The Long and The Short Of It

21. Ask

Episode Summary

Jen's cappuccino machine sparks a conversation on the importance of asking because "you never know, unless you ask."

Episode Notes

Jen's cappuccino machine sparks a conversation on the importance of asking because "you never know, unless you ask."



Episode Transcription

Peter: Hey listeners, it's Pete, which is an obvious thing to say, now that I think about it, because, I mean, with an accent like this and a voice like mine, it's clearly not Jen; but in any case, we just wanted to let you know the sound in the upcoming episode is a little bit wobbly - we had some troubles with the internet. But we still think it's an episode worth sharing, so please enjoy. Thank you for your patience, and thank you so much for listening.

Jen: Hey Peter.

Peter: Hello Jen.

Jen: Remember a couple episodes ago when I was lamenting this cappuccino machine?

Peter: The famous cappuccino machine, I remember.

Jen: Well, one of our listeners wrote in, because he wants it.

Peter: We've found someone who wants the cappuccino machine.


Jen: And lucky for me, he lives in New York, so we're going to make arrangements for him to come pick it up. And this leads me to the thing I want to talk to you about, which is, you never know unless you ask.

Peter: Oh, I like where this is going. This is The Long and The Short Of It.

Okay Jen, talk to me about what you mean when you say, "you never know unless you ask." Also just to throw it out there, I had been thinking something along these lines just this morning, which just is a highlight to how crazy our brains are. But anyways, sorry, tell me.

Jen: Well, there have just been a series of events recently that could be summed up by that phrase: you never know unless you ask. So I mean, in this case, with the cappuccino machine, the guy could have just assumed, "It would be weird for me to reach out to Peter and say, 'If you were serious about the cappuccino machine, I'll take it.' But on the other hand, you never know unless you ask." And on my end, I'm thinking to myself, "Thank you, listener, for the act of service, because what you've just done for me and for my husband is cleared an entire cabinet in our kitchen." And in fact, when I told my husband last night, "Someone's coming to take the cappuccino machine," he shouted, "Hallelujah," so this actually has greatly improved my life. So thank you, listener, for asking about the Cappuccino machine. So that is just, like, one minor example of something that seems so trivial, but now because he asked, he can have a delicious cappuccino, and I can have a place to store things. So, win-win. But here's the sort of bigger thing that recently happened that I want to unpack through this lens. So on Friday, I opened my LinkedIn - for some reason, I don't go on there that often - but I opened my LinkedIn, and I had a bunch of connection requests waiting for me. So usually I just click "manage all" and then accept everyone, but on this particular day, one of the names stood out to me because it was very profane. So I was like, "Huh, maybe I should stop this practice of just accepting everyone and actually, like, click the names I want to accept." So as I was doing this, I realized that one of the requests I'm getting is from the leader of a major, major organization that I am familiar with, and so of course I accept the request. It doesn't come with any message or anything, and I immediately go into this imposter syndrome mode where I'm like, "Why would this person be connecting with me? This must've been one of those, like, oh, 'people you should know' that popped up, and he was just mindlessly clicking, and what would I possibly have to offer this person? This is so stupid, Jen, you don't deserve," you know, it was just like, over and over. And then I was like, "Stop it, stop it. What if, just what if this person was intentionally seeking to connect with you? What could it be about? Why would this person do this?" And so I said to myself, "You never know unless you ask." So in an effort to beat imposter syndrome, knowing that I can sometimes get in my head if I see my words when I'm typing, I gave myself two minutes and no more to compose a message and hit send. So it was a first draft that I sent out into the universe, and I could hear another voice in my head of a friend of mine saying, "There are givers and there are takers, there are givers and there are takers. Show up to give. You have nothing to take, so just show up to give." So the message I sent basically was like, "Hey, this is some cool stuff that's going on, and perhaps you would want to be involved in this. Let me know." Oh, and then right away he wrote back and was like, "Absolutely I do. Let's set up a meeting." So now, a couple of weeks from now, we have a meeting in the books to - for me to go meet with this person who I assumed I had nothing to offer to, but then of course quieted the gremlins, and of course I have something to offer. Otherwise why would a person reach out? So you never know unless you ask. In this case I asked, I got the information, and now something really cool could come out of it.

Peter: Wow, what a cool story.

Jen: Oh, it's such a cool story. So then I'm like, "Well, where else can I be applying this in my life? There are a lot of things that are going on in the world around me that are bugging me. What if, instead of assuming that everyone was comfortable with the status quo, I just asked. You never know unless you ask." So I, yesterday, had coffee with a friend of mine who is on the agenting side of the business, and - in the theatre busines - and we got to talking, and I asked, "Hey, when was the last time you or your colleagues really investigated the new findings in effective communication, cultivating empathy, personal development, et cetera, and would you be interested in sharing some of those things with them? I would happily lead a couple free workshops to make things better in this industry." And she was like, "Yes, we would be interested." And of course I had assumed previously, no, of course they wouldn't be interested, but they are. So you never know unless you ask.

