The Long and The Short Of It

Episode 262 - Ask For What You Want

Transcript:

Jen: Hello, Peter.

Pete: Hello, Jennifer.

Jen: I wanted to talk to you today about something that has come up so many times in the last month or so, that I cannot even count. And that is this idea of, "Ask for what you want."

Pete: Ah-hah, asking you for what you want. I feel like we did an episode three thousand weeks ago on asks, so this feels like a very timely revisit. This is The Long and The Short Of It.

Pete: So it was Episode 21 I think...I just had a quick look.

Jen: Whoa. Whoa, whoa, whoa.

Pete: It was many moons ago. And if you look at the transcript, it looks like it was back in the days when we just used to do monologues to one another. It was like, it's just wall of text, wall of text, wall of text, wall of text.

Jen: Oh my gosh, that's so funny. I guess we were just figuring out how we were really going to structure this thing.

Pete: We were excited. We were excited. I feel like they're a little more conversational now.

Jen: Oh my gosh, yeah. The version of us from back then had not yet heard our episode on monologue meetings.

Pete: Very true. Very, very true. Okay, tell me about asking. Why is this coming up? I love your idea already of asking for what you want. I feel like you have a very direct and New York opinion of this. And I'm excited to hear more.

Jen: Well, this came up because about a month ago, I guess, I did my negotiating seminar for the artists who were a part of my summer coaching program. And I could just sort of see their minds melting at the thought that they could actually negotiate. And so on the heels of that, I got so many questions, and so many conversations were started. And basically, at the center of it is: If you ask, they could say no. But if you don't ask, they can't say yes. And people are so afraid of getting the no that they hold themselves back from asking for what they want. And on the heels of this seminar, I had a bunch of clients who actually were entering contract negotiations, who ended up having a much better deal because they were willing to ask for what they wanted or what they needed.

Pete: Mmm. Okay, let me say that again, just to make sure I clarify. I feel like this is one of those Brené Brown moments where you're like, "I need a minute to process," because it's so good. It's like a mic drop. If you ask for what you want, they could say no. But if you don't ask for what you want, they can't say yes. And obviously, the goal is to get them to say yes. So like, you have to enter the arena. You have to give them an option of saying yes. (Which also means they have an option of saying no.) But I love that. That's so good.

Jen: And from where I'm sitting, I would prefer a no in the land of the known, than the, "If I had asked, would they have said yes?" I would just rather know where I stand.

Pete: Yeah, agreed. It feels like so many things and concepts we've talked about all come together in this one topic, right? Like, clear is kind. What am I trying to ask for? What does success look like with this reach out or this ask? How might I position it in a way that makes it easy for them? Like, all of these things feel like they're coming to the surface for me.

Jen: This makes me want to tell you a little theater story.

Pete: Yes, I love Jen's theater stories. Buckle up, listeners.

Jen: Okay, once upon a time, I was directing a production of Spring Awakening, which is a really awesome musical. And I received an email from a young woman who had the previous year been a part of a lab company at a theater that I was running at the time. And the lab company is basically like an emerging artists program. So in my mind, I was associating her with being this actor-in-training. And she reached out to me and said, "I'd love to come in and audition for Wendla, which is the lead role in Spring Awakening. Okay, so I say to her, "I don't really see you in that role. But you're right for the show, and I think you might be good in this other role. Would you want to come in and read for that?" And she wrote me back and said, "Jen Waldman, if there is anything I learned from you, it is ask for what you want." And then, she went on to say, "I'm not asking you to cast me. I'm asking you to let me audition."

Pete: Wow.

Jen: And I was like, "Touché, and damn. Come on in and audition." Pete, I'm sure you've guessed the punchline of this story. What do you think happened?

Pete: She crushed the audition and you cast her.

Jen: Yeah, she absolutely ended up being cast. And she was incredible. So, she got the no. And then, she asked in a different way, a second time. Now, I'm sure there are some people listening who are like, "Oh my gosh, isn't that pestering? Isn't that annoying?" No, she reflected my values back to me.

Pete: Hmm. I love that. That's so good. Well played. I feel like she played the Jen Waldman game perfectly.

Jen: Yes, she did. Kelsey Lake, if you're listening, you were amazing in that show.

Pete: Shout out, Kelsey. Okay, I have all these like random thoughts and ideas, some of which I think are tangentially related to what you said, some of them are a little more related. So, let me put one out there in particular. When this pops up in my world, it is often for people who are proposing a product or solution or workshop, an idea, a business, a putting an idea forward, essentially. You know, whether that's within a corporate, or if it's a small business, perhaps they're trying to get relationships or connections within another company and so it's like a business-to-business transaction, and they're like, "I'm asking for something." So that's, I guess, a little bit of context. And one of the things I heard so early on in my starting business journey, was this idea of kind of gamifying the no.

Jen: Mmm.

