4. Favo(u)rite Questions

Pete and Jen discuss some of their favo(u)rite questions.

Peter: Hey Jen.

Jen: Hey Peter.

Peter: I've got a question for you, and it's a little bit meta.

Jen: Okay.

Peter: Do you have any favorite questions at the moment that you like to ask either of yourself, or of your clients, or your friends, or other people in your life?

Jen: Yes.

Peter: Then I would like to hear them.

Jen: Okay.

Peter: This is The Long and The Short Of It.

Okay. So Jen, you and I have discussed our favorite questions a lot over the last, you know, ten months, and so I was curious as to, at this point in time, what are some of your favorite questions to ask? And I've got a few as well, and maybe we can just unpack each one.

Jen: Great. I'm going to reserve the top two questions for you to unpack because I love hearing you talk about them. The first thing that came to mind when you asked me that question was a question that I learned from someone else maybe about a year ago, which is super simple, and it is: What do you mean by that?

Peter: Ooh

Jen: So this question became a very powerful script in my life that I use when there is a disagreement, confusion, some sort of heated political conversation; if someone says something that immediately triggers an "I'm offended," response in me, instead of calling that person out or questioning their beliefs or their motives or supplying my own contrary opinion, I simply say, "What do you mean by that?" because I assert nothing and I really give that person a chance to explain themselves before I start laying my assumptions on the table.

Peter: Yeah, I mean, I love this question because it's one from a curious place, right? You're seeking to understand. You're giving them the opportunity to explain to you their opinion, which is, yeah, that's quite powerful. I really like that.

Jen: Yeah. It's a really good one for those of us who want to cultivate more empathy and who have deeply-held political and social opinions; so entering into conversations with someone who's coming from a different point of view, it can be so tempting to assume that you are right and they're wrong and to start sort of shoving your opinions down their throat, but asking a question like, "What do you mean by that?" can really help deflate the tension and help you to engage in more meaningful conversation.

Peter: Okay. I have a question along a similar theme then, that is, again, seemingly quite simple, and I think a lot of my favorite questions, a lot of the most powerful questions are really simple at the surface, but they can often be quite powerful when you start to unpack them. So my question is: What is on your mind? And this I think comes from a similar place to where you just were, which is giving people a genuine chance to feel heard, to have a space where they can talk about what is actually on their mind and I think a couple in question with this is, and what else? It's from a book that I know you love, Jen, called The Coaching Habit.

Jen: Love that book.

Peter: Yeah. I think if you couple of these together, it can be really powerful. So you might start a conversation with, well, "What's on your mind?" and then, I mean, the most important part of asking these questions, I guess as a disclaimer, is you actually need to shut up and let them listen - sorry, shut up and let them speak - which is a whole separate conversation. But if you let someone have space to unpack what's on their mind, they might start with, "Oh, well, I'm just a little bit worried about work," or, "I've got this thing on at work," and then if you couple that with, "and what else?" what you'll often find is there something else that's on their mind that they want to talk about, or that they want to get out there - that they want to unpack. And just giving someone the chance to even talk about that I think is really powerful. So that would be what I would throw out there. Have you got another one?

Jen: Yes. This question comes from a book called Fierce Conversations. The question is - well, a little backstory: if you are engaged in a conversation with someone and you ask a question to which they respond, "I don't know," then this question is the follow-up to that: "What would it be if you did know?" I have used this with so many of my clients, and it is extremely powerful, because in some ways it's noncommittal because they've already expressed, "I don't know," so whatever comes next, they don't have to wholeheartedly subscribe to, but often it is the thing that they were scared to say when they instead chose to say, "I don't know."

Peter: Wow. Yeah, you give them permission to un-attach themselves from the right answer by doing that, I think, too.

Jen: Exactly. What's another one of yours?

Peter: Well your question reminded me of a Tim Ferriss question, which is, "What would this look like if it were easy?" I don't think we need to go into it, but that's a similar question I think to the one you just asked.

Jen: You've asked me that question many times. The other question that you often ask interchangeably with that one is, "What's the hard part?"

