The Long and The Short Of It

Episode 188 - Ask Better Questions

Transcript:

Pete: Hey, Jen.

Jen: Hey Pete.

Pete: I got a very meta question asked of me a few weeks ago by an executive at a big global company, that I feel like you, as a Questioner, could get even more meta about, but also just like have some insight into.

Jen: Alright...

Pete: And the question is: How do I ask better questions?

Jen: Oh, yeah. As a Questioner, I do love this meta question. This is The Long and The Short Of It.

Pete: So let me, I guess, set some context. I was running a workshop for a group of executives at a large multinational, and we were talking about, specifically, the benefits of coaching your people. So these are senior leaders at a company that have teams, and are very much on board with the idea of coaching their people to be better leaders. And we were talking about the amazing book by Michael Bungay Stanier, called The Coaching Habit, which I'll pop in the Box O' Goodies...just a brilliant, accessible, very easy to implement book on how to be a better coach for your people. And I think importantly, embedded in that book which was embedded in this conversation, is, you don't need to have a qualification or label yourself as a coach in order to be able to coach your people. It's a posture. It's a practice of asking great questions and being curious. So anyway, we were talking about this. And this particular executive was like, "I'm on board with this. I love coaching my team. And I understand it's all about asking questions. But what happens when you ask a question, and then they respond? Like, what do I say next? What question do I ask next?" And ultimately, where we got to was...basically, I'm asking, "How do I ask better questions?" And apart from being super meta, I just think it's a great question. I've written a blog about it recently, just in trying to like put on paper what I've responded in the moment. But before I even get to all of that, I just think that Jen Waldman is a very curious, questioning human, and I know you would have some ideas and some insights, so please drop it on us.

Jen: Well, first of all, high-five to your client. Because it's easy to kind of learn the script and go like, "Okay, well, next time I'm with one of my team members, I'm going to ask this question," and then be completely ill-prepared for what comes next.

Pete: He preempted that part, yeah.

Jen: Right. So like, yay, high-five. Well, we were talking about the concept of asking better questions in our recent KYA (kick your ass) Questions episode. And you have your story backpack where you keep your stories that you're collecting, you can have a question backpack (or as you and I like to call it, a Bowl O' Noodles) that you can actually reference. You can keep a list of questions going for yourself, so that you actually have a menu to pull from. So that's like, just on a tactical level, like actually select good questions, the way you would collect interesting...well, or the way I do, collect interesting quotes, or collect books, or whatever it might be. You can collect questions. But the other thing I feel compelled to ask, in a meta way, is, to what end? Like, what are the questions for? Because what the questions are for will determine what "better" means, in that context.

Pete: Ooh, I like that. What are the questions for? This is meta. What are the questions for? In the context of the conversation we were having, you know, the questions are for promoting independent thinking and brainstorming of your team. Often what happens in a corporate setting is a team member might say to their boss or their leader, "What do I do with this problem? Or, how do I move forward?" And it's very tempting for a manager or leader to say, "This is exactly what you should do." But instead, if you take on a coaching posture, it's like, "Well, what do you think you should do?" So it's trying to empower the individual, put them on the hook in a generous way, in a safe way, in order to think more creatively, think more independently, perhaps, and come up with a solution that maybe they feel more, you know, enrolled in or bought into because they came up with it. So it's like, it's a very empowering place or posture to take on in that particular context that I was talking about.

Jen: Yeah. You know, I'm going to quote Pete Shepherd and ask, "What is the question behind the question?" Because when someone comes to you and says, "How do I do this? Or, how am I supposed to come up with ideas,"...I'm not saying that you have to ask this question out loud to the person, like, "What is the question behind your question?" But you internally ask yourself, "What is the question behind the question?" Because, "How do I think creatively," might actually mean, "Do I have your permission to think creatively?"

Pete: Ooh, yes. Yes, yes, yes, yes.

Jen: You know? So, context makes everything mean something. So as the coach, as the leader, as the conversationalist, I think part of the job of asking better questions involves being aware of the context in which the questions are being asked.

Pete: Yes, context is everything. And I think overlapping that, like you mentioned, that tactical idea...I've actually, I've been part of a very, very high-performing team of coaches right around the world, and we actually had a shared document, I think it was called "130 Questions You Could Ask When Feeling Stuck" or something ridiculous, very literal. And you open that document, and it's just like seven pages of questions. Like, it was literally 130+ questions. And if feeling stuck, I used to go to that document with my context, obviously. And you would try and like see which is the question that is going to help you, based on your context. So I think the combination of both those things, context and like a backpack of questions or a dock of questions, it's actually a really good tactic.

