The Two Piers Podcast

The Leadership Skill of Asking Better Questions with Thea Charles and Bob Greene

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Episode Summary

In this episode of the Two Piers Podcast, Erica D’Eramo is joined by Thea Charles and Bob Greene for a discussion about the power of questions in leadership.

Together, they explore why asking better questions is such a valuable skill for leaders, coaches, facilitators, managers, and anyone responsible for helping people think more clearly. The conversation covers open-ended questions, delegation, active listening, performance conversations, team development, and the shift from being the person with the answer to being the person who helps others find their own.

Erica, Thea, and Bob also discuss why “why” questions can sometimes create defensiveness, how leaders can use “what” and “how” questions more effectively, and why giving people space to answer is just as important as asking the question itself.

In This Episode

Erica, Thea, and Bob discuss:

  • Why powerful questions are a practical leadership skill
  • How leaders can move away from the pressure to have all the answers
  • The difference between being a bottleneck and becoming a multiplier
  • How questions support better delegation
  • Why open-ended questions often create better insight
  • The limits of “why” questions in interpersonal conversations
  • How to ask questions without leading people toward a predetermined answer
  • Why space, silence, and follow-up questions matter
  • How questions can support team ownership, creativity, and problem-solving
  • Why coach education can be valuable for leaders, even if they do not plan to become professional coaches

Key Takeaway

Better questions help leaders build trust, develop people, and create more ownership across teams.

For leaders who are used to being rewarded for having answers, this can be a meaningful shift. The value is no longer only in knowing what to do. It is also in creating the conditions for better thinking, stronger conversations, and more sustainable action.

Interested in Building Your Question-Asking Skills?

Erica, Thea, and Bob all teach in the University of New Hampshire Certificate in Professional Coaching program.

This live online program is designed for people pursuing professional coaching as well as leaders, managers, and professionals who want to bring coaching skills into their work. The program includes hands-on coaching practice, reflection, mentorship, and real-time feedback, with a focus on skills such as active listening, powerful questions, ethical practice, accountability, and supporting growth in others.

Enrollment is open for the Fall 2026 cohort.

Learn more about the UNH Certificate in Professional Coaching:
https://training.unh.edu/coaching

About the Guests

Thea Charles

Thea Charles, PCC, is a mentor coach, leadership coach, educator, and consultant whose work includes coach education, mentor coaching, leadership development, and support for coaches pursuing ICF credentials.

Connect with Thea:

Bob Greene

Bob Greene, MS, ACC, is a coach, consultant, facilitator, and trainer who works with individuals and teams on leadership development, career development, team effectiveness, communication, conflict resolution, and organizational development.

Connect with Bob:

More from Two Piers

Erica D'Eramo:

Hello and welcome to the Two Piers Podcast. I'm your host Erica D'Eramo, and today we'll be talking about the power of questions. I'm joined by Thea Charles and Bob Greene. Thea is a mentor coach, leadership coach, educator, and consultant. She specializes in developing coaches and leaders through mentor coaching, coach education, and leadership development, she teaches in university and professional coaching programs, mentor coaches pursuing ICF credentials, partners with leaders across a variety of industries. Outside of coaching, you'll likely find her at a theater or music performance or planning her next travel adventure. Bob has extensive experience as a consultant, coach, facilitator, and trainer. He works with emerging and established professionals on leadership and career development, building real teams, supervision skills, diversity, equity, and inclusion, communication, and conflict resolution. He's consulted a wide range of local and national mission-driven organizations, and worked with numerous individual coaching clients. He's also an avid photographer. Really excited to have both Thea and Bob on the podcast to talk about one of my favorite topics: questions. Okay, welcome to the podcast, Thea, Bob. So good to have you on. Thanks for joining.

Thea Charles:

Thanks for having us, Erica.

Bob Greene:

Absolutely great to be here. And Erica, just we were wondering this this topic of asking great questions. Why? What was it about this topic that you found so important for having on your podcast?

