What I Learned from "The Mom Test" - A Developer's Guide to Customer Conversations - Part 2

Chapter 3: Asking Important Questions

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Table of Contents

• The Trivial Question Trap
• Finding Scary Questions
• Learning to Love Bad News
• The Lukewarm Response Problem
• Look Before You Zoom
• Premature Zooming: A Common Mistake
• Gaze Upon the Elephant
• Does This Problem Actually Matter?
• Prepare Your List of 3
• Key Takeaways and Rules of Thumb

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The Trivial Question Trap

Here's something I realized after reading this chapter: it's possible to ask non-biasing questions that are completely useless.

Once we learn The Mom Test, we might over-compensate. We start asking safe, neutral questions — but they're so trivial they don't move our business forward at all.

Asking someone "How old are you?" isn't biasing, sure. But it also tells you nothing useful about whether they'll buy your product or whether you're solving a real problem.

The Key Insight

You have to apply The Mom Test to questions that actually matter. Otherwise, you're just spinning your wheels — having nice conversations that feel productive but lead nowhere.

⚠️ Watch Out For

• Asking demographic questions that don't help you understand the problem
• Sticking to "safe" topics because important questions feel uncomfortable
• Leaving conversations feeling good but having learned nothing critical

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Finding Scary Questions

This section hit me hard. Fitzpatrick argues that beyond avoiding trivialities, you need to actively search for the world-rocking, scary questions you've been unintentionally avoiding.

We all have questions we're afraid to ask because the answers might destroy our business idea. But those are exactly the questions we need to ask.

How to Find Scary Questions

The book suggests a thought experiment:

1. Imagine your company has failed spectacularly
2. Ask yourself: what had to be true for that to happen?
3. Find ways to learn about those critical pieces

How to Identify Important Questions

Here's a practical test: a question is important when its answer could completely change (or disprove) your business.

If you get an unexpected answer and it doesn't affect what you're doing, it wasn't an important question to begin with.

A Real Example from the Book

Fitzpatrick shares a personal story that cost him dearly. One of his companies had legal ambiguities around content ownership. The theory was okay, but they lacked strong precedents.

A key customer's executives were excited, and their creative team was thrilled. But Fitzpatrick never asked the lawyers about the legal concerns — he was afraid of the answer.

The result? Not asking that scary question cost them at least half a million dollars.

The Hard Truth

There's no easy solution here. For unpleasant tasks, the book offers this advice: imagine what you would have someone else do if you were delegating it. Then do that yourself.

You're a startup. You're allowed to ask about money. You're allowed to ask uncomfortable questions. It's okay.

Rule of thumb: You should be terrified of at least one of the questions you're asking in every conversation.

✅ Do This

• Identify the questions you've been avoiding
• Ask yourself: "What could kill this business?"
• Make yourself ask at least one scary question per conversation

❌ Don't Do This

• Avoid topics because they make you uncomfortable
• Assume things will "work out" without verification
• Leave critical assumptions untested

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Learning to Love Bad News

This concept was a mindset shift for me. We avoid important questions because the answers are scary. They might reveal that our beloved idea is fundamentally flawed, or that a major client will never buy.

But here's the reframe: bad news is actually good news — if you get it early.

The Economics of Bad News

Think about it this way:

Scenario	What Happens
One shot, bad news	Your bungee cord doesn't work, your café fails, your $50k startup idea flops — that's genuinely bad
Early bad news, resources left	You spend $5k to learn an idea is dead, but you still have $45k and all your new knowledge to find a viable path

If you have $50k and spend $5k to discover you're heading toward a dead end, that's actually a great result. You've saved $45k and gained valuable learning.

Why We Fish for Compliments

We go through the futile process of asking for opinions and fishing for compliments because we crave approval. We want to believe that the support and sign-off of someone we respect means our venture will succeed.

But here's the reality: that person's opinion doesn't matter. They have no idea if the business is going to work. Only the market knows.

The Real Victory

Similarly, if you have an exciting idea and talk to a few potential customers who don't actually care, that's a great result. You just saved yourself months of building and selling something nobody wants.

Bad news early is good news. Bad news late is disaster.

✅ Do This

• Actively seek information that could disprove your idea
• Celebrate when you learn something won't work (early)
• Remember: finding out now saves you time and money

❌ Don't Do This

• Avoid conversations because you might hear "no"
• Seek validation instead of truth
• Interpret silence or politeness as approval

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The Lukewarm Response Problem

This was one of the most valuable insights for me. We often think that positive feedback is good and negative feedback is bad. But there's something worse than both: the lukewarm response.

