However, if one party shuts the other one down with destructive words and tone, they hinder the process of getting to a healthier conclusion that will benefit them as well.

The “Too Uncomfortable” Scenario

While it’s crucial to maintain a general consensus to move forward with the conversation, what happens if someone becomes extremely emotional or raw in sharing their feelings?

Often tears will accompany a difficult conversation. That isn’t always a bad thing! Likely, topics are being discussed that affect families, livelihoods, and careers. All are things that people have a ton invested into. It makes sense that they are passionate to defend them.

Remember, becoming more effective at difficult conversations doesn’t cease to make them difficult. It just gives you the tools to go through the pain, through the insecurities, and through what hurt without getting stuck.

If someone is emotional, and that emotion is leading towards more puzzle pieces getting on the table, along with helping them process through the pain—then it is absolutely helping the conversation stay on track.

If someone is emotional, and that emotion is turning destructive and causing them to disengage from effective process—then it is getting off track and it’s time for a break.

Often, people get very uncomfortable when someone is sharing strong emotions. The temptation may be to halt the conversation. If healthy process is happening, don’t stop it.

It is more likely that the conversation will go off track by having someone shut down the other’s healthy processing than by the actual emotions themselves.

Often, we are going to feel tense, uncomfortable and vulnerable in difficult conversations. There’s no avoiding that. The opposite is a much worse fate—avoiding the issue and letting the chasm grow wider and deeper.

Encourage those who are “too uncomfortable” that it is better for all involved to go through a short period of awkwardness, rather than a long time of unhealthy results from avoiding the conversation.

The “Leave Too Soon” Scenario

Finally, an often-overlooked way that a difficult conversation can get off track is by thinking the conversation is over prematurely.

Say all parties agree on the picture that all the puzzle pieces have painted, but are simply exhausted by the emotional processing. They may say a quick “I’m sorry” to one another, but in search of respite leave the room in a hurry.

What happens next? What consensus was gathered about changes that will accompany what has been discussed? Who oversees keeping everyone accountable for the shifts in culture and behavior that need to be put in motion?

It’s one thing to agree about the hurt of the past, but it is crucial to ALSO agree upon the action steps needed to ensure that same hurt isn’t repeated in the future!

One without the other will simply land the same parties in an even more difficult conversation soon.

Consensus, agreement, and accountability must be the tangible conclusions of the conversation. If time or participant energy doesn’t allow for this last piece, then a separate time needs to be agreed upon to accomplish it.


Difficult conversations are difficult enough—even with healthy process and dialogue! They become exponentially more so when the conversation goes off track…whether through a blow-up, a wrong-frame, inappropriate environment, or lack of hard-fought conclusion and accountability.

It’s time to get unstuck! With proper training and experience, you can become more effective at having difficult conversations. It is possible to strengthen your relationships in life and expedite your career track with this necessary skill set.

Are you ready to be more effective at the difficult conversations in your life? Download our FREE PDF entitled, 9 Reasons Why Difficult Conversations Are So Hard (and what to do about them).

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