Erica D'Eramo:

I mean, I think it's it's probably part of my brand at this point that I am an avid question asker, and I think it's probably always been a part of my brand, considering I went into engineering, right? And I, I mean, I think this predates that. Actually, it probably goes back to when I was a kid, right? Taking things apart, being like,"Why does this work this way? Why, why, why? I was that kid, so, so yeah. This is probably what brought me to coaching is like a love of question asking, and I thought this is a topic I definitely want to talk about on the podcast, and who better to have this conversation with than two of my fellow favorite question askers and question experts? But to answer your question a little bit more tactically, I think that this is a this is a topic that comes up continuously with my leadership coaching clients around the value of open-ended questions, what makes a good question, how questions can be used for stakeholder management, for for performance management. It really intersects at almost every point in a leader's journey and skill set, so that's that's why I think it deserves a place on the podcast.

Bob Greene:

Great, thank you.

Erica D'Eramo:

What do you think about questions?

Bob Greene:

No, I, you know, Erica, I agree with you so much that asking great, powerful questions is a real skill, and it's one that isn't typically taught to leaders yet. It's critically important, particularly as leaders move up and are trying to build their teams and build build the effectiveness of their teams and help individuals grow. Asking those great questions is empowering, and and and incredibly helpful. So I think we have a lot to talk about here.

Erica D'Eramo:

Yeah, Thea, how are you? How are you feeling about questions?

Thea Charles:

I love questions. I love answering asking a powerful question. I don't always like answering them because they can be a little difficult, but I do. I love the questions, and like Bob, I think it's a great leadership skill. It really helps leaders who sometimes feel like they have to have all the answers. Sometimes you could just ask a really good question.

Erica D'Eramo:

Yeah, yeah. Well, I hear this a lot too when folks are even navigating, say, imposter phenomenon, and they're like, "I'm not even the expert in the room. What am I bringing? And it's like, "Well, just as you mentioned, Bob, right? There's a point at at development, like as you're developing in your career path, where you won't have all the answers, and you're not supposed to have all the answers. And being able to learn how to be the person in the room without the answers and still bring value can be valuable at any career stage, right? Like the intern all the way through to the senior executive. So,

Bob Greene:

and having answers can be really valuable. There are times, you know, in a crisis situation. For instance, that it's great to have an expert kind of leading the charge. Fantastic, and it's so often the case where leaders feel they have to have the answers in every situation, and they're not gaining from the wisdom and expertise of the people they're working with, who may be closer to the action and may have lots of great ideas and lots of great things to share.

Erica D'Eramo:

Yeah, I see that a lot with, especially new leaders who feel like they are supposed to intuit what motivates their team. They'll be like, "Oh, I tried this, and I tried this, and I tried this. Nothing seems to work, or like performance management issues, right? I tried like giving them structure. I tried doing making it easier. I tried giving them the answers, right? And nothing is working. Like, have have you asked them what might work? And it just doesn't occur a lot because I think that piece around that pressure to have yeah like I'm just we don't even question it right like we just somehow internalize that narrative

Bob Greene:

right

Thea Charles:

yeah and often when people move into leadership positions it's because they're really good at their job so the thought is if I'm really good at the job I should know all of the job and do not start to not notice where the bottleneck comes in of being the person that has to have all the answers all the time. Your your team's not able to grow,

Erica D'Eramo:

right? Like if you were really good at delivering that job of executing that piece of the work, that means that you were adding to the organization in one way, but when you shift into that like leadership role, and even if this is as a peer leader, right? Even if it's not a formal leadership role, you're shifting into empowering other people. Then you become this multiplier effect, right? Instead of like it all has to go through me, I have to have the answer, I have to figure it out, I have to do it, I am responsible now. It's even if you're accountable for it, being able to ask those questions really starts to create these multipliers in the organization.

Bob Greene:

Great. That distinction between being a multiplier or being a bottleneck is so important, and that it so many leaders become bottlenecks and slow down progress because of that. So, particularly as we grow as leaders, you know, of course, we want to accomplish goals. We're doing great things, and we want results absolutely. And paying attention to how we get those results is critically important, and a lot of leaders aren't considering the how. They're so focused on the what that they're not paying attention to the how, which they could really improve and even get better results.

