Purpose & Dreams

Episode #335 – Dare to Ask: Turn Your Wants into Wins

March 26, 2024

I’m Cherylanne.
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Get ready to step into the world that opens up when you learn to ask for what you truly want in life. In this episode, Cherylanne shares her personal insights on the power of asking for what you want and how it can lead to incredible outcomes.

From navigating through fears and societal norms to honing the essential skill of effective asking, this episode is packed with real-life examples and eye-opening experiences that will empower you to break free from hesitation and start claiming your desires confidently. 

It’s time to embrace the courage to ask and turn your wants into wins.

Show Highlights:

  • Discover the intriguing dynamics of sibling personalities. 00:59
  • Do you know the power of asking for what you need? 04:10
  • Learn how to navigate tasks at home with ease and confidence. 07:16
  • What happens if you don’t express your needs? 08:28
  • How to overcome the fear of judgment? 09:36
  • Say goodbye to societal norms and conditioning that hold you back. 12:07
  • How to deal with a positional power differential? 16:30
  • Can shortcuts help you in getting what you need? 18:11

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So, I was thinking about this topic of asking, and it is not surprising that this topic would be top of mind for me these days. I have three children. If you’ve listened to this podcast for a while, you know this, and one of my children is not afraid to ask for anything. The three children have very different personalities when it comes to this. Maybe yours do too, or maybe if you had siblings, you recognize that there was a disparity in the way your siblings approached your parents back in the day. But in our household of our three kids, one of them just was sort of born not being afraid to ask for what they want, and the reality is, because of that, they often get it. This particular child is often the one who gets what they want because they’ve figured out or were born naturally with this ability to be clear about it, articulate it, and sort of unapologetically ask for it. And you know I’d be lying if I said it didn’t cause conflict sometimes, both in my heart and my husband’s heart, or between this child and their siblings because it really is something that is so unique to this particular member of our family, right? I’m being appropriately cautious. I’m trying to anonymize which child this might be on purpose.

So, the reality is that knowing how to ask for what we want is a skill that does open a lot of doors. It does change the outcomes for people who know how to do it, and there are some things in life that we don’t have because we haven’t earned them, right? There’s some things in life that we don’t have, and I’m talking about as adults, where it’s because we didn’t make choices to steer our lives toward them. Like, I don’t have a house at the beach. I didn’t make choices in my life to say, “I’m going to choose to live in a coastal location because that’s really important to me.” Sometimes we don’t have things in our life because we didn’t make time for that. We just didn’t prioritize learning to play the violin or learning to be fluent in Italian. But there’s some things that we don’t have simply because we haven’t asked. That is one of the reasons that sometimes we have blocked ourselves from having something. I love this Nora Roberts quote. I’ve heard this before: “If you don’t go after what you want, you’ll never have it. If you don’t ask, the answer is always no.”

If you don’t step forward, you’re always in the same place. And I think we get evidence of this same idea in so many famous quotes. I mean, biblically, you may know the verse “Ask and you shall receive,” right? And you may also know the Wayne Gretzky quote: “You miss 100% of the shots you don’t take.” And I think that one is similar. I always think about that one as, remember back in the mall in the ’90s, they had that store called Successories and I swear that particular Wayne Gretzky quote lived on a plaque at Successories. And then I think Michael Scott famously quoted Wayne Gretzky’s quote. That’s a meme that’s gone around the internet. So, “You miss 100% of the shots you don’t take” is just another articulation of this same idea, right? If you don’t ask, it’s not going to happen.

And I think when we think about the circumstances in life where we want to ask for things or where we want to ask even for something that we need, right? Maybe it’s not just a want. Maybe it’s something we actually need. There are lots and lots of examples that come to mind for me, and I want to go through some of these just to ground you in this, in case there’s any little part of your brain going, “Well, it’s, you know, it’s selfish to ask for what I want,” or it goes against the practice of gratitude to ask for something that you know is more than what I already have.

But let’s think about some of the things where this skill is actually really, really important. One of them would be within the work environment, something like a flexible work arrangement. You know, a less than full-time schedule or the ability to work from home or to change your typical working hours, I think flexible working arrangements are not something that typically gets handed out on a silver platter. You know, when I did several versions of flexible work arrangements during my corporate career, and each time, I had to ask for the arrangement that I thought might work best for our family and have a conversation, you could call it a negotiation, about how that was going to play out, right? So that’s one example. Also in the workplace, raises, you know, any kind of compensation change, changes to responsibilities, asking for a promotion, asking for more responsibility, asking to be able to be a part of a particular project, right? There’s a lot of things where we may have to raise our hand and say, “Hey, I’d like to do that.”

