Curiouser and Curiouser: Crafting Questions and Attending to the Answers

Adjacent skills—some of which are referred to as “soft” skills (such an inappropriately diminutive moniker)—can serve you both personally and professionally. My goal in this article is to share what I hope will be a new perspective on the value of both asking questions and attending to the answers you receive as well as offering techniques and resources to help you hone your curiosity. 

For data visualizers, I thought it might be instructive to consider the upstream activity of data collection, which is a process fueled by questions. This article contains a mix of synthesis from folks like Sheila Heen, Erica Hall, Adam Grant, Dr. Tasha Eurich, Brandon Stanton, Rob Walker, Ximena Vengoechea, Rebekah Modrak and Jamie Vander Broek, and many others. It also reflects some techniques I’ve picked up after many years of trial and error conducting user research. 

Why bother exhibiting curiosity?  

Let’s base this discussion in our personal lives. Conversation IS our means of relating to others. A Harvard study of dating conversations (online chats and in-person speed dates, what user researchers refer to as dyads) revealed that people who demonstrated curiosity were more likeable. In online chatting situations, the folks who asked many questions got to know their partner better and were thus better liked. Among speed daters, those who asked more questions got more dates. In fact, asking one additional question of their conversation partner meant more second dates.

Note to hopeful online daters: follow-up questions are the most successful. They signal to your partner that they’ve been heard and that you want to know more. Plus, they’re often spontaneous and don’t require much preparation (provided you’re listening actively).

Where might we apply these findings professionally? What about during job interviews, networking at industry events, waiting for Zoom calls to start, or in proactive outreach to your less-frequent professional contacts?

But why are curious people more likable?

People like to talk about themselves. That same Harvard research found that 40 percent of everyday speech is spent telling other people what we think or feel—basically, talking about our subjective experiences. In fact, research shows that talking about ourselves, regardless of the platform, triggers the brain’s pleasure sensation.

Besides feeling good, asking questions also communicates humility—that you know the limits of your own knowledge. Inquisitiveness conveys a powerful combination of “soft skills”—empathy and curiosity—in addition to humility. Admitting what you don’t know gives others the chance to share their perspective AND can help shape your understanding.

Again, how can we apply these findings in our professional lives? Would it surprise you to learn that most people are too self-promoting during a job interview? Asking questions can help you better understand the contours of the opportunity. Even a question like, “what am I not asking you that I should have?” can reveal critical attributes when weighing decisions. The answers to these questions can help you evaluate prospective career shifts. 

You can be intentional about developing adjacent skills. Adjacent skills are those skills that border your existing capabilities and these can encompass “soft skill” development. Anne-Laure Le Cunff, founder of Ness Labs, recommends brainstorming as many potential new skills relevant to your current role as possible. I applied this advice in my own career when expanding my market research practice into user experience research. Brandon Stanton, the creator of Humans of New York (HONY), is one of my favorite examples of wildly-successful adjacent skills development. When he began the HONY project, he was focused on developing his photography skills, instead he honed the ability to build rapport and tell stories that have the power to change people’s trajectories and beliefs–and these are the skills for which he has become known.

What value is there in learning to ask questions?

Asking questions can unlock value. Demonstrating curiosity about others can demonstrate knowledge to prospective clients and promote bonding among team members. Asking questions can uncover and aid in avoiding project pitfalls. The act of questioning can:

• Spur learning and idea exchange
• Fuel innovation
• Improve performance
• Build rapport
• Mitigate risk
• Signal engagement

And, this is a virtuous cycle skill: asking questions improves emotional intelligence, which in turn makes us better questioners. Try this: the next time you catch yourself getting ready to make a judgement try asking a question instead.

There are typically two categories of goals in questioning: information exchange and establishing a positive impression. Understanding your objectives can help you choose the right mix of questions. What do you need to know? What do you want to do with the answers to your questions? Different goals necessitate different methods of inquiry. Quantitative questions are typically close-ended. Survey questions are often quantitative, with answer choices like yes or no or questions that ask you to rank or rate your options. Qualitative questions are usually open-ended. They allow for a broader range of—sometimes unexpected—answers. Design researcher, Erica Hall, explains the difference between qualitative and quantitative questions like this: a quantitative question might be, “How much money are people spending on dining during COVID?” while a qualitative question is, “How are people deciding what to have for dinner during COVID?” 