Pete: I can't remember the name of the book, I'll try and dig it up and put in the Box O' Goodies. The paraphrase version was, "The reason we don't get enough business or clients (we, being small businesses) is we don't ask enough, or we don't ask specifically, or we don't give ourselves permission to get a no." Like, we're so terrified of someone saying no, thank you, that we just like dance around the ask but we don't even send the email in the first place. And we like perfect our little website, because maybe someone will come and discover it.

Jen: Yeah.

Pete: And that the takeaway of this like prompt or call to action was, "Chase the no." Like, collect as many nos as you possibly can in a week, and define success by how many nos you get. Because the punchline kind of to that was, if you collect enough nos, you will get a bunch of yeses within that as well.

Jen: That's right.

Pete: Right. So like your work is for someone, but it's also not for a bunch of people. But in order for you to get the yeses, you need to also get the nos. So I found that like almost gamifying the no, it really unlocked a lot for me around, "It's not personal. It's not an attack on my values. It's perhaps a way to play a game and get to no, which then means I'm closer to a yes." That is one idea that I've been using for years and years and years. Every time I'm putting a proposal in the world, I'm like, "Oh, if I get to no then that's success. Like, I chase the no.

Jen: I love that so much. I love that so much. And embedded there in what you said is something super important. I want to make sure we don't just let it pass us by, which is the specificity of the ask.

Pete: Yes.

Jen: It's fascinating to me how much fluff we put around an ask, because it's so scary to ask that we try to obscure the fact that we're asking.

Pete: Yes.

Jen: I was telling you right before we hopped onto this call that I was helping a client with an invitation that she was sending to offer someone free tickets to see an amazing show that she's going to be in. And in the first draft of the email that she was sending out to someone who's, you know, fairly powerful in our industry, the word "invite" or "invitation" just wasn't in there. And so, I had to go back and say, "Are you inviting her? Are you offering her free tickets?" And it was like, "Yes." And I'm like, "Oh my gosh, you must make the ask so crystal clear. Because if the ask is unclear, how will you ever know what they were saying yes or no to?"

Pete: Right. Yes. Again, that clear was kind idea. I'm so obsessed with that. Like, when I'm thinking about this in a context of an email...because a lot of the asks I see is via email. I think about this as if I'm sending an email with a proposal and there's an ask within it. And the ask might be, "Do you want to proceed with this proposal?" Or it might be, "Do you want to have a phone call to talk about this proposal?" The way I think about it, just visually, is like there should be one line in this email that is one sentence long or maybe two sentences, that is my ask. And it's the kind of line that I'd be comfortable putting in bold. And in fact, sometimes I do, so it stands out as like, "This is the most important thing in this email, this one sentence, this one question. There's one line." And so that's, visually, how I think about it, is like one line in an email that's bold. And hopefully, if you've done this well, hopefully it's not surrounded by walls of text.

Jen: Right.

Pete: It's like clear and concise. And like, "This is exactly what I'm asking."

Jen: I am stealing that from you, as of this very moment. As I'm looking at clients' emails, I'm going to ask them to put the ask in bold.

Pete: Yeah. I feel like it's a version of something I borrowed off you, which is like, "Can you summarize it on the back of a napkin? What are you asking?"

Jen: Right.

Pete: And once you've got it on the back of the napkin, i.e. in one sentence, can you put it in bold? And I mean, I use it in a lot of my proposals in corporate world because everyone's just drowning in email. And so, you open an email...and it's so rare, in my experience, that everyone reads every single word of your email. You scan the email and you go, "What's the ask? What do I need to do with this? Do I need to delete it? Do I need to forward it? Do I need to reply? What exactly is this asking me to do?" So in my mind, if I'm that person (like, I'm trying to put myself in the shoes of a busy executive or a leader), I look at it and I go, "Boom, what's this bold thing? There's a question. Oh, I can reply to that question." In fact, I want to make it easy for them to respond.

Jen: Yes, I love that so much. It's also making me think about where in the email it falls. I find myself giving the same note over and over again, which is, "The ask needs to come sooner." Like, please don't give me six paragraphs of context, and then the ask. Give me the ask up top. Give me some context, and then double down on what you asked me at the end.

Pete: Yeah, I would agree with that. I feel like if you haven't provided enough context but you've got a clear ask, they're always welcome to ask you for further context.

Jen: Correct.

Pete: Like, they can reply and go, "I would be interested in doing this, maybe. But could you tell me more about this, this, and this?" And then, you can tell them about it. So I don't know if I fully agree with that in every situation, because sometimes like the context is key. But I feel like we could probably err on the side of like, to your point, a little less context in six paragraphs.

Jen: Right, right.

