How to gain an information-edge by asking better questions

The success your decisions depends on the quality of information you use to inform them.

How to gain an information-edge by asking better questions

The quality of decisions you make directly depends on the quality of information you use to inform them. While some of the data you need to make those decisions may exist in print, that information tends to be public. That means it won't give you much of an advantage in competitive domains like hiring, entrepreneurship or investing.  To gain a true information edge you'll need to get your information from other people. To illustrate, consider the following typical Silicon Valley scenarios:

  • A job candidate wants to learn about a company's recent performance so she can decide whether to accept an offer there.
  • A hiring manager needs to know whether candidate is qualified for a role before he offers her a position.
  • A founder tries to learn best practices in a new function to assess whether a direct report is doing a good job
  • An investor wants to understand the dynamics of a market to determine whether to invest in a startup

In each of these situations, the information the decision-maker needs is locked in the brains of other people.

How does one access that information? By asking good questions.

What makes for a good question?

Since you were a baby you've been asking questions as a way to understand the world around you. Why did she say that? How do you spell Mississippi? Where do we go when we die? Questions are so second nature to us, that few have put the time into learn how to ask good ones.

The quality of a question can largely be judged by the usefulness of the response it elicits. So, perhaps it's best to start with some principles that make for a good response, and how you can phrase a question to increase your chances of getting one.

Characteristics of Useful Responses

On Topic

You want to make it as easy as possible for your respondent to surface the information you're looking for in their memory. If your question is long or complicated, you'll create too much cognitive load, and get a lower quality answer. To focus your subject ask questions that are:

  • Short – Avoid stuffing a question with too much upfront exposition. Often this can come in the form of qualifiers that make the question overly confusing. "How long have you been working at this company in the context of your function on this project?"
  • Properly framed – If you need to focus someone on a specific topic, start with a short framing statement like "I'm now going to ask you about your previous role..." that can help focus them on the topic you want to know about. With that out of the way you can ask shorter follow up questions.
  • About only one thing – Asking about more than one topic in a single question will lead to confused and muddled answers as people try to gather information from multiple areas and weave it together. If you need to know about more than one thing, use two separate questions to ask.


People have both a natural desire to tell others what they want to hear and to conceal information from those they don't trust. If you want truthful answers, you'll need to:

  • Avoid biasing your subject by indicating the kind of answer you're looking for – All it takes is one extra word to indicate to the respondent what kind of answer you're looking for. Even a simple question like: "How much will will the market grow next year?" contains the assumption that the market will grow. Instead a question like: "Where will this market be one year from today?" will prompt the respondent for a more accurate answer.
  • Build rapport and trust with your subject – A subject that trusts you and likes you is more likely to divulge the information you want to know.


When exploring a new topic, you'll find there are lots of questions you won't even know to ask. By getting subjects to offer longer narrative responses you're more likely to pick up useful information that you wouldn't have known to ask for. To get narrative responses, ask questions that:

  • Don't prompt a yes/no answer – openers like "do you," "could you," or "can you" don't lend themselves to elaboration.
  • Start with interrogatives – these are words like "why," "when," and "how" that will prompt longer answers.
  • Are followed up by asking "what else?" – instead of moving on after a question has been answered, probe deeper when you think the subject may still have more detail to share.

Of course, open-ended questions don't always make sense. If you find yourself in a competitive situation, like a negotiation where the other party doesn't want to reveal information, open-ended questions can leave them a way to dodge or lie by omission. In this case yes/no questions may be more effective at getting them to open up.

You will rarely be asking single questions in isolation. More often you'll have a sequence of questions that you'll need to adapt on the fly based on the responses you get. Here are six common types of questions that tend to be useful for drawing out information.

Six types of good questions

Direct questions are useful when you know exactly what you want information about. These questions often start with an interrogative, contain one verb and one noun or pronoun.


  • "How long have you worked in design?"
  • "Why did you join that company?"
  • "How large is the market?"
  • "Who is doing the most interesting research in your field?"

Control questions are ones that you know the answer to before asking. They can help you determine if the subject is lying, uninformed or not paying attention.

Example: When assessing someone's level of expertise you might start a conversation by asking a question about the subject matter that you already know the answer to.

Repeat questions are designed to get at the same information in different ways to help determine the validity of an initial response.

Example: If a founder tells you his company is on a steep growth trajectory, you might ask him how many customers he's signed in the past quarter, or his year-over-year revenue growth and look for inconsistencies.

Persistent questions help you get more complete answers by pulling out more details on a topic.