Jen: Yeah. Well, you know, you and I have been having a conversation offline (which I guess I'm bringing online now), which is about how we use the tactics and strategies and methods that we use with our clients on ourself. Like, how do we as coaches coach ourself? And how do we help our clients to start coaching themselves? And something that's perhaps a trap that's kind of easy to fall into when you're in the leadership role, "coaching" people with your newly learned strategies without ever experimenting on yourself first, to see what it feels like and how far you can get. And I wonder if your client would benefit from doing some self-coaching. Like, asking himself the questions that he might use in the context of a conversation with someone on his team, to see how far is he willing to go to answer that question and where does he get tripped up, so that he can help that other person sort of navigate through it.

Pete: Yeah. Have you ever had the experience of someone asking you a coaching question, and you're just either not in the mood or that's not what you need right now in the moment?

Jen: Yes. And also, have I offered the coaching question that someone has not been in the mood or did not need at the moment? Yes.

Pete: Absolutely. I've definitely done the latter many times. I mean, I have a few clients where it became like a, actually a helpful mental model or tactic that we would use, which I would encourage them to ask for what they need, because my default in a coaching conversation is, "You're paying me as a coach, so I'm here to coach you. So, I'm going to ask you a bunch of questions and take that posture." And every now and then, I have a couple of clients, in particular, that would be like, "I don't want you to coach me right now. I need your opinion." So, I would actually say, "Alright, let me just remove my coaching hat for a second, and I'll just give you Pete's opinion on this." Because I think this ties into what you were saying, with like, "Have you tried this on yourself," because coaching can be so effective and so helpful to help someone propel themselves forward, and it can also feel frustrating or even disingenuous if you're not seeing or hearing what that person is, perhaps, struggling with. Like sometimes, I think it's just worth saying, "I see you. I hear you." Not literally, but like through the response that you give, rather than just deflecting to a question or defaulting to a question...which I've learned the hard way, and still proceed to learn most days. Like, when is the appropriate time to ask a question, and when is the appropriate time to be silent or give an opinion?

Jen: This is reminding me...I feel like I must have spoken about this at some point on the podcast, because it was such a jolting experience for me. I went to this event that had an expert panel of people talking about gender issues in the workplace. And there was an audience that was invited to participate in this conversation. And the moderator set up the rules of engagement at the beginning of the event, and said, "This is a no questions space. So if you raise your hand, I'm going to ask you to state what would have been your question as an assertion."

Pete: Mmm.

Jen: And it was wild. My mind was kind of blown. And I've experimented with this with some of my clients, in certain situations, where I'll say, "Let's have a conversation where neither one of us can ask a question. We just both have to stand behind these assertions." So in the case of, let's say, someone going to their leader and saying, like, "How do I think creatively," okay, so how would you say that without the question mark might be, "I'm afraid you're going to be disappointed in the ideas I bring to the table."

Pete: Oof. Wow.

Jen: You know, whatever is actually going on. So sometimes the best way to dig in to a question is to actually not ask it, but to make an assertion instead.

Pete: That's such a brilliant flip. I've had...oh my gosh, I think the conversation I'm referencing with this executive is an example of this. I've had situations where I do the exact opposite. Which is, yeah, all you're allowed to do is ask questions. Because depending on who I'm working with, often they may, if someone's in a senior leadership position, they're often there because they have strong assertions or ideas or strong vision. And so it can actually be the opposite, is, training them to ask questions as opposed to always making assertions is the skill I'm trying to help them cultivate.

Jen: When one thing is true, the other polar opposite is also true. Right? It's so useful to be able to speak in assertions, and it is equally useful, for different reasons, to have a completely question-based conversation. I mean, you know, again, it's, "What's it for? What's it for?"

Pete: Yeah, yeah, yeah. Yeah. So like, some tactical responses or some things I came up with in the moment, that I've actually...I've written a blog about this just recently, so I'll put it in the Box O' Goodies. I think there's like, I probably have twenty-seven responses to that, "How do I ask better questions?" But I tried to boil it down to three or four. And the four I came up with, I'm happy to share. But the first one was just (which I think we've touched on, which is why I bring it up), is just, "Be curious." So I was sort of saying to him, "If nothing else, just remember A-B-C, always be curious." And that, to me, the best question is one that's rooted in a genuine curiosity of what's been said. And in that sense, you know, I've talked about on this podcast before and you and I've talked about, it's kind of like improvised comedy. You hear what has been said and then you have to respond to that, not knowing what is going to be said next, where it's going to take you. But it's like, you have to respond to what's being said, you, "Yes, and..." it with a question. And I guess, you know, I think our podcast is a reasonable example of how we do this. Like, we recently got a message from a listener saying, "Are you sure you guys don't script what you say? Because it sounds a lot like you both know what you're going to say." And I said, "No, this is us practicing A-B-C. Always be curious."

Jen: That's right. What were the other points in the blog?

Pete: There's three others, one...I think you've probably heard me talk about many of them. But the second one was, "Ask one question at a time."

Jen: No question stacking. Yes.

