Difficult Conversations

An excerpt from a book I’m working on, 20 Principles to Try to Live and Relate By And Other Tips For Healthy Relationships.. If you want to support me on this, I have a Patreon page.



Sometimes we have to have difficult conversations with those we love.  If you take the time to prepare and go into the difficult conversation consciously you’ll find that solutions to whatever the problem may be will come easier than you think.

Getting Ready for the Conversation

1. Purpose for the conversation

Ask yourself these questions.

Why are you having this conversation?

Be aware of any hidden purposes for the conversation.  Look deeply at yourself so that you enter the conversation with support and good intent.  Is this about support or do you want to punish the other person for some reason?

What is the problem?

Difficult conversations are usually necessary because there is an issue or problem that needs to be addressed.  Make sure you are very clear on what that is and that you are not making up stories about what it may be.

What is its impact on you?

Is the issue causing you distress?   How is the issue impacting you and your relationship with the other person.

What do you think is the impact on the other person?

While you do not want to make up stories about what they may be thinking or feeling about this, consider how the issue may be impacting your partner.  This will assist you in having empathy during the conversation.

What would be your IDEAL outcome?

If all things go perfectly, how would you like the conversation to end?  This is a good time to begin to  look at your motives for having the conversation.

What is non-negotiable?

Are there any hard limits to the outcome?  Establishing what’s non-negotiable up front will help steer the conversation.

What support are you committed to providing?

If this is about something that you feel the other person needs to change or do, how will you support them in their efforts.

What do both of you agree to?

What do you think you’ll both agree on?  Are there areas that you can come to agreement on, early on in the conversation?

2. Assumptions being made

Think about any preconceived notions you may feel.  You may feel intimidate, ignored, disrespected or marginalized by the other person.  It’s important not to assume that this is their intention.  This may simply be your reaction to the difficult conversation.  If you are going to make an assumption, assume that they are just as nervous and uncomfortable as you are and they also have good intentions.   Remember, impact does not necessarily equal intent.

3. Buttons being pushed

Emotions are normal and they arise sometime without warning.  While we can’t control the emotions we can control our actions.  Are you emotions getting the best of you?  There may be a “backstory” that has nothing to do with the person and/or the conversation you are preparing for.   What personal history is being triggered?  We can avoid being overly triggered by being mindful of preserving the person’s dignity—and treating them with respect—even if we totally disagree with them.

4. Attitude toward the conversation

If you tell yourself that it’s going to be a horrible difficult conversation, it probably will be.  And on the other hand, if you believe that whatever happens, that the end results will be good, then that will most likely be true.

5. Who is the person?

Do they even know that there is an issue or concern?  No one likes to be blindsided by a “We need to talk” conversation.  I highly advise that you share these steps  with the person that you are having the conversation with so they can prepare as well.Open communication prior to the conversation is important.

If they do know that there is a problem or issue, what might they be thinking about what is going on?  How do you feel that they perceive the problem?  What might be their needs?  Their fears?  Do you have an idea what solution they might suggest?  Do not forget they are your partner, not your opponent,

6. Your needs and fears and their needs and fears

Think carefully about what your needs are (write them down in fact) and what your fears are.  Consider what their needs and fears may be.  Remember this is not a battle or a contest with winner and losers. Look closely at any common concerns you may share.

7. Your contribution to the problem

This one is the hardest for many of us.  Self-reflection.  What have we contributed to the problem?  We can probably make a long list of how they contributed to the problem.  That’s the easy part.  It’s what our contributions are to the problem that is harder and very important as we prepare for the conversation.

The first steps to take.

1. Choose the right place and time for the conversation

The more neutral the place the better.  And while it may seem counter-intuitive, someplace that is semi-public can make the conversation work better.  Maybe a coffee shop or a park will do.  The library is a great place because it forces you to keep the conversation at a respectful volume.  Be aware of both of your needs.   Some people may need to not have constant eye contact while discussing difficult issues.  So maybe a car trip or sitting side-by-side in the café or park will make it easier.

The time of day can be important, too, as well as having a full stomach.   Being unrushed, well rested and fed will make a huge difference in having a successful conversation.  No drugs or alcohol, please.

2. Inquiry

Cultivate an attitude of discovery and curiosity.  State the issue or concern then give them opportunity to talk.  Pretend you don’t know anything (you really don’t), and try to learn as much as possible about them and their point of view.  Let them talk until finished  Whatever you hear, don’t take it personally. It’s not really about you. Try to learn as much as you can in this phase of the conversation. Be open to hear first what the other person has to say before reaching closure in your mind. You’ll get your turn, but don’t rush things.  Give them all the time they need.  Listen carefully to what they are saying.  Stay present and in the moment.

3. Be comfortable with silence

There will be moments in the conversation where a silence occurs. Don’t rush to fill it with words.  Be present and conscious and listen to both the words and the silence.  This is difficult, especially for us extroverts.  Some people may need to even get up and move away from the conversation for a short period of time. That is an acceptable way of dealing with discomfort and a conscious way of handling emotions that may arise.