Thea Charles:

Agree with that, Bob. By asking those questions, you also get more insights, different perspectives from other people. It also helps you to be a better delegator because now you know what the people on your team know and what their where their skill sets are and where they can bring their best value to to you as the leader. Right.

Erica D'Eramo:

Yeah, I talk sometimes when I talk about delegation and some of the like key steps in delegating, I think it surprises people how many questions are in those steps. Like, what would you need to accomplish this? What could you see getting in the way of this? How did you hear what I just said? Like, how are you perceiving the success of doing this? Like, what have you done before that's similar to this? Like, and what what will happen if you encounter a bottleneck or if you encounter a barrier? Like, what's the plan? But there's a lot more questions in delegation than I think a lot of people. I hope in good delegation than I even in the act of delegating than I think a lot of people plan for.

Thea Charles:

Yeah, one thing to notice with the questions that you just asked, they were all really open. So open being that people are able to explain their thought processes rather than this or that or something that you can answer with yes or no. Can you do this tomorrow? Yeah, or no. Or instead, you're asking like, what could possibly get in the way? Well, I have so many reports and this and that, so it really opens up conversation by asking an open question and being able to really get better insight into what your employees are doing, and even to I don't know, just knowing what's happening within the business that you may have blinders to.

Bob Greene:

Yeah, such an important point, and open-ended questions typically start with what or how. You know, what what are you thinking about this? What makes it difficult for you? How have you approached this in the past? So those are open-ended questions that really encourage people's thinking and help them build the problem-solving skills, as opposed. To those closed questions, right, which are often very leading questions, like why would you do that?

Erica D'Eramo:

Which is like a lot. I love this that you went there because I joke that why is like a closed question hidden as an open ended question because a lot of people think why is a is a open ended question, especially the engineer types who do things like five whys analysis, right? Like the why, or even like Simon Sinek talks about, like start with why. But I, but why is a tricky one, right? Right, because it has

Thea Charles:

that has that. It sometimes it brings up other people's defenses.

Bob Greene:

Yes,

Thea Charles:

like there are very few times where someone asks you why, where you don't think, well, well, why not? What did I do wrong? Oh no, where did I go wrong here? You start to think a little bit differently rather than just explaining why you did the thing,

Erica D'Eramo:

right? There's the when you were talking about the closed-ended questions that are leading. One of the my favorite ones there is like, was I clear? Like, was that clear? Are the expectations clear? It's like, you're gonna get a yes on that one, but like that, like, what what was your understanding is very different. The why question and that defensiveness is a similar like quick reaction where you don't actually get deepened knowledge, you get like a rationale that people are giving to try to protect, instead of maybe a deeper insight. So I I truly believe though that any why question can be rephrased as a as a how or what, like oh how did you know? What inputs did you use when you came to that decision, or how did you plan for this, or how did you assess your risk profile when you were about to do this? How did you think through it when you were wanting? I guess I'm I'm kind of laughing because like what were you thinking is just I hope everyone on that's listening to this knows that that's not really a good example of like an open-ended question, even though it starts with what. So there are caveats here.

Bob Greene:

Oh, for sure.

Thea Charles:

Always the caveat.

Erica D'Eramo:

Yeah,

Bob Greene:

right. The key is it's a helpful guide to think about you know a what question being more open, but not always. Is the question truly open? Is your question truly trying to get at what the other person is thinking, helping them understand it, helping them think it through, or not? So, or are you really trying to lead them? Are you trying to get a specific answer? So, you know, it's it's a nice shortcut to think of starting with a what question, but it doesn't make it necessarily an open question.

Erica D'Eramo:

Yeah,

Thea Charles:

I can often see that if I'm talking to my kids,"What are you doing? is this question that comes with a lot of defense. Why aren't you doing your homework? If I were to ask,"How much homework do you have today, or what? This is a what question, but like, what are some challenges that you're having with your homework? Or I get a different response rather than when I'm like, why are you doing that?