Peter: Yeah, that's one of my favorite questions. So that question I love so much that I have a calendar invitation with myself once a week - it pops up on my calendar with the question, "What's the hard part?" And I try to, most days when I get that, so it's on a Wednesday, I grab a piece of paper and I take five minutes and I just write out what I think the hard part is right now, and by doing so, so often what you realize is A) it's really not that hard - it's all just in your head, and B) you start to realize that there are quite easy, quite implementable ways to get around that quote unquote "hard part." So I try and use that on myself quite a bit once a week, and I also ask a lot of people that question too. Do you want me to throw another one out there?

Jen: Yeah.

Peter: Okay. So this is literally two words, and I think it's really cool, and the question is, "So what?" And this has to be used in the right context, because it can be used passively-aggressively, or even aggressively, but I think if you use it when you're coaching someone or pushing someone to get out of their own way, or when you sense that somebody is limiting themselves with excuses like, "Oh, I can't possibly, you know, start this new project because I don't have the time or the capacity or the money, or I don't have the resources," and if you just say to them, "So what?" what can happen is they start to have to try and answer that and unpack - again back to this, the question of what would this look like if it were easy - you almost force them to un-attach themselves from the outcome that they have to be able to do this and just kind of free-flow ride of, "Well, so what? I need to be able to do this, this, this, this and this." And it's like, "Well, yeah. So, so why don't you?” Does that make sense?

Jen: I love it. It reminds me of a game I play with my daughter, which we call "The 'Why' Game," where she'll ask me a question, and I'll answer it, and then her response to my answer will be, "Why?" And then I'm not allowed to think; I have to just answer. And then her response to that answer will be, "Why?" So, you want to play real quick?

Peter: Let's do it.

Jen: Okay, so ask me a question.

Peter: Jen, what's the hard part for you right now?

Jen: Getting up the guts to actually post all of this stuff.

Peter: Why?

Jen: Because I know that imposter syndrome is creeping up and saying things like, "Oh, people are gonna think you're crazy."

Peter: Why?

Jen: Because some of the ideas and assertions that I might make might actually be different.

Peter: Why?

Jen: Because I have very specific ideas and a very specific point of view about the world.

Peter: Why?

Jen: Because I've had the chance to step into the skin of many different characters and see what the world looks like through their eyes.

Peter: One more: Why?

Jen: Because, I guess, my whole life, all I've ever wanted to do was show people that there's more than just one way.

Peter: What's amazing is that last line that you just said is the exact reason why you should make this podcast.

Jen: Right. Well, this is - this is why Kate and I love to play this game, because even though she's eight, she understands that there is some truth that gets uncovered when you keep asking questions.

Peter: Yeah, so there's that famous line, right: the quality of your life can be determined by the quality of your questions, and I think that's true of the questions you ask each other, but also the questions you ask yourself. So, I love that your eight year old already has that wisdom. She's a genius.

Jen: She really is. I've got another one.

Peter: Okay, let's do it.

Jen: This was a question that I had specifically started using for a certain context and set of circumstances and have now repurposed. So the original purpose and the original question was, "Is there anything you want me to know?" And this original purpose was something that I would tell the actors that I work with to ask in a call back audition when they are meeting the director of the show that they're auditioning for for the first time. So that would allow a conversation to be started, but they, the actor, would not be sort of "leading the witness," and instead get the information that was actually on the director's mind. The new repurpose - I still, I still recommend that if there are actors in our audience - the repurpose is that I've realized that, with a lot of my interactions with people, that I sort of steer the conversation in a certain way. And one of the things I like to do at the end of the conversation - whether it is a one-on-one with someone, or if someone is registering for a class, or applying for one of our scholarships - the last question is always, "Is there anything else you want me to know?" Because that allows them to really release whatever they've been holding back, if they felt that it didn't answer the question that I had specifically asked. So this kind of leaves everything open for them to share whatever's on their heart and make sure that their ideas are truly heard.

Peter: Yeah. I have another one that's down a different path.

Jen: Let's hear it.