Pete: Right. Exactly, question stacking. I was laughing with a friend about when you hear an interviewer who, I don't know, maybe they're a bit nervous, or maybe they don't realize they're doing it, maybe it's on a podcast and they say something like, "So Jen, what are you excited about right now? I mean, like what are you working on? What's really grabbing your attention? Is there anything that comes to mind? I heard you've been kayaking recently, Jen, could you tell us about kayaking?" And it's just like question after question after question. And then, you're there going, "What do I respond to? Like, what just happened?"

Jen: Right. Well, I think one of the reasons people question stack is because of our collective discomfort with silence. And you and I talk about this, usually when someone says, "Is your podcast scripted," part of what we answer is, "Sometimes we sit in silence. Well, you know, we might cut the silence, but we try to let each other finish our thoughts, which makes the conversation flow smoothly." And when you ask a provocative question, you've got to give people the space and time to come up with an answer.

Pete: Yeah. It's sort of wild, the tics that we have because of a discomfort of silence. I think that's why a lot of folks say, "I'm in awe," because they're uncomfortable with silence. I think that's why people question stack, because they're uncomfortable with silence. Yeah. So that, yeah, that was the other one, the question stalking. And then, the final two. One was, "Avoid binary questions." I do break this rule, every now and then. But I just think that the default, often, can be to ask a question like, "Are you okay?" And that's a binary question, in that there's a yes or no answer, which doesn't necessarily promote an open discussion rooted in possibility or curiosity. It's kind of like a...it's a yes or no. So I would, instead for that one, you might ask like, "What's on your mind," as opposed to, "Are you okay?" Or instead of, "Do you agree with this approach," you might ask, "How would you solve this problem, Jen?"

Jen: You know a question I love in place of, "Are you okay," is, "What's it like to be you right now?"

Pete: Yes. I asked that question in a keynote about three hours ago, and had everyone in chat put their response in chat. Yeah.

Jen: Love that.

Pete: Then, the final one is...I think I've said this tagline before, it's something I learned from an incredible human by the name of Paul Jun. And it's, "Don't steal the revelation." So this is more like when you're asking a question and then trying to sit in that often silent discomfort, or you can predict, perhaps, where you think that person is going to go in responding to your question, there is a temptation to want to fill that gap, to state the aha moment before they've had the aha moment, because you can see it. And Paul always reminded us, in this group I was a part of, to not steal the revelation, to let that person have that aha moment themselves, that that is their revelation to have, don't steal that from them.

Jen: Mmm. I love that. Can I add a number five?

Pete: Please. I'm sure there's so many more that I missed.

Jen: My number five would be, "Play to volley instead of play to score." Because sometimes when you're in the coaching position, there's like this hierarchy that can happen. So instead of trying to like win a point by asking a question that like makes something happen, what if instead, you just played to keep the game going, to keep the conversation going, that you're sparring with someone who is as skilled at conversing as you are?

Pete: Yes.

Jen: As curious as you are, as ready to dig in as you are?

Pete: Yes. Yes. And I guess a sixth...which, now we're just piling on more of them.

Jen: Here we go.

Pete: The sixth, which has come up maybe in the early episodes of this podcast, which I need to remind myself as a coach very often, and I think it can be a helpful just like mental model, which is around the idea of being a lamppost.

Jen: Yeah.

Pete: So, the idea is...it comes from a book called The Prosperous Coach, and the story they tell is that one would benefit from talking to a lamppost once a day and saying, "Here's what I'm struggling with. Here's what I'm working on," and just verbalizing the thing that you're thrashing with or struggling with. And of course, the lamppost doesn't respond, doesn't say anything, it's all just standing there. It's being a lamppost. So a useful prompt when adopting a coaching posture, when you feel like you want to jump in or you feel like you want to hit the return serve or the return question, like win that point, is to just be a lamppost. i.e. Be quiet, hold space, trust that having them say something out loud is as effective as you having to hit a winner or, you know, say something that's so good that you drop the mic. That what we're trying to do in these coaching conversations is encourage someone, ultimately, to think out loud and create the progress, revelation, aha moment, whatever, that they have themselves.

Jen: Mmm. Okay, the timing of this episode is so perfect. Today (literally, today), I started a session of this nine-week class I teach called Preparing a Role, where actors pick a role and we dig very, very deep. And the first three weeks, we're focusing on analyzing the script, and so many questions come up during this time. So I warned them today, "I won't be answering questions for the next three weeks, but you should keep asking them and see if you can answer them." So I also wonder how asking better questions is not necessarily an assignment that you give yourself so you can ask other people better questions, but an assignment you give yourself so that you can ask yourself better questions. "Where are the questions? I'm feeling stuck. What questions might I be able to ask myself to get unstuck, rather than needing someone else to ask them for me?"

Pete: "What are the questions I need to ask myself to get unstuck?" That is The Long and The Short Of It.