Most disagreements between people share the same underlying anatomy, even when the stakes are wildly different. A bickering couple deciding where to eat dinner is using the same psychological machinery as two business partners arguing over equity.
Indeed, almost every conflict gets worse for the same reasons. People stop listening because they’re rehearsing their next point. They argue against a position rather than the person actually in front of them, so they end up swinging at a straw man. They confuse their preferences with their principles, which makes any compromise feel like a betrayal.
They are exchanging arguments instead of trying to understand the point of view and interests of the other person. And they let emotion run the conversation while pretending it isn’t there.
The basic strategies that help are also similar. Listen properly, which means letting the other person finish without composing a rebuttal in your head. Reflect back what you’ve heard before responding, even briefly, so the other person knows they’ve actually been heard. Try to find the interest underneath the position. Be honest about what you want and why. Be willing to discover you were wrong without treating the discovery as a humiliation.
Some related reading on the question-asking side of this:
Tone and timing matter regardless of context. A reasonable point delivered when someone is exhausted, emotional or already defensive is perceived as an attack. The same point made at a calmer moment can be agreed with promptly. Similarly, there is almost never an emergency that requires a difficult conversation to be had at this exact instant; a few hours, sometimes a few days, often improves the outcome substantially.
Sometimes, we approach the conflict totally disconnected from the other party and the context, unaware of what is happening with the people around us and of the system in which we all operate. For example, entering the office of a colleague and engaging in a discussion about the missed project deadline with determination and resolve, not knowing that they just had a heated argument with their partner over the phone and are still emotional — something totally unrelated, which will however significantly affect how they approach the work-focused conversation.
You might reasonably ask at this point: if it’s all so straightforward, why are we so consistently bad at conflict and difficult conversations? Could you just stop reading the article at this point? Not really. Knowing the moves and applying them well at the right scale are two different problems, and that gap is where most of us lose.
What changes as the stakes climb is the calibration of those instincts and the amount of structure you should build around them. The listening skills that resolve a row about the washing-up are not, on their own, adequate to a contested divorce; the formal apparatus that fits a divorce would be ridiculous in the kitchen.
People also make characteristically different mistakes at each level, which means the failure modes are worth exploring as well as the techniques. Let’s dive in.
Low-stakes conflicts
Examples: a flatmate not doing their share of the washing-up, a friend who keeps running late, a small irritation at work.
When the stakes are low, the main risks are letting the tension accumulate or overreacting. People often do both at once. They say nothing for weeks, then erupt about something trivial in a way that’s confusing for the other person and embarrassing for them. Unfortunately, conflicts don’t fade away on their own: they require attention and effort, and avoidance is not a good strategy.
The accumulation problem deserves a bit more depth: because each individual instance feels too small to mention, you don’t say anything. But the irritation doesn’t go anywhere. It just deposits itself somewhere, and after enough deposits the next instance lands on top of all the previous ones rather than being weighed on its own. By the time you do say something, your reaction is calibrated to the running total, while the other person, who has only experienced the latest instance, reasonably thinks you’re being disproportionate. They are right that you are, and you are right that the underlying issue is real. Both can be true at the same time, and the conversation goes badly because neither of you is talking about quite the same thing. This case is an example of the proverbial “straw that broke the camel’s back.”
The right response at this level is usually to mention things early, lightly, and without making them into a verdict on the whole relationship. “Hey, can we figure out the washing-up rota? I’ve been doing most of it the last couple of weeks and it’s starting to bug me” is a complete conversation. It doesn’t need to be solemn. Because the cost of getting it slightly wrong is small, you can be more direct and less rehearsed than you would be in a more loaded situation. The mistake is treating every minor mention as if it were the start of a Big Conversation. That’s exactly how a thirty-second exchange turns into an awkward evening.
Here’s an example:
Sam and his flatmate had a good arrangement, or so Sam thought. The bins, the recycling, the occasional shared shop. It mostly evened out. What didn’t even out was the kitchen. Sam’s flatmate cooked elaborately and cleaned up slowly, sometimes a day later, sometimes not until Sam did it himself rather than look at it over breakfast.
Each time, it felt too small to raise. It was one pan. It was one evening. Mentioning it would have made him feel petty, so he wiped down the surfaces and said nothing.