What Lukewarm Looks Like

When you're learning about a problem or testing your product positioning, you might get responses along a spectrum:

Response Type	What They Say	What It Means
Strong Positive	"This is exactly what I need! When can I get it?"	Real problem, real interest
Strong Negative	"That's completely wrong for us because..."	Useful data, clear direction
Lukewarm	"That's pretty neat." / "Yeah, maybe."	Danger zone

Some responses tell you clearly: you're not getting paid, but it's also a bad result. When someone doesn't care at all, at least you know they're not your customer.

Lukewarm responses are the most dangerous because they feel somewhat positive but indicate no real interest.

Why Lukewarm Kills Businesses

As the book puts it: "Meh" responses are more reliable information than "Wow!" responses.

You can't build a business on lukewarm interest. If people aren't excited, they won't pay, they won't change their behavior, and they won't tell their friends.

Rule of thumb: There's more reliable information in a "meh" than a "Wow!" You can't build a business on lukewarm responses.

How to Handle Lukewarm

When you get a lukewarm response, dig deeper:

• "You don't seem too excited about this — is it not a big problem for you?"
• "On a scale of 1-10, how painful is this issue?"
• "What would have to be true for this to be a must-have for you?"

✅ Do This

• Recognize lukewarm responses for what they are: a "no"
• Push for clarity when responses are ambiguous
• Value strong negative feedback over weak positive feedback

❌ Don't Do This

• Interpret "that's interesting" as validation
• Count lukewarm responses as potential customers
• Proceed without genuine enthusiasm from your market

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Look Before You Zoom

This section addresses a mistake I've definitely made: getting lost in details before understanding the big picture.

The Problem with Premature Details

Another way to miss important questions is by obsessing over ultimately unimportant nuances. We get stuck in the details before understanding whether we're even solving the right problem.

Here's what happens:

1. You ask about specific features or implementation details
2. The person knows about those details, but doesn't actually care enough to fix the problem
3. You lead them through questions about that semi-problem
4. They happily answer, drowning you in unimportant details
5. You zoom in on a super-specific problem before understanding the big picture

Zooming in too quickly on unimportant details can irreparably confuse your learning.

A Really Bad Conversation Example

The book gives a great example of how this goes wrong:

You: "Hi, thanks for taking the time. We're building phone and tablet 
     apps to help people stay in shape. How do you stay fit?"

Them: "Okay." (I never exercise, so this should be quick)

You: "How often do you go to the gym?"

Them: "Not really ever." (Well, looks like we're done here then!)

You: "What would you say is your biggest problem with going to the gym?"

What went wrong here?

1. The opener mentioned the idea — now everything is biased
2. Asking "how often do you go to the gym" is demographic data that tells you what kind of person they are, not whether there's a real problem
3. Asking about "your biggest problem with the gym" prematurely zooms into whether staying fit is a real problem

Any response you get is going to be dangerously misleading. You're asking someone who doesn't care about fitness to tell you about fitness problems.

A Good Conversation Instead

You: "How often do you go to the gym?"

Them: "Um. Not really ever."

You: "Why not?" (Instead of taking it for granted that staying fit is 
     one of their top priorities, let's dig into the motivations)

Them: "I don't know, it's just not something I'm that worried about, 
      you know?"

You: "When's the last time you did try? Have you ever joined a gym or 
     taken up jogging or anything?"

Them: "Oh yeah, I used to be into sports in high school. It just 
      hasn't been a big deal since I settled down. Running around 
      after the kids gives me all the cardio I need!"

You: "Haha, gotcha. Thanks for the time!"

Why this is better:

• We learned this person isn't our customer
• We didn't bias them with our idea
• We can move on and find people who actually care about fitness
• The conversation was pleasant and we didn't waste time on details

Rule of thumb: Start broad and don't zoom in until you've found a strong signal, both with your whole business and with every conversation.

✅ Do This

• Start with broad questions about their life and priorities
• Find out if they even care about the problem space first
• Only zoom into details after confirming genuine interest

❌ Don't Do This

• Jump straight into specific questions about your solution
• Assume everyone has the problem you're solving
• Spend 30 minutes on details with someone who doesn't care

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Premature Zooming: A Common Mistake

The book expands on this with another example about fitness apps:

Bad Conversation: Zooming Into Nothing

You: "Hi. Thanks for taking the time. We're building phone and tablet 
     apps to help people stay fit."

