We attempt or avoid difficult conversations every day – whether dealing with an underperforming employee, disagreeing with a spouse, or negotiating with a client. Douglas Stone and the Harvard Negotiation Project provide us a step-by-step approach to having those tough conversations with less stress and more success.

These are my reading notes from this book. Any errors, omissions, or misrepresentations are mine.


Many efforts fail because people do not skillfully manage difficult conversations – they have different views on priorities, levels of investment, measures of success, and what constitutes correct implementation. Progress can grind to a halt when everyone takes for granted that their own view is correct, and that any opposition stems from self-interest. Simultaneously, we blame our organizations for being dysfunctional while difficult conversations are being ignored.

What makes a conversation difficult?

We fear the consequences, whether we choose to engage with the issue or avoid it. Even being tactful may not work – delivering a difficult message is like throwing a hand grenade, and there's no way to deliver it nicely, outrun the consequences, or keep it to yourself.

Of course, it's important to keep your goals realistic – the purpose is mitigating, instead of completely eliminating, anxiety and consequences.


The structure of difficult conversations

All difficult conversations share a common structure, much of what is left unsaid: what people are thinking and feeling, and the gap between that and what they are actually saying. These thoughts and feelings fall into three categories:

  1. What happened? Who said what, who did what, who's right, who meant what, who's to blame?
  2. Feelings. Are my feelings valid or appropriate? Should I acknowledge or deny them? What do I do about the other person's feelings? What if they're angry or hurt?
  3. Identity. What does the conversation mean to me – does it mean I am competent or incompetent, a good or bad person, worthy of love or unlovable? How does it affect our self image, self esteem, our well-being? Do we feel balanced or off-center during the conversation?

It's easy to make errors responding to each of these three categories:

  1. We assume we know all we need to know, instead of exploring what information the other party has that we don't.
  2. We try to hide our feelings, or let loose in a way we'll regret, instead of working to manage them constructively.
  3. We treat the conversation as if it doesn't say anything about us, instead of exploring the identity issues that may be at stake for both us and them.

Let's visit each of these categories separately.

The "What happened?" conversation

Who's right? Who meant what? Who's to blame?
We make a faulty assumption when answering each of these questions.

Truth: who's right? We don't question the crucial assumption that I'm right, you're wrong. Difficult conversations are rarely about getting the facts right; they're about conflicting perceptions, interpretations, and values. They're not about what is true; they're about what is important.

Shift away from proving that you're right; instead, try to understand the perceptions, interpretations, and values of both sides. Don't just deliver a message; ask questions and explore how each party is making sense of the world.

Intention: who meant what? We assume we know the intentions of others when we don't – and we invariably assume the other party's intentions are bad. But intentions are complex – the other party can have mixed intentions, none at all, or even good intentions that nevertheless hurt us.

Blame: who's to blame? We spend too much attention on who's to blame, and it's too easy to just blame the other person instead of trying to see how we contributed to the problem as well. And when we feel like we're blamed (especially when we feel it's unfair) all of our energy goes into defending ourselves.

Most difficult situations are a result of something both parties did (or failed to do) – and playing the blame game distracts us from what we should be doing: exploring why things went wrong, what kept us from seeing them coming, and how we can correct them going forward. Focus on how each party contributed to the issue, instead of putting blame on anyone.

The Feelings conversation

What do we do with our emotions? How do we handle the strong feelings that will invariably arise?

When we have strong feelings, we try our hardest to stay rational – getting into feelings is messy, clouds our judgment, and makes us feel vulnerable and uncomfortable. What if the other party dismisses or doesn't understand our feelings; what if it ruins our relationship; what if they start dumping their feelings on us too?

But is the best solution really to "stick to business"? It misses a key fact about difficult conversations: they are at their very core about feelings, and having such a conversation without addressing feelings in reality accomplishes nothing – the feelings will just keep resurfacing and resurfacing, and even months from now we'll still harbor the negativity simmering from what was left unsaid.

It's hard to understand, talk about, and manage feelings. But we can try our best and slowly get better and better – both at knowing how to communicate our feelings, and knowing when to just let sleeping dogs lie.

The Identity conversation

Look inward and ask: what does this say about me? How does this affect my self-esteem, my self-doubts, my self-image? How does this impact my future? What is it that is at stake for me, below the surface of this conversation?

The impact of the conversation on your self-image can topple your inner balance. You lose confidence in yourself and your decisions, anxiety skyrockets, and you react in a way that you'll regret later.

Keeping your inner self stable during difficult conversations – when your self-image of being a reliable employee is impacted by receiving negative feedback; when your image of being a helpful coworker is impacted by having to cancel someone's project – can be tremendously difficult, but absolutely crucial. Again, mindfulness and practice will help develop your skills over time, and eventually turn a source of anxiety into a strength.

Moving toward a learning conversation

Don't just deliver a message or prove a point. Instead, invite the other party into a learning conversation, where you prefer mutual understanding of points of view, sharing your feelings, and working together to manage the problem going forward. By doing so, you're much more likely to reach a satisfactory conclusion, as well as reaching a higher level of understanding of the problem.


The "What happened?" conversation

Stop arguing about who's right; explore each other's stories

Why do we argue in a conversation? Because we think we're right, and the problem lies with them – if only they'd see things our way, but they're too selfish, naive, controlling, irrational. Why can't they just realize that?

Because they think we're actually the problem – in both our stories, we make sense and the other person doesn't. Our arguing is actually preventing us from realizing the issue is just that we have different stories, and preventing us from learning about how the other person sees the world.

Where do our individual stories come from? Why do they differ?

  1. We have different information and context, and we notice and focus on different things. We know all our own mitigating factors, the tough things that we ourselves are going through, and assume we have the same level of understanding of the other person.
  2. We have different interpretations of and give different meaning to the same facts and observations. Our past experiences have a huge impact on how we see things now and the "rules" by which we live our lives, but we tend to make snap judgments of other people without thinking of the experiences and rules that could have shaped their reaction.
  3. Our conclusions frequently reflect our own self-interest – we cherry pick information that supports our conclusion while giving less thought to everything else.

People almost never change without first feeling understood, and when we argue, we inhibit change by inhibiting understanding. Instead, making progress requires us to understand their story well enough to see how their conclusions make sense, and vice versa.

How do we begin to understand their story?

  1. We need to move from certainty to curiosity. What information do they have that we don't? How do they see the world so that their view makes sense? And what don't we know about ourselves and why we feel this way?
  2. Embrace both stories by realizing that you can understand their story without giving up your own – it matters how both of us feel. Take the And Stance – I feel this way and you feel that way. The world is complex – you can be right and wrong at the same time; you can love and hate at the same time. Even if your stories never align, no matter how well you understand each other, you can at least shift towards "how can we manage this problem?" instead of "who's right?"
  3. Even if you're certain you're right or justified, that's not what the conversation is about – rather, it's about both parties' complex feelings that are best managed with mutual understanding.

Enhancing understanding doesn't mean all views are equally valid, but it will help you decide whether your strong views make sense in light of new information, and help the other party appreciate the strength of your views. Understanding should always be the first step – just imagine yourself in the other person's story and start from there.