By the time he did say something, over a single mug left in the sink, on a Tuesday, it came out as a short speech about respect and consideration and whether his flatmate actually valued living there. His flatmate, who had registered none of the previous two months, heard an enormous reaction to one mug and concluded that Sam was impossible to live with.
They were both right. The mug didn’t warrant the speech at all on its own. But the pattern genuinely did. And because Sam had saved it all up, the conversation was about his accumulated frustration rather than the thing he actually wanted to fix. As a result, the flatmate left the exchange feeling unfairly ambushed rather than thinking about the kitchen at all.
There’s also a category of low-stakes conflict that needs to be dealt with separately: the kind that gets expressed obliquely. Sarcasm, eye-rolls, pointed silences, slightly cold replies, the well-aimed sigh. These are how a lot of people register dissatisfaction without feeling they’ve started a fight. The trouble is that the other person registers them too, but doesn’t get a chance to respond to anything explicit, so resentment builds on both sides about a conversation that hasn’t actually happened. If you find yourself doing this, it’s usually worth saying the actual thing instead. If you find someone else doing it to you, asking gently and without irony what’s going on tends to work better than matching the tone. Focus on facts, numbers, observable behaviours, not opinions or judgement. And avoid talking too much about the past — rather, discuss future behaviours or actions, only using the source of the current frustrations as a starting point.
A useful reframe is that low-stakes conflicts are often early signals of larger patterns. The argument about the washing-up isn’t really about the washing-up; it’s about feeling that your time is taken less seriously than the other person’s. Treating these small frictions as data, rather than just nuisance, lets you spot patterns while they’re still cheap to address. A medium-stakes conflict is, very often, a low-stakes conflict that nobody dealt with in time.
And, by the way, there is a very much alive myth that the closer we are to the other person, the fewer conflicts should emerge. Exactly the opposite is true: the risk of tension and friction increases as we get more intimate. A strong relationship is usually one where the people involved have the skills and ability to resolve small, low-stakes conflicts early and smoothly.
The Art of Asking Questions is a reader-supported publication. To support my work, please consider becoming a paid subscriber.
Medium-stakes conflicts
Examples: ongoing tensions at work, disagreements with partners about money or parenting, frictions with siblings or in-laws, disputes with neighbours.
Medium-stakes conflicts are where most adults spend a lot of their lives. The defining feature is that the relationship is going to continue and the issue is likely to recur in some form. That changes the calculation in two ways. You can’t just win and walk away, because you’ll see this person on Monday or at Christmas. And you can’t avoid the topic indefinitely without the avoidance itself becoming the problem.
These conflicts reward more structure. It helps to pick a deliberate moment to talk rather than letting the conversation erupt opportunistically, and to flag it beforehand so the other person isn’t ambushed. That gives them time to think rather than time to defend, and signals that you’re taking the issue seriously enough to plan for.
It helps to separate the specific incident from the larger pattern, so the other person isn’t being asked to defend a year of behaviour all at once. Most people will dig in if they feel everything is up for review, whereas they will engage if the conversation has visible edges (this is what we discussed as the ‘Movie Scene’ in a recent article and live with Maurizio). If the underlying pattern really is the issue, you can come back to it once the specific incident has been talked through. Trying to do both in the same sitting tends to produce a row about the wrong thing.
Writing things down beforehand, even only for yourself, clarifies what you actually think and stops you drifting onto tangents under pressure. The exercise often reveals that you want several things, some of which are in tension, and that you haven’t yet decided which matters most. If a workplace issue is heading anywhere that might involve HR or a tribunal, these notes become genuinely useful rather than just reassuring. Ideally, all conflicting parties should come prepared — improvisation from a blank page usually ends badly or takes too much time and energy.
A particular trap at this level is the difference between airing a grievance and trying to solve a problem. They look similar from the outside but have very different shapes:
Airing tends to be one-directional and complete in itself: you say the thing, the other person hears it, the air is somewhat clearer.
Solving requires both parties to commit to specific changes, which means both parties have to bring something to give up.