Peter: Sounds like a new catch phrase for the life of Jen Waldman.

Jen: Well, I want to hear your thoughts on this, and then I have a couple sort of ideas to share.

Peter: I have so many thoughts on this, so let me just throw a few out there and see if they stick. The first is, are you familiar with the book, The Art of Asking by Amanda Palmer?

Jen: Yes.

Peter: Yeah. So this - at the start of the show, I mentioned that this idea of asking was on my mind before you even launched into your story, and it was because I'd, I'd seen pop up on my feed the book, The Art of Asking, which I read about six months ago. And basically, I mean, Amanda Palmer is a phenomenal human being and performer and artist, musician, speaker, and she writes this book about how, how as creatives, and also as humans, we find it so hard to ask; that there's, like, a bunch of stories that we tell ourselves about why we shouldn't ask, that we're being annoying, that people don't want to hear from us, like all of these imposter related and fear-driven stories are things that we tell ourself. And she does a lot of things in the book, but one of the things she suggests is reframing it as, exactly like you have, Jen, as being generous to the person you're asking. So she talks about it in a way that she raised money for one of her, I think it was one of her albums, or got payment for one of her pieces of music - I'm sure I'm butchering that - but basically -

Jen: No it was, it was basically raising money for her to make her music.

Peter: Right. And so the original story I think she'd struggled with or, or one might struggle with, is like, "Who am I to ask people to pay me for my music?" And essentially the way she talked about it, I really liked, which was, these people follow you for a reason, and they are looking for a way that they can support you. So it's actually generous to them if you give them a mechanism to help you. And so it's not about you, Amanda Palmer, it's actually about serving the people that want to help you. And that I just have become a little bit obsessed with it and think about quite a lot: this idea of it's not about you, it's about the people you seek to serve and how you're being generous to them. So that was one direction (not the band, but that was one direction where my brain went). The other one I was just noodling on is that you decide that you can never know till you ask, it's really interesting, because the inverse of this I've, I feel like - I don't know how to articulate this - I feel like we as coaches, so you as coaches, you as a coach of creatives and performing artists in particular, and, you know, all of the other change-makers that you coach, and me too, the change-makers and the leaders that I coach, we actually do this with them in that we, we ask them questions in order to help them unpack ideas, situations, problems, examples that they are working through in their head. So it's almost like, we don't know, we seek to understand, to use one of my favorite phrases, by asking our clients. But what you're saying is actually almost applying that to yourself in the way that you can ask other people for things. Is that making sense? Did I just butchered that?

Jen: No, there was no butchering involved. This was absolutely vegetarian.


Peter: I feel like I'm talking in circles.

Jen: No, it makes a lot of sense. I mean, maybe it's worth holding up two words against each other to see the difference. There is a difference between "asking" and "taking."

Peter: Yeah.

Jen: If you think of asking as an act of service, that you're coming at asking from a place of service, you can't really come at taking from a place of service. That is selfish and all about you. But when you ask, you give someone the opportunity to participate; you invite people to be a part of something. So even with, like, the silly example of the cappuccino machine, the guy asking was totally an act of service. He knew I needed to get it out of my house.

Peter: Yeah.

Jen: So this leads me to a story I heard once from a client of mine probably ten years ago, and I have no idea where she is in the world, so when she hears that I'm referencing her story, reach out and say "hi." So once upon a time, she was a burgeoning singer-songwriter, and had a very particular vision for who would be her manager, and the person she had in mind was managing an artist who that year won so many Grammys that they were unable to hold them all at the same time.

Peter: Wow.

Jen: It was, you know, like, a superstar. And so this young artist reached out, found out who this established artist's manager was, reached out to the manager and included, I think it was like one or two songs from a demo or something, and said, "Do you represent new artists? I love the artists that you represent and would love to work with you," you know, whatever she said. And she received in response a one-word reply: "No." And she, the way she tells the story, it's like wisdom fell upon her, and in that moment she knew that "no" was the answer to the question that she had asked, and that was the only thing it was the answer to. So she asked a different question. She wrote back and she said, "Thank you so much for that information" - I'm paraphrasing, of course - "Thank you so much for that information. It would be so helpful to me if you could listen to my demo, and if you think there's anything in there, would you be willing to write me one or two sentences that I can share with other managers so they can see that someone like you believes in what I'm doing?" And the manager wrote back, "Yes, I listened to your demo, I think it's phenomenal, you do have a future in this. Good luck to you." So the manager wrote a couple sentences, and then this person was able to use that to generate interest. She ultimately went on to develop a successful music career, ended up being nominated for her own Grammy, and I, I don't think I'm making up the end of the story, but maybe like this is my fantasy ending: I believe what ended up happening ultimately was that when she became a Grammy-nominated artist, she was managed by this initial person she had reached out to years and years prior. So the point of the story is that the answer that you get is the answer to the question that you asked, which is why it's so important to know what you asked.