Don't assume they meant it; disentangle intent from impact

Intentions are a huge part of how we judge others. We are more understanding of those we see as having a good reason for inconveniencing us or not doing what we want them to do, versus those who we feel don't care at all or are downright malicious. But if we're not careful, were likely to assume others' intentions are bad and defend ourselves, while ignoring the impact of our own actions on them.

There are two major mistakes we make with regards to intentions:

Mistake 1: Our assumptions about intentions are often wrong

We care deeply about others' intentions, but it's impossible for us to know what they actually are. As a result, we tend to assume intentions based on their impact on us – we feel hurt, so of course they intended to hurt us. And we assume the worst by default, without giving any thought to mitigating circumstances or what they actually mean. Conversely, we are much more charitable and understanding towards our own behavior, and don't give any thought to how it could be hurting others.

When we assume their worst intentions, we often also assume their bad character – and after that judgment, we can only see their future actions through that lens, making our impression even worse. The worse our impression is, the more we're likely to avoid them or talk behind their backs, potentially ruining our relationship completely.

Instead, we should dive deep into why we feel someone has a bad character – if it's because we feel powerless or manipulated or frustrated, then we're deriving a conclusion only based on their impact on us, which is far from enough to actually understand someone's intentions or character.

One dangerous consequence of our bad assumptions is on our conversations: our statements become more accusatory (though of course we feel we're just helping them understand our hurt), they feel we're attacking or maligning them, and either (from our POV) become defensive or attack back. Each party feels victim to the other's bad intentions, and the result is completely destructive.

Another consequence is that our assumptions can become self-fulfilling – they eventually become true, even if they weren't to start with. Our behavior changes for the worse, which triggers how we're treated, creating a vicious cycle.

Mistake 2: Good intentions don't sanitize bad impact

We can cause great pain even with the best intentions; even if we don't mean to hurt the other party – and when they invariably call us out for hurting them, we focus more on defending ourselves (maybe by clarifying our intentions) than the fact that they have been hurt.

Our intentions are also very often unclear to ourselves – maybe we are asking them to eat less or lose weight not for them, but for us, and that's coming through in how we speak to them. We need to think hard about our own intentions, which has the added benefit of showing the other party how much we care.

Focus on both where your intentions lie, as well as how they are perceived (and felt) by the other party. Only then can you begin to work through your issues constructively.

Avoiding these mistakes

First, separate impact from intentions; separate "I was hurt" from "You intended to hurt me". Ask the following questions:

  1. Actions: what did they actually say or do?
  2. Impact: what was its impact on me?
  3. Assumption: based on this impact, what assumption am I making about their intentions?

Of course, this is just a hypothesis based on little evidence that you must verify. Verification happens through the difficult conversation:

  1. Share what the other party did, its impact on you, and your assumption about their intentions, being clear that it's a hypothesis.
  2. Don't pretend you don't have a hypothesis about their intentions – it's inauthentic to say "I know you didn't intend to hurt me..."
  3. Anticipate and try to mitigate defensiveness – the less they try to defend themselves, the easier for them to understand what you're saying. Encourage them to think in a more balanced way about the information you are bringing to their attention by saying something like "I was surprised when you said that – it seemed uncharacteristic of you..."

To avoid the second mistake, when accused of having bad intentions ("you hurt me on purpose"), remember that you must address both ideas they're communicating: (1) they think you have bad intentions, and (2) they were hurt, frustrated, or embarrassed. The best way to do this is to start with listening to their feelings, and then address the intention issue. The other party will be much more likely to consider your feelings if they feel theirs are being heard.

Abandon blame; map the contribution system

When something goes wrong and someone's to blame, we tend to call it out in one of two ways: either blaming them explicitly, "I can't believe you let this happen!"; or implicitly, "Let's do better next time".

Either way, our conversation still revolves around who's to blame – and focusing on blame injures relationships, causes pain and anxiety, and prevents us from learning about and meaningfully correcting what's really causing the problem.

We blame because we misunderstand what has really given rise to the present issues, and because we fear being blamed ourselves. To move away from blame, let's try to understand its underlying motivation, and shift towards something more constructive instead: the idea of contribution.

Blame is about judging, and looks backwards

When we ask "who's to blame?" we're actually asking three questions:

  1. Did the person cause the problem?
  2. If so, how should their actions be judged? Are they incompetent, unreasonable, unethical?
  3. If the judgment is negative, how should they be punished?

When we say "this is your fault", we're actually giving condemning answers to all three questions – and their first reaction is, of course, to defend themselves in any way, perhaps redirecting the blame by pointing fingers at someone else.

After blame is assigned or punishment is threatened, it's natural for the accused to become less forthcoming, less willing to apologize. They may even actively resist changing positively after the fact, in case it seems like an admission of guilt or incompetence.

The blame game also hinders problem-solving – focusing on blame doesn't help you understand the problem or fix it going forward. It makes surfacing systemic issues hard, as someone in the blame frame has to feel confident that others (and not themselves) are at fault to feel justified in raising an issue – and as there's always ways they have contributed, they're likely to never bring it up.

Contribution is about understanding, and looks forward

Contribution acknowledges that when things go wrong in human relationships, everyone has contributed in some important way. It asks a slightly different set of questions, exploring the joint contribution system:

  1. How did we each contribute to bringing about this situation? What did we each do or not do?
  2. Having identified how we each contribute, how can we change it going forward?

The goals of contribution are understanding and producing lasting systemic change: how you interact in the future, how decisions are made. Looking at the system from all angles can help surface issues, misaligned incentives, and bad policies or processes that could have all contributed to the issue at hand.

There are several key misconceptions about contribution:

  1. Misconception 1: Focusing only on your own contribution. But finding your contribution doesn't negate their contribution, and it took both of you to get into your mess.
  2. Misconception 2: Putting aside your feelings. There are undoubtedly strong feelings involved, and sharing them is essential. Expressing your feelings directly – "I feel devastated" – actually reduces the impulse to blame. Ask yourself, "What feelings am I failing to express? Has the other person acknowledged my feelings?"
  3. Misconception 3: Exploring contribution means blaming the victim. Blaming the victim is suggesting that they brought it on themselves, that they deserved to be victimized. This is terribly unfair and can be very painful – it's not their fault they were attacked. However, to solve forward, focusing on contribution is useful: you did contribute to being mugged by choosing to walk alone at night, and you can change your contribution to reduce the likelihood it will happen again.

It can sometimes be hard to find contribution. You can try to see yourself in the opposing party's eyes, asking "What would they say I'm contributing?" Or, play the role of a disinterested observer, and try to describe in a neutral, nonjudgmental way how each person is contributing.

Here's 4 common contributions that are often overlooked:

  1. Avoiding until now. You allowed the problem to continue unchecked by not addressing it earlier, or even worse, by only complaining about it to a third party instead of the person with whom you're upset.
  2. Being unapproachable. If your interpersonal style is being uninterested, unpredictable, short-tempered, judgmental, punitive, hypersensitive, argumentative, or unfriendly, others may be less likely to raise things with you which becomes part of the system of avoidance between you.
  3. Intersections between people of different background, preferences, communication style, or assumptions about relationships. In intersections, no one is to blame; people are just different. Only after understanding the intersection can communication improve, and often we will have to compromise our preferences to stay together.
  4. Problematic assumptions about your role in a situation. Issues can arise if your role assumptions differ from others', but also when they are shared. Commonly shared assumptions like "leaders set strategy; subordinates implement it" have limitations and potential negative impact. However, it's hard to change unless people have an alternate model that everyone thinks is better, and the skills to make that model work at least as well as the current approach.

