Truth-seeking is the main thing. It is like excavating an archaeological site. Every question may bias the person so answers would be irrelevant. Asking the wrong question is worse than doing nothing at all because when you know you’re clueless, you tend to be careful.
The usefulness of a conversation is whether it gives concrete facts about customers’ lives and world views.
Rules:
| Question | Good/Bad | Reasoning |
|---|---|---|
| “Do you think it’s a good idea?” | ❌ | Opinions are worthless. Only the market can tell if the idea is good. [1] |
| “Would you buy a product which did X?” | ❌ | Anything involving the future is an over-optimistic lie [2] |
| “How much would you pay for X?” | ❌ | People will lie to you if they think it’s what you want to hear [3] |
| “What would your dream product do?” | ❌ | Sort of okay, but only with follow-ups. People know what their problems are, but they don’t know how to solve those problems. [4] |
| “Why do you bother?” | ✅ | Points toward their motivations |
| “What are the implications of that?” | ✅ | Some problems exist but don’t matter. This question helps to distinguish between I-will-pay-to-solve-that problems and that’s-kind-of-annoying-but-I-can-deal-with-it “problems” |
| “Talk me through the last time that happened.” | ✅ | Watching someone do a task will show where the problems and inefficiencies really are, not where the customer thinks they are |
| “Talk me through your workflow.” | ✅ | Same |
| “What else have you tried?” | ✅ | If they haven’t looked for ways of solving it already, they’re not going to look for (or buy) yours |
| “Would you pay X for a product which did Y?” | ❌ | It is about the future where people are overly optimistic. It is about your idea instead of their lives. If far along, ask for money [5] |
| “How are you dealing with it now?” | ✅ | While it’s rare for someone to tell you precisely what they’ll pay you, they’ll often show you what it’s worth to them. |
| “Where does the money come from?” | ✅ | Necessary to figure out decision maker. Especially important in B2B context |
| “Who else should I talk to?” | ✅ | Should work by default. Not working if you screwing up the meeting or they don’t care about the problem |
| “Is there anything else I should have asked?” | ✅ | People want to help you, but will rarely do so unless you give them an excuse to do so. Discard it as you get better at asking good questions and knowing the industry |
Deciding what to build is your job. You do that by figuring out customer’s problems, cares, constraints, and goals. You aren’t allowed to tell them what their problem is, and in return, they aren’t allowed to tell you what to build. They own the problem, you own the solution.
Bad data gives us false positives and false negatives about the idea. Types:
Compliments are almost certainly lying. Try to avoid them completely but if they happen ignore them.
You don’t need to end up with what you wanted to hear. You need to get to the truth.
3 types of fluff:
Always get back to specifics.
Avoid triggering fluff answers by avoiding:
You may use those to transition to concrete questions
Startups are about focusing and executing on a single, scalable idea rather than jumping on every good one. When you hear a feature request/idea, you should understand which motivation led to it. Ask questions like this to do so:
If people are feeling emotional, just let them speak:
So ideas and feature requests should be understood, but not obeyed.
Compliments are dangerous. So it is better to avoid situations when they may occur.
If you’ve mentioned your idea, people will try to protect your feelings.
Anyone will say your idea is great if you’re annoying enough about it.
Even if they are talking about something you’ve already thought of.
Unexpected answers are really important and should affect what you’re doing. You should be asking questions that have the potential to destroy an imagined business.
For unpleasant tasks, you can imagine what you would have someone else do if you were delegating it. Then do that.
Do not avoid important truths. We are not selling, we are learning. “meh” response is more reliable than a “Wow!” one.
Avoid being stuck in details before understanding the big picture. You could get a lot of details of a problem that a person does not care about.
When it is not clear whether a problem is a must-solve-right-now (e.g. selling a painkiller) or a nice-to-have (e.g. selling a vitamin) it is possible to clarify via questions like this (for example with personal blog):
Start broad and don’t zoom in until you’ve found a strong signal, both with your whole business and with every conversation.