Example: if a candidate revealed a red flag in an interview, you might need to ask multiple questions about the incident in order to get to the truth:

  • "Why did you have conflict with your previous manager?"
  • "What did your manager do that annoyed you most?"
  • "How did you handle your strained relationship with your manager?"

Summary questions allow you to feed information back to the respondent to confirm or disconfirm your interpretation of what they said.


  • "If I'm getting this right, you're saying the market is about to have explosive growth in Q1 of next year?"
  • "You're saying that if I submit an application to the company, the CEO will personally look at it?"
  • "You really think that the CEO is about to resign?"

Non-pertinent questions aren't asked to get information about the topics you care about. Instead, they serve other purposes like building rapport, putting the subject's mind at ease or stalling while you decide what to ask next.

Example: If you're doing a reference call for a candidate and find that the other person is uncomfortable answering your questions, you might try asking them about their weekend plans as an easy question to mitigate the tension.

Which of these questions you use will depend on the behavior and personality of your respondent. Here are some common types of respondents along with advice for how to handle them.

Respondent Types

Integrators will revisit their initial answer to your question until they're satisfied that they've given the best possible answer.

How to handle: Since this type will often change their answers, you may want to try a repeat line of questioning to get the same information from another angle to ensure it lines up.

Dictators like to deliver definitive answers, often presenting their personal opinions as fact.

How to handle: Use a persistent line of questioning to probe the true depth of the subject's expertise.

Commenters often give far more detail in their answers than a question requires, which can drag a line of questioning off track.

How to handle: Try framing your questions to narrow the scope of acceptable answers as much as possible.

Evaders avoid answering your questions because they may feel uncomfortable or have something to hide.

How to handle: Asking the question from another angle can make the subject more comfortable with providing an answer. If the person is shy, you may have more luck warming them up with a non-pertinent question before asking what you really want to know.

Of course, asking good questions is only half the battle. Unless you closely listen to what you hear, it will be hard to pull out useful insights.


For most of us it's hard listen without getting distracted by our environment. From the buzzing of a phone to worries about what the other party thinks of us, it's easy to lose track of the responses we're hearing.

One technique to help focus the mind is active listening. While hearing is a passive activity, listening forces you to hear sound with deliberate intention. Some general principles of active listening:

  • Pay attention – not just to what the speaker is saying, but how they are saying it. Listen for pauses and words they use repeatedly. As you listen, look at the speaker directly and avoid getting distracted by your environment. While you may be tempted to think about what you want to say next, don't pull your attention away from the speaker.
  • Show you're listening – keep eye contact, open body language and a slight lean toward the speaker. Every so often, offer the speaker a signal that you're still paying attention like a nod, a smile or short verbal affirmation. Sensing that you're interested and attentive, the speaker will want to keep revealing information.
  • Provide feedback – as the speaker reveals new information, ask follow-up questions to clarify things that don't make sense. Periodically you can ask summary questions to make sure you understand what the other person is saying, and show them you're listening.

Here's a quick demonstration so you can see these techniques in action:

When it comes to getting smart on new topics, perhaps the most important part of the process is making sure that you're sitting in front of someone who actually has the knowledge you need.

Identifying Experts

When you're new to a topic it can be challenging to determine the difference between an expert and a charlatan. Here are a few strategies that can help you find and vet potential experts:

  • Ladder up – You may not know an expert on a given topic, but you probably know someone who's smarter than you on that topic. Start by having a conversation with that person to get some basics. At the end, ask them for the name of the smartest person they know on the topic. You only need to do this a few times before you're sitting with a real expert. This strategy will also help ensure that by the time you're sitting in front of a true expert you're able to have a more fruitful conversation.
  • Vet the expert with mutual connections – Once you reach someone who seems to have legitimate expertise, try cross-checking them with mutual connections. While your mutual connections may not be able to gauge the depth of their knowledge, they can probably tell you if the person generally tells the truth.
  • Do some background research – In the age of Google, there's a lot you can learn online about anyone. Do some homework to look for legitimate signals of expertise in that topic including where they've worked, who they know, what they've studied and the topics they've published on.
  • Test their knowledge –Use a mix of control, persistent and repeat questioning to test how much they know about a topic and spot inconsistencies in their answers.

Become a Conduit for Value

You've now got the foundations for a toolkit that will help you get useful data from anyone. To press your advantage, start thinking of yourself as a conduit for valuable information. Perhaps the expert in data science would love to know more about the latest trends in design systems, or the nutrition expert would appreciate learning about commodities markets. By becoming a broker of expertise, you'll be able to cultivate relationships with experts. In turn, those experts will want to continue suppling you with valuable data that you can use to make better decisions on an ongoing basis.

Source: A good deal of the research for this post came from this book.