Moving from blame to contribution

Always ask, what is my contribution? What is their contribution? Who else is involved?

Shifting from assessing blame to exploring contribution will take hard work and persistence – you must be vigilant in course correcting when you see yourself or others slip back into the blame frame.

Some of us might be "shifters", more prone to focus on the other person's contribution, while others are "absorbers" who tend to feel responsible for everything. Knowing your predisposition can help you fight it and get a better balanced picture.

It can be difficult to get the other person to shift from blame to contribution. One of the best ways to show you want to leave blame behind is by acknowledging your own contribution early in the conversation. You can subsequently help them find their own contribution by:

  1. Making your observations and reasoning explicit. Share very explicitly what you saw or what you recall they did that triggered your reaction.
  2. Clarifying what you would have them do differently. Make a specific request for how the other person can change their contribution to help you change yours. Both of you must realize what you each need to do differently to improve the situation.

Once both parties understand better what's happened, you can finally talk constructively about where to go next.


The Feelings conversation

Feelings matter, and are often at the heart of difficult conversations. And since you can't have an effective conversation without talking about the primary issues at stake, neither party will be satisfied with the outcome unless they also talk about how they are feeling.

However, managing feelings can be overwhelmingly difficult. When we share our feelings, we risk hurting others and ruining relationships, and it puts ourselves in a position to get hurt.

We're tempted to frame the feelings out of the conversation, and focus only on using our problem-solving skills – but our emotions will leak into the conversation in unhelpful ways anyway. Our tone of voice, body language, and facial expression will change, and we can become aggressive, impatient, or defensive. Our long-unexpressed feelings may burst in the conversation in an embarrassing or destructive way, where we cry or explode when we'd rather act composed. Or our feelings create so much tension that we'd rather disengage, choose to cut contact, or become distant.

Having unexpressed feelings also makes it difficult to listen – we're not going to be open and have an honest curiosity about the other person, if our emotions about them are buried and waiting to explode. It's hard to hear someone else if we're feeling unheard, even if we're feeling unheard because we're choosing not to share.

When we don't express important feelings, we suffer a loss of self-esteem (why didn't I stick up for myself?) as well as deprive others from the chance to learn and change in response to our feelings. As a whole, our relationship suffers – by keeping our feelings out, we're keeping an important part of ourselves out of the relationship.

Sharing your feelings requires three steps:

  1. Sort out what your feelings are
  2. Negotiate with your feelings
  3. Share your actual feelings, not attributions or judgments about the other person

Finding your feelings

It's challenging to recognize our feelings – they're usually more complex than we can imagine, and they're good at disguising themselves. Feelings we're uncomfortable with can disguise themselves as emotions we're better able to handle; groups of contradictory feelings can disguise themselves as a single emotion; and feelings can transform themselves into judgments, accusations, and attributions.

We each have a unique "emotional footprint": which feelings we believe are OK to have and express, and which feelings are not. This can vary in different relationships: our awareness of and ability to express emotions changes if we're talking to our parents, our friends, our boss.

To raise awareness of what we are feeling, we can ask ourselves questions to find out the contours of our emotional footprint in different contexts: anger is easy to express, but shame or failure is hard. Disappointment may be easy to express, but not affection, pride, or gratitude.

There are some assumptions that people incorporate into their footprint than can be damaging:

  1. Damaging assumption 1: There's something wrong with having feelings. Feelings are normal and natural, and nothing to be ashamed of.
  2. Damaging assumption 2: There are certain emotions "good people" should never feel. Everyone feels anger, everyone has the urge to cry sometimes, everyone fails, and everyone needs other people. Everyone has conflicted emotions sometimes, and it has nothing to do with whether we are a good person.
  3. Damaging assumption 3: Other people's feelings are more important than ours. Many times in life, we choose to put someone else's feelings ahead of our own. Does this make sense? Why do they express their feelings and preferences, but we cope with ours privately? Don't undervalue your own feelings and interests.

In many situations, what seems to be a single emotion (e.g. anger at someone) actually contains an entire spectrum of emotions (confusion, fear, love, pride, shame). We can be blinded to the complexity of our feelings by one strong feeling that trumps all the others.

Sometimes hard-to-find-feelings:

Another common pattern is when there is an underlying feeling that we are not even aware of, but interferes with our experiences – for example, buried anger can interfere with the ability to express love.

It's dangerous to translate your feelings into attributions, judgments, and accusations, which can lead to defensiveness and misunderstandings. Sometimes, the attributions themselves are so powerful that we fail to see the real feelings underneath.

Judgments can feel like feelings when we are saying them – they're motivated by anger or hurt, but the result is judging, attributing, and blaming. There is a huge difference between "You are thoughtless and self-absorbed" and "I feel hurt, confused, and embarrassed". Find the feelings lurking under your judgments, and use the urge to blame in a conversation to find important unexpressed emotions.

Negotiate with your feelings

Get everything you are feeling into the conversation, but before saying what you are feeling, negotiate with your feelings. Our feelings are not static and nonnegotiable, as they are based on our perceptions and our perceptions are negotiable.

Our feelings are formed in response to our thoughts and the story we tell ourselves about what's happening, and as our thinking is often distorted in predictable ways, there is generally fertile ground for negotiation:

  1. First, we examine our own story and its impact on how we feel, and find the gaps where it's missing information or differs from the other person's story.
  2. We then explore our untested assumptions about the other person's intentions. Could they have acted unintentionally, or with conflicting intentions? And what about our own intentions and motivations, and how our actions could have impacted them?
  3. Finally, consider the contribution system. Can we see our own contribution to the problem, and can we describe each person's contribution without blaming?

Of course, some of these questions can only be resolved during the conversation – but even just raising the questions making hypotheses can take the edge off our anger or our hurt.

Don't vent; describe your feelings carefully

You can express emotion well without being emotional, and you can be extremely emotional without expressing much of anything at all. Here are some guidelines for expressing your feelings:

  1. Frame feelings back into the problem. Remember that feelings are important, and even if you have to preface their expression with an admission that you're uncomfortable with the feelings, make sure you follow up by expressing them. Get them out.
  2. Express the full spectrum of your feelings. Take the time to paint a more complete picture of your feelings, which adds depth and complexity to the conversation: "It's hard for me to talk to you about this, but I feel a couple of things..." The conversation doesn't end with the expression of feeling; rather, that's just the beginning.
  3. Don't evaluate – just share. Get everyone's feelings on the table before you start to sort through them. Premature evaluation of feelings will undermine their expression. Save problem-solving until later.
  4. Express your feelings without judging, attributing, or blaming. Look at the actual words you are using, and whether those words are conveying what you want them to. Stay away from blame, even implied; focus on the pure feeling first.
  5. Don't monopolize; both sides can have strong feelings at the same time. Get both sides' conflicting emotions on the table.

Beginning your conversation with "I feel..." keeps the focus on feelings and makes it clear you're only speaking from your perspective. It helps stay away from judging or accusing.

The important of acknowledgement

Each side must have their feelings acknowledged before you can start problem solving. This is letting the other person know that what they have said has made an impression on. you, and you are working to understand them: "Wow, I never knew you felt that way", "I kind of assumed you were feeling that, and I'm glad you felt comfortable enough with me to share it". Let them know that you think understanding their perspective is important, and that you are trying to do so.