Another way to think about your objectives is in terms of the type of conversation you expect. Are you anticipating a cooperative discussion? A competitive one? A bit of both? Framing—things like setting, tone, group dynamics, etc.—is critical to the effectiveness of your efforts. Think about establishing a disarming environment for asking questions. For example, I have found that I am best able to have hard or sensitive conversations with my kids when we’re in the car. We are less distracted. Neither of us can leave the “room” and we are both facing forward, thus we aren’t forced to make eye contact. 

If the conversation is competitive and you anticipate reluctance, NYTimes best-selling author, Sheila Heen, recommends starting with the most sensitive questions first. Her techniques include using direct, close-ended questions and phrasing questions so that it is easy for your conversation partner to respond affirmatively. For example, if you think a supplier is going to miss a delivery date, you’d ask, “So, it looks like you’re going to miss the deadline?” It turns out that people are less likely to lie in response to a pessimistic assumption. Conversely, in a tense environment, close-ended questions (e.g., yes/no questions) work better because they don’t allow for much “wiggle room.”

If the conversation is cooperative, but you anticipate avoidance, start with the least sensitive questions first, to build rapport. Use open-ended questions to draw your conversation partner out, and again, use negative assumptions to frame tough questions. Casual questioning works better when building rapport than using a formal tone. People are more responsive if you give them an out (e.g., there are no “right” or “wrong” answers, you can change your responses at any time). An individual in a group setting may respond differently than they would one-on-one. Quiet or closed-off respondents can derail group sessions or leave important topics unexplored. With that in mind, a skilled facilitator can vastly improve a group session like a workshop or a design sprint. 

What about the inevitable awkward silences?

Though much-maligned, silence is extremely useful in conversation—especially when awaiting the answer to a question. An extended pause can mean that the person is still processing. Pausing can encourage a mindset shift from fixed to reflective—resulting in expanded possibilities for both sides. Sharing silence can be a means of reinforcing rapport. Silence can create space that can change the tenor of the conversation. Sometimes, especially in a difficult conversation, silence is necessary to give a person the grace to calm down. As such, avoid the inclination to interrupt or move on too quickly. This is much easier said than done! Giving someone a chance to speak without interruptions is a gift. It requires patience and self-discipline. In practice, if the answer you receive is something like, “I don’t know how I feel about this…” a gentle nudge that can be effective without interrupting is, “Because?” This approach invites your conversation partner to finish their thought. 

What if you find it difficult to ask questions of others?

Fellow introverts, you may need a little more prep time before a conversation, or an alternative format to in-person. One resource you can consult is the Question Formulation Technique (QFT). You can use this technique to interview candidates, evaluate prospective service providers, or even develop a podcast interview. The QFT steps are:

1. Develop a list of questions
2. Categorize the questions either open end (qualitative) or closed end (quantitative)
3. Determine how you plan to use the question and, if necessary, change closed to open
4. Prioritize your questions: what do you need to know? What will you do with the information you collect? What answers will have the greatest impact? How much time do you have?

The Complete Guide to Writing Questions is another resource I’ve used, especially valuable when writing survey questions. Yet another option for building your question-formulation muscles is to practice active reading–which you can do by yourself and at your own pace, using your own library. Ask yourself pre-reading questions like, “What do I already know about this topic?” “Why would an instructor assign this book?” Summarize the text by writing questions in the margins. At the end of each paragraph practice asking the questions, “What does it say?” and “What does this mean?” or “Where could I apply this?” Write your own exam questions based on the reading. 

In terms of live interactions, in the pre-COVID world, I found networking at conferences drained my energy. To address this challenge, I learned to narrow my focus and pick out someone who looked uncomfortable with whom to strike up a conversation, usually by asking some questions I’d developed in advance. And, even though we have all become accustomed to video conferencing, you can still opt for other, less-intrusive types of interchange. One option is the good old-fashioned phone call. Like the kids-in-the-car example, a phone conversation can be less-intimidating. You can still hear people “smile” in their voice and this format may put your conversation partner more at ease–especially if the topic is sensitive. Live chats can sometimes be preferable to a written exchange, too. In an in-person conversation you can make mistakes and correct them in a way that you cannot in email or text. 

