“Judge a man by his questions rather than by his answers.” ― Voltaire
“...For seven and a half million years, Deep Thought computed and calculated, and in the end announced that the answer was in fact Forty-two - and so another, even bigger, computer had to be built to find out what the actual question was.”
― Douglas Adams, from The Restaurant at the End of the Universe
Answers are Overvalued; Questions are Undervalued
Organizations hire and reward people who know the ‘answers’. Those who know ‘how to’ do the work. Efficiently and effectively, without much help. How to code, how to sell, how to write marketing copy, how to build a financial model…the list goes on. To date, having knowledge (acquiring, processing, and retaining it) combined with confident answers has been highly valued.
By contrast, picture a person asking a question. The image you likely conjure up is someone with shoulders raised and a look of confusion on their face. We've been unconsciously trained to associate asking questions with ignorance, weakness, and a plea for help.
We are living through a sea change in the value of questions and answers.
In an AI-driven world, knowledge is being commoditized. Answers to most questions are available in seconds from LLMs, in better formed sentences than many of us could write.
Going forward, asking ‘good’ questions — thought provoking, with multiple layers, and follow-ons exploring nuances — will become a more important determinant of career success. And we’ll ask those questions of both other people and machines (LLMs etc.).
The Benefits of Questions
Build relationships. Interpersonal relationships are core to being human. Questions from a place of curiosity build and sustain relationships.
Questions signal that you are interested in others. In what matters to them — their experiences, perspectives, insights and feelings.
Questions lead to greater information exchange. Through information exchange, we discover commonalities with others.
Shared experiences increase likability. We are more drawn to and more likely to trust people with whom we have multiple things in common. We prefer to spend time with and do business with people we like. And that virtuous circle of time spent together deepens connection.
Likeability is a precursor to trust. Trust is built through reciprocity where both parties are contributing to and benefitting from the information exchange.
Trust drives deeper information sharing. We only share more ‘vulnerable’ or ‘risky’ information with people we trust. Trust creates the bedrock on which deeper friendships, romantic relationships, and business partnerships are built.
Make better decisions.
Take the ‘outside view’ as a consultant might. When you are too close to the material, ask questions about underlying assumptions, especially those that no one has recently questioned. Rely upon historical data or benchmarks (‘base rates’ in Bayesian terms) and draw upon ‘similar’ cases to reset assumptions.
Identify weaknesses faster. Asking questions, especially when phrased as a pre-mortem (‘What could go wrong or What might cause this initiative to fail?’) helps identify hidden flaws, overlooked challenges, or unintended consequences.
Reduce the chances of groupthink. Questions, phrased well, are a softer way to disagree. When everyone is in agreement, ask aloud what new information or events would weaken their conviction. Questions such as "What behaviors or outcomes do you hope to achieve?” allows for finding common ground in the outcome while changing the prescription to get there.
Learn.
Benefit from the wisdom of crowds and surface ideas that hadn't occurred to you. Questions asked of a large group of people — such as in a group brainstorming session — allow each person to build on prior thoughts and riff off each other. Typically, the outcome is better overall insight.
Question your own beliefs and judgments. Asking questions of someone who disagrees with you can reveal blind spots. Your ‘sparring’ partner might offer a new perspective based on unique experiences.
Model behavior you want to encourage.
People copy the behavior of leaders. Especially when leaders make the behavior consistent. Model being a novice yourself. Suggest that everyone asks questions. Clarify that there are no ‘dumb’ questions.
Remind people that slowing down is ok. While questions take time — slowing down is directly opposed to current tech wisdom that reveres speed — they can re-orient everyone to the direction that matters or the values that are most important and thus lead to a better outcome.
Advocate for experimentation, even when things are going well. Experiments are the outputs from curious questions about trying different things. Done correctly, experiments offer the chance to learn quickly at a relatively low cost.
Create space to ‘unlearn’. In our rapidly changing world, questions expose beliefs and theories that may no longer be relevant or useful. In a world where continuous learning is praised, we need to make space for new information by discarding that which no longer serves us well.
Reduce unnecessary or unproductive work.
Clarification. Questions are opportunities to clarify requests and minimize misunderstandings. As a result, increasing the likelihood your end product will meet the needs of those requesting it.
Understand motivations. Questions get at why the person making a request is asking. What concerns are their highest priorities - which might well be different from what you think.
What defines ‘Good’ Questions?
Here are a few thoughts on how to construct better questions.
Ask ones to which there is no simple or short answer. Reduce the number of questions you ask which can be answered with a ‘yes’, ‘no’ or simple factual answer (unless the question is for clarification purposes.)
Questions which prompt a story or revelation. These create learning opportunities and increase understanding.
Require perspective shifting. Questions that put people in someone else's shoes. It's very easy to become overly attached to one's own best interests.
Hypothetical queries probing second and third order effects. ‘What if’ questions, especially those which assume the first outcome has happened, help expose unintended or unforeseen consequences.
Questions that signal an openness to new information. Particularly valuable when dealing with people who disagree with you. They signal your willingness to challenge existing beliefs.
Evaluating Answers
Doubt simple answers. Particularly, lists claiming that doing a small number of things will get you to a desired and difficult outcome. We're all naturally lazy and want the easy path to success and happiness in life; I am as guilty as the next person of overconsuming this type of content.
Words have signaling value. Pay greater attention when you hear these words in answers. It can be worth asking these people for more detail.
It’s complicated; there are nuances;
There is no simple answer;
There are tradeoffs;
I don’t know;
The Path Forward
I recommend doing your own thinking to devise the questions. Yes, AI can do it for you, but it is worth the hard work to learn for yourself. When we outsource tasks to others, our ability to do those tasks atrophies. This will happen with asking good questions as well, so use AI wisely. Be willing to add friction to your life (i.e. being less productive) by spending time to figure out questions to ask.
When you do use AI (and we all will and should), here's a format recommended by OpenAI President Greg Brockman for writing quality prompts. Equally importantly, realize that any prompt is only the first question in your effort to gain relevant, valuable knowledge. Ask multiple follow-on questions of the AI.
We’ve been told, mistakenly, that smart people have all the answers. Actually, smart people have good questions. And, anything worth doing or having takes hard work.