In the commercial space, you know, thinking about your everyday life, you may have to go and ask for a refund of something that the product or the service didn’t live up to your expectations. In the nonprofit space or your civic kind of engagements, you may need to go ask for donations. I remember being a part of a fundraiser for our church community. They were hosting a big live auction and silent auction a number of years ago, something that became an annual tradition there. And early on being on the committee planning that, you know, we had to go and ask for donations, and some people were like, “I will do anything except that. Like, I will literally do any task on the entire committee just don’t make me go ask for donations,” right? Which I think is so indicative of how hard we find this as a society. You may need to ask for an introduction to someone who could help you, right? Professionally or personally. You may need to say, “Hey, I know you know this person. Could you introduce me?” And oh, if that’s hard to do, another example would be asking for permission, like, “Hey, I need permission to be able to do this thing. That’s not standard. It goes against the rules.” Sometimes we need to ask for advice, and that can be scary, just saying, you know, sharing our story to ask someone who’s been there before for their perspective or their advice.

At home, thinking about examples at home, because I had interviewed Eve Rodsky recently about fair play, you know, asking someone to handle a task at home that typically has fallen to us, a task that maybe has traditionally been in our wheelhouse. That’s another example. Sometimes socially, asking someone to join us for a walk or for coffee or to join a book club or having people come over for a party, like those can be really anxiety-provoking moments if we’re not comfortable that they’ll say yes. We’re like, “I don’t know, what if they don’t say yes? I can’t possibly risk that.” Sometimes just saying what we want for dinner is a lot, you know, telling someone else that what we want might be different than what they want. And as I started writing these out, the examples are endless. I mean, you just think about how many times in life we need to be able to ask for what we need or what we want, and yet it’s so challenging. The stakes can actually get pretty high on this because if we don’t ask and we don’t get what we want, we run the risk of living someone else’s life, right? We’re just sort of going along to get along, or we’re living a substandard version of our own.

So, I want to get underneath this today, and I want to look at the reasons why we don’t ask, right? If you’re somebody who’s listening to this and saying, “Yeah, this is me. I really have a hard time asking for what I want,” I want to get underneath what some of the reasons are that we don’t ask so that you can confront whichever one might be in your way. And then I want to talk a little bit about a process for asking and a couple of things to remember when we start to build this muscle, right? Build this skill that might be rusty.

The first reason that I think we don’t ask is probably the first one that comes to your mind immediately, which is we’re afraid, right? We’re afraid in some way. We are afraid, probably of rejection, that the person is going to say no. And I think we tell ourselves that that’s what we’re afraid of, that the person is going to say no to my request. But even if they say yes, or even if we think there’s a chance that they’ll say yes, we can be feeling a fear of judgment, like, “Well, what will they think of me because I asked?” Even if they’re going to say yes, we can be worried about how they’re going to feel about the request, or we could be experiencing a fear of conflict, like, “I might be able to get to a yes, but it might not be easy.” Go back to the example about a flexible work arrangement. You know, if that doesn’t easily land with a yes, if there is a discussion about it or a negotiation or somebody is frustrated by our request, even if we get what we want on the other side of it, the perception of that conflict can be enough to stop us.

And I think the fear of potential rejection or you could call it failure is a big one because I think sometimes we literally choose the certainty of a no before we’ll risk an uncertain yes. We will just double down. The only way that we have certainty is by not asking, and sometimes that is more powerful than tolerating the uncertainty that comes with asking, so that fear is something to really maybe become more precise about, try to really understand what exactly am I afraid of? Am I afraid of rejection, you know, what it would feel like to have them say no, or is it more about conflict or more about their opinion or judgment of me, or is it that I’m having a hard time tolerating the uncertainty? I think those can all get a little twisted together, and they can really keep us at the starting line where we just walk away from it altogether, right? We just don’t ask at all. Fear is one bucket, but it’s not the only one. The second one that I was thinking about is sometimes we don’t ask because we think we’re not supposed to, like somehow, asking for what we want is going to break an unwritten rule or a cultural norm.

So, for example, we might think that it’s impolite to ask, right? That asking is somehow crossing an invisible boundary of politeness, and that when we ask, the person is going to feel like we’re being rude or we’re being too forward or we’re being impolite. Also, sometimes we think we’re not supposed to because we’re like, “This just isn’t how it works, you know, like this is just supposed to come to us. I’m not supposed to ask for it.” And sometimes there’s a lot of cultural conditioning that is involved in that. You know, I think a lot of women, in particular, certainly women in my generation, were taught like good work speaks for itself. Results speak for themselves. So if you are going to go into your boss’s office and ask for a promotion and basically lay out a case for why you think you deserve one and it’s time for one, if you were told, “Listen, good results speak for themselves, and you don’t need to toot your own horn or brag about things like that,” you can feel like asking is breaking some kind of rule, right? You also can feel like you’re supposed to be discovered, right? Like someone is supposed to just show up, and you know, Oprah is going to one day cross paths with our work and say, “Oh, look at how amazing this is,” and your platform is going to grow. And we think like, it’s not our job to go asking people to share our work, right? Or to give us feedback about our work and tell us how it can be better. And there’s like a belief that that’s just not how it’s supposed to work. You’re supposed to get discovered.