Them: "I guess the time it takes to get there. I'm always kind of 
      busy, you know?"

You: "Perfect. That's great. And could you rank these 4 in terms of 
     which is most important to you in a fitness program: convenience, 
     personalisation, novelty, or cost?"

Them: "Probably convenience, then cost, then personalisation, then 
      novelty."

You: "Okay. Awesome. Thanks so much. We're working on an app to help 
     you exercise in the convenience of your own home..."

Them: "Cool. I'd love to try it when it launches."

What's wrong here?

• The opener biases the conversation — you're now fishing for compliments
• Asking them to rank features assumes they actually care about fitness (they might not)
• The "convenience" ranking doesn't tell you if this person actually cares enough to pay
• "Cool, I'd love to try it" is a non-committal compliment and a stalling tactic
• You totally missed the point: You're misinterpreting the conversation as validation when you're prematurely zooming into irrelevant details

Good Conversation: Finding What Matters First

You: "What are your big goals and focuses right now?"

Them: "The big one is that promotion at work. And we just bought our 
      first house, so I've got to find a bit more time for the missus. 
      Things have been pretty busy lately."

You: "You're buying a new house and expect to be less busy?"

Them: "Can't blame a guy for hoping."

You: "Is getting healthier on that list?"

Them: "I'm actually feeling pretty good at the moment."

Why this is better:

• We asked about their big goals first — fitness wasn't even mentioned
• We learned what actually matters to them (work, house, relationship)
• We discovered they're not worried about fitness right now
• We know this isn't our customer without wasting either person's time

The Leading Question Trap

The book makes an interesting point: sometimes leading questions are okay, as long as you're careful.

We probably already know the answer when you're about to abort the conversation anyway. If they come back with a positive, just be extra careful in making sure they aren't lying.

You: "Is getting healthier on that list?"
Them: "I'm actually feeling pretty good at the moment." 
      → Not a customer.

✅ Do This

• Ask about their overall goals before zooming into your topic
• Be willing to end conversations when someone isn't your customer
• Check if your problem area even registers as a priority for them

❌ Don't Do This

• Assume everyone cares about the problem you're solving
• Ask detailed questions before establishing relevance
• Interpret polite interest as genuine need

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Gaze Upon the Elephant

This section teaches us to look for the big, scary, obvious problems — not just the ones we want to solve.

De-risking the Business

Sometimes we comfort ourselves by asking questions which don't actually de-risk the business. We resolve the easy questions about our tools and features, but ignore the elephant in the room.

The book shares this scenario:

Let's say we suspect that teachers from the poorest schools are completely overloaded, and that yes, they are completely overloaded. We then spend weeks with them, figuring out exactly what their dream tool would do.

But we've missed the elephant: We go talk to them and confirm that yes, they are completely overloaded. Unfortunately, we've missed the elephant: the schools may not have the budgets available to pay us.

What We Tend to Ignore

Startups tend to focus on multiple failure points — problems of the teachers and the ability of the schools to pay. If any of these conditions doesn't exist, we must overhaul our idea.

The book says it's tempting to obsess over the most interesting of several failure points and ignore the others. But we miss important questions when we:

• Focus only on problems we find interesting
• Ignore risks related to our customers and market
• Skip over the "boring" business model questions

Beyond the risks of our customers, we also have challenges with our own product. Overlooking product risks is just as deadly as overlooking the goals and constraints of our customers.

What to Consider

Ask yourself:

Risk Type	Questions to Ask
Product risk	Can I build it? Can I grow it?
Customer/market risk	Do they want it? Will they pay me? Are there lots of them?

Is it full of good data or bad data?

✅ Do This

• Identify all the major risks to your business (product AND market)
• Address the scariest assumptions first
• Ask about budgets, decision-making, and buying processes

❌ Don't Do This

• Only focus on the problems you find interesting
• Ignore the "elephant in the room" (usually money or market size)
• Assume if the problem exists, people will pay to solve it

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Does This Problem Actually Matter?

At some point, you need to figure out if the problem you're solving is a must-solve (painkiller) or a nice-to-have (vitamin).

