Lean Customer Development will help you ask those hard questions and build smarter MVPs. Get a physical or e-book version now.

It's uncomfortable to ask questions that might prove you (or your boss) wrong. It's also essential to success.
Customers
are what make a product successful.
Everything you do in customer development is centered around testing hypotheses.
"...you will be actively trying to poke holes in your ideas, to prove yourself wrong, and to invalidate your hypotheses."
Confirmation bias is our innate tendency to pay more attention to information that confirms our beliefs.
"I was shocked to find that so many people were willing to talk to a total stranger who didn't even have a product..."
Customer development doesn't mean asking customers what they want and building exactly that!
If you're reaching out to people who would consider it a burden to talk with you, you're approaching the wrong people.
... most of us are unrecognized experts in the things we do every day -- whether it's keeping the family fed or debugging code or coordinating large meetings. It's a pleasant change to hear from someone who doesn't take that for granted.
Don't try to save time by sending a mass email. An individually crafted message is asking a personal favor; a generic email with recipients in the Bcc: header is an easily ignorable spam.
Customers may not know what they want, but they can't hide what they need.
The specific actions that customers take are important, but equally important are the adjacent factors of how, why, when, and with whom.
"Forget about what's possible. If you could wave a magic wand and solve anything, what would you do?"
Who can loosen up and feel like an expert when they're worried about how their hair looks on camera?
When you're doing customer development, you don't know what's important yet.
"Using product X is literally the worst part of my entire week," ... is not the same as "Customer doesn't like product X."
Emotion -- and by that, I mean complaining, anger, enthusiasm, disgust, skepticism, embarrassment, frustration -- is prioritization.
...you don't want to hear the official process; you need to know all the secret grumblings and workarounds that people have patched together to get their jobs done.
"One person might just be a nutcase.
Ten people are not all nutcases."
You may not realize that you just asked a leading question, but if your interviewee starts an answer with "yes" or "no," you probably did.
Interviewees aren't trying to hold back information; they just haven't thought about it from an outsider's perspective before.
If someone says "maybe",
write it down as "no".
No matter how excited someone sounds about your product, the real test is whether or not he is willing to throw down money...
"You're not going to discover the truth by talking -- you'll find it by doing." - Kevin DeWalt
If you can't explain your MVP in a couple of sentences, it's probably not minimum.
In the enterprise world, if you are embarrassed by your first version, you may not get the chance to show a second version.
Customers don't talk about features -- they talk about the benefits they're getting, the feeling they get from using your product, what it replaces, and how much better their life is.
Conducting customer development without revealing your company affiliation doesn't need to be complicated. All you really need is a different domain name!
"Just to be clear for my notes, if you had feature X, can you repeat what that would allow you to do?"
Replaceability -- or the lack thereof -- is an important qualitative metric to pursue.
It's not uncommon for power users to clamor for improvements to a feature that 90% of users have never even tried.
Using a "how many times have you done X?" framing (instead of "have you done X?") is also helpful if you are asking about behaviors that are less socially acceptable or that the customer is embarrassed about.
The surprising truth is that questions are an extremely effective tool for defusing negativity.

Interested? There's a lot more information and how-to awaiting you in Lean Customer Development.