I think actors and musicians can go through that same process of feeling like I’m not supposed to ask to be on that stage or to be in front of that bigger audience. Someone is going to come and find me, and that can really get in the way. So this notion of societal norms or even family norms and conditioning around what we are allowed and not allowed to do, even think about something as simple as expressing an opinion on what you might like to do on a weekend if you as a child weren’t really allowed to have an opinion about that. Everything was sort of dictated for you. Then it’s a skill that may not have been built. And so feeling like, “Okay, well, I’m not, I just am supposed to do what everybody else wants to do, that’s how it’s supposed to work,” and can cause us to not actually get to explore the things that are intriguing or fulfilling or exciting to us. That’s the second piece, and remember, the first one was fear and all the associated fears. The second one is sort of rules, like we think we’re not supposed to do this.

The third one is skills, like we don’t know how to ask? So even if we push past the fear, even if we don’t think we’re breaking rules, we can lack the skill in how to effectively ask. So if this hasn’t been modeled for us, if every time we watch someone ask for something, they got embarrassed or awkward, or you know, they just couldn’t find the words, then we don’t know how to do it in a way that holds enough power, enough authority to sound like we’re somebody who deserves to get the yes, right? So the communication skills or the language that we have to conjure up to be able to make the ask, particularly if there is a power differential, right? Particularly if you’re talking to your boss or you’re talking to someone who has more perceived prestige or power than you do, when that exists, it can be more difficult to find our words, right? Because we’re so intimidated by the person that we have to ask that we just don’t. I watched my kids go through this with teachers, right? Or in college, professors having to go and approach a teacher or a professor to ask for something, even if it’s like, I mean, some things you can argue are objectively more difficult, asking for an extension or something that really is maybe asking them to bend a published rule can be tricky, but even just asking for clarification of a concept, you know, “Hey, you went over this in class, I didn’t quite get it. Can you go over it again?” That is terrifying. And if you’re dealing with the positional power differential, and I think we carry that into adulthood where, particularly in cases where there is authority, we get tripped up.

Another place I think this gets in our way is if we start to project how they’re going to receive the request. I was thinking, earlier this weekend, one of my neighbors who has a teenage son, the teenage son came over because he was selling a fundraising, you know, like a coupon book or something for the baseball team. And I was thinking about, you know, he kind of just bravely came up and made the ask, and I dutifully turned over my money and bought this coupon book that I will probably never use, right? Happy to support his team. But honestly, what was running through my head was, I want to reward the ask, you know, I want this person to have the experience of, I walked up to somebody’s door and did something difficult, and wow, that went better than I expected it to. And I think that is the reason I always stop at lemonade stands. Same reason, right? Is I want those kids to be rewarded for putting themselves out there. And you know, even if I’m going to pay a dollar for a dixie cup of lemonade, it’s like, I want them to have that experience of, I asked you if you wanted this, and someone said yes. So that’s how we build those skills, we learn how to ask in a way that is direct and simple, and you know, brave and polite, and sometimes it’s not going to get the yes, but that the more times that we do it, the more the skill gets built around how to do it.

One more reason that I think gets in our way, so we have fears, and we have rules, and we have skills. I think the other reason is we want a shortcut. Like, it just feels like it’s work, and we’re honestly kind of annoyed that we have to ask, right? We want things to just fall into our lap readily and easily, we want people to ask us, we want people to come to us, we want them to know what we need, right? We want to be so obvious, and we just think like, there has to be an easier way than this, and so that can result in apathy, where we’re so attached to the story that we shouldn’t have to ask, like we shouldn’t have to do this, right? It’s different than a rule where we’re like we’re not allowed to do this. This one is that we shouldn’t have to do this. And so we’re kind of annoyed by that, and we’re just, we’re like, you know what? If they want me to do this thing or if they want to give me this raise or if they want to know what I want for my birthday, they’re going to ask. They’re going to come to me. And the reality is, that’s just not how it works, so we must ask, right? We must find the way, find our voice, find our courage to be able to ask for what we want, and sometimes we have to ask more than once.

Because it turns out, all the way back to that story about my child who is so good at this, persistence pays off. In fact, if we look at the world of sales, okay, here is a statistic that is just mind-blowing because it applies not only if you work in sales. It applies to anything you’re trying to get someone to do or agree to. Here’s the statistic: 80% of customers across industries say no four times before they say yes. Okay, so it’s the fifth or later request that finally gets the yes. 80% of customers say no four times before saying yes, and you’re ready for this one: half of all salespeople never make even a single follow-up, so they never get to two. So you need five for eighty percent of customers, but half of salespeople don’t even get to two, so the most successful salespeople are the ones who are really good at follow-up. We always think it’s like, oh, they’re so glib and they’re so convincing and they have the best argument. Well, there’s I’m sure truth to that, I’m sure there’s merit in that idea. But really, what it is is the persistence and the system in place to continue to make the follow-up, right? Not. I think we don’t do this because we think we’re going to be annoying, we don’t do this because we think we’re going to ruin relationships, but in reality, persistence pays off.