Peter: So it's actually one I've only really heard and appreciated recently from a friend of mine, and it's three words. I don't know why I keep telling you the length of it - and it's actually four words, now that I think about it - so that was smooth. Yeah. And the question is, "Is it worth it?"

Jen: Peter, that's four words.

Peter: Yeah, I know. I corrected myself, didn't you hear? I knew you were going to say that. It's four words everybody. But the question, to get back to it, is: "Is it worth it?" And again, it sounds so simple, but like, I've heard my friend say this question could haunt him at times, because when you ask it at the right time, what you may realize, if you ask it of yourself, is that you're spending a bunch of time on stuff that you don't actually get - like you don't actually see any value in it. It's not worth it. So if you're getting really hung up on a conversation that you've had with someone at work, or with a friend, or an acquaintance who, you know, may have said something that is just getting all up in your business, you can ask yourself, is it worth it? Like is it worth me tearing myself to pieces internally because of this one throwaway line that my boss said, or my friend said, or my acquaintance said? And more often than not, I think the answer is going to be no. But also in the work that you do, is this work worth it, you know, is what I'm doing today worth what I want it to be worth? I think it can be really - a little bit haunting, but it can be a really powerful question. And it is four words.

Jen: I thought of another one. Do you over on the other side of the world know who Dr. Phil is?

Peter: Wait, was that the question, or is there a question?

Jen: No, it's a follow-up. I am legitimately asking you, do you know who Dr. Phil is?

Peter: We are familiar with Dr. Phil. He is on daytime television in Australia.

Jen: Cool. So he has this famous question, which is, "How's that workin' fer ya?" And I love this question because the default response is, "It's not." And he goes, "No, no, no, it must be working for you somehow. Figure out how it's working for you." So if someone is, let's say, approaching a situation from a fear-based perspective, and then you call out, "How's that working for you?" and they go, "Well it's not," and then I can say, "Well it must be, because you're continuing to do it. So let's talk about how it is working for you: it's making you feel safe, it's keeping you from having to discover what you really want in this world, it's keeping your relationship stable but static." And once we start laying all of that out, then that person is able to realize that it actually is working for them, but not in a way that is productive, or meaningful, or useful for their own progress. Then they can really see how they need to make a shift, instead of just sort of throwing their hands up and saying, "Well, I know it's not working." But it is, otherwise you wouldn't keep doing it.

Peter: Yeah, Dr. Phil with the wisdom. I like that: helping you unpack the stories that you may not realize you're telling yourself. Huh. Have you got any more, other than our two or three favorites?

Jen: Okay, so Peter?

Peter: Yeah?

Jen: There are a series of questions that have come up quite a bit on this podcast that I know are your personal favorites, so can you please explain, "Who's it for, what's it for, who's it not for?"

Peter: Okay. I should say these are not my own questions, but these are questions that have had a significant impact on my life and the work that I do and the people that I work with. So, "Who's it for?" is a question that forces you to put audience to the work that you do, right? It forces you to add intention to something, whether it's an email, you know, who is this email for, or whether it's a new business that you're creating a side project, a podcast for example. And what it forces you to realize is that your work cannot be for everybody, right? You cannot create something that is for everybody, and if you try to, what will usually happen is it won't be for anybody. No one will be interested in it. So you hear people say that you need to get really niche and create a persona of, you know, people who are into badminton that live in North Carolina - I just made that up - but getting really specific about who your work is for is so critical so that you can speak to those people and tailor your message to those people. And it's actually - it's an exercise in empathy in a lot of ways. So this question of "who's it for?" is so powerful, and it's something that I asked at the start of any project, and we used it in this podcast in our trailer, Jen. So, "Who's it for?" and then literally listing the types of people that it's for, and then like, going really deep on the characteristics of those people. So I often, when I write about who's it for, I'll write about what podcasts do they listen to, what books do they read, who do they hang out with, what do they do on the weekend, what jobs do they have? Getting super specific about who my work is for, having that intention will then I think increase the likelihood that you can talk to those people, you can meet them where they're at, and that they'll get value out of it. So that's who's it for - and please interrupt me if you have anything to add.

Jen: I love hearing you wax philosophic about these questions, so I'm just sitting back with my martini and enjoying this.

