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  • Writer's pictureNathan

How to have difficult conversations

Updated: Dec 29, 2019

Most of my adult life, I was not capable of having difficult conversations with another person. I mean, I knew how to sit there and witness the conversation as it essentially happened to me. And I even knew how to listen, though understanding was often beyond me. But engaging in the conversation? Understanding it to be not only a necessary thing but also a good thing, and using that understanding to guide my actions within that conversation? Those were not skills I had.

I've learned much since then, from a lot of people. What I've learned I've put to practice, often to dismal result. Over time, I became able to intuit some common principles that I, at some point, realized could be put into explicit form if I could just articulate them.

In the end, these articulations were forced out of me unexpectedly over the course of conversations with friends who were telling me about difficulties in their own conversations with other people. These friends would tell me about problems that were confusing and frustrating them; problems that seemed to never go away but rather kept popping up in new iterations; problems that were exactly the same ones I'd been working to articulate my entire adult life. In those moments of realization, I would go into a kind of trance and verbally chart these articulations for the first time. This had a certain irony to it, as I could not initially articulate these principles for myself but I could articulate them for others. Either way, once the articulation was made, then it was available for me to access and use in my own difficult conversations with other people. By this time, quite a few people had thanked me for helping them think about communication more clearly and systemically, I began to understand that perhaps I had something of value in these conversational principles, something that deserves to be made more widely available so that fewer people have to guess and stumble their way toward them like I have.

This list is my first attempt to write down and publicly share those conversational principles. These are specific strategies for having hard conversations in a productive, healthy way. When I am conscientious about using these principles, my conversational partners and I tend to have much better experiences that teach us a lot and help us simply feel better all around. Hopefully these strategies will help others do the same, by approaching hard conversations in a more conscientious, meaningful way. Hard conversations will still be hard, but they will also be safer, healthier, and more productive, and build trust and empathy between conversational parties instead of eroding both.

One thing to keep in mind is that all of these articulations assume a conscientious listening partner, who is engaging with you in good faith and trying their best to understand your needs. If this does not describe your conversational partner - if they are refusing to listen or engage honestly, or they're just being mean - then you will probably not be able to feel safe or understood in a conversation with them, and this list will not help. In that case, let this person know you don't feel safe having a conversation with them until they are willing to honestly listen and earnestly engage with you.

Another thing to keep in mind is that you will never be able to change a reflexively selfish conversational partner into a conscientiously collaborative one within the timeframe of preparing for a single hard conversation, so don't even try. You will only hurt yourself and waste your time. These strategies are intended to help boost gradual growth. They will not work miracles. That said, if someone seems like a lost cause, you can still feel free to send them this list to read. Maybe they will learn and grow from it in time for their next hard conversation, with someone else or a future you.

With all of that out of the way, let's get into the list.


This isn't a competition or a battle. Trying to "win" will ruin the entire conversation for everyone in it, including you. What this means is don't use rhetorical trickery, don't try to overwhelm the other person with arguments about your "rightness", and for fuck's sake don't try to hurt the person you're talking to. If you don't understand something they are saying, ask them to clarify. The next point is an especially important extension of this.


You may or may not know these things. Similarly, they may or may not be important. But if you don't know, and if it's important, then ask the other person. Explicitly. Try this: "What do you mean when you say that?" Or perhaps: "Why do you think that?" And so on. Simple as that. Just ask. Don't build any implications or traps into your questions, either.


Vulnerability is good for connection, understanding, honesty, all that goodness. So, the more defensive you feel, the more explicitly you should try to remain vulnerable. Defensiveness derails trust and understanding, and will drive you down rabbit holes that make the conversation more combative and lengthy while simultaneously covering less meaningful ground. You will want very badly to be defensive sometimes, and you must figure out ways to defuse that compulsion. The conversation needs to be vulnerable. Speaking of which....


You can add on to those words if you like, but don't replace them with synonyms. You need to actually use the specific phrase "Thank you". Alternative phrases like "I appreciate that" will not cut it on their own. This is because "Thank you" is ultimately a statement that is about the listener ("You gave me something I needed") while "I appreciate that" is a statement about the speaker ("I now have something I needed"). They are thus orthogonally different kinds of statements that perform different functions. Our brains react differently to them, and that can make a lot of difference in an already emotionally fraught context. Thus, these phrases may complement one another, but they cannot replace each other. To build trust and vulnerability, you always need to say "Thank you".