Pete: So one of the other tangential threads that came up...just this story that came up for me when you were sharing. I was like, I really heard what you said, and I just thought of this person who is this very senior leader in this very large organization. Incredible woman, highly, highly capable and successful. I was coaching her and she had been offered a fellowship that is recognizable around the world, like a once in a lifetime, you got this three-month traveling fellowship that is like, oh, my god, incredible. And part of what we were talking about was, "How do you negotiate with work or ask work for three months off, so you can really go hard and focus on this three-month fellowship?" That was what she wanted to do. And she was kind of laughing and lamenting the fact that she negotiated with herself, which is something we so often do, when she said to her manager like, "Here's the fellowship I got. I'm really excited about it." And her manager was like, "Great. So, what does that look like? How do we support?" And it was something like in her head, she wanted four months, but she was willing to take three months. And so, she said, "Well, so I'd love to take three months off," and like completely negotiated against herself, without ever giving the manager a chance to respond to the four-month request. And so, the ask was not even made, because of the story she told herself about how that was inconveniencing her boss, and all these things. And so, I don't know, I just feel like that story in my mind is so human and so common, that we have a position and then we have a like, "I'll accept this," and sometimes we just kind of negotiate against ourselves, because it feels uncomfortable asking for what we actually want.

Jen: So true. It's so true. And maybe what we need to consider more is what it might be like to be in the shoes of the person being asked. Like, maybe it would be delightful to be able to say to someone, "Yes, go do this fellowship. Take all four months. Keep me posted. Send me updates. Can't wait to brief everyone here on how it's going for you." Or like in my case, I'll have people ask me for introductions to other creatives. And it never occurred to me to put those two people together. And then, the second the person's like, "Could you introduce me to so and so," I'm like, "Yes. Oh my goodness, that's a magical combination. I can't wait to do that." So, I think we're too quick to assume that we are a burden or we're causing problems or we're being selfish. I know for me, when I am able to help make something happen for someone else, it gives my life meaning and purpose and fills me with joy. It does not make me feel like, I don't know, put upon.

Pete: Yeah. So I'm absolutely obsessed with this idea of when making an ask, start with the person that you're asking. Like, empathize with them. Put yourself in their shoes. What might be going on for them? What are their priorities, their incentives? What's the story they tell themselves? I totally agree with that. And I feel like sometimes people do that through the lens of a pre-mortem, to your point. They focus on all the ways this will go wrong, "because I'm going to upset this person, because this person is busy or senior or not interested or whatever." And that idea that I've liked and mentioned, I think, on this podcast a few times is like the opposite of the pre-mortem is the pre-parade. And so, I feel like what you're articulating is, put yourself in their shoes, but through the lens of a pre-parade. What if this is like the best ask they've ever received? What would they do with it? What would that look like? What would that sound like? How would that be exciting, for them and for you? Then, I imagine if you do that, it shifts the way you then approach the reach out or the ask, and that comes through in the way that it's written.

Jen: Absolutely. You know, the other thing with that empathy exercise of, "Put yourself in their shoes," is you can actually create the conditions for the person who might under certain circumstances have to say no, to possibly get the yes. So, here's an example. Sometimes in my world, the person who is making the offer and negotiating with the actor is not actually the person who has the capacity to say yes to more money or yes to different terms. So one of the things I do with the actors that I work with is if they're negotiating their own contract, I tell them to say, "I understand there may be other people you need to speak to about this, and that I won't get an answer right away. I'm okay with that. Talk to whoever you need to talk to, and then get back to me." And then, that sort of like alleviates the urgency that often surrounds a negotiation.

Pete: Yeah. In your world, can I ask, would it be appropriate to say, "I'm happy to get on a call or speak to the other people that you need to speak to?"

Jen: Oh, yes. Yes. It would be totally appropriate. Get me off of email, people. Get me off of email. That is my ask for the world at large: Get me off of email.

Pete: But I think the point in there though, is, "Yes, you might need to speak to other people. But also, I'm happy to speak to them too, if that's helpful."

Jen: Absolutely.

Pete: That's something I do a lot, of like, "Look, Jen, I know you might need to run this up the flagpole about this workshop that we want to run in this company. Let me know if it's helpful, I'm happy to jump on a call and answer any questions that your boss might have." And often, they take you up on it, and they love it. Or just the fact that you asked and offered, they're like, "I really appreciate that. Thank you."

Jen: Oh my gosh, I feel like we could do a twenty-five part series called The Art of Asking, or The Art of Negotiating, or How to Actually Meaningfully Converse With People.

Pete: I know, we're like twenty minutes in and we haven't even mentioned Chris Voss yet. There's so much more content to go.

Jen: Oh my gosh. Okay, well, listeners, if you want to ask us for further episodes on this topic, of course you can. And you can ask us really anything by emailing hello@thelongandtheshortpodcast.com. In fact, I want to challenge some of you who are scared about asking to use us as a training ground for yourself. Send us an email. Ask for what you want.

Pete: Please do. Please do. And I look forward to reading and replying to all of those emails, because Jen's relationship with email is such that...

Jen: Truer words were never spoken.

Pete: We'll both read and reply to your ask, don't worry.

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