Though, text-based conversation has its benefits as well. Consider whether a text-based conversation or collaboration (e.g., using a virtual whiteboard or an activity-based, online research platform) would work–for even part of your questions. A text-based exchange may allow for interaction with folks who would be less likely to speak up in group settings or who are more comfortable expressing themselves in a format that allows for some on-the-fly editing. 

How else can you condition your curiosity?

I have found that self-reflection, or the act of asking myself questions, can help me overcome feelings of frustration and powerlessness. For example, Mariame Kaba (h/t Ann Friedman’s newsletter) offers these questions to ask yourself when you are outraged by injustice:

1. What resources exist so I can better educate myself?
2. Who’s already doing work around this injustice?
3. Do I have the capacity to offer concrete support & help to them?
4. How can I be constructive?

Similarly, the team at OpenMind has a tool you can use to ask yourself questions before navigating difficult conversations. Their Conversation Simulator gives you the chance to practice your skills in anticipation of your upcoming holidays with family, for example.

Data analysis cannot answer a question that you did not think to ask

Asking questions is a form of data collection. Most of what we’ve discussed so far are qualitative lines of questioning; these produce unstructured data. The alternative approach is quantitative inquiry, for example, sending out a survey. Those results are structured data. Quantitative approaches are thought by some to be more efficient or ‘cleaner’ to conduct. It is true that structured data analysis is often more straightforward. However, qualitative methods are more conducive to identifying faulty assumptions or prospective pitfalls. And, organizations are frequently surprised by how few customer or stakeholder interviews it takes to yield actionable insights. From a study cited in Harvard Business Review, the team harvested actionable insights about company performance after 18 – 20 interviews. In user experience research, we are often able to inform design and development decisions with as few as five users.

This same study found that client and manager priorities coincided only 50 percent of the time. The authors conclude that quantitative studies are usually written based on what managers think clients want. If you missed the mark on capturing those wants, the error is then compounded with techniques like ranking. For example, if the question asks you to rank requirements based on your own usage, but you are not the primary user of said functionality, the study results may suggest that you don’t care about something that you do indeed value, but for which you are not the primary user. Generative or exploratory steps can inform further quantitative options to help reduce the occurrences of questions you didn’t ask.

No one is omniscient. Yet, we are often making decisions with the best information we have available at the time. Asking questions to supplement our own understanding improves the quality of this decision-making process.

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Now that you know how to ask questions, how can you pair that skill with listening?

Active listening can be transformative. Documentary filmmaker Valarie Kaur posits that, “We risk being changed by what we hear.” We are always listening to the thoughts in our own heads. Active listening requires us to quiet those thoughts. Listening, like allowing a person to speak uninterrupted, can change a narrative. One way to signal that you are listening actively is to repeat back a bit of what you heard the person say in a follow-up question. This essential practice gives the person a chance to clarify or correct their statement and it reinforces that you understood what they meant.

Journalist and author, Rob Walker, observed, “One of the wince-inducing rituals of my job as a journalist is transcribing interviews and listening to myself fail to listen.” As a user researcher who watches and listens to herself interviewing people regularly, I have made the same cringy observation in my own work. 

I have the opportunity to practice active listening frequently. When I cut someone off, it’s usually due to one of four things:

• I’m worried about the time (running over my promised allotment or feeling pressure to get specific information in the limited time window).
• I’m excited to add in something related to their point and I don’t want to forget it. It could help reinforce rapport (but not if I interrupt).
• I think I know what the person is going to say (and sometimes I’m wrong).
• I’m showing off (know-it-all syndrome). 

Look for low-stakes opportunities in your daily life to hone your active listening skills. Practice devoting your complete attention during phone calls with family and friends, with your kids, and in casual co-worker interactions (e.g., what did you do this weekend?).

How is listening foundational to productive negotiation?