Painkiller vs. Vitamin

The book introduces this framework:

Type	Description	Customer Behavior
Painkiller	Solves an urgent, painful problem	They're actively looking, willing to pay, will switch
Vitamin	Nice improvement, not critical	They're interested but won't prioritize it

Questions to Determine if the Problem Matters

The book calls these "Does-this-problem-matter" questions:

• "How seriously do you take your blog?"
• "Do you make money from it?"
• "Have you tried making more money from it?"
• "How much time do you spend on it each week?"
• "Do you have any major aspirations for your blog?"
• "Which tools and services do you use for it?"
• "What are you already doing to improve this?"
• "What are the 3 big things you're trying to fix or improve right now?"

These questions help you understand if the problem is top-of-mind or just an occasional annoyance.

A Good Conversation Example

The book shares a conversation about talking to a blogger:

You: "Hey Rob, what are the top problems with your blog?"

Me: "I'm grumpy that Google Reader disappeared — I lost like half my 
    followers. And this book is consuming all of my interest in 
    writing, so I haven't really posted in months. And Wordpress 
    seems so slow these days."

You: "That Google Reader thing is a mess. What are you doing about it?"

Me: "Nothing, really. I don't know what to do. But it sucks."

You: "Have you looked into what your options are?"

Me: "No, I just caught the drama on Hacker News."

You: "Are you spending a lot of time working to build your audience 
     back up?"

Me: "Probably just keep on writing when I have something to say. 
    It's more of a hobby than a business, really."

What we learned:

• The Google Reader problem sounds annoying, but they haven't done anything about it
• It's not a big deal for them despite being "annoyed"
• The blog is a hobby, not a business — so they won't pay much to solve problems
• This isn't a customer worth pursuing for an audience-building tool

An Ambiguous Conversation

Sometimes the signal isn't clear:

Them: "...I get paid 2 or 3 grand per talk. Sometimes more if it's 
      corporate work."

You: "Where do you get your gigs? Do you have an agent?"

Them: "Yeah. He kind of sucks though. Most of my work comes through 
      people who just know me from my blog or have seen my other talks."

You: "What's wrong with the agent? And why do you still work with him?"

Them: "I'm one of the lowest-paid people they work with, so I get 
      ignored a lot. But sometimes he brings in deals, so whatever. 
      It's free money."

At this point:

• Getting gigs is important to them (they mention income)
• They have a workaround (the agent) but it's not perfect
• The current solution isn't painful enough to actively change

Next step: Zoom in to introduce the problem and see if they care:

You: "I'm building a marketplace to cut out the agents and connect 
     event organisers directly with speakers. It should help you get 
     more gigs and keep the agent fees. How would that fit into your 
     speaking life?"

Them: "Man, that's awesome. If you could get me more gigs — or better 
      paid ones — I'd happily drop my agent and pay you 20% of the 
      boost. I know a bunch of other people who would love to as well."

Now we have signal:

• This is a real problem for them
• They're willing to pay (20% of the boost)
• They're offering to refer others
• This is worth pursuing

Product Risk vs. Market Risk

The book makes an important distinction:

• Product risk: Can I build it? Can I grow it?
• Customer/market risk: Do they want it? Will they pay me? Are there lots of them?

You can't overlook either one. The book shares a story of a founder who spent 3 months on worthless customer conversations. He was building gadgets to track farm animal fertility. The farmers responded like: "If you can build what you say you can build, I'll equip my whole herd."

The problem: He couldn't build it. The risk was in the product, not the market. He should have talked to technical experts, not just customers.

When Conversations Aren't Enough

For some businesses, you can't fully validate through conversations alone:

Situation	Why Conversations Aren't Enough
Online advertising	Advertisers will pay if you have traffic — you need to get traffic first
Affiliate products	You need traffic and ability to sell — the risk is in execution
Heavy product risk	The market exists but can you build the tech?

In these cases, the conversations give you a starting point, but you'll have to start building product earlier with less certainty.

✅ Do This

• Ask questions that reveal how much they care about the problem
• Find out if they've tried to solve it before
• Understand if this is a top-3 priority for them
• Differentiate between product risk and market risk

❌ Don't Do This

• Assume complaints equal willingness to pay
• Build without understanding if the problem is "must-solve"
• Ignore product risk when the market seems interested

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Prepare Your List of 3

The final section gives practical advice for preparing for conversations.

Why Pre-plan Your Questions

Pre-planning your big questions has several benefits:

1. Makes it easier to ask questions that pass The Mom Test — you're not improvising
2. Reduces biasing — you've decided on questions in a calm environment with your team
3. Helps you face tough questions — it's easier when you've already committed to asking them
4. Keeps you focused — you won't drift into trivial topics

How to Create Your List

For each type of person you talk to (customers, investors, industry experts, partners), pre-plan the 3 most important things you want to learn.