Sometimes the person on the other side needs to be familiarized with that idea more than once. It’s not easy to give a quick yes sometimes, sometimes we need to warm up to the idea and sort of look at it or think about it from different angles before we finally say yes, okay. So when we do make the ask, when we do kind of get our courage together and make the ask, this is a really important point to remember that we could get a variety of responses. I think we tell ourselves we’re afraid of the no. But. These requests are not always a simple yes or no. Sometimes it’s the beginning of a conversation. And I just I want to get into this a little bit before I close the episode of a variety of responses that you might encounter when you ask. Of course, the dream is you could get an immediate yes, right? The relief. Like my neighbor got with the fundraising coupons, like that’s relief. Wow, that one worked. Best-case scenario, you could also get an immediate no, right? A different person could just slam the door in your face or say just immediately tell you, absolutely not, and we’ve all given those responses to our kids, right? They come in and ask for something, and we’re like, that’s a hard no. It’s immediately a no, but I don’t think those two answers are the most common.

Um, I think there’s a big overlap here with how people make decisions and actually our challenges with decision-making as a culture, which is a whole separate episode. But there’s a few other things that could happen. One thing that could happen is we could get some questions back, and I didn’t say this earlier, but I think that could be another reason that we get nervous about asking is we’re not sure how we’re going to handle that part of the process when someone asks us questions or they want us to kind of further our case or clarify our request. That can be uncomfortable. Um, especially if we feel like we’re on trial, right? And sometimes people can put us on trial about this, like we owe them an explanation for why we’re asking, and sometimes we’re like, well, can’t I just ask? Do I have to have a rationale behind it? But getting questions is really a positive response. It means they’re considering it. They’re intrigued enough to find out more, so we need to be ready for questions, and we need to be ready to answer them in a way that is not defensive or argumentative, but is clarifying, right? Helps move the conversation forward.

We might get what I would call a soft no, and this is a no that isn’t really definitive, but it’s a no for now, right? Like I don’t have enough information. I’m not sure this is the right timing. I don’t know enough about your situation. It’s a soft no. And that can be really disappointing when it happens, but it’s not the same as a hard no. It’s not a definitive no, so that’s also something to be ready for. You might get a not yet, right? Like I’m not ready for this yet, but I might be in the future, or I’m not able to do this yet, but I might be in the future. That’s also a positive response because it leaves the door open for a future conversation. And then lastly, I think sometimes we get a yes, but, right? Like it’s a conditional yes, it’s a yes, but I want to know more about this. I want to, you know, understand more about your situation or the timing. I want to negotiate more about the terms, right? So it’s a yes, but, it’s a yes with conditions. And all of those answers except the immediate no are the beginning of a conversation, right? So I think that’s really important to remember is that sometimes the ask is the start of a negotiation. It’s the start of a dialogue, and we have to be ready for it to not be easy. It’s going to be uncomfortable. It’s going to be hard, but it might be worth it, right? Because the dream, the yes is a yes, and that’s what we’re going for.

So here’s what I want you to do. If you’re sitting there going, “Okay, I see myself in this episode. I am the one who has a hard time asking for what I want.” The first thing I want you to do is get clear about what it is you’re asking for. Sometimes we’re not even clear about what we’re asking for, or we’re afraid to say it out loud. It’s like we want it so badly that we’re afraid to articulate it because what if we don’t get it, right? So get clear about what it is you’re asking for. That’s step one. And I would write that down, right? Get it out of your head onto a piece of paper.

And then step two would be to get honest about why you’re afraid to ask. Like, what is the thing that’s causing the fear? Is it rejection? Is it judgment? Is it conflict? Is it uncertainty? What exactly is it that’s causing the fear? And then the third thing I want you to do is to choose one place where you are going to ask for what you want. One place. Maybe it’s going to be at home, maybe it’s going to be at work, maybe it’s going to be in a volunteer context, maybe it’s going to be in your social life. I don’t care where it is, but I want you to choose one place where you’re going to ask for what you want. And I want you to think about how you’re going to do it. Like, how are you going to do it? What are the words that you’re going to say? What’s the context? How are you going to follow up if it’s not an immediate yes? How are you going to follow up on that? And then I want you to do it. That’s the hard part, right? Is to actually do it and then see what happens. See what happens and come back and let me know. I’d love to hear how it goes for you.

And I will be back with you again next week. Until then, let’s be brilliant.

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