Much like "Thank you", "I am sorry" cannot be replaced by synonyms. If you have hurt your conversational partner in some way, you need to actually apologize or you will destroy the ability for either of you to remain trusting or vulnerable. The phrase "I'm sorry" will not always be sufficient on its own, but it will always be necessary.


Don't wander down rabbit holes chasing minutiae or details unrelated to your actual conversational purpose. Presumably, you have a clear and simple overarching need that you would like the other person to understand about you. Your goal is to clearly and simply explain that need to the other person, and then clearly and simply ask them if they are capable and willing to help support you in that need. This is one of your main conversational goals; the other one is making sure your conversational partner is understood in their needs the same way that you expect to be understood in yours. The more you deviate from these two goals, the more likely your conversation will frustrate and confuse you both. So keep these goals in mind and stick to the point, which is discussing your mutual interpersonal needs, and the feelings that flow to and from them.


Don't just say "I need more space". That could mean anything. State your need in such a way that your partner can reasonably understand it and act on it. Instead of "I need more space", try "I need more alone time during the week", or "I need you to stand slightly farther away from me when I am chopping vegetables", or "I need you to stop defending me without first asking me if I would like you to", or whatever your need actually is. Because whatever your need is, it is more specific than "I need space". So say the specific need, not a generic version of it. Of course, if you don't know your specific need yet, it's fine to start with a general version and think through it (by yourself or with others) until you can articulate the specific version. Just don't leave it in a general format and assume that this will be sufficient or even useful by itself.


The important thing is what each of you needs. Presumably, if you are having a fraught and difficult conversation with someone, it is because they are someone with whom you strongly wish to share understanding, and so you will want to tell them why you feel what you feel and need what you need. This is fine. What is not fine is explaining your needs and feelings as though you are trying to convince the other person to feel your feeling or need your need. They probably will not, and they should not need to. They are, after all, a different person from you. This is where trust and respect come in. Providing excuses for your expressions of deep feelings and needs will only degrade your relationship with the other person, without getting you any closer to shared safety or understanding. What matters is that your conversational partner respect your needs and vice versa, not that either of you makes the other person's needs their own. It's also important that you trust each other's articulations of your respective feelings, even if neither person actually feels what the other one is feeling. What matters is trust and respect. That's it. The only acceptable answers to "Can you help me with this need?" are "Yes", or "No", or possibly "I don't know yet but I am trying to understand myself and will let you know later, once I am able to know the answer myself". In none of these cases should there be any quibbling over whether your needs match social norms, or seem "logical", or are by any other external metric "justified". None of that stuff actually matters.


Never ever bargain over how you feel or what you need. Your needs and feelings are what they are. They may (and probably will) change over time, but any change that arises through bargaining will not be healthy or sustainable. Thus, while your conversational partner may be able to help you understand your needs and feelings by talking through those things with you, they should not be bargaining with you about those things, and the same is true in reverse. No bargaining should be happening at all; it simply should not be an aspect of why your difficult conversation is difficult. Don't haggle over particular cases of your needs and feelings, either, for instance: "Well I can give you more space when you're chopping green peppers but not when you're chopping cilantro". That kind of haggling is a freeway to codependency.


Difficult conversations are always about the participants in the conversation. No one else. Even if it's about the participants in relation to a third party, and even if you are actually having this conversation because of that third party, the conversation itself is still not about that third party. It's about you and your conversational partner. So talk about you and your conversational partner. Speak in terms of what you are feeling, what you are needing, and what you are wanting, and help your partner do the same. Don't talk about other people. If it is actually critical to mention some third party, for instance to illustrate a conceptually unfamiliar point that is well-exemplified by that third party, make it clear that this is what you are doing, and that you are not comparing this person to yourself or to your conversational partner in any way. A good example of this might be: "I didn't understand this about myself until after all those conversations I had with Ibram". A bad example of this might be: "You haven't talked to me about this like Ibram has". A truly terrible example might be: "Ibram understands this about me just fine, so I don't get why you can't".

Many of these tips are applicable in many other kinds of conversations, not just hard ones. Feel free to use them everywhere! However, you should not feel obligated to carry out these recommendations with anyone you don't trust, no matter the context.


I will add to this list as I remember other principles, articulate new ones, or refine old ones.

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