3 big questions and a discussion guide

Sofia's call with Andrew went well, and not by luck. The evening before, she wrote her questions down, and whenever she felt like drifting into small talk, the list was right there. Two scary answers came out of it: he has never paid for anything cat-related in advance, and he changed shops only once, when prices went up.

Make that a habit. Before every round of conversations, write down your list of 3: the three most important things you want to learn from this type of person.

Why three and not ten? Ten turn into a questionnaire you rush through, ticking boxes instead of listening. Three fit in your head, even in a five-minute chat by a shop till.

Choosing them in advance matters as much as the number. Mid-call, when a moment gets awkward, the easy questions always win. If you decided calmly the evening before what you must learn, the scary questions survive that moment. Keep the list where you can glance at it.

Turning a big question into something you can say on a call is a small, repeatable move. Take the goal and ask yourself: what would someone have done if the answer were yes? Then ask about the last time that happened.

• “Do they ever pay ahead?” becomes “When did you last pay for something for your cat a month or more in advance?” If the honest answer is “never”, you've learned it without a debate.
• “Does running out cost them real time or money?” becomes “What happened the last time you ran out? How long did it take to sort out?”
• “Who decides and pays?” becomes “Who bought the last bag, and whose card was it?”

Each call question points at one moment in the past, so there's nothing to guess and nothing to be polite about. Write two or three of them under each big question before the call, so you don't have to invent them while you're also listening.

Your three big questions are things you want to learn, not lines to read out. Sofia's draft for cat owners was: does running out of food cost them real time or money; do they ever pay for pet things in advance; who decides on the food and pays for it. All three are good goals, and all three would be bad questions if asked word for word.

Asked straight, “Do you ever pay for pet things in advance?” invites a quick, flattering guess about yourself. People describe the person they'd like to be, not what they did.

So on the call you reach each goal through honest-answer questions about the past. “Who decides and pays?” becomes “Who bought the last bag, and whose card was it?” The big question is the destination; the conversation is the route. Nobody should be able to guess your list from what you ask. That's also why the list stays short: one goal can take several small, concrete questions to reach.

To choose your three big questions, ask yourself: what's the riskiest thing we believe right now, and which answer would change the plan? Good items test beliefs the whole idea rests on: whether running out of food really costs owners something, whether they ever switch where they buy, whether anyone pays in advance. At least one of them should scare you.

Items about packaging colour or a product name don't belong. They collect opinions about details, and no answer would change much. Don't agonise over the wording either: the list will change as soon as you start learning.

Choose them together. Fifteen minutes before a round of calls, everyone involved brings their best guess and their scariest question, and you agree on three. Invite the developers too: they spot product risks the rest of the team misses, and once they've helped choose the three, they'll trust the answers. This is conversation prep: short, shared, before every round.

When the team of Megan, CatChow's head of sales, got ready to call the pet shops that stock CatChow, she asked to borrow Sofia's list. It wouldn't work: Sofia's questions are about cat owners, and a shop owner can't tell you how Olivia feels about paying ahead.

Each type of person gets its own list of 3, because each knows a different part of the picture:

• a cat owner knows her own habits and what running out costs her;
• a pet shop owner knows the shop's business, and how it reacts when a brand starts selling directly;
• a courier knows what delivery really costs;
• your own sales team hears customers' complaints every day.

Ask each person for what only they can tell you, and put the scariest question for that group first. For shops, that's how they'd react when CatChow starts selling directly to their customers. Half of CatChow's revenue goes through those shops, which is exactly why that question can't wait.

Sofia wondered whether to ask shops how many cat owners live in their district. The question back is simple: could you find that out without them? City statistics and the shop's own online reviews would probably do.

A conversation is expensive: your time, the other person's time and their patience. Don't spend it on facts that are just lying around. Anything you can learn from the web, the CRM, sales records or the analysts, learn before the call.

How many bags a shop ordered last quarter is already in CatChow's sales data. How long someone has been a customer is in the CRM; Sofia nearly asked Andrew that one. Save the conversation for what only that person knows: who really decides which brands to stock, and what they did the last time a supplier changed its terms. Doing your homework also makes you sound prepared, which earns more patience for the questions that matter.

The list of 3 is for a whole round of conversations, not for each single one. A short call may cover only one question, and that's fine: question one from Olivia, two and three from Andrew, and together they complete the picture. Nobody needs to answer all three for the data to count.

Once a question has solid, consistent answers from several people, stop asking it and spend the time on what you still don't know. This keeps every conversation shorter, and short conversations are far easier to get.

The list itself changes as you learn. After eight calls, Sofia's question one had an answer: for owners with a shop nearby, running out is cheap, ten minutes and no drama. A vitamin. But two owners had cats on prescription diets, and one had driven across the city twice last month for food. New segment, new risks, new three. A list that changes means it's working; a list that never changes means you've stopped learning.

A discussion guide turns your list of 3 into a one-page plan for a call: the questions you need answered and a few prompts to reach each one. It isn't a script to read aloud. It keeps the call on track while the talk stays natural. It has four parts, in this order:

1. A broad opening about their world, such as “How do you order stock for the shop now?”
2. The three big questions, the scariest first, while there's still time.
3. Under each, two or three prompts about past behaviour: “When did that last happen? What did you do then?”
4. One closing ask at the end.

For the scariest shop question, prompts could be: “When did a brand you stock last start selling online? What did you do about it? What happened to your orders?” Each asks what they did, not what they would do. Keep the whole guide short enough to glance at mid-call: one opening, three questions, nine prompts at most, one ask.

A discussion guide ends with one closing ask: a small request that costs the other person a little, such as a look at last month's orders or an intro to another shop owner. It shows whether their interest is real, and it moves things forward. A friendly “thanks for your time” shows neither.

A good ask fits the stage. Compare four endings for a first call with a shop:

• “We'll be in touch when we launch” asks for nothing at all.
• “Would you recommend CatChow to other shops?” asks for an opinion about the future, which costs nothing to give.
• “Would you sign a twelve-month exclusive deal today?” is far too much, too soon, and a no teaches you little.
• “Could you show me last month's orders, so I can see where stock-outs happened?” costs them some time and trust, and gives the team real data.

Pick something they can agree to today that still means giving up a bit of time or reputation.