Asking great questions, I believe, can be worth hundreds of thousands of dollars in your lifetime. It could be the difference between getting the job, date, knowledge, or opportunity versus never seeing the chance. We cover question structure this week and really break down what makes a great question and how to ask the same types of questions slightly differently to receive great answers and achieve successful outcomes.

052 – The Art of Asking Great Questions

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Today I’m going to evangelize the power of questions. Specifically, the power of asking good questions.

There are several reasons this has been so top of mind lately and it compelled me to share. As regular listeners have likely picked up, I work professionally in tech sales and of course host a podcast that has to this point featured nearly 20 interviews and will aim to do at least another 20 through the rest of 2018, and likely more. My livelihood and my hobby depend completely on the quality of my questions, the quality of my listening, and the quality of my next question. Rinse and repeat.

A few things have stuck out lately, and this for a moment is going to sound like me tooting my own horn so please bear with me because I hate coming off that way but it’s what inspired this episode. In my career, in professional networking situations, and in the podcast, I’ve received a noticeable frequency of feedback that my preparation or questions were exceptional. I genuinely mean this when I say it: this feedback surprises me constantly. What it tells me is that many people even in a profession of asking questions, such as sales or podcasting, people are underperforming on average. Imagine the implication of this for people who don’t get as much practice asking questions — imagine how many people are navigating personal and professional arenas either without asking questions, or asking questions poorly.

The impacts of this are monumental: asking better questions can help you understand your customer, understand your manager, your colleague, your boss, your significant other. Asking better questions can make deeper connections quicker and make you the most unforgettable person at a networking event. Any time you’re interviewing for a job, regardless of what that job is, part of the battle is won in the questions you ask of the prospective employer. Sure, this might be less the case for, say, a labor job, but for anyone who ever does anything remotely white collar for work, or anything interpersonal in life, asking better questions can set you so far apart and net you so many great answers that you will make connections and learn new information faster than your peers. I feel completely comfortable suggesting that asking great questions can make you hundreds more connections and hundreds of thousands more dollars in your lifetime.

That being said, today I want to share a few strategies around asking, crafting, and practicing great questions. And when I say practicing I really do mean practicing! Asking great questions is a skill and for most people, it’s not something that will just some naturally. There are definitely those who are naturals but if you show me ten people who seem excellent at the art of asking questions, what you’ve really found are at least nine people who have a ton of hours booked practicing and reworking questions and failing a ton by asking the same question the wrong way a dozen times. It may seem daunting to have to find ways to book these hours, but we’re going to break down some question structure today which will shave off a ton of that practice time so you’re aiming in the right direction from the jump.

Let’s start with conventional wisdom. There is a ton of conventional wisdom around questions that most people have heard, but the problem in my mind is that the advice is far too unspecific. “Ask open-ended questions” is basically the advice everyone will tell you ahead of a first date or interview, but there are so many ways to botch this by asking questions like, “what music do you listen to?” or “what are your favorite movies?” In essence, this advice sort of ust feels like the broader way of saying, “avoid questions with a ‘yes’ or ‘no’ answer.” This is often pretty good advice, but then that leaves your options as almost any question that doesn’t start with the word “are,” as in “are you hungry?” or “are you from the area?” Needless to say this advice is well-intentioned, but will only get you one or two tiny steps closer to asking tons of interesting questions that will net tons of interesting answers.

Of course, we all know questions can only start with certain words, but these opening words are extremely important to how the question is received on the other end. For example, “Why did you choose that career path?” has about a 50% chance of being received as judgment against the career path, and may cause the answer you receive to come out defensive. Some people will not receive it this way at all, but part of the art of asking great questions is to completely minimize any potential lack of clarity or intention. Ask the question asker, you could phrase the exact same question as “What made you choose that career path?” which has almost no potential to sound accusatory or judgmental but carries the exact same meaning you intended. We’ll come back to “what” questions because they are probably one of the two most effective ways to practice asking great questions and they are very easy to make small adjustments to.