Don't skip over feelings in the pursuit of addressing the problem and making things better. Being able to communicate effectively with each other will not only resolve the current problem more soundly, but also benefit your relationship in the long term.


The Identity conversation

Some conversations are overwhelmingly difficult as we're not just facing the other person, we're also facing ourselves. The conversation threatens to disrupt our sense of who we are, a threat to our identity – which can be profoundly disturbing. Even as you're trying to communicate clearly and effectively, you're suffering a private identity quake.

Three identity issues are particularly common:

  1. Am I competent?
  2. Am I a good person?
  3. Am I worthy of love?

There's no quick fix to identity crises, and you can't "quake-proof" your sense of self. But you can recognize and cope with them better by thinking clearly and honestly about who you are.

The all-or-nothing syndrome

The biggest contributing factor to a vulnerable identity is "all-or-nothing" thinking: I'm either competent or incompetent, good or evil, worthy of love or not. This makes our identity unstable and hypersensitive to feedback – we can only deny negative feedback altogether (which requires ever-increasing mental gymnastics), or exaggerate it to a crippling degree (acting as if it's the only pertinent information to our identity).

The bigger the gap between what we hope is true and what we fear is true, the easier it is for us to lose our balance.

Step 1: Become aware of your identity issues

This is the first step in grounding your identity. Oftentimes during a difficult conversation, it seems our ability to hold a conversation has deserted us – we stumble over words, can't stop arguing, and boil over with anger. We don't realize how much the conversation has impacted our identity.

Are there patterns to what knocks you off balance in your conversations? Why do they do so? What about your identity feels at risk? How would it feel if what you fear were true?

Step 2: Complexify your identity

A self-image that allows for complexity is healthy and robust. Move away from the false choice between "I am perfect" and "I am worthless", and instead try to get a clear picture about what is actually true about you: your mix of good and bad behavior, noble and less noble intentions, wise and unwise choices. Life is complex; we can feel good about many of our actions and choices, and ambivalent or regretful about others.

There are three characteristics that are especially important to accept about yourself:

  1. You will make mistakes. This helps you understand and accept the legitimate aspects of the other person's story. A positive side effect is that competent people who take mistakes in stride are actually seen as more confident than those who resist acknowledging even the possibility of a mistake.
  2. Your intentions are complex. Be honest with ourselves (and the other person) about the complexity of our motivations.
  3. You have contributed to the problem. Assess and take responsibility for your own contribution.

Learn to regain your balance

The question isn't whether you will get knocked over (you will) – it's whether you are able to get back on your feet and keep the conversation moving productively.

You can do these things before and during the conversation to help maintain and regain balance:

  1. Let go of trying to control their reaction. It's good to not hurt the other person during your conversation, but don't try to smooth over or stifle their reaction ("Look on the bright side; it's not so bad after all"). It will make things worse – you might just look like you don't understand or care. Apply the And Stance: give the bad news, take responsibility, show you care how they feel, and try to be helpful.
  2. Prepare for their response. Take time in advance to imagine the conversation and how they might respond. Do any of their potential responses implicate identity issues for you? Is it OK for you to make someone cry? How will you respond if they attack your character or motivation?
  3. Imagine that it's three months or ten years from now. Eventually you'll feel better, and someday it might not seem so important. When looking back at this period, what do you think you'll have learned? How will you feel about how you handled it? What advice would your future self give your current self?
  4. Take a break. Sometimes you're just too close to the problem and too overwhelmed by your identity quake to engage effectively. Ask for some time to think about what they've said – even ten minutes to untangle your thoughts, weighing all the information you have about yourself, can help. In what ways is what they're saying true?

Their identity is also implicated

Even as we're having our own identity quake, the other person is likely grappling with their own identity issues. We can help lead them away from all-or-nothing thinking, or
remind them of the positive things that are true of them that are important to us.

Make the Identity conversation explicit

In some cases, you can share your Identity conversation to directly get to the heart of what's going on: "I'm sensitive to X", "I've always regretted Y".

Find the courage to ask for help

Some issues are easier dealt with if we get help from family, friends, colleagues, or professionals. If someone you loved were in the situation you're in now, would you think it was OK for them to ask for help?


Creating a learning conversation: When to raise it and when to let it go

You can't have every difficult conversation you come across. How do you decide if and when you'll raise an issue, and how do you let go of the ones you don't raise?

There's no right choice, and no way to know how things will turn out. Instead, try to think clearly and make a considered choice. Work through the Three Conversations: think clearly about what you do know and what you don't know; get a better handle on your feelings, identity issues, and perception distortions or gaps.

There are several kinds of conversations that don't make sense, and may not be worth pursuing:

  1. Is the real conflict inside you? Maybe the difficulty of the situation lies in what's going on inside you rather than what's going on between you and the other person.
  2. Is there a better way to address the issue than talking about it? Sometimes actions are better than words, and a change in your behavior is the optimal solution
  3. Do you have purposes that make sense? Are you sure about what the point is, or what a good outcome would look like?

It's important to have the right purpose in difficult conversations. Here are some purposes that don't work:

  1. We can't change other people. When we try to change someone, we're likely to argue with and attack their story and less likely to listen, causing them to feel defensive. Change can only happen if they think we understand and respect them, which only happens in a conversation with mutual learning as the goal. People are more likely to change if they feel free not to.
  2. Don't focus on short-term relief with long-term cost. If your purpose is to change the person's behavior, to vent or tell them off, having the conversation may actually produce the negative consequences you fear. You will jeopardize the relationship, hurt their feelings, and provoke a defensive reaction. Instead, negotiate with yourself to shift your purposes.
  3. Don't hit-and-run. If you're going to talk, really talk. And if you're going to really talk, you can't do it on the fly – you have to plan a time, be explicit about needing ten minutes or an hour. If hit-and-run is all you can do ("Late again, eh?") then it's better not to raise the issue at all.

Letting go

Sometimes, you have to let go. You consider your purposes and some possible strategies, and decide not to have the conversation. Instead of painfully holding onto the issues, you decide to move on. This will take time and be very complex: it's hard to find a place where you can set free the pain or shame from your experiences, a place where you can accept yourself for who you've been and who you are.

A good place to start is in the Identity conversation, by adopting some liberating assumptions:

  1. It's not my responsibility to make things better; it's my responsibility to do my best. Let go of the fantasy that things can be better.
  2. They have limitations too. They are as imperfect as you are, and no matter how cleanly you share your feelings and perspectives and you each agree to change your behavior, they can continue to do it. They may not have the capacity to be different, at least not right now.
  3. This conflict is not who I am. When we integrate the conflict into our sense of who we are, it's especially hard to let go. The prospect of reconciliation can actually be threatening, as it robs us of our role and our identity as a community. Take a step back, and remember why you're fighting: you're fighting for what is right and fair, not because you need the conflict to survive.
  4. Letting go doesn't mean I no longer care. You can let go of the emotions and identity issues in a difficult conversation; you can let go of anger while holding to love and memories.

Letting go is about how to handle with skill and grace not having a difficult conversation.