Sometimes we fall to asking questions that don’t actually de-risk the business or resolve those critical, big, scary, lurking questions.
There are two types of risks:
Do not overlook one or the other. Videogames, for example, are a pure product risk. If more product risk maybe start building earlier.
Pre-plan the 3 most important things you want to learn.
There are suggestions to separate meetings into 3 to avoid bias: the first about the customer and their problem; the second about your solution; and the third about selling a product. But the first one doesn’t even have to be a meeting. Learning about a customer and their problems works better as a quick and casual chat than a long, formal meeting.
Do not try to relegate every opportunity for customer conversation into a calendar block. It sets expectations. Reduce it from a meeting to a chat. Leave room for the unexpected. Symptoms of formality:
At their best, conversations are a pleasure for both parties. If it feels like they’re doing you a favor by talking to you, it’s probably too formal.
Early conversations are very fast. Chat grows longer as you move from the early broad questions (“Is this a real problem?”) towards more specific product issues. It takes 5 minutes to learn whether a problem exists and is important. Learning how someone achieves a certain goal is quick as well. Scheduling and going to a meeting has a lot of overhead for a 10-minute chat. Just leave the idea out.
Keep it casual even in more formal meetings. Give as little information as possible about your idea while nudging the discussion in a useful direction.
Once we’ve learned the key facts about the industry and customers, it’s time to zoom in again and start revealing ideas and show some products. But compliments! To distinguish we may ask for commitment in some form or for an advancement.
Not trying to convince anybody. If they don’t care we can leave. But we have to put them to a decision in order to get the answer. Symptoms of a bad meeting:
Two concepts of moving forward:
“Customers” who keep being friendly but aren’t ever going to buy are a particularly dangerous source of mixed signals.
If you don’t know what happens next after a product or sales meeting, the meeting is pointless.
Compliments aren’t data because they don’t cost anything.
Time commitment:
Reputation risk commitments might be:
Financial commitments:
The more they’re giving up, the more seriously you can take their kind words.
| Phrase | Good/Bad | Reasoning |
|---|---|---|
| “That’s so cool. I love it!” | ❌ | Compliment. Zero data. Obviously fluff. Deflect it and get back to business |
| “Looks great. Let me know when it launches.” | ❌ | Compliment plus a stalling tactic. Find a commitment to ask for today to make a signal clear, for example, an introduction or push to an alpha user. |
| “There are a couple of people I can introduce you to when you’re ready.” | ❓ | Some data, but it is too generic. Clarify what “ready” is and who he wants to introduce to. |
| “What are the next steps?” | ✅ | Need to know what the next steps are. |
| “I would definitely buy that.” | ❌ | Shift from promises into concrete current commitments. |
| “When can we start a trial?” | ❓ | Depends on what starting a trial means for them. If it is a big effort then good. What are they giving up to try it out? |
| “Can I buy the prototype?” | ✅ | Rare. |
| “When can you come back to talk to the rest of the team?” | ✅ | In case of B2B. |
Meeting that you leave with neither rejection nor advancement. Won’t learn anything until I take the next step. Maybe pushing for a commitment at the end while you receive compliments. But don’t be annoying, you aren’t trying to get into their wallet. You are trying to cut through polite rejections.
Q: aren’t polite rejections bad already?
Even product-focused sales meetings start with open-ended learning. Hard pitching gives binary feedback whether you nailed it or you didn’t. That’s not ok for big questions like if anybody cares about your product at all.
Buying from a startup is already weird. First customers are crazy in some way. They really, really want what you’re making. It is good to keep an eye out for the people who get emotional about what you are doing. These might be early evangelists:
They might give you money even for pre-orders and duct-tape prototypes. If someone isn’t emotional it’s pretty unlikely that they are crazy enough to be the first customer.
In early-stage sales, the real goal is learning. Revenue is just a side effect.
