Six Steps to Becoming More Effective at Difficult Conversations

Everybody has difficult conversations. Few people want them. But everybody needs them.

Difficult conversations are part and parcel of everyday life. As much as we have them, whether we realize we are or not, it’s wisdom to learn some tried and true methods of getting better at them.

More than simply learning new techniques, we can actually learn the posture of a receptive, understanding heart that can and most often will be reciprocated by the other party.

If you crave the results of genuine breakthrough in difficult conversations, such as increased understanding, rapid productivity, and stronger team unity, here are SIX solid steps to becoming a difficult conversations PRO.


Be proactive to understand that something is not right and needs to be talked about. Waiting for the issue to simply go away does not work!

Let’s be clear, difficult conversations will never go away completely.

The goal is not to eliminate the often necessary difficult conversations in personal and corporate life, but to learn how to be more effective at having them.

In fact, learning some key insights will actually enable these conversations to happen earlier than they usually do, when the conversation MUST be had because of a rapidly approaching crash.

We are often thrust into difficult conversations because we failed to take the initiative to have them when a crash point wasn’t so near. Learn to read the warning signs in people’s tone, words, or body language that shows they are uncomfortable in a certain area or topic.

Take some time to initiate a “listen-first” conversation where you understand where that person(s) is coming from. Perhaps you will be able to see their current thought trajectory and help avoid a collision before the wrong path is taken in the first place.

If we can learn to read the signs of a collision point and how the people are responding to the existing communication structures and culture, we will go a long way in preventing blow-up.


Find the right time to talk. Find the right place to talk. Find the right participants (who needs to be in the conversation) and lastly, find the right ‘frame’ for the conversation.

What’s appropriate for this convo? Is breakthrough possible with just two people, or does a third-party need to be brought in to help moderate?

Finding the right amount of people present, without under-loading or overloading the system with too many voices is an important balance to strike.

Sometimes, the conversation is front and center and must be had presently, but if you can plan a time do it, and do it wisely!

Late Friday afternoon or first thing Monday morning for example, are some of the worst times. You want all parties present and available, not still waking up or longing to rush out. Find a time that dignifies both the parties present and the conversation itself.

Picture walking into a difficult conversation in your boss’s corner office, full windows on all sides with his plaques and trophies lining the office. Feeling comfortable, ready to be vulnerable? Hardly.

Environments that clearly favor one party, intimidate, or provide no sense of privacy are terrible choices to have your conversation. Pick an inviting, neutral ground with respectable privacy and you have a winner.

Finding the right frame is actually the part that may take the most time. Being proactive about what exactly you are getting at in the conversation is important to set from the get-go.

“Hey, I’d like to talk to you about ______” puts a box around the conversation and provides comfortable boundaries that both parties can work within. What exactly are you looking for within that box? Puzzle pieces.


The problem that produced the need for the difficult conversation is not that there is no solution; the problem is we don’t have all the puzzle pieces to solve the problem.

Commit to the right framework on the conversation – we are here to collect puzzle pieces: those important angles, perspectives, thoughts, emotions, and even faulty conclusions that have built us into the ‘stuck’ mode we find ourselves in.

Often we are in a rush to fix things but what we are really doing is patching the part of the problem we think we understand, which usually makes thing worse.

Be careful not to get into “fix-it” mode before you collect all the pieces of what’s broken in the first place. Really effective processing tools can make the conversation move forward in a healthy way and will encourage all parties to lean into the conversation and work together towards a healthier conclusion.

Take time to get people’s perspective on the table and learn as much as you can from that. The heart posture of being empathic is critical! You are seeking to hear them from their perspective with listening skills that promote an environment of learning and not judging.

Even if you completely disagree with their narrative, you are simply in ‘collection’ mode. Listening (collecting) is not the same as agreeing! There will be time for evaluation later, but making room for the hard work of listening while processing is taking place is worth the investment.

And as you do, you’ll soon find what I call the ‘squishy’ spots …

STEP FOUR: MANAGE P.I.E. (Perspective, Insecurity, & Emotions)

Three elements that can powerfully help or radically hinder the process of working through a difficult conversation.

When people don’t allow another person’s perspective, cutting them off, making light, interjecting side comments; this tears down the effective work that’s happening to remove the obstacles in the way of success.

Don’t conclude before you engage! Honestly, this is especially difficult for strong, gifted personalities who have enjoyed much success due to their ability to come to quick conclusions.

These especially need to balance their quick wit with the courage it takes to hear another person’s perspective. When we hear the other, we win. When we understand where they are coming from, even if they are abjectly wrong – we win.

What’s a win? A win is when we identify the ‘squishy’ spots – the parts of the process where we encounter the awkwardness, the pain, the frustration, even the anger when a certain topic or point of perspective is raised.

Without allowing those puzzle pieces to even get on the table (by cutting them off or concluding too quickly) we miss the opportunities right in front of us to work through the cause of that pain, those emotions, that frustration.

What is making me angry right now? Why does that point raise sincere insecurity in me? Why am I feeling the emotions I do when they bring that up?

Even if you don’t speak them in that moment, write down what you are feeling, and why you believe you are ‘squishy’ in that spot. This clarity will be very helpful in the later stages of the conversation.

Learning to manage your heart regarding your emotions is critical – because typically our biochemical response to being uncomfortable is – FIGHT OR FLIGHT!


It’s important to try to engage the other person’s perspective as much as possible, but the goal is to move towards a healthier dialogue and ability to work together, not the opposite.

This is why a third party can be extremely helpful to keep things on track. If one party is starting to attack another (verbally), perhaps it’s time to take a time out.

Slow down, take a step back, let’s figure out what’s happening and remind ourselves that we are here to collect puzzle pieces.

Managing the process, not just the content, is critical in difficult conversations. Over and over again we find that the issue we THOUGHT was the issue going into the meeting is RARELY the issue.

If we learn to stay on track, we will become better to be like a detective, analyzing deeper to get to the ROOT issue of the difficulty.

Remember, how you say it is just as important as what you say! Our training teaches tone over content, managing emotions, exploring perspective and collecting puzzle pieces towards engaging the real issues.

Often we get derailed because we start having multiple conversations, talking past each other about different events because one aspect of our discussion reminded each of us of something else.

Ask often – are we moving forward in our frame of the conversation?

Other valid issues may come up and are worthy of their own time and consideration, and if they are helpful towards advancing or current framework then it’s fine to include them. However, don’t be afraid to ‘park’ that separate issue or event and make room for another time for both parties to speak into that.

We are moving forward because we want (and often have to) work more effectively together, and come to the place of consensus, consensus, and accountability.


These are all key to a healthy conclusion to your difficult conversation.

If something broke, we have to talk about what happened and how to fix it, and so the words ‘I’m sorry’ and ‘I forgive you’ are important words we should be (authentically) using.

It’s amazing how often the ‘aha!” moments of realization – “I didn’t realize …”, “I judged your intentions … ”, “I didn’t think about …” – become keys to unlock the conversation and the relationship.

When both parties see where they got off track (consensus), they can begin to recommit to work together (agreement), and will be ready to keep up that newfound commitment in the future (accountability).

This may look like meeting again in a week or a month to revisit the conversation and make sure things are still on track with what was committed and agreed upon mutually.

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