If you raise it: Three purposes that work

The better you are at engaging difficult conversations, the fewer you will have to let go of. Having sound purposes is crucial, ones focused on mutual understanding:

  1. Learning their story. Go into of the Three Conversations to explore the other person's perspective: their information, past experiences, intentions, feelings, reasons for what they did; how our actions impacted them and how we're contributing to the problem; how the situation affects their identity.
  2. Expressing your views and feelings. Express your story to your own satisfaction – you can hope the other person will understand what you're saying, but you can't guarantee that. Just say, as well as you can, what is important for you to say in the Three Conversations.
  3. Problem-solving together. Given what you both have learned, what would improve the situation going forward? Is there a creative solution that satisfies both of your needs? Can you come up with fair standards to resolve when your needs conflict in the future?

Shift your internal orientation from certainty to curiosity, from debate to exploration, from simplicity to complexity, from "either/or" to "and".


Getting started: Begin from the Third Story

The beginning of a difficult conversation is the most stressful yet most crucial moment – it's fraught with peril, but also an opportunity to influence the entire direction of the conversation. Take advantage of this to start on the road to understanding and problem-solving.

Why our typical openings don't help

We take a deep breath and jump in, then realize we're over our heads. The other person is hurt or angry, we feel defensive, our preparation goes out the window. What went wrong?

  1. We begin inside our own story. When we jump into conversations by describing the problem from our perspective, we're beginning from the exact place the other person thinks is causing the problem – and they'll either defend themselves or counterattack.
  2. We trigger their Identity conversation from the start. Our story contains a judgment about them, and inside our version of events, they're the problem. By starting with "I was very upset when you did X", we leave no room in our agenda for their story.

What's the best way to open instead?

Step 1: Begin from the Third Story

Take the vantage point of the Third Story, an invisible one that a keen observer or mediator would tell – one where both sides have valid concerns that need to be addressed; one that rings true for both sides simultaneously.

Initiate the conversation from the gap between your story and the other person's story, to include both perspectives and invite joint exploration: "You and I seem to see this situation differently. I wonder if it's something we could talk about? I'd like to share how I'm seeing it, and learn more about how you're seeing it."

Without judgment about who is right or whose view is more common, both sides can buy into this; each feels their story is acknowledged. This keeps communication open and helps both parties understand the feelings and perspectives involved – which sends the message that even when we disagree, we care about each other. At the very least, we can separate the substantive disagreements from the importance of the relationships.

You can step into the Third Story even when difficult conversations are forced on you. Take what the other person says, and use it as their half of the Third Story description – "It sounds like you're pretty unhappy with X. I have trouble with X too, so I think we have different preferences and assumptions around that. It seems like it's a good time for us to talk about..."

Step 2: Extend an invitation

Now that you've described the problem in a way that both parties can accept, next propose mutual understanding and problem-solving as purposes, check to see if it makes sense with the other party, and invite them to join you in a conversation.

  1. Describe your purposes: Let them know up front your goal is to understand their perspective better, share your own, and talk about how to go forward together.
  2. Invite, don't impose: Your offer (and your Third Story) should be open to modification.
  3. Make them your partner in figuring it out: Don't cast them in an unappealing light. Say, "Can you help me understand...?" (offering the role of advisor), "Let's work on how we might...?" (inviting a partnership), "I wonder whether it's possible to...?" (throwing out a challenge, for them to play the hero). The role you offer has to be genuine – but chances are you actually need their help to make real progress anyway.
  4. Be persistent: Their initial reaction may be defensive by default, so be both persistent and open to their response.

Some specific kinds of conversations

Third Story, their story, your story

Once you've begun with the Third Story, you have to have the real conversation. The description of the problem is on the table, and now you will need to spend time exploring each of the Three Conversations from each person's perspective. They'll share their views and feelings, and then you'll step back into your story and share yours.

Each of the Three Conversations gives you a useful path to explore, with what you choose to do dependent on the context and the relationship:

How to talk about it: Listening, expression, and problem-solving

The Three Conversations provide a useful map for what to talk about; next we'll dive deep into how to talk about it.

To be able to see the other person's story, you'll need skills in inquiring, listening, and acknowledgement.

To share your own story with clarity and power, you need to feel entitled and be precise in speaking only for yourself.

To keep the conversation on track when it starts to go off the rails, you'll need to manage the interactive process and direct it towards problem-solving.


Learning: Listen from the inside out

Listening to someone doesn't just help us see issues from their point of view – it also helps them listen to us. People don't listen to us because they don't feel heard, they don't feel we care enough – we must demonstrate we understand what they are saying and what they are feeling to remove that block.

Some popular strategies for being a good listener include asking questions, paraphrasing what they say back to them, and acknowledging their view. However, without authenticity, without genuine curiosity or caring, you will sound phony and mechanical.

To become a good listener, we must master our internal voice: what we're thinking but not saying. When we listen to someone speak, our internal voice is also chattering away, making assumptions and judgments. Instead of tuning it out, we need to negotiate with it into curiosity and a learning mode. Remind it that we can never fully understand how someone else feels or what they are trying to say; there's always more to learn. We must shift our internal stance from "I understand" to "Help me understand".

Keep focusing on the purpose for the conversation – if our purpose is to understand the other person instead of just to persuade or win, our internal voice will naturally ask more questions like "What else do I need to know for that to make more sense?"

Sometimes, it's impossible to convince our internal voice to listen to the other person – in that case, it's better to let them know that we really want to listen to them, but we feel overwhelmed and just can't right now.

There are three primary skills that good listeners employ: inquiry, paraphrasing, and acknowledgement.

Skill #1: Inquire to learn

The only good reason to ask a question should be "To learn". Otherwise, if you don't have a question, don't ask a question. Make sure your questioning follows these guidelines:

  1. Don't make statements disguised as questions. Although it feels safer, never ask a sarcastic question instead of making a request or sharing our feelings: "Are you going to leave the door open like that?" instead of "Please close the door"; "Is it impossible for you to focus on me just once?" instead of "I'd like you to pay more attention to me". We lose more than we gain by doing so – the other person just focuses on the attack, and is distracted by the need to defend themselves.
  2. Don't use questions to cross-examine. Don't use questions to shoot holes in their argument: "If it's true that you , how do you explain _?" It's too focused on who is right and who is wrong, instead of trying to learn. Instead, share them as perceptions and ask for their response: "I understand you feel . But to me, that seems inconsistent with _. What's your thinking about that?"
  3. Ask for more concrete information. Ask them to be more explicit about their reasoning and their vision. Ask, "What leads you to say that?", "Can you give me an example?", "How would we test that hypothesis?"

Use each of the Three Conversations to feed your curiosity:

If the answers aren't entirely clear, ask for clarification.

If all of your questions are met with defensiveness, just leave them as open invitations to answer in the future – make your caring intent clear, make it their choice, and eventually they may open up again.

Skill #2: Paraphrase for clarity

Express to the other person, in your words, your understanding of what they are saying. This both helps you check your understanding, as well as showing them that they've been heard. This is especially important when you see someone repeating themselves a lot in conversation: they've noticed you're not taking in what they're saying.

Skill #3: Acknowledge their feelings

When you paraphrase, try to respond not only to what they say, but also to their feelings. Feelings crave acknowledgement – each feeling comes with a set of invisible questions attached: Are my feelings OK? Do you understand them? Do you care about them? Do you care about me? It's hard for us to move on in the conversation until we know the answers.