Another example of the importance of the opening word can be seen with words like “when” and “how” versus “if” and “are.” Let’s use the idea of time or scheduling as an example. “If you’re available, I’d love to get together for coffee” is not a terrible question, but it’s not a strong one either. Words like “if” leave a lot of room for immediate “yes” or “no” classification and can even convey a lack of confidence as the question itself becomes almost flimsy and uncommitted, like you are afraid to be rejected and are doe-eyed and hopeful that they will grace you with their presence over a coffee. This is totally appropriate in some contexts, but often times the exact same question can be tweaked slightly to come off stronger. “Are you available to get together for coffee?” is also not a terrible question, but again leaves a ton of room for “yes” or “no” classification. This is especially problematic over text or email because a person can more easily read that, answer in their head, and leave you hanging with no answer and no ability to follow up naturally. Even if the answer is simply “yes,” you now have to do additional work to determine details like location and scheduling.

The same intention, however, is heard in the question, “When are you available to get together for coffee?” or very similarly, “How does your schedule look this week to get together for coffee?” Notice now the words “yes” and “no” are not options — our brains naturally recognize these types of questions in a way that indicates a totally different form of recall beyond a simple “yes” or “no” answer, and it’s pretty clear that you can’t answer the question “When are you available to get together for coffee?” with, “No.” I suppose you could, but obviously this would be rude and sending quite the message, and in all likelihood you’ve done something to offend or turn off the recipient well before you asked the question. The more important thing to note here is that this same ask — to get together for coffee — can be phrased slightly differently in the opening word and you will naturally leapfrog the first mental line of defense. Whether the response is positive or negative, you’ve placed the ball in the recipient’s court. They will either respond with a time and date, or they will respond to tell you why they are unavailable to get together. In this case, that means even the negative outcome will net you some information that you can use to formulate a clearer picture of the person you are interacting with. Why are they unavailable? What was the tone of the response? Perhaps they tell you, “I’m actually traveling this week to perform with the orchestra!” Sure, it would be great if they followed up with, “but I’d love to schedule for the week after! How’s Tuesday morning?” but even if they don’t, you now know a lot about this person that you potentially might have missed learning about simply due to phrasing the question in a way that it’s more likely to receive a “no,” a defensive response, or no response at all. Now you know this person is in the orchestra — did you know that already? Some personality traits you might glean from this include musical, talented, creative, dedicated, worldly, consistent. And now your follow-up, even if they don’t make the move to schedule at a later date, can lead naturally into many questions about them: “That’s awesome! What instrument do you play?” “Where are you traveling to?” “How long have you been playing music?” “What type of orchestra is it?” “What do you enjoy most about performing?” In fact, this leads to another point about asking great questions: great questions will beget great answers, which make it significantly easier to identify ways to keep the conversation going with more excellent and thoughtful questions. If you learn just the basics of asking better opening questions, it’ll make it that much easier for you to latch onto the next subject to keep the conversation interesting, flowing, and about them.

This is another important thing to note about asking great questions. The purpose of asking questions should be to learn more about them and to allow their answers to lead naturally into tangents before you return to asking them questions about themselves. In general people love to talk about themselves and their interests, which is a beautiful thing nature did to human beings. Sure, without a doubt this sometimes gets you stuck in a conversation about a topic you could not possibly care any less about, but in many cases you are likely to learn something yourself, learn about the person you’re interacting with, and make them feel amazing and cared about and listened to, which will in turn reflect well on you and in all likelihood they will remember how you made them feel. Asking great questions is almost as much about listening, and asking great follow-up questions communicates that your attention is completely within the conversation. If you ask a great conversation-opening question and then as soon as they answer you take the pause as an invitation to talk about yourself for five minutes without taking a breath, you’re likely going to come off self-centered and, if you do this on more than one isolated occasion, you will be bucketed in that person’s mind as someone who will pretend to be interested in something other than themselves as a way to trap people into listening to a tirade about themselves. It will not take long for people to go out of their way to avoid individuals like this, so it’s important to learn how to take a deep and genuine interest in the answers to the questions you’re asking and to identify excellent follow-ups that form from their answers.

