April 29, 2026

The Biggest Mistake You're Making with Your Ask that's Leaving Money on the Table

The Biggest Mistake You're Making with Your Ask that's Leaving Money on the Table
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Tell me if this has ever happened to you. You were solid with your messaging. You had that dialed in, and you'd engaged the decisionmaker and gotten them to the point where they're interested in your stuff.

And then when you pivoted to the pitch and named the price, they didn't buy.

Maybe they said things like, maybe next year. Or, I'm not sure this is right for us at this time. Or some other thing that tried to let you down gently, but didn't result in the investment you were asking for.

I hear some version of this scenario from Nonprofit leaders all the time. And when I have them replay the lead-up and the pitch for me, it almost always turns out they were making the same big mistake that lots of folks make, that winds up trampling their great messaging and reducing its effectiveness.

When we're able to fix that, the results change pretty fast. But the catch is, it's really hard to analyze that mistake yourself, because it's very likely something you're doing completely unconsciously. So the first thing we have to do is notice it before we can get to work on fixing it.

Today, I'm going walk you through how this set of mistakes shows up and some things you can do right away to start solving this problem.

In this episode, I’m sharing:

  • The wrong conclusion so many people draw when their big ask fails to get a yes
  • How an attempt to make it easier for the decisionmaker to hear a big ask is actually planting doubt
  • Three common language and voice shifts during the ask that cause the decisionmaker to back away
  • Two simple ways to identify the language and voice mistakes you’re making
  • How to uncover the hidden obstacles that are causing these mistakes
  • The 3-step process to fixing the mistakes that are costing you the most in your ask