Acknowledgement is any indication that you are trying to understand the emotional content of what they are saying: "This seems really important to you.", "If I were in your shoes, I'd probably feel confused too.", "It's been a tough time, hasn't it?". There's no perfect thing to say, and sometimes you may not need to say anything – you can acknowledge with a nod, or the look in your eyes.

Make sure you acknowledge before you start to problem-solve. Our best intentions can skip over the acknowledgement, and the resulting loss is significant.

Be sure to distinguish between the Feelings conversation and the What Happened? conversation – you don't have to agree with what they're saying to acknowledge their feelings: "I feel badly about how it's turned out, but I do think it's the right decision."

Empathy is a journey, not a destination

The deepest form of understanding another person is empathy: the shift from mere outward observations to looking at the world from their eyes, with their set of experiences and background. It's a journey with a direction but no destination – we will never be able to say, "I truly understand you."

Embarking on that journey is all it takes – as humans, we just want to know our peers are trying to empathize with us, that they are willing to struggle to understand how we feel and see how we see. This struggle to understand communicates the most positive message of all.


Expression: Speak for yourself with clarity and power

Understanding the other person isn't the end of the matter – they need to hear your story too.

In a difficult conversation, your primary goal shouldn't be to persuade, impress, trick, outwit, convert, or win over the other person – it is to express what you see and why you see it that way, how you feel, and who you are. You need to understand yourself, and believe that what you want to share is important.

You are entitled

No matter who we are, no matter how high and mighty or low and unworthy, we all deserve to be treated with respect and dignity. My views are feelings are as legitimate, valuable, important, and as worthy of expression as yours.

Audre Lorde writes: "What is most important to me must be spoken, made verbal and shared, even at the risk of having it bruised or misunderstood. What I most regretted were my silences... We can learn to work and speak when we are afraid in the same way we have learned to work and speak when we are tired. For we have been socialized to respect fear more than our own needs for language and definition..."

There may be risks in expressing ourselves, but the costs of silence are even greater. A relationship takes hold and grows when both participants experience themselves and the other as being authentic – such relationships end up being more comfortable, relaxing, and nourishing to the soul. Conversely, by failing to share what's important to us, we detach ourselves from others and damage our relationships. When we hide parts of who we are, we end up hiding everything, and we appear to others to be lifeless and removed.

Beware of self-sabotage – waiting to speak until it's too late can make us feel like we tried, with the same outcome as if we hadn't. When you feel that vaguely sick or confused feeling, engage in the Identity conversation and ask yourself, "Why aren't I entitled? What would I need to feel fully entitled?"

Speak the heart of the matter

The next step is to figure out exactly what you want to say.

Start at the heart of the matter for you: "For me, what this is really about is...", "What is most important to me is...", "What I'm feeling is..."

Bring it up directly, not through subtext – doing so via jokes, questions, offhand comments, and body language ends up triggering all the problems you worried you'd create by bringing it up, without the benefit of being able to clearly say what you want to say.

Don't rely on the other person to read your mind and know there's a problem – over time, we may start to know better how we each think and feel, but we will never be perfect.

Don't ease in: don't soften the message by delivering it indirectly through hints and leading questions. Easing in increases both sides' anxiety and defensiveness by conveying three messages: "I have a view", "This is too embarrassing to discuss directly", "I'm not going to be straight with you". State your thoughts straight out, while indicating (honestly) that you are interested in whether the other person sees the situation differently: "Based on what I know, it seems to me that you might have gotten more done. However, you know more about what happened; in what ways would you see it differently?"

Use the Me-Me And technique to express your complex thoughts, feelings, assumptions and perceptions instead of just focusing on being concise. Connect two aspects of what you think or feel with an "and": "I do think you are bright and talented, and I think you're not working hard enough." "I want to share my view on this, and I have to say I'm nervous about doing so because I'm afraid it may sound self-serving. So if you see anything in what I say that doesn't seem legitimate, please say so and let's discuss it."

Telling your story with clarity

When you share something important, do so in a way that will maximize the chance that the other person will understand and respond productively. Clarity is key.

Don't present your conclusions as the truth. We often experience our beliefs, opinions, and judgments as facts, and presenting them as such invariably creates resentment, defensiveness, and leads to arguments. Be vigilant about the distinction between actual facts and everything else.

State where your conclusions come from. Share the information you have and how you have interpreted it, and the past experiences that have influenced your thinking.

Don't exaggerate with "Always" and "Never"; give them room to change. When you use polarizing words, you can often get into a useless argument about frequency or finding edge cases, and it makes it harder for them to change their behavior. Instead, invite and encourage them to consider new ways of behaving. Proceed as if they are unaware of the impact of their actions on you, and as they are a good person, they would certainly wish to change their behavior once they became aware: "I wish I could feel more often like you believed in me. It would really feel great to hear even something as simple as, 'Good job!'"

Help them understand you

You'll need their help in understanding them, and they'll need your help in understanding you.

Express your feelings in terms they might understand. Recognize that different people take in information at different speeds and different ways; if they are visually-oriented, use visual metaphors or (in business settings) charts; if they prefer to look at the whole problem first, share that with them before getting into the details.

Ask how they see it differently, and why. Don't just ask for agreement ("Does that make sense?") as they may be reluctant to share their doubts and reservations. Instead, ask explicitly for how they see it differently to discover their true reaction.

Final thoughts

You are the ultimate authority on you – you are an expert on what you think, how you feel – and you are entitled to say it; no one can legitimately contradict you. You only get into trouble if you try to assert what you are not the authority on – who is right, who intended what, what happened.

Speak fully the range of your experience and you will be clear. Speak for yourself and you can speak with power.


Problem-solving: Take the lead

Don't count on the other person to understand how to engage in a learning conversation. Most likely, you'll talk about understanding, and they'll talk about who's right. You'll talk about contribution, while they're stuck in blame. You'll listen to and acknowledge their feelings, and in return you'll be attacked, interrupted, and judged.

Skills for leading the conversation

You're gonna have to take the lead for the conversation to go anywhere. Use these techniques to help keep the conversation on track:

Reframe, reframe, reframe

Reframing is taking the essence of what the other person's saying, and translating it into concepts that are more helpful – concepts from the Three Conversations framework:

You can reframe:

One sentence alone is unlikely to do the trick – you'll need to be persistent, and expect to be constantly reframing the conversation to keep it productive.

Another reframing you should do is the "You-Me And" – instead of focusing on a false dichotomy between what you think and what they think, what you feel and what they feel, use "and" to embrace both stories. This way, you can assert yourself without invalidating the power and importance of their concerns.

It's always the right time to listen

You can't move the conversation in a more positive direction until the other person feels heard and understood, and they won't feel heard and understood until you've listened.

Even they act like their story is the only version that makes sense, continue listening – then paraphrase what you're hearing and ask questions about why they think that way, to move the conversation into constructive territory.

Name the dynamic: Make the trouble explicit

Sometimes, reframing and listening aren't enough – no matter how hard you try, the other person will continue to interrupt, attack, or dismiss you; they act upset, then say nothing's wrong when you ask about it.