Now, I alluded earlier to the fact that “what” questions are a great place to start because they tend to be open-ended and less likely to be misconstrued as judgmental. Another great opening word is “how.” “What” and “how” questions can lead you to getting great answers out of people when asked correctly, and when paired with a soft but upbeat tone that communicates confidence and genuine interest in the answer to the question, you are more likely to get an uninhibited answer, or to ask enough questions to make the recipient less defensive and more comfortable trusting you with their honesty and vulnerability. Again, a beautiful thing to be trusted with.

Let’s get a little more advanced, focusing on questions that start with “what” and “how.” Take for example a few questions with a very similar intention and nearly the exact same words:
What do you enjoy most about music?
What do you enjoy most about performing music?
What do you enjoy most about writing music?
And another example:
What is your favorite book?
What is your favorite fiction book?
What is your favorite non-fiction book?
What book has inspired you most?

In both cases, you can see how the questions progressed, but the progression was in the specificity. A question like “What do you enjoy most about music?” is a little too open-ended. Unless the context is very clear, the recipient may have to filter through all of the possibilities as to what the question means: “what do I enjoy most about music? Like, listening to it? Or playing it? Boy, I don’t know either way. I love so many things about music.” This is an example of an open-ended question that is so open-ended that it becomes really difficult to recruit a great answer from your brain. You should always aim to ask questions where the mental work done by the recipient is never around what the question itself means but rather only around the recall of their answer to your question. Further, the recall should be easy. Even in a question like “What is your favorite book?” which is a less confusing question, the recall is still really difficult for most people. Unless that person just happens to have one single book that rules above all else they’ve read in their life, they’re likely to ask you to clarify to narrow their mental search for the answer they’d like to give you. You can again leapfrog this first step by asking more specific questions, especially on a topic you might know about more. If you like non-fiction more than fiction, ask about non-fiction specifically. Their answer will likely either be something like, “Oh, I love non-fiction! I’d say X and Y are my favorites.” They may elaborate naturally and if they don’t, you can of course ask follow-ons to learn more about the person. Every single answer they give you will net you new information — maybe one of their favorites is one of yours. Maybe one of their favorites is something kind of silly and you can go further there. The type of person who likes “Eat, Pray, Love” as a favorite book of theirs is probably a pretty different type of individual from one who says “The 48 Laws of Power by Robert Greene.” Or perhaps they answer, “Oh, I don’t really read non-fiction. I love fiction though, it’s my escape from the real world and gets my imagination going!” Great, you just learned a ton about this person and you have a variety of follow-on questions you can ask.

Back to the topic of openers, I want to make sure I cover a few openers that I feel make great set up questions to lead into smarter questions. The words “was,” “did,” and “do” tend to be followed by a fairly specific, narrow ask such as, “was it any good?” or “did you grow up around here?” or “do you like Thai food?” Of course you can find ways to frame these questions in a way to be smarter on their own, but these are really easy ways to start or continue a conversation and get enough information out of a simple question in order to find the follow-up. I’m not going to dive too deep on these because I do personally think many other openers will serve the same purpose better, for example comparing, “do you have any familiarity with cybersecurity systems like this?” to “how familiar are you with cybersecurity systems like ours?” — the first might lead a person to lie about their familiarity so as not to come off inexperienced, and the latter gives them a gradient on which to answer more honestly without feeling self-conscious. Nonetheless, “was,” “did,” and “do” questions rarely need much practice so when you need to fall back to something more easy and automatic to keep a discussion going and find your new topic to inquire about, you can navigate to one of these.