Erica D'Eramo:

Right. In coaching, a lot of times we talk about like asking questions that are either to get information or to get deeper understanding. Right. Like, there's a difference there. We centering the deeper understanding, and and that's part of that shift that I think we can see in organizations when leaders really do try to center in curiosity, like take a breath, manage your nervous system, and whatever that reaction is or frustration is, and then come back to that true curiosity, so that it's not leading, and you're not trying to get a certain answer or defend. You know, like the goal should be to have more accurate understanding and information with all parties than you had before you started out.

Bob Greene:

Accurate information and also creative information that you know we deal with so many complex issues that having a team where you're hearing creative ideas from a variety of folks can often lead to a brand new solution that no one person, including myself as the expert, would come up with. So that that curiosity piece is so valuable.

Thea Charles:

Yeah, along with the take a breath that you mentioned, Erica, giving people space to answer these questions. Answering a closed question is really easy. It's really quick. It's just a yes or a no. But if you're asking someone how, they have to actually like cognitively think about what it is that they did, how they did it, how they're going to now speak that to you in a way that you understand. So, giving a little bit of space in between the questions is very helpful to let someone else process.

Bob Greene:

And giving space, and and even after you ask the question and receive an answer. Are not jumping right in now with your thoughts, but asking a follow-up question. So continuing to do a deeper dive, perhaps, and really help build the other person's problem-solving creativity, and and to really hear from them.

Erica D'Eramo:

Yeah,

Thea Charles:

Yeah, actively listen to what they're saying, because if you they start to respond and then you come up with a question while they're still speaking, you're not really listening to the full answer anymore. So really, just kind of sitting there with that person, letting them explain, and then taking what they just said to create your follow up.

Bob Greene:

Absolutely,

Erica D'Eramo:

yeah. I think so. It's it's interesting because sometimes I get pushback on this type of I don't know thinking philosophy around well in the heat of the moment though in command and control structures we just need to kind of like we don't have time for this, and and the fact is that actually in emergency response training, they they build this in to the to the way we ask questions. So instead of looking around the room, the on scene commander, instead of looking around the room and saying, "Did I miss anything?" they look around the room and they say, "What did I miss?" Which is a very different question because it's very easy to say, "Did I miss anything?" Can't think of anything. Nope, sounds good. Versus like, what did I miss? I probably missed something. What did I miss? Like looking at each person and giving it the spaciousness for somebody to respond that like, oh, you missed this step in the procedure that is really important for people's safety.

Bob Greene:

What a great example of of multiplying rather than being a bottleneck of really bringing the entire team into the work rather than it all being focused on this one individual. No matter how brilliant and experienced the individual is they're not going to have all the answers.

Erica D'Eramo:

No, and even I think when somebody is brilliant and has the answers, I think there's a lot of research out there that people are not swayed by facts and figures nearly as much as when they examine their own thought process and come to their own conclusions, which I I know we in the coaching sphere I often talk about that video, the advice monster with Michael Bungay Stanier. But he talks about how like advice is ineffective for a variety of reasons. One of which is that it's usually answering the wrong question, right? It's usually like we need a few more questions, like you mentioned, Bob. Follow up questions first, but it also creates this kind of power differential of like I know better than you do, and people don't really want that or like that. So even when somebody's asking for advice and they're like, "Tell me what to do," it's actually way more effective when we just say,"Well, what is it that you want, and what do you know about this, and what is important here?" I don't know. What are your thoughts?

Bob Greene:

No, you know, I worked for quite a while with a coaching client who was an executive in a field that I know nothing about. But what the coaching was about was leadership development and team building, so he would bring situations to coaching, and say,"What do you think I should do?" And I don't know. So guess what? I asked him questions. I asked him open questions, including,"What have you done in similar situations? What's coming up for you? What makes this difficult for you?" And invariably, he would come up with great ideas, try them out, and then the next time we met, he would give me an update. And invariably, things worked out really well. So, but again, he you know, he was seeing me as the expert, which I, of course, appreciated. Except, I wasn't. I wasn't the expert. Certainly not in his field.