Peter: I'm obsessed with this. I wonder, I was going to ask you, do you think it's got something to do with uh, asking a yes or no question, or being maybe being mindful of whether you've asked a yes or no question, and if, if that is the question you actually want to ask, or if you want someone's thoughts on something, you need to reframe it as a question that doesn't have a yes or no answer so that they can give you their thoughts?

Jen: Well, I'm of two minds about this, because one of the things that drives me absolutely crazy on the receiving end is when someone asks me a question like, "How open would you be to..." fill in the blank. The reason this drives me crazy is because it requires that I gauge my level of openness. I should have to do an openness assessment. If they had just asked, "Are you open to forwarding these materials for me?" I could say "yes" or "no." So I think it depends on the circumstance. If what you need in order to move forward is a definitive answer, then ask the definitive question and get the definitive answer so you know where you stand. You know, in Brene Brown's new book, she says, "Clear is kind, unclear is unkind," and when someone asks an unclear question, it is unkind, because it generates homework for the person they're asking.

Peter: Yeah, I love that. So it's not necessarily a bad thing, a yes or no question or not a yes or no question, but it's about the clarity. It's about, you know, it's been, it's been about three episodes since I mentioned my favorite question: it's about being clear in "what's it for?" What is this email for, what is this question for, what is it that I'm seeking to get out of this person, and framing the question in a way that serves the purpose of the email, the "what's it for?"

Jen: That's exactly right. And I know you and I both are working with a lot of clients who are in pursuit of something that is different than what they are currently dealing with, so it might be that they are making a career transition, or are seeking to make a big change in the world, to affect the culture, so there's a lot of asking that goes along with that, because you must be able to enroll people in your vision. There's a lot of asking. So the art of the asking is actually indeed an art, but there's also some science to it. Close the loops, help people close the loops.

Peter: Yeah. And so, to go back to your example where you gave yourself a time constraint, which I love, of two minutes, was there a question you asked yourself in drafting that ask, or was there a way that you thought about the "what's it for" of that ask that helped you get clear in two minutes on the question you wanted to ask?

Jen: Well, I think this might be a whole other episode, but the reason I was able to generate the ask in two minutes is because I am fully immersed in the world of the person I was reaching out to, meaning I didn't have to do even ten seconds of research because I've already done the research. I was very prepared for the opportunity to reach out. So, you know, had I been in a situation where I was knocked off guard by seeing the connection request come through and wanting to do something about it, if I had not already been impassioned by the kind of work this person was doing, it might've taken me weeks to put an ask together to have enough information to speak from the heart with honesty about why I think the work that person is doing is important.

Peter: Yeah.

Jen: So I guess the point is, immerse yourself in the stuff that you love so that when opportunity shows up, you can go after it.

Peter: Yeah, I think it, I don't want to bring this back to one of my other favorite questions, but I'm going to, which is, clarity in your "who's it for?" Like, who are the people that create work that inspires you, that you can surround yourself with or not surround yourself with physically, but surround yourself with their work so that when an opportunity presents itself or if you decide to create an opportunity, because you never know until you ask, you already know enough of their context, of their work, of their ideas, because you live and breathe it and surround yourself with it all day, every day.

Jen: Yes, and this goes back to something I say to my clients all the time, which is, "If I can poke a hole in your story, it's not a very solid story." So in other words, if, if for example, someone comes to me and says, "You know, I've really been thinking about this: I only want to work for organizations that are led by women." And then I'll say, "That's a wonderful realization to have. Which organizations are those?" "Uh..." It's like well you have, you haven't done the work to make that vision real yet. You must fully immerse yourself in the world of women-led organizations to really understand what that's about, and why you would be so impassioned and intent on making that change. Can you hear singing behind me?

Peter: I can hear some spectacular singing behind you, which maybe our listeners can hear, also.

Jen: Yes. Listeners, I am recording this from my office, which is, I mean other than Disney, it's the happiest place on earth, because basically for eight hours a day, Broadway singers sing in here. It's just the best. It's the best.

Peter: It's truly remarkable, and so in the spirit of this episode, I would ask our listeners to be patient and generous with some of the sound in the background. And also, something we've literally never done before, Jen, and in the spirit of this episode, if you're enjoying this podcast, please tell a friend, or feel free to write and review us on iTunes, or on your podcast player of choice, or visit our website. I don't even know if we've mentioned our website,, or send us an email like our friend did who got the cappuccino machine, which is

Jen: Yes. We invite you, we ask you to please let us know what you think of what we're doing because we want to get better so that we can better serve you, our listeners, and you never know unless you ask.

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