Earlier this year, we had Harvard Business School professor Alison Wood Brooks on the show to talk about talking—specifically, how the questions we ask (and how we ask them) influence how people see us as leaders. 

She joined me and a program manager named Meagan, who wanted to get better at asking questions that showcase her executive presence and leadership potential. Meagan wasn’t the only listener who volunteered to be part of this episode. In fact, so many of you raised your hands that we knew we’d need to follow up in some way. 

So, in this newsletter, with Alison’s help, we’re going to answer some of the additional questions we got about asking purposeful questions. Three volunteers shared their situations and what specifically they needed help with. Below are their questions and Alison’s advice, lightly edited for length and clarity. 

Listener #1: This listener is a consultant who works with very senior people in high-pressure environments. Managing these clients requires asking pointed questions. She notices that some of her peers have a natural skill: They’re succinct and get the information they need in just one or two questions. She’d like to get to that level. She asks:

How can we ask meaningful questions without making the other person feel like they’re being interrogated?  

Alison Wood Brooks: In cooperative conversations, there is no evidence to suggest that you can ask too many questions. In more conflicted conversations, where the other person has different or opposing goals, you need to be more sensitive about how many questions you ask. On average though, people are still more likely to not ask enough. 

If you’re heading into a more conflicted conversation, such as a sales call or negotiation, it can help to prepare. Write out some key questions you might want to ask—as well as the questions you’re afraid you might get asked in return. Jotting them down helps you think through which questions are most valuable, how to frame them, and how to answer them succinctly, without disclosing too much (or too little) information. 

How can we use questions to build stronger professional relationships without coming across as transactional?  

AWB: To expedite and maintain meaningful relationships, both people need to share things about themselves. Don’t be afraid to ask about non-work topics. Does the other person have kids? What are their favorite hobbies? What are their favorite foods? What are their likes and dislikes? People often hesitate to ask these types of questions at work because it feels too intrusive or unprofessional or inefficient, but it’s the most direct pathway to mutual trust, shared knowledge, and understanding. My research shows that people like talking about sensitive topics more than you might think, especially in one-on-one conversations.

Are there specific types of questions that make people feel more seen and valued in a conversation? 

AWB: Yes, follow-up questions! They show the other person that you’re listening to them and care to know more, and they lead to more learning and liking between conversationalists.

Open-ended questions that start with the word “what” elicit more information exchange and relationship building compared to “why” questions, which can come off as accusatory. For example, “What did you have for breakfast?” is better received than “Why did you have avocado toast?” and “What do you worry about when you’re running late?” will go better than “Why were you late?” or “Why don’t you leave earlier?”
 
Listener #2: This listener is a physician trainee in the field of cardiology and the mom of two young kids. She’s finding herself out of her depth and unable to keep up with her peers on all of the technical knowledge she needs to know and retain for her specialty. When she knows she needs to ask a question, her feeling of inadequacy puts her into a full-on panic, even holding back tears. She asked:
 
How do you recommend asking questions when the material feels beyond your grasp and you don’t want to completely invalidate your position? 
 
AWB: This sounds so hard, and it’s also a problem that many people face. You’re trying to reconcile two conflicting goals at the same time: 

One idea is to find a confidante or ally. Maybe you already have the right person in mind, or maybe you need to foster a new relationship (which, I know, can sound like a daunting time investment, especially for a mother of two). But developing a relationship with someone who won’t judge you when you ask “dumb” questions can be incredibly helpful and save you time in the long run.

An ideal confidante shouldn’t have formal power over you or see you as a competitor (bonus points if you already have a trusting relationship with them). Ideally this person would be an expert, so they can answer your questions directly or at least point you toward other resources and people who know the answers. And they should be someone far enough outside your current circle that you won’t feel embarrassed or ashamed to ask even basic questions. 

How do you overcome the negative self-talk of “you’ll never be able to ask the right questions,” especially when you’re pursuing a job that requires asking questions?

AWB: Here’s a reframe that might be helpful: The “right questions” in conversation are literally any questions that serve people’s needs. Often, good questions are not particularly advanced, complex, or insightful, but instead might call out a point of ambiguity that many people are secretly confused about, prompt clarification on basic concepts, or direct people’s attention toward something seemingly unimportant that turns out to be very important. 