Thea Charles:

Yeah, can certainly relate to that. I find that the best coaching happens when I know nothing, and also like to think of it in like, in a term that everyone is probably experienced in some way. Like, when you're starting a new routine and someone prescribes what to do, how sustainable is it? You know, like I think of like exercise. If someone told me to start running, I would not do it for very long because I don't like running, but if someone said go dancing, I would most likely do something that that you know I came up with on my own. I would come up with an idea like, oh, you know what? I really like playing tennis with my friends. I could I could keep doing that and have like make a routine that way. So when you come up with the idea yourself, it's more likely to stick. So even when, if you have a leader that's trying to move a team in a certain direction, if the team comes up with the idea or has ownership over that idea, it's more sustainable and likely to continue rather than if they just said this is what you need to do.

Bob Greene:

I really agree with what you're saying, Thea, and and real ownership. So I once worked with a a client, and she had great ideas, and that and wanted the team to own those ideas. So in team meetings, they would ask questions to lead to the solution they already had, and so no, that was not empowering. And so we had a conversation about that, so that how to encourage the team to develop their ideas.

Erica D'Eramo:

Right, I think that those leading questions they can be tricky because sometimes we don't even know we're doing it. Like coaches, I think, work on this a lot to ensure that they're not leading the witness. Right, we're not like asking questions. But well, and what did what did the manager say to that? And what did you think about in terms of the timing? You know, that like they'll insert a little bit because they're kind of trying to lead. And the reality is that like I think when people sense that it's not true open curiosity that there is a hidden agenda or that they are being pulled or pushed. That it's people become much more wary about what's happening and less open to the ideation and definitely don't take as much ownership because it's still somebody else's idea that they're just executing. And so, I when you said like true curiosity, I think it's tough like to really stay in that true curiosity, and yet it is probably the most effective way for people to come to. I'm going to use heavy scare quotes, and people can't see it, but like the right answer, which means like the right answer for them, which might not be the same as the right answer for us.

Thea Charles:

Yeah, I agree with that.

Erica D'Eramo:

So I know we're talking a lot about like all these good practices and and philosophical frameworks around or theory around around powerful questions. But for our listeners who might be hearing all this and thinking like, okay, I'm sold. I want to become a a powerful question asker, an expert on questions. What are your thoughts? And I am leading the west. I am leading the witness here. What are your thoughts, Thea and Bob, on how people might develop some of their question skills?

Thea Charles:

Well, it's a practice for sure, because asking these types of questions are not how we normally speak in everyday conversation. We're not normally asking really open, powerful questions all over the place. So to flex that muscle, sometimes it's doing less. So if you find yourself over-explaining or using a lot of words in your question, most likely you have a little bit of a hidden agenda in there. So if the question's a little bit shorter to let that person really explore, you get a you might get a more open and honest answer.

Erica D'Eramo:

Yeah, I think one of our our coaching's program participants said, like, what was it? Talk, say less, ask more. Say less, ask more. I think was what they went. Say less, ask more. And then, why am I talking? Is the other one that we know a lot about. W A I T, right? Why am I talking right now? So, yeah, Bob, what are your thoughts?

Bob Greene:

Yeah, a couple things I'm thinking of that I always encourage people to think about what hat are you wearing in the moment? Are you wearing the boss hat, the mentor hat, teacher, or coach, supervisor? So what? So what is needed in the moment? And very often, so what we're talking about today is not just for coaches. Everyone can use it. So if I'm supervising, okay, do I need to get something done right away in one particular way, and I need it done now? Okay, then maybe telling, right, is the thing to do. But a lot of times, it's about building others' power, building others' potential, helping them grow, and then powerful questions that help others think things through and develop is what we want. So to really pay attention to what is my intention in this interaction is one. And then the only other thing I'll add is sometimes taking a pause is really powerful. Not to jump right in, pause, let others speak, and even to think, okay, what question can I ask here rather than jumping in with my brilliant idea?

Erica D'Eramo:

Yeah, which kind of speaks to that shift in value that I think early in coaching, I see a lot of folks struggle with this shift of being the person who has the good advice, who has the value by having that answer, to really starting to get that like little dopamine circuit from having the the most insightful question that gets to the heart of what this person really needs, or like what what's at the heart of the matter, and that takes a little time to relearn our value coming from holding the space, being the observer, asking the question instead of having the answer. And I hope leaders also start to feel that reward cycle come through a little bit.