You should be honest with yourself about which one you’re going for. Going in claiming to want a solution while actually wanting to be heard is a reliable way to end up worse than you started:
Anna has been carrying what she privately calls “the invisible architecture of this family’s life”: the grocery lists, the school admin, the low-grade permanent logistics. One evening, it boils over. Her husband, Victor, listens, doesn’t get defensive, and says genuinely, “You’re right, I’ll do more, just tell me what you need.”
Anna nods. They hug.
But what Anna wanted was for Victor to see it without being told. The telling him is the exhausting part, that’s the whole point. Victor heard something different: problem identified, fix agreed, she’ll delegate, he’ll execute. He’s not wrong exactly. He just answered a question she wasn’t asking.
Next Sunday, Anna is making the grocery list. Victor is nearby, waiting. She doesn’t ask. She’s stewing.
Three weeks later, same kitchen, same argument. Now with the added bruise of “we already talked about this.”
Solving this would have been messier: Anna saying she doesn’t want to delegate, she wants Victor to own things without being managed. Victor asking what that actually looks like. Both sitting with the discomfort of a real negotiation rather than a successful venting session. What they had instead felt like resolution, but wasn’t.
A third party can help at this level, though they don’t have to be a professional. You mainly need someone who can slow the conversation down and reflect back what each side is saying. The point of a third party is to break the loop where each person keeps hearing the worst possible version of what the other one said (“He always takes me for granted!” or “She won’t tell me what she wants from me!”).
The judgment call at this level is when to escalate something towards more structured handling and when to keep working it out informally. The signals that something has outgrown informal handling are reasonably consistent:
The same conversation keeps happening with no progress.
One party is using power they didn’t previously have, such as a manager who has started writing things up or a partner who’s started talking about leaving.
The issue is starting to spill into other parts of your life, like your sleep, your work or other relationships.
None of these on their own mean the situation has become high-stakes, but they suggest the informal approach has stopped paying off.
High-stakes conflicts
Examples: divorce and custody, major financial disputes, business breakups, serious workplace allegations, deep estrangements within families.
High-stakes conflicts are the ones where the outcome can reshape your life. Here the rules change in ways that can feel very uncomfortable if you’re used to handling things informally.
You generally need professionals, like a family solicitor, a mediator, an employment lawyer or a therapist. The consequences of a misstep at this level are large enough that you want someone whose job is to think clearly while you can’t. People often resist this on cost grounds and end up paying far more for the consequences of going it alone.
The choice of professional matters. A specialist in your kind of dispute is generally worth more than a generalist with more years on the clock. Personal recommendations from people who’ve been through something similar are more reliable than online reviews, which over-represent the very pleased and the very angry. It’s normal to have an initial conversation with two or three before picking one: you’re buying someone whose temperament you can stand for the next year, and whose willingness to tell you uncomfortable things you actually trust.
Here’s an example of how the choice of professional often goes wrong:
Daniel and his co-founder Marie had built the company together for six years before things stopped working between them. When the time came to split, Daniel hired his regular solicitor. This was the man who’d handled his house purchase, who knew the family. Marie hired someone who did nothing but shareholder disputes.
The specialist told her things she didn’t want to hear in the first meeting. That her position on the IP clause was weaker than she thought. That some texts she’d sent two years ago were going to be a problem. That what she was hoping for wasn’t realistic. She went home and complained to her partner about the lawyer. But she stuck with the lawyer anyway.
Daniel’s solicitor was not a bad lawyer. He was just a generalist who liked his client; and, when you like your client, you tend to agree with them. Daniel spent eight months being surprised by things that Marie apparently wasn’t.
The final settlement landed close to what the specialist had told Marie to expect in month one, and several points up from where Daniel’s solicitor had assured him things would settle. Daniel spent eight months and a lot of money arriving at an outcome that was worse for him than the one Marie had been braced for since the start — the difference being that she’d spent those months preparing for it while he spent them being surprised.
You also need to be more careful about what you say and where, and slow your communication down. Things written in anger by text or email have a habit of being read aloud later in rooms that you didn’t expect.
If you have seen recent high-stakes trials (like the Musk v OpenAI one), you will know that this isn’t paranoia. High-stakes disputes routinely involve people you trusted last year and don’t trust now:
Priya, going through a custody dispute, was by her lawyer’s account keeping her head. The process was ugly but she was managing it.