Negotiating a deal or navigating conflict are skills which require training, according to The New York Times best-selling author, Sheila Heen of Triad Consulting. It is counter instinctual to give someone else the benefit of the doubt. Your best strategy for persuasion is to listen and learn. Developing your second-position skills—the ability to see someone else’s point of view—affords you:

• Insight into a person’s position and better understanding of their perspective
• Input on what’s fueling their feelings, what they care about, how much risk they’ll tolerate 
• Access to their feelings by either naming what you’re hearing OR sharing how you’re feeling
• An opportunity to shift your mindset away from getting an apology or advancing your agenda to obtaining a better understanding of what’s going on with your conversation partner

If the conversation feels difficult, it’s likely signifying something about you: you feel wronged by the discussion, you are reacting to the person themselves, or the content of the discussion is threatening your identity. If you need help identifying your own triggers, try asking yourself: “If I know nothing else about myself, I know that I am a BLANK person.”

Honestly, how coachable are you, really?

Seeking feedback is yet another way of asking questions. And receiving feedback is a different kind of listening. This reciprocity can be difficult. In a study by Sheila Heen and Douglas Stone:

• 63 percent of human resources executives surveyed said their managers were unable or unwilling to have difficult conversations
• 55 percent of employees said their review was unfair and inaccurate
• 36 percent of managers completed appraisals thoroughly and on time
• 25 percent dreaded evaluations more than anything else in their working lives

Yet, people who seek critical feedback tend to receive higher performance ratings for the reasons we’ve already addressed. When you ask for feedback you communicate humility and a personal desire to excel. Try orienting your mindset to receive feedback as coaching or advice, even if that was not the spirit in which it was delivered. Unpack the information with follow-up questions, if necessary. Validate the feedback with input from those whom organizational psychologist and keynote speaker, Dr. Tasha Eurich, dubs “loving critics.” When in doubt, ask for just one thing (e.g., what ONE thing is holding me back?). Alternatively, organizational psychologist and bestselling author, Adam Grant, recommends motivating your evaluators to coach you by asking them, “How can I get closer to 10?” In applications beyond performance reviews, for example if you regularly deliver high-visibility presentations, you might try sending out a regular email to collect top-of-mind questions the week prior in order to address the answers upfront and avoid being caught off guard.

Prioritizing asking questions and listening actively can promote a culture of learning

Contrary to the misperception that they will look like they don’t know what they are doing, leaders who ask inspiring questions signal their humility, which instills trust. Questions like: “Where do we have the opportunity to deliver more value to stakeholders than we have in the past?” model that questioning is valued, especially if these questions are posited openly and often. Domino’s Pizza famously demonstrated this skill when they asked customers how their pizza tasted. When customers told them their pizza tasted “like cardboard,” Domino’s launched a public campaign to show customers what they were doing to improve the taste. In this example, Domino’s also demonstrated the importance of sharing the answers to questions asked to both communicate that they were listening and to jumpstart idea generation. 

And, speaking of idea generation, rather than running idea brainstorms, consider assembling a multi-disciplinary group to brainstorm questions and rank them in order of potential outcome. This mini-design sprint approach establishes a collaborative rather than a competitive environment, resulting in a sense of collective responsibility. Organizations that can learn rapidly and apply what they’ve learned tend to survive and thrive. 

In addition to the abundance of applications we’ve discussed in our professional lives, like job interviews, networking, performance reviews, negotiating, and concept development or prototyping, on a personal level, honing your curiosity exercises a growth mindset and provides daily opportunities for learning, joy, and transformation. Take a moment to ask yourself: what is ONE application where asking questions and attending to the answers would enrich my life?

Many thanks to Katie Kilroy and Data + Women Ireland for encouraging me to develop this material (based on an old blog post) into a presentation, which served as the foundation for this article.

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Additional resources:

If you listen to podcasts, pay close attention to questions the host asks. Anand Giridharadas, author of Winners Take All, demonstrates his Q+A skills in his newsletter The Ink (interview format).

If you need inspiration, Rob Walker’s Ice Breaker of the Week is a running, crowdsourced list of great questions. Nightingale has fun exercising our curiosity chops in our Three Questions With… section.

I synthesized ideas from several books in this article. These include: Radical Humility by Rebekah Modrak and Jamie Vander Broek; Difficult Conversations by Douglas Stone, Bruce Patton, and Sheila Heen; Listen Like You Mean It by Ximena Vengoechea; The Complete Guide to Writing Questionnaires by David F. Harris.