Thea Charles:

Yeah. And also recognizing that people process differently. So some people will answer that question by talking. Some might need a break to think about it first. And if this is a new skill for you, it's also a new way of experiencing you as the person receiving the question, they may need to step away and come back and give you the answer later. So, you know, it's a learning process on both ends on how to answer these questions that make you really think and how to ask them.

Erica D'Eramo:

You bring up a really important point, which is like how people are experiencing that, and I do want to give one, like not word of warning, but one thought to have, especially in high power differential organizations, it can be unsettling for a leader to turn to somebody and say, "Well, what do you think?" And so that can feel like a deflection of authority. You know, it can feel like, well, you're the boss. You should be responsible for the outcome here. Why are you putting that on my shoulders? So sometimes, just creating the safety of like, I, I am, I'm happy to make a decision here, and I genuinely want to know what your thoughts are, so that I make an informed decision. Right, like meeting people where they're at, and not just suddenly like shifting your way of operating to to a way that folks don't know how to interpret. So, yeah, really good point.

Bob Greene:

Yeah, and and and I'm just going to say the same thing. Really good point, Erica. That again, that's an example of a leader paying attention to how they lead, and not only being the being the expert, not only the results. Of course, we need the results, but how we lead and building new skills as a leader is so important.

Erica D'Eramo:

Yeah,

Thea Charles:

And being transparent about your intentions. Yes, so that other people understand why there's a shift happening. Like, why are you asking these open questions now? What is going on? At least to explain what you're doing can help in the trust process.

Erica D'Eramo:

Yeah, it doesn't need. We don't need to hold our our cards close to our vest on this. We can be open about what what the process is. And I I'm going to do a little bit of a shameless plug because, well, before I do my shameless plug, I will say that there's also lots of great books out there. There's podcasts. There's people are doing a lot of research around what good questions look like, what's most effective. I just read read a book recently on how minds change. Really fascinating. It turns out they change not from facts and figures, right, but from questions. But yeah, shameless plug. One of the ways that leaders can become much better question askers is by doing some coach training, and you don't need to become a coach. Like, there's lots of training opportunities out there, including the program where we are instructors at UNH, and there's continuing ed. There's International Coaching ederation. There's IOC. Lots of stuff out there. So, thoughts, Thea Bob? Anything you recommend?

Thea Charles:

Well, I'll piggyback on coach education, and I have we've trained lots of different people in different industries. People who are going into coaching, people who are not, and I can even say from my own experience that learning more about coaching and how to ask questions and be quiet and listen to people has helped me all throughout any leadership position that I've had, whether that's a volunteer position, whether that's working within the hospital organization that I worked in-it helps all over the place. So it's just a different way of relating with people, and it's a really great way of building trust.

Erica D'Eramo:

Yeah,

Bob Greene:

Absolutely. No, it just totally agree. And it's also to remember, it's not only one-on-one. So we've been focusing on one-on-one, but it's also great skill in terms of team building and really engaging engaging the team actively, so that you're gaining the wisdom of the entire group rather than again just just telling.

Erica D'Eramo:

Yeah. Meeting facilitation, senior stakeholder management, so many different applications, dealing with partners, friends, kids, siblings, all sorts of different uses. Yeah, I I do wish I'd done coach training earlier in

Thea Charles:

All of the above. my life, but hey, we can't rewrite history. Well, I do want to say thank you so much, Thea and Bob, for being on the podcast, sharing your wisdom. I will definitely include some information for how folks can connect with you if they want to follow up, and some information about the program that we teach in, and some other resources on the on the podcast episode. So, if listeners are hearing this and they want to go find that they can find it in the show notes or on our website. We'll have a summary and we'll include links so you can connect with Thea and Bob there as well. So thanks for being on. Thank you so much for having us.

Bob Greene:

Absolutely, thanks so much, Erica.

Erica D'Eramo:

Yeah, thanks, and we'll see you next episode.

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Erica D'Eramo

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