The questions will be different for each:

Person Type	Example Questions
Potential Customer	What's your current process? What have you tried? What would make you switch?
Industry Expert	What are the biggest changes in the market? Where do new entrants fail?
Investor	What concerns you about this space? What would make this a big opportunity?

Don't Over-stress About "Right" Questions

The book reassures us: your questions will change as you learn. Just choose whatever seems murkiest or most important right now.

• You might get answers 1-3 from customer A
• Answer 4 from customer B
• Answers 5-7 from customer C

There's overlap and repetition, but you don't need to repeat the full set of questions with every participant. Pick up where you left off and keep filling in the picture.

The Serendipity Advantage

Knowing your list allows you to take advantage of serendipitous encounters.

Instead of running into a dream customer and asking to exchange business cards for a formal meeting later, you can "grab a coffee" (like everyone else) and just pop off your most important question.

This keeps it casual, which has advantages the book discusses later.

Rule of thumb: You always need a list of your 3 big questions.

✅ Do This

• Write down your 3 most important questions before conversations
• Update the list as you learn new things
• Have different questions for different types of people
• Be ready to ask your questions in casual encounters

❌ Don't Do This

• Wing it and hope you'll remember what to ask
• Ask the same trivial questions every time
• Miss opportunities because you weren't prepared

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Key Takeaways and Rules of Thumb

Let me summarize all the rules from this chapter:

Rules of Thumb

Rule	What It Means
You should be terrified of at least one question in every conversation	If you're not asking scary questions, you're not learning what matters
There's more reliable information in a "meh" than a "Wow!"	Lukewarm responses are actually worse than negative ones
Start broad and don't zoom in until you've found a strong signal	Don't get lost in details before understanding the big picture
You always need a list of your 3 big questions	Pre-planning helps you ask what matters and stay focused

My Personal Checklist

Before every customer conversation, I now ask myself:

Preparation:

• [ ] Do I have my 3 big questions written down?
• [ ] Is at least one of them scary?
• [ ] Am I ready to hear bad news?

During the conversation:

• [ ] Am I starting broad or jumping to details?
• [ ] Is this person actually in my target market?
• [ ] Am I getting lukewarm responses? (If so, dig or move on)

After the conversation:

• [ ] Did I learn something that could change my business?
• [ ] Did I ask about the elephant in the room (money, priorities)?
• [ ] Can I describe their current situation in detail?

Quick Reference: Important vs. Trivial Questions

Trivial (Avoid)	Important (Ask These)
"How old are you?"	"What's your biggest challenge right now?"
"Do you use apps?"	"What have you tried to solve this?"
"Would you like this feature?"	"What would happen if you couldn't solve this?"
"Do you like our idea?"	"How are you dealing with this today?"

Quick Reference: Good Signs vs. Bad Signs

Good Signs ✅	Bad Signs 🚨
Strong emotion (positive OR negative)	Lukewarm "that's interesting"
Detailed description of their problem	Vague agreement with your pitch
They've tried to solve it before	They've never looked for a solution
They ask when they can get it	They say "keep me in the loop"
They want to introduce you to others	They're politely ending the conversation

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Wrapping Up

This chapter fundamentally changed how I think about customer conversations. It's not just about avoiding bad questions (compliments, fluff, ideas) — it's about actively seeking the questions that matter most.

The biggest shifts for me:

1. Embrace scary questions — The questions you're avoiding are probably the most important ones
2. Bad news is good news (if it's early) — Better to learn now than after building
3. Lukewarm kills — Strong negative feedback is more valuable than weak positive feedback
4. Start broad, zoom later — Don't get lost in details before confirming the big picture
5. Always have your 3 questions ready — Preparation makes everything easier

I'm still working through the book, and I'll continue sharing what I learn. These concepts aren't just for startups — they apply to any developer who wants to build things people actually want.

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Have you ever avoided asking a scary question and regretted it later? Or spent time on conversations that went nowhere because you zoomed in too fast? Share your experiences in the comments!

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This post covers Chapter 3 of "The Mom Test" by Rob Fitzpatrick. I highly recommend reading the full book if you're serious about building products people actually want.

Sharing what I learn as a developer expanding into product thinking. If you're on a similar journey, feel free to explore my blog for more posts like this.

👉 Read the rest of the posts from here...

Currently reading: Chapter 3 ✅ | More insights coming soon...