In these case, you can try naming the dynamic – raise for discussion what's happening in the conversation itself:

Naming the dynamic clears the air as it brings what both parties are really thinking and feeling but not saying onto the table for honest discussion. It can stop frustrating interactions immediately, by making the other person aware that they are doing something that is upsetting to you. On the other hand, it can escalate tension – so generally do this only when nothing else has worked.

Now, begin to problem-solve

Problem solving is gathering information and testing your perceptions, creating options that would meet both sides' primary concerns, and, where you can't, trying to find fair ways to resolve the difference.

It takes two to agree. Don't think of problem solving as persuading the other person; it requires compromise and mutual accommodation from both parties. You always can turn the tables, inviting them to persuade you and insisting that they do. Persuasion must be a two-way street.

Gather information and test your perceptions. Divergent views are often rooted in conflicting assumptions or hypotheses, and if these are identified, you can discuss what would constitute a fair test of which assumption is empirically valid, or to what extent it's valid. Of course, such a test must be accepted as fair and adequate by both parties.

Say what is still missing. When you follow their reasoning, what's missing that would make their version make sense?

Say what would persuade you. Be open to persuasion, honest and firm with your current views but receptive and listening to theirs.

Ask what (if anything) would persuade them. You've offered some good reasons, yet they're still adamant in their view. Ask them if there's anything you could say or show that would persuade them otherwise.

Ask their advice. "Help me understand how you would feel and how you might think about the situation, if you were in my shoes. What would you do? Why?"

Invent options. Determined joint brainstorming can find creative solutions that meet most of everyone's needs: "I wonder if we can work to find a creative way to meet both interests here. What do you think? Are you willing to try?" If you wish to maintain your relationship, you will need to work together to find a solution that satisfies everyone.

Ask what standards should apply. Look for standards or fair principles to guide a resolution, rather than haggling with or trying to intimidate the other person. Industry or local practices, legal precedents, and ethical principles can all offer ways to settle the matter – but of course, not all standards are equally persuasive.

The principle of mutual caretaking. A good resolution will usually require each party to accommodate the somewhat to the other's differences, or to reciprocate – going one way on some issues and the other way on others.

If you still can't agree, consider your alternatives. If you're going to walk away without agreeing, you need two things:

  1. You need to explain why you're walking away. What interests and concerns aren't met by the solutions you're discussing?
  2. A willingness to accept the consequences. If you can't live with the possibility of negative outcome, then your best choice may be to renege – as long as you feel you've ultimately handled the conversation skillfully and made a wise choice at the end.

It takes time

Most difficult conversations aren't a single conversation – they're a series of exchanges and explorations that happen over time. You should always have followup conversations to check in, and, if necessary, look for new ways to cope.


Putting it all together

Step 1: Prepare by walking through the Three Conversations

  1. Sort out What happened.

    • Where does your story come from (information, past experiences, rules)? Theirs?
    • What impact has this situation had on you? What might their intentions have been?
    • What have you each contributed to the problem?
  2. Understand Emotions.

    • Explore your emotional footprint, and the bundle of emotions you experience.
  3. Ground your Identity.

    • What's at stake for you about you? What do you need to accept to be better grounded?

Step 2: Check your purposes and decide whether to raise the issue.

Step 3: Start from the Third Story

  1. Describe the problem as the difference between your stories. Include both viewpoints as a legitimate part of the discussion.

  2. Share your purposes.

  3. Invite them to join you as a partner in sorting out the situation together.

Step 4: Explore their story and yours

Step 5: Problem-solving


Ten questions people ask about difficult conversations

It sounds like you're saying everything is relative. Aren't some things just true, and can't someone simply be wrong?

First, we need to distinguish very clearly between actual facts, and opinions, assumptions, values, interests, predictions and judgments. Facts can be clarified, verified, and measured, but even they are hard to pin down sometimes – memories are not wholly reliable, and it's possible to have selection bias in choosing the facts to remember and surface. As a result, even when discussing facts, it's important to find out what the other is seeing and how they make sense of it.

Furthermore, disagreements are often about interpretations and judgments – what the facts mean. This requires a careful learning conversation about one another's stories. Of course, not all stories are equally valid – some stories reflect having more context on the situation, others rely on fewer, less extreme, or more relevant assumptions, others have fewer logical leaps or internal contradictions – but in order to compare stories by these standards, you first have to explore each story, where it comes from and what it's based on, and how they intersect.

When you think their view is just wrong, take a moment to re-examine your assumptions – there's always a chance that they know something you don't, and there's no downside to testing your view and seeking to understand theirs. Look for the sense rather than the nonsense in their view.

When dealing with people who hold particular beliefs as absolute truth – e.g. people with religious views, or conversly those who hold only observable, measurable evidence as true – the strategy is the same as with any difficult conversation: be respectful, and seek to understand the sense in how they see it. When it's us that hold such beliefs, we need to avoid hubris and be careful not to force it on them; one-way persuasion usually results in increased resistance rather than greater understanding. Even within absolute truths, there may still be disagreement on the implications and meaning of those truths – both religious scholars and scientists have a healthy skepticism of what we currently understand and what we are capable of understanding.

With a passionate viewpoint comes the responsibility to be informed about the issues involved, and to listen to how people with a different point of view see them.

What if the other person really does have bad intentions – lying, bullying, or intentionally derailing the conversation to get what they want?

We can't know for sure what is motivating another person, but sometimes people do lie and have bad intentions towards us. In those situations:

  1. Be careful about rewarding bad behavior. Giving in is justified if you're persuaded the other person is right; when the other person cares a lot about the outcome and you care little; when any solution is better than no solution and you need an answer immediately. But giving in and giving them what they want just to avoid the hassle is not a good long term strategy – it rewards bad behavior, and what gets rewarded gets repeated.

  2. Beware of reacting in kind or "playing their game". Your behavior can affect your reputation far beyond this one interaction, so it will rarely serve you to act poorly in return and undercut your reputation for integrity. How can you deal with it then?

    • You can try naming the dynamic and making the trouble explicit from a Third Story perspective.
    • Clarify the consequences of no change. Make it clear that things aren't working for you as they are. Think about what the real consequences of no change will be, and describe them clearly to the other person.
  3. Seek to understand why they think their intentions and actions are justified. We tend to ascribe bad behavior to bad character – but if we make that assumption, we've already marked them as hopeless. In reality, people tend to feel that their negative intentions and actions are somehow justified, that we're leaving them no choice but to act out. Accordingly, it's still helpful to understand their logic as it keeps open the possibility that you can persuade them that another approach makes sense.

What if the other person is genuinely difficult, perhaps even mentally ill?

There are many mental illnesses that can create huge interpersonal challenges, and even when they're less extreme, they can still cause rifts in our relationships. Good communication skills and support of peers, family, and professionals can mitigate these challenges somewhat, and additionally we should keep in mind that:

Watch out for your own blind spots – tone of voice, facial expressions, and body language all serve to communicate our feelings, and often the listener is very aware of these whereas the speaker is not.

How does this work with someone who has all the power – like my boss?

Use the power of influence. Distinguish between two forms of power: control and influence. Your boss has the power of control over you – they could fire you, dump projects on you, etc. But explicitly acknowledging that they are the decision maker could make them more receptive to listening to your input – likely more open to influence, since they don't need to push back or defend their turf.

Use the language of request instead of the language of joint contribution: "Something else that would be really helpful to me is if I had more lead time on the more complicated projects...