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You're listening to the Nonprofit Power Podcast. In today's episode, we share the biggest mistake you're making with your ask that's leaving money on the table. So stay tuned. If you wanna have real and powerful influence over the money and policy decisions that impact your organization and the people you serve, then you're in the right place. I'm Kath Patrick, and I've helped dozens of progressive Nonprofit leaders take their organizations to new and higher levels of impact and success by building powerful influence with the decision makers that matter. It is possible to get a critical mass of the money and policy decision makers in your world to be as invested in your success as you are, to have them seeking you out as an equal partner and to have them. Bringing opportunities and resources to you. This podcast will help you do just that. Welcome to the Nonprofit Power Podcast. Hey there folks. Welcome to the Nonprofit Power Podcast. I'm your host, Kath Patrick. I'm so glad you're here for today's episode because the chances are really good that you've run into this problem and maybe have drawn the wrong conclusion when it happens. Tell me if this has ever happened to you. You were solid with your messaging. You had that dialed in, and you've engaged the decision maker and gotten them to the point where they're interested in your stuff. And then when you pivoted to the pitch and named the price, they didn't buy. Maybe they said things like, uh, maybe next year or, I'm not sure this is right for us at this time. Or some other thing that tried to let you down gently, but didn't result in the investment you were asking for. I hear some version of this scenario from Nonprofit leaders all the time. And when I have them replay the lead up and the pitch for me, it almost always turns out that they were making the same big mistake that lots of folks make that winds up trampling their great messaging and reducing its effectiveness. When we're able to fix that, the results change really fast. But the catch is, it's really hard to analyze that mistake yourself because it's very likely something you're doing completely unconsciously. So the first thing we have to do is notice it before we can get to work on fixing it. Today, I'm gonna walk you through how this set of mistakes shows up and some things you can do right away to start solving this problem. The thing is, it's easy to know if this mistake is happening because there's direct evidence. Your decision makers either aren't buying or they're not investing at the level you know they should. That's your red flag. Now, with a caveat, if they're not interested at all, that's a separate problem, which is totally solvable, but is not our focus today. When they're interested, you've gotten them that far and they're engaged, but then they don't buy when you make the pitch, there's something else going on. And here's what's happening. Your messaging is great. You're in the meeting and you're nailing that messaging right up until the part where you pivot to the ask, the investment, the big scary number. And that's when everything shifts. Suddenly there's a hesitation that happens in the voice and it manifests in a number of different ways. Sometimes there's suddenly a bunch of qualifiers and filler words that start showing up to soften or distract or minimize the ask. And almost always, there's something happening in the actual quality of the voice that shifts and that tells the decision maker that you're not bought in. And if you're not bought in, then they're thinking to themselves, whether they're aware of it or not, well, if they don't believe in this, if they don't think that this is worth that investment, why should I? And so what might very well have been a yes becomes a not now or maybe later. And here's the worst part of it. When that happens, and you've already felt like this was a really big ask, it was a stretch ask. And you were a little bit nervous about it'cause it's so big. The conclusion that folks often draw when they swing for the fences like that and then get turned down. The conclusion they draw is, See, I knew it. We asked for too much. Next time, we better dial it back. And guess what? If the core mistake is happening, it will still happen when you dial the number back. Unless it gets all the way down to some number that's way too low and that is gonna cause other problems for you. Sometimes we can deliver that with great confidence and fantastic delivery. And we get a yes to something that's not in our best interest. The investment's just too low. Let me expand on this just a little bit to help you understand how this comes about.'Cause this is really common. And I see versions of this happen every single day. One of the things that's very common is a lot of filler words start coming into the conversation. All of a sudden there's a lot of likes and you knows, and ums and ahs and all the things. All those little filler words that, you know. Like I just did that we toss into everyday conversations, sometimes unconsciously. It's a little bit of a vocal tic. And in moderation, on occasion, no big deal. But if what's happening is that's suddenly starting to show up, just as you move into your pitch and it wasn't there before. That's an indicator that you are making a move to, basically sabotage that pitch. Another way it shows up is with qualifying language. So you get these, well, we're thinking this amount, but. Well, you know, our stretch goal is X. Our dream number is blah, blah, blah. All of those things signal to the decision maker that you are quite ready to accept quite a bit less. And so they may take one of two courses of action. One, they may just offer you a bunch less. Or they may translate in their subconscious to, oh, well this person doesn't really think that the thing they're selling is worth that level of investment, so what's wrong with it? Why are they asking for that, but they're kind of saying that it's not really worth that. Well, what does that mean? Is it a bad investment? Maybe I shouldn't do this. We do these things because what we hope we're doing is sort of softening the blow and making it easier for the decision maker to hear the big scary number, when in fact we're planting doubt. Maybe not in their conscious mind, but that's how their subconscious is receiving it and processing it. And it's leading them directly to a no or to a substantial underinvestment. Which is the exact opposite of what you're looking for. The third thing that happens, and this is universal. If you are making any of these sets of mistakes and you're having this experience, I promise you that something is happening to your voice in the process. And that can show up in a lot of different ways, but basically what's going on is you're rolling along confidently. You're engaging the decision maker. You're talking to them about the substance of the work, About why it's exciting, why it's visionary, why it's groundbreaking. However you're framing it, to get them really excited and invested in getting on board with this amazing thing that you're offering them. Or maybe it's just the amazing outcomes that you're offering and they're excited about that. And you're in the groove because that's your happy place. You believe in this 100%. If somebody asked you, does your stuff deliver the outcome you're saying? You'd be like 100%. There is no question. It is awesome. You can't believe the transformations we get. So you're rolling with that level of investment that is reflected in your voice. You're fully present in your voice. Then you get to the pitch. And maybe your voice gets a little softer. Maybe you start hesitating. Maybe you say, well, you know, so the, so there's those fillers again, you know, so the, the, um, the investment we're looking for is XYZ dollars. But, you know, um. I realize that's a lot. It's a pretty big ask. Or yeah, the impact is incredible. And the investment is um, XYZ dollars. There may be hesitation, we may get quieter. Something happens in the voice where the energy drops, the level of certainty drops. And all of those sounds are processed in the listener's subconscious as this person doesn't believe in what they're saying. They're not bought in, so why should I be? Those are the three biggest ways that this problem manifests itself. And the end result is the same whether you're doing one or all of the versions of this mistake. It's resulting in either a lower investment or just a no, a not now, a maybe later. Here's why this is happening. What's at the root of this on some level, is that we're uncomfortable with some aspect of what we're asking for. We think the ask is too much in some way. Now, maybe it's too much money. Maybe if it's a policy ask, it's too much in that it's too ambitious. It's asking for too bold an action. Whatever the case, on some level we believe it's too much. Now the reason for why it's too much. That gets complicated. And we'll get into that in a minute. But because on some level we think it's too much, we're already anticipating pushback and maybe rejection, maybe even anger or hostility because we were so rude as to ask for so much. And all those things, the pushback, the rejection, the hostility, the anger. All of that feels very unsafe to your subconscious. So your subconscious gets to work protecting you from that scary outcome by minimizing, by deflecting, by otherwise finding ways to signal to the decision maker that they don't really need to make that big investment that's obviously too much. It's very important and very useful to understand that's what's going on. But unfortunately, fixing it is not as simple as just saying, oh, okay, uh, I won't do that anymore. It's a little more complicated. But that said, if you don't know you're doing it at all, then you can't even begin to fix it. So awareness is absolutely the first step. But the reality is, if you're doing these behaviors, making these mistakes. If you're doing that it's also important to realize that very likely you've got some beliefs and stories running in your subconscious that are causing you to do those things, to step on your own messaging. There are beliefs and stories around why something about this is unsafe or not okay. So if we're gonna actually fix it, we've gotta get at those underlying beliefs and stories that are causing our subconscious to feel unsafe in asking for something big. Otherwise, that pesky subconscious will just keep doing whatever it can to try and keep you safe by sabotaging those big asks. Now we work on all of this in my coaching programs, and we go deep on not just the messaging, but on all of the engagement and energy and the vocal aspects of it, because they're all tied together. You could have the best messaging in the world, but if you're stepping on it in some way with other behaviors, then that great messaging won't perform for you the way it could. So we work on that in great depth in my coaching programs. But there are some things you can do right away by yourself, to begin to address this before it costs you any more money. So first thing is how to tell if you're making this mistake. All right. You've got some kind of a red flag that you've already noticed. If every time you go in with a big ambitious ask, the response is, yeah, baby, where do I sign? You're good. You probably stopped listening a while ago. But if you're still here, chances are this is resonating for you and you're wanting to know, so what do I do? How do I fix this? One of the most effective things you can do is to actually watch and listen to yourself. Watch some recordings. If it happens that you have been doing some of these meetings with decision makers over Zoom, then you probably already have the recording. If not, and you've been doing