A similar way of moving conversations forward is not technically in the form of a question but acts as one: “tell me about” and “walk me through” are similarly not strong questions on their own, but are great ways to tee up an easily answered question and move from there to find new and smarter questions to ask. This is particularly powerful as an easy set-up if you can provide some context based on something you know. This may require you to do research before your conversation, but as long as you stay away from the overly-personal, this type of background context shows a lot of care and consideration. For example, it’s probably not appropriate to say, “I know you have three kids and a dog and live on Sierrawood Avenue, tell me about your family!” whereas the dialed back, “You play in an orchestra right? Tell me about that!” or “You recently knocked out all of your student loan debt right? Walk me through how you did that!” are much more palatable and have the opposite effect: you’re not freaking them out as much as you are showing you did some research or paid attention. In the podcast you’ll see most interviews I’ll use about two or three of these in order to queue the guest to tell me a story, and within that story I can almost always find at least one or two things I can dive deeper on and ask a more thoughtful question that shows I was listening closely to the answer.

Another way to practice asking great questions is to dig another layer deeper with empathy. After you’ve started an animated conversation and can tell you have formed some trust and connection in the conversation, begin to ask questions that may be a little more personal or require them to be more vulnerable. Of course, you can’t just walk up to someone and ask, “How did that make you feel?” because you’ll come off like a totally crazy person. But maybe ten minutes into a flowing conversation, finding areas to ask questions that will speak to the person’s emotionality, values, philosophies, beliefs, hopes, dreams, visions, code of ethics etc. can spark amazing conversation, shows a deep thoughtfulness about the other individual. This is key – these questions must come from a place of empathy, as any intention to harmfully manipulate will often be picked up on and, just morally speaking, is pretty uncool. You also want to avoid coming off as prying or being too pushy, so it’s important again to ask from a place of empathy to reduce the chance that it’s received negatively, and then gauge the comfort and depth of the answer you receive to understand whether the question was too personal and you need to dial it back or whether you have transcended to a new plane of connection and can go back and forth with more intimate thoughts and feelings. Asking these follow-up questions with empathy — “how did that make you feel?” “Where do you think you got that trait?” “How did you overcome that hardship?” “Did you feel any sort of doubt going in?” — these types of questions can put you into contact with a lot of interesting and meaningful information about the person and can help color how you approach them in all of your future interactions with them. Great questions can quickly lead you to identify whether a new person is introverted or extroverted, by-the-book or free-spirited, anxious or confident, optimistic or pessimistic, heavily emotional or heavily logical, and so forth. These learnings should be internalized so that you become more and more able to modulate your interactions with them such that they consistently go smoothly and feel positive and that you never say something that is misconstrued as offensive where you meant no offense at all. Remember that the exact same question asked the exact same way could be offensive to one person and exciting to another — it’s important before you ask these personal or risky questions that you develop a sense in every single conversation for how this person might respond. Keep in mind that you are one Google search away from finding a ton of studies that confirm that people tend to like other people who ask questions, especially follow-up questions. Understand as well that if you are not a natural, you can develop this skill by giving it a shot and internalizing the response — I mentioned at the top that I work in sales professionally and of course host this podcast, so it has taken me a lot of reps to go from terrified to order a pizza over the phone to navigating a complex sales environment with a C-level executive and showing them a ton about who I am as a professional without having to say a single word about myself.

All right folks, let’s recap some key points since we went through a LOT today!
Avoid questions with a “yes” or “no” answer
Avoid open-ended questions with a difficult recall
Ask questions with a certain specificity that makes the recipient’s mental search much simpler
Put intentional thought into how the opening word might color the implication of the question i.e. “Why did you do that?” vs. “What made you decide on that?”
Progress naturally — don’t ask personal questions right out the gate, but don’t be afraid to ask them after the conversation warms up
Once you do ask personal questions about emotions, values, philosophies and so forth, seek to understand the person through their answer when you ask the question
Listen closely to the answers to questions to identify areas to latch onto for follow-up questions, areas to relate to the person, and areas to avoid

Listeners and readers we’d love to hear from you, whether you’re a regular or brand new, if you haven’t yet you can check out our blog and other content on thewealthyhealthy.co and follow us on instagram @thewealthyhealthy

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