Listen. It quiets their internal voice, letting them hear you, and additionally lets you know what they care about.

Say what's in it for your boss. Explain how having a conversation is in your boss's best interest, and be open to learning – your goal should be to figure out what you might be missing.

Do the necessary reading or research, and try everything you can think of beforehand to deal with the issue on your own. Then, schedule time on your boss's calendar (this will never work as a hit-and-run conversation), and to start the conversation, frame it from the Third Story: "I want to talk about how we raise things, as I think it's affecting morale and productivity...", "I want to talk about the best way to disagree with you in a meeting. What's your advice?"

What if your boss is actually abusive? Firstly, reframe the abuse as something that's not your fault, and don't take their feedback at face value; try to find other ways to evaluate your work so as to preserve your self-worth. Then, it may help to deal with them only when required, treading carefully when you are forced to, and cultivating as many other relationships as you can. Be aware that there are other jobs out there!

If I'm the boss/parent, why can't I just tell my subordinates/children what to do?

You can – make your decisions as early and efficiently as possible, explain them clearly, and take responsibility for their implementation and effectiveness.

But be sure to distinguish between times when you are Commanding (I decide, and I tell you my decision), versus times when you are:

Whatever category you choose, be sure to communicate it effectively and make sure the roles are clear.

When trying to influence someone else's behavior, we often fall into the pattern of repeatedly trying to tell them what to do – even when we don't get the results we expect. We should engage in two-way communication, and by taking the And stance, we can keep our role, rights, and responsibilities (and decision-making prerogative) while still having a learning conversation.

When bringing up an issue, it's useful to be assertive at the start, putting the problem on the table – "Let's talk about X. It was three days late. Let's figure out why, assess the impact, and decide how to avoid this going forward." – and then switch into inquiry mode. Use a mixture of inquiry and assertiveness in the pursuit of your purpose.

Isn't this a very American approach? How does it work in other cultures?

The underlying structure of difficult conversations tends to be the same around the world – and so no matter the culture, make the mental shifts in your internal voice as described earlier, find out ways to talk about the unintended impacts we are having on each other, and a good working relationship will follow.

What about conversations that aren't face-to-face? What about phone or email?

Email allows for reflection and carefully crafted responses, and keeps an ongoing record of a conversation. But it's terrible for difficult conversations: it's not dialogue, but serial monologue. There's no opportunity for clarification, course correcting, or testing our assumptions about their intentions. It doesn't convey tone of voice, facial expressions, or body language.

Yet email can become the most emotional channel of communication in our organization – emotions often suffuse the text, trigger emotional reactions, which get fired back in a vicious cycle of frustration, resentment, and attributions. There's also often an audience (everyone else who's on the email, including your boss) upping the stakes and putting identity more deeply on the line. How can we avoid this?

When reading email:

  1. Question your attributions. You don't actually know their intentions, and you don't know if it was actually your previous email that triggered what you perceive as an attack on you.
  2. Hit pause. If you get a strong emotional reaction, just stop. Do nothing. Wait for an hour or overnight, then come back when you're feeling more balanced.
  3. Talk in person. Once any emotion enters the arena, it's time to switch your mode of communication.

When writing email:

  1. Be extra explicit about your intentions, reasoning, and (when appropriate to share) your emotions. Go out of your way to be clear to ward off potential misunderstanding. Being explicit with your feelings invites a conversation, whereas being curt feels like judgment.
  2. Let them know if there will be a delay – don't leave them hanging. If you can't answer right away, explain why and when you expect to be able to answer: "Let me check with X and get back to you; if you haven't heard from me by Tuesday, please send me a reminder – thanks!"
  3. Take it step-by-step. If you're wondering about their tone or intent, instead of making assumptions, write them a short note to check: "I can't tell if you're annoyed. Was I supposed to respond earlier?"

On the phone:

The phone conveys tone of voice, but not facial expressions – it's still a perilous medium for having difficult conversations.

Why do you advise people to "bring feelings into the workplace"? Shouldn't business decisions be made on the merits?

Every organization has feelings that are accepted and expressed often (stress, frustration, pride, loyalty, enthusiasm), and others that are supposed to remain hidden (disappointment, self-doubt, jealousy, hurt). All in all though, we're supposed to stay on task and check our feelings at the door.

But we can't just leave feelings behind. Positive emotions are necessary to drive us to come to work and do our best, to make good decisions. Negative emotions in reality only distract from productivity when they are unacknowledged and dealt with them directly, efficiently, and honestly.

A difficult conversation at the workplace tends to involve both a business issue and a people/feelings issue, and it's hard to address the former without understanding and addressing the latter.

Remember to use acceptable language ("I often leave these meetings frustrated, and I imagine the you do too sometimes. Can we talk about why that is and how we might design a better process?"), and pick the right timing, location, and context to start these difficult conversations. You can talk about your feelings without being emotional.

Start with sharing less risky feelings – appreciation, admiration, curiosity, enthusiasm; even admitting you're confused about your role or the scope of a task, or anxious about the potential impact of decision you've made on others – and when that's taken hold in your corporate culture, you can go deeper from there.

In business decisions, feelings should be considered as another factor to be weighed on their merits – and bringing them up helps us scope them and avoid them insidiously overwhelming our thinking. No matter the context, listening to feelings and trying to genuinely understand others will improve relationships and morale.

Who has time for all this in the real world?

No one does. Opening up a messy conversation when you have all those other things to do isn't particular appetizing. But that's not the choice we're making here – it's not as if the problem will magically disappear if we choose to ignore it.

We're already spending time and energy dwelling on these unresolved conflicts with people: our time spent complaining to coworkers or spouses about them, our time lying awake thinking of how we should have responded to or confronted them, our time on the Internet trying to diagnose their personality disorders. And all of those things only serve to make our relationship with them worse.

Instead, we should aim energy in useful and efficient directions – why don't we ask third parties for genuine advice and coaching, instead of just complaining? Why don't we go through the preparation checklist, and actually tackle the problem? The earlier we raise the issue, the sooner we clear it up and move on. And issues only grow with time – we can spend seven minutes now, or seven hours arguing or stressing about it down the line.

My identity conversation keeps getting stuck in either-or: I'm perfect or I'm horrible. I can't seem to get past that. What can I do?

Sometimes it's really hard in the moment to not act out when our identity feels threatened – why is it so hard to change these behaviors and assumptions about ourselves? It's because our identities develop from our life experiences and the story we tell about these experiences, and our image of ourselves cannot change unless we can overcome years of hard wiring to change the story we tell.

We need to identify the unrealistic all-or-nothing assumptions we make, then dive deep – look under simplistic identity labels like "competent" or "incompetent", put events in context, come to terms with things that happened in the past. Create new, positive experiences that stimulate and produce positive reinforcement for behaving and seeing yourself in different ways. Enlist help to keep you on track ("Tell me when I'm being defensive"). And give yourself some empathy – we're not perfect, and accepting and forgiving our whole selves, failures and shortcomings and all, is essential to finding balance now and growth in the future.


Final thoughts

For most of us, this will be a lifelong project of small adjustments and daily reminders. As you start to change, look for tiny signs that things are shifting: glimpses of warmth, no argument when you were expecting one - these are often enough to sustain you on your path to improvement. Know when to give up with individual people, though be sure to extend invitations for them to join you on this path. Good luck!