What she hadn’t thought about was her sister.
Her sister, Meera, was her closest person and completely on her side. During the worst months Priya had sent her long voice notes, screenshots, a running commentary. The kind of thing you only say to someone you trust completely, in the tone you only use when you’re sure nobody else is listening.
Then she and Meera fell out because old family money, nothing to do with any of this. And, at that point, her ex-husband got a call.
A string of messages were submitted as evidence by his lawyers. Nothing criminal, just a year’s worth of anger about his parenting, his finances, something her daughter had said about weekends at his place that she’d passed along without thinking about how it would look written down.
It looked bad written down.
The messages didn’t lose her the case, but they cost her. Her ex-husband’s lawyers used them to paint her as someone whose hostility might colour what the children heard at home, and the question of how the weekends were being talked about (something she’d mentioned to Meera in passing, never to her daughter directly) became a thread the other side kept pulling. Her own lawyer spent time she’d rather have spent elsewhere explaining context, walking back tone, reassuring people that a year of private venting wasn’t a parenting style. The arrangement she ended up with was workable, but it came with conditions she might not have been carrying if she hadn’t shared her frustrations in writing.
Her lawyer had told her in the first meeting to treat everything as potentially visible. She’d nodded and thought: yes, but not my sister.
So, a useful working rule is to assume any message you send during a high-stakes dispute might end up in front of a judge, an arbitrator or someone else’s lawyer. Most won’t, but writing as if they might removes a whole category of regret.
When it comes to high-stakes conflicts, friends and family are a complicated resource. You’ll need people to talk to, and the people who love you will want to help. They are also, in many cases, poor sources of strategic advice, because they care about you rather than about the outcome and they will often tell you what they think you want to hear. The healthier pattern is to use them for emotional support and use professionals for advice, and to notice when those two things are getting tangled up.
That kind of emotional support is important, because self-care is part of the strategy rather than an indulgence. Sleep, food, exercise and someone to talk to who isn’t a party to the dispute are what keep you from making decisions that look reasonable at midnight and disastrous in the morning. Long, high-stakes conflicts wear people down, and the side that holds itself together better often does better, because they’re still capable of clear thought when the other side isn’t.
The hardest skill at high stakes is knowing when to settle and when to hold out. Most people swing between the two extremes, capitulating early to make the discomfort stop, or digging in past the point where winning costs more than losing. A good, detached adviser helps you see the realistic range of outcomes and the actual cost of the fight, so the decision is made on something other than how you happen to feel that day or week.
The cost of the fight includes months or years of your life, the relationships that survive the dispute and the ones that don’t, and the version of yourself you’re becoming while it’s going on. So you need to avoid becoming the conflict. When something occupies enough of your attention for long enough, it can take over your sense of who you are, so that even when the dispute ends you’ve lost the ability to think about anything else.
The people who come through high-stakes conflicts best tend to be the ones who keep some part of their life ring-fenced from the dispute, even when that feels frivolous or disloyal to the cause. A weekly tennis game, a project at work, a friendship that has nothing to do with the matter: these things are how you preserve the person who will have to live the life that comes after.
A throughline
The counterintuitive thing about stakes is that most people get worse at conflict as the stakes rise, when actually they need to get better. The pull is in the wrong direction at exactly the wrong moment: less sleep, more fear, fewer reliable advisers, a stronger urge to win. All when the cost of winning badly is highest.
It also helps to remember what you’re actually trying to preserve. In a small dispute, it’s usually the ordinary functioning of a relationship you don’t want to have to think much about. In a larger one, it’s a partnership or a working arrangement you’ll need to keep using. In the worst kind, it’s something deeper: the version of yourself you’ll be living with when the matter is finally over, and the people you’ll still want around you then.
The unhelpful instinct in any of these is to treat the conflict as a contest with a winner. Most disagreements between people are problems to be solved together, even when one party has been clearly in the wrong. The aim throughout is a state of affairs both people can live with going forward, with as little damage along the way as possible.
Enjoyed this piece? Become a paid member and get my Consulting with AI prompt library, the full Asking Questions Like a Pro course ($199 standalone), practical templates from a decade of fieldwork, and discounts on many other resources. 🔗 See everything included in the paid tier.