Advanced professionals often look back on their careers and remark that the more expertise they gain, the more they realize they have more questions than answers—even as they learn more, they get a clearer picture of all the stuff they don’t know. So it’s a common feeling for experts to wish they’d had the courage to ask more questions earlier in their careers, back when they put too much pressure on themselves to know more than anyone could possibly know. 

How do you suggest asking questions of those superior to you when you both have limited time?  

AWB: Ask peers first. If no one else can answer your question, then you can send a short, pithy email (bullet points and headings help). For more advice about how to send compelling texts and emails, I recommend Writing for Busy Readers by Todd Rogers and Jessica Lasky-Fink. [Editor note: HBR also has some great resources on this. For example, check out “How to Write Better Emails at Work.”]

Listener #3: This listener works on an international team with whom she doesn’t share a native language. She faces an insecurity about asking questions of superiors with the added complication of a language barrier. She asks:

How do I ask questions appropriately in another culture? What considerations do I need to keep in mind?

AWB: Are you thinking about asking questions in one-on-one conversations or in groups? Group conversations are much more complicated (and tend to be more intimidating and dissatisfying) compared to one-on-one chats. So, my advice is to have more one-on-one or small-group conversations where you can practice asking questions and check that you’re understood, then work up your courage during large group meetings or conversations. 

That said, if you find yourself in a group conversation, one thing that can help is writing down your questions ahead of time. If the opportunity arises to ask one, you’ll be in a more confident place to say it out loud.

What’s the best way to get over my insecurity about asking questions, especially when there’s a language barrier?

AWB: Practice! There are lots of conversational AI bots that are specifically designed to help you practice difficult conversations (for example, Virtual Sapiens and Hyperbound). You can even tell your AI partner that you struggle to ask questions, especially when there’s a language barrier, and it will push you and give you the opportunity to get reps asking lots of questions in your non-native language. Between the repetition and feedback, you’ll learn so much (with no fear of negative judgment!).

For more from Alison, check out her book Talk: The Science of Conversation and the Art of Being Ourselves.

How You Can Contribute to the Show

For an upcoming project, we’d love to hear about a piece of advice you gained from the show and how it helped you. Perhaps it was a research finding from an expert we featured in one of our episodes, an insight from a fellow listener, or a tip from this newsletter (maybe from Amanda’s How I Got That Raise series). What was the advice? How did you use it? And what changed in your work life because of it? Email and let us know at womenatwork@hbr.org.

Here are two of our latest episodes and a couple of recent articles from HBR.org that I suggest you check out: 

Podcast: What We Can Learn from Taylor Swift: Our colleague Kevin Evers wrote a new book called There’s Nothing Like This: The Strategic Genius of Taylor Swift, and we knew we had to talk about it. So we got four diehard HBR Swifties together to talk through how the pop icon has become a case study in relevance, resilience, and connection. Whether you’re a Taylor fan yourself or just curious, this episode has great insights on knowing your strengths, bouncing back from criticism, and staying connected to your audience.

Podcast: Managing Up, One Conversation at a Time: Ever realized partway through a project that you and your boss aren’t aligned? Maybe the expectations were murky or your work styles just didn’t click. Executive coach Melody Wilding joined me for a discussion, based on her new book Managing Up, about the two foundational conversations every manager–employee relationship needs: one about goals and one about working styles. She shares scripts and strategies, then we dive into real listener dilemmas, including bosses who micromanage, give vague feedback, or make you feel like you’re walking on eggshells.

Article: Research: Women’s Complaints of Workplace Abuse Get Ignored More Than Men’s: New research analyzing thousands of workplace reports reveals a troubling pattern: When women report workplace abuse, they’re less likely to be believed than men making identical reports. This credibility gap widens when there’s limited supporting evidence, which is unfortunately common in these cases. The authors, four organizational behavior professors, argue that, to build truly equitable reporting processes that employees can trust, leaders need to first acknowledge these gender biases exist and then take concrete steps to counteract them in their policies and training.

Article: How Women in Leadership Can Shape How Others See Them: As we’ve discussed often on the show, women leaders face a double-bind: They’re seen as either competent but cold, or likeable but ineffective. But what if, instead of fighting these biases head-on, women could take control of their own narratives? Authors Deepa Purushothaman and Colleen Ammerman make the case that women leaders need deliberate tactics to counter the assumptions others make that limit their advancement. Their advice includes crafting a counternarrative, using positive associations to shift perceptions, and transforming feedback into a source of power.

As always, thanks for reading, listening, and contributing—

 
Amy G