Questions to Ask Smart People
Questions for a conversation with someone who knows a subject far better than you do, whether that is a mentor, a specialist seated next to you, or a researcher who agreed to half an hour, with notes on what to listen for in the answers.
The questions
Open any question for the note
What are you working on right now that you cannot stop thinking about?
Why ask it
Unfinished work draws a more candid answer than finished work, because there is no conclusion to defend yet. It also points at where a field is actually moving rather than where it has already been.
What do people outside your field consistently get wrong about it?
Why ask it
Most specialists keep a short list of these and rarely get asked. The answer also shows how they treat non-specialists: some correct the record patiently, some sneer at the public, and that difference tells you whether a longer conversation is worth having.
What is the best question anyone has asked you about your work?
Why ask it
This lets you borrow someone else's good question. It also reveals what they wish people would notice, which usually sits one layer below the topic they get invited to speak about.
What did you believe about your subject five years ago that you no longer believe?
Why ask it
A changed mind is the clearest evidence that someone is still thinking. Watch for changes that cost nothing: a shift in emphasis is not the same as abandoning a position they used to argue for in public.
What took you longest to genuinely understand, rather than just repeat?
Why ask it
The distance between reciting a concept and using it is where the real learning happens. Whatever they name is usually the same thing you are about to underestimate.
When you get stuck, what do you actually do?
Why ask it
Ask for the behavior, not the philosophy. The useful answers are mundane: reread the original source, write the problem out by hand, call one particular person, stop pretending to work and go outside.
How do you decide what not to read?
Why ask it
How someone filters transfers better than what they have read. Anyone senior in a busy field has a working policy on this, and hearing it will change your own habits more than a reading list would.
What are you following at the moment that is outside your own field?
Why ask it
Ideas tend to arrive sideways rather than from above. This also gives them permission to be an amateur for a minute, which usually loosens up the rest of the conversation.
What is overrated and what is underrated in the way people talk about your subject?
Why ask it
This asks for a judgment instead of a summary. Someone who cannot name anything overrated in their own area is either being diplomatic or has stopped evaluating the field they work in.
What is a standard piece of advice in your field that you think is wrong?
Why ask it
Advice survives because it is easy to repeat, not because it holds up. People who have done the work usually have one piece of orthodoxy they believe costs newcomers years.
Who do you disagree with most in your field, and what is their strongest argument?
Why ask it
Anyone can caricature an opponent. Stating the other side's best case is the harder test, and someone who cannot do it has usually not examined their own position closely either.
What does your field measure because it is easy, rather than because it matters?
Why ask it
Disciplines drift toward whatever is cheap to count, and insiders know exactly where that has happened. The answer tells you which published numbers to treat carefully and which questions nobody is funded to ask.
What would change your mind about the thing you are most confident about?
Why ask it
This separates confidence from stubbornness. A real answer names a specific result or observation that would count against them; a weak answer is a modest-sounding claim to have no exposed positions at all.
What is the last thing that genuinely surprised you?
Why ask it
Surprise means a prediction failed, so the answer marks the edge of what they actually understand. If nothing has surprised them lately, they may not be testing anything.
What do you know that would be hard to write down?
Why ask it
Tacit knowledge is what does not survive documentation: when a result smells wrong, how long a task really takes, which corners are safe to cut. Practitioners can usually name theirs once someone asks directly.
How do you tell someone who knows this subject from someone who only sounds like it?
Why ask it
A filter you can reuse for years. Experts know the specific tells of fluent nonsense in their own field, and they are almost never the ones outsiders are watching for.
What did you get wrong publicly, and what happened after?
Why ask it
Public error is where the interesting story usually is, and volunteering it is rare. Notice whether the lesson they draw concerns the substance or only how it looked.
What advice do you give that people agree with and then ignore?
Why ask it
There is usually a reason it gets ignored: the advice is slow, boring, or costs status. That resistance is the part worth discussing, more than the advice itself.
What would you work on if funding and permission were not a problem?
Why ask it
Constraints on money and approval hide what someone actually thinks is important. The answer often describes a field's real open problem more honestly than its published agenda does.
What should I go and learn that I did not think to ask about?
Why ask it
A good closing question because it hands them the frame. You will get either a concrete recommendation or the news that your questions were aimed at the wrong thing, and both are worth having.
Getting a real conversation out of an expert
Practical guidance for the conversation itself
Before you start
- Do the reading that is already public. Asking what someone's book argues, when the argument is in its first chapter, spends your credibility inside a minute.
- Pick two questions rather than twenty. A short conversation goes further down one thread than across ten.
- Write down the specific thing you are confused about. Vague admiration gets a vague answer; a stated confusion gets an explanation.
- Decide which you want: a decision made, a concept understood, or a relationship started. Those are three different conversations and they need different questions.
While you are in it
- Say when you have lost the thread. Nodding along through an explanation you do not follow throws away the only part that mattered.
- Ask for the example rather than the principle. People state principles they do not follow and examples they actually lived.
- Resist showing that you know things too. Time spent proving competence is time not spent learning.
- Follow the energy. When someone's pace picks up you have found what they care about, so stay there instead of moving to your next prepared question.
- Let a few seconds of silence run after an answer. The second half of an answer is usually better than the first.
Questions that tend to go badly
- What is the secret to your success. It flatters, and it gets a platitude back.
- Anything a search would have answered in ten seconds.
- Asking them to settle a disagreement you had with a colleague.
- Asking for predictions about markets or timelines. You will get a hedge, and it will be the question's fault, not theirs.
- Asking for their whole field summarized in five minutes.
Afterwards
- Send one specific thing you did because of the conversation rather than a note listing everything they said.
- If they recommended something, read it before asking for more of their time.
- Write your notes the same day, including the parts you did not follow. Within a week you will not remember which those were.
- If a question of yours landed badly, note that too. The failures narrow down what this person is actually able to help with.