You will be able to ask questions that show what the other side cares about, without making them feel interrogated.
Before you put a figure on the table the next time someone makes a demand of you, find out why the demand matters to them. Lesson 1.1, "What people ask for is not what they need", showed that one position usually sits over several interests. To find those interests, you need the other side talking about their problem. The conversation should come across as interest in that problem and shouldn't feel like an interview.
Take Arjun, who edits videos for a living (he and his clients are an invented example). A property developer's marketing team wants six short clips for a launch. They need them in two weeks, when he would normally get four. His instinct is to name a rush fee and brace for the pushback. Doing that would be a position meeting a position, which means answering their stated demand with a counter-demand without looking at the reasons behind it. Arjun holds off on any number and asks what's behind the date.
The marketing manager tells him the clips are for a preview event for existing buyers, held on a date that can't change. Only two of the six clips will play at that event. The remaining four go out on social media over the following weeks. What she needs, then, is something good to show on one particular evening, and two clips cover that. Arjun can offer to deliver those two within two weeks and the other four on his normal schedule, with either no rush fee or a smaller one. Neither of them had suggested this when the talk began. A single answer about the real interest can reshape a negotiation like this and turn up an option nobody put forward at the start.
Of all the questions in a negotiation, "why" is the simplest. It is also the easiest one to get wrong. Asked bluntly, as in "Why do you need it by the 14th?", it can come across as a challenge, as though the other side owes you a justification. Asking what the demand is for carries the same curiosity and goes down better. You might ask what getting it by the 14th would allow them to do, what lies behind the date, or what would happen at their end if it slipped a week.
In the book Getting to Yes, Fisher and Ury recommend asking "why?" and following it with "why not?". It helps to have both ready. The "why not?" question is about your own proposal. It makes your offer the topic, and it asks the other side what is wrong with it from where they sit, so you aren't left defending it. You could ask what makes it difficult to accept, what their boss would object to, or what would have to change before it could work for them.
Inviting objections can feel like a risk. They are there whether you raise them or not, though, and asking gets them into the open while there's still time to act on them. Sometimes an objection reveals that the amount was never the real constraint, and that the issue is something else, such as who has to approve it. Picture Arjun proposing a rush fee and the manager going quiet. If he asks "What makes that hard?", he might learn that the marketing budget was signed off months ago and that anything extra needs the director's approval. The constraint is then approval. A smaller fee inside the manager's own limit could be easier to agree than a bigger one that has to go up to the director.
Hardly anyone lists their interests from most to least important. What matters to them shows up in what they repeat, so listen for the words and worries that come up more than once. The worry someone keeps returning to is often the interest the deal will turn on. Say the manager brings up the preview event three times, the director twice and the budget once. In that case the event and the director are probably what matter most to her. Or take a landlord who keeps saying "last time the tenant left the place in a mess". For them, the state of the flat may weigh more than the rent figure.
When the setting allows, jot those repeated words in a notebook or on your phone during the conversation. Later you'll recall the numbers but lose the exact words, and the exact words hold the clues. You can also use reflecting back, which means putting a word or worry they keep repeating back to them as a question. Arjun might ask whether the event is the part that can't move. This tests your guess, shows them you were paying attention, and makes them more willing to tell you more.
A long run of questions can start to feel like an interrogation, more so with someone you've only just met. The remedy is to offer something of your own, because when you tell the other side a few of your interests they often become more open about theirs. Arjun could say that his main concern is doing two rushed jobs back to back, because the quality suffers. He could add that if he knows which clips matter most for the event, he can plan around it. He says nothing about the lowest fee he'd accept or how much he wants the job. Once she has heard his concerns, it's natural for the manager to explain hers.
The line to draw is between interests and numbers. Be generous with interests, since they help both sides find options. Keep numbers such as the lowest fee you'd take to yourself. They do nothing to help the other side find options and only show them where they can stop. Module 2 deals with your numbers in detail.
None of these questions works unless it sounds like you, so change the wording to suit how you talk and who you're talking to. A question that comes out naturally from a colleague can sound stiff from a stranger. Where you go back a long way, you can be more direct. With a landlord you've known for three years, you could just ask whether the increase is about the market or about something else. With a new client, soften the question and add your reason for asking it.
How you say it counts as much as the words you choose. Be genuinely curious when you ask, wait for the reply, and don't meet each answer with another question straight away. A pause after a question gives the other person room to say the thing they almost held back.
Now go back to the negotiation you picked in Lesson 1.1. Imagine the other side sitting across from you just after they've stated their position. In the activity below, write the questions you would ask next, then judge which of them you could say out loud without sounding scripted.
Write six questions you could ask in your next negotiation to find out the other side's interests. Rank them by how natural they would sound when you say them.
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