Cold calls
The goal of cold calls is to stop getting them by treating the first one or two respectfully trying to solve their problem and getting warm intros from them.
Seizing serendipity
Sounds weird to unexpectedly interview people but you should think of a conversation instead. People love talking about themselves and their problems. Don’t make excuses about why you are there or mention that you are starting a business. Just have a good conversation.
Find a good excuse
For example “Hello, I’m doing my PhD research on a problem around X and it would be a huge help if I could ask you a couple of questions”
If it’s a topic you both care about, find an excuse to talk about it. Your idea never needs to enter the equation and you both will enjoy the chat.
Immerse yourself in where they are
Landing pages
Get your product out there, collect emails, and reach out.
When you are finding ways to have conversations, you’re on the back foot. You approached, so they are suspicious and trying to figure out if you’re trying to waste their time.
Organise meetups
Speaking & teaching
Conferences, workshops, online videos, blogging, consulting, office hours.
Industry blogging
Get clever
Business-specific hacks.
These are the goals.
7 degrees of bacon
Research the network.
Industry advisors
They might create incredible intros. They might come from early customer conversations.
Universities
Professors are easy to reach out and they get grant funding from high-level industry folks.
Investors
Cash in favours
Everybody who said “Keep me in the loop and let me know how I can help”
You are going to be ignored a lot, but so what? You aren’t trying to minimize failure rate; you are trying to get conversations going.
It might be unclear what the meeting is for. So it is important to frame it:
Or, in shorter form: Vision / Framing / Weakness / Pedestal / Ask
Better to start in person.
Be with a mindset of looking for advisors instead of customers.
Keep having conversations until you stop hearing new stuff.
Every company starts small, otherwise it is too generic; the marketing message is generic.
If you have a fuzzy sense of who you’re serving, you end up talking to a lot of different types of people, which leads to 3 problems:
Talking to an industry expert can provide a taxonomy of the industry.
If you aren’t finding consistent problems and goals, you don’t yet have a specific enough customer segment.
Start with a broad segment and ask:
Having those answered, we will have segments and motivations. How to find them:
If groups are unfindable then slice into finer pieces. Now that we have those, we may start with the most:
Good customer segments are a who-where pair. If you don’t know where to go to find your customers, keep slicing your segment until you do.
3 ways to do so:
It is a bad pattern for a single guy to do all the meetings and tell everybody what to do because it’s easy to misinterpret what customers say.
Symptoms of a learning bottleneck:
Ensure you know your current list of 3 big questions. Scary questions should be there as well. If some questions could be answered using desk research – do it.
Questions to unearth hidden risks:
We are trying to figure out:
If you don’t know what you’re trying to learn, you shouldn’t bother having the conversation.
Say you’re building an app to help construction companies manage their suppliers. You might ask them to show you how they currently do it. Talk about which parts they love and hate. Ask which other tools and processes they tried before settling on this one. Are they actively searching for a replacement? If so, what’s the sticking point? If not, why not? Where are they losing money with their current tools? Is there a budget for better ones? Now, take all that information and decide for yourself whether it’s a good idea. | ↩︎
Ask how they currently solve X and how much it costs them to do so. And how much time it takes. Ask them to talk you through what happened the last time X came up. If they haven’t solved the problem, ask why not. Have they tried searching for solutions and found them wanting? Or do they not even care enough to have Googled for it? | ↩︎
Just like the others, fix it by asking about their life as it already is. How much does the problem cost them? How much do they currently pay to solve it? How big is the budget they’ve allocated? | ↩︎
The value comes from understanding why they want these features. You don’t want to just collect feature requests. You aren’t building the product by committee. But the motivations and constraints behind those requests are critical. | ↩︎
Ask about what they currently do now, not what they believe they might do in the future. Common wisdom is that you price your product in terms of value to the customer rather than cost to you. That’s true. And you can’t quantify the value received without prodding their financial worldview | ↩︎