Peter: Related to that I think is: "Who's it not for?" And this is an equally simple but equally powerful question, and equally as important, and it reemphasizes this idea that your work cannot be for everyone. And so it challenges people, this question, because they'll say often, the default response is, "Oh but, I don't want to exclude anyone from my work. I want anyone to be able to get value out of my work." But there's always this other pool of people. There is always a very large portion of people that your work is not going to be for, and by calling out who these people are, you can actually celebrate in a way, in a weird way, you can celebrate even when you get negative feedback from these people. So I know we've spoken about this in relation to the podcast. This podcast is not for people who are seeking the right answer or seeking an answer, and so if we get a one star review on iTunes from someone who says these two just wax philosophical and they don't actually give me any answers, we'll high five each other and say, "Perfect. That's the type of person who this podcast is not for, and we succeeded in it not being for them. That means we served the people we seek to serve. We served our 'Who's it for?' so that's actually a good thing." So I think that question can be equally as powerful.

Jen: Yes, it allows us to celebrate and release the trolls.

Peter: Exactly. Be Gone, trolls, be gone! And the third and final question that I have to riff on is: What's it for? It's actually, I think of it as another way of asking, "Why?" in a lot of ways, but I know there's some - and I'm no neuroscientist - but there's some logic behind this idea that people struggle to answer a question that starts with "why," and they actually find it a lot easier to answer a question that starts with "what" or "how," which is why I love this question. So, "What's it for?" is kind of like asking, "Why should I do this?" or, "Why am I creating this thing?" And again, I think you can use "What's it for?" for everything, whether it's an email, whether it's a meeting, whether it's a podcast, a project, a blog, a business; if you start with, "What is this thing for?" and add intention to it, and force yourself to write down, "Well, this is for a select group of people who I want to go from a to b. That's the goal. That's what this is for. That's the mission," you then have a measurable way of deeming whether or not you got there, whether or not you achieve that particular thing. But also it just - it just gets rid of ambiguity. I mean, having worked in corporates and startups in the past, I've sat through so many, so many pointless meetings that didn't have a clear intention. They didn't have a clear "what is it for," and that just by taking five minutes to ask that question at the start, I think we can all save ourselves a whole lot of trouble, but also just add a lot more intention and a lot more purpose to the lives that we live. So I just ranted - it felt like for ten minutes, Jen - I don't know if that made sense, but I'm going to throw it to you.

Jen: It made total sense, and it just sparked an idea for another episode, which is how to meaningfully communicate with people - meaningfully, and effectively. And I've got a framework that I'll share the first two bullet points right now, and then we can do a sort of long form version of this on another episode, but I call this my "rules of engagement," and these are rules that I put in place when I'm writing an email, if I'm doing an interview, etc., etc. And the first one is: know your audience, and the second is: know your objective. So this is another way of saying "who's it for, what's it for" - the subheading under "know your objective" is: "what do you want this person to do, and how do you want them to feel when they do it?" So it's not just about your intention in terms of what the finish line looks like, but how you want that person to feel when they crossed the finish line. So if for example, I'm reaching out to a colleague, or someone I met at a cocktail party or something, and I want to ask for their feedback on this episode, let me say. So, this is a person who has some expertise in this area and I would really love for them to provide some feedback before we release this to the world. So I have to identify all of the things that make that person my specific audience. And then I know that the objective is: I want them to listen to the podcast and deliver feedback, but to take that one step further, I want them to feel proud that there's was the expertise that was sought, and excited to provide the feedback. What I don't want is for them to feel obligated, or like it's a slog, or encumbered by all of this weight. So knowing that there's a feeling attached to the action, I want to make sure that the way I set up the ask is going to help me to achieve that desired outcome.

Peter: Yeah, that feeling question is such a good one, as we wind up this episode. So I would ask you, Jen, how do you want people to feel at the end of this episode?

Jen: I want them to feel curious. I want them to feel confident that they are now equipped with a whole new set of scripts to bring into conversations, and I want them to feel excited to share this with someone else.

Peter: And that is The Long and The Short Of It.

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