4. Acknowledgement

Acknowledgment means showing that you’ve heard and understood. Try to understand the other person so well you can make their argument for them. Then do it. Repeat back to them what you heard them say.  Acknowledge whatever you can, including your own defensiveness if it comes up.

5. Advocacy

When you sense your partner has expressed all their energy on the topic, it’s your turn. What can you see from your perspective that they’ve missed? Help clarify your position without minimizing theirs. Be careful not to impose your ideas on them, simply state your concerns and thoughts.

6. Problem Solving

Now you’re ready to begin building solutions. Brainstorming and continued inquiry are useful here. Asking them what they think  might work. Whatever they say, find something you like and build on it. If the conversation becomes adversarial, go back to inquiry. Asking for the other’s point of view usually creates safety and encourages them to engage. If you’ve been successful in centering, adjusting your attitude, and engaging with inquiry and useful purpose, building sustainable solutions will be easy.  Don’t not end the conversation without clear action items.


It’s not easy to have these conversations no matter how much we prepare.  Mistakes happen and we screw up.  Being aware of possible mistakes will make them less likely.

1. When difficult conversations turn toxic, it’s often because we’ve made a key mistake: we’ve fallen into a combat mentality. This allows the conversation to become a zero-sum game, with a winner and a loser. But the reality is, when we let conversations take on this tenor everyone looks bad, and everyone loses. The real enemy is not your conversational counterpart, but the combat mentality itself. And you can defeat it, with strategy and skill.

2. If the subject of your argument were straightforward, chances are you wouldn’t be arguing about it. Because it’s daunting to try and tackle several issues at once, we may try to roll these problems up into a less-complex Über-Problem. But the existence of such a beast is often an illusion. To avoid oversimplifying, remind yourself that if the issue weren’t complicated, it probably wouldn’t be so hard to talk about.

3. The key to avoiding oversimplification is respecting the problem you’re trying to resolve. To avoid the combat mentality, you need to go further – you need to respect the person you’re talking to, and you need to respect yourself. Making sure that you respond in a way you can later be proud of will prevent you from being thrown off course if your counterpart is being openly hostile.

4. Fear, anger, embarrassment, defensiveness – any number of unpleasant feelings can course through us during a conversation we’d rather not have. Some of us react by confronting our counterpart more aggressively; others, by rushing to smooth things over. We might even see-saw between both counterproductive poles. Instead, move to the middle: state what you really want. The tough emotions won’t evaporate. but with practice, you will learn to focus on the outcome you want in spite of them.

5. Lying, threatening, stonewalling, crying, sarcasm, shouting, silence, accusing, taking offense: tough talks can present an arsenal of thwarting ploys. (Just because you’re trying to move beyond the combat mentality doesn’t mean your counterpart is.) But you also have an array of potential responses, ranging from passive to aggressive. Again, the most effective is to move to the middle: disarm the ploy by addressing it. For instance, if your counterpart has stopped responding to you, you can simply say, “I don’t know how to interpret your silence.”  Disarm the ploy by labeling the observed behavior.

6. Everyone has a weak spot, a trigger. And when someone finds ours – whether inadvertently, with a stray arrow, or because they are hoping to hurt us – it becomes even harder to stay out of the combat mentality. Take the time to learn what hooks you. Just knowing where you’re vulnerable will help you stay in control when someone pokes you there.

7. This is my personal downfall.   If we’re sure a conversation is going to be tough, it’s instinctive to rehearse what we’ll say. But a difficult conversation is not a performance, with an actor and an audience. Once you’ve started the discussion, your counterpart could react in any number of ways – and having a “script” in mind will hamper your ability to listen effectively and react accordingly. Instead, prepare by asking yourself: 1. What is the problem? 2. What would my counterpart say the problem is? 3. What’s my preferred outcome? 4. What’s my preferred working relationship with my counterpart? You can also ask the other person to do the same in advance of your meeting.

8. Optimists tend to assume that every disagreement is just a misunderstanding between two well-intentioned people; pessimists may feel that differences of opinion are actually ill-intentioned attacks. In the fog of a hard talk, we tend to forget that we don’t have access to anyone’s intentions but our own. Remember that you and your counterpart are both dealing with this ambiguity. If you get stuck, a handy phrase to remember is, “I’m realizing as we talk that I don’t fully understand how you see this problem.” Admitting what you don’t know can be a powerful way to get a conversation back on track.

9. The key in any tough talk is to always keep sight of the goal. Help prevent this by going into conversations with a clear, realistic preferred outcome; the knowledge of how you want your relationship with your partner to be for example; and having done some careful thinking about any obstacles that could interfere with either. (Remember, “winning” is not a realistic outcome, since your counterpart is unlikely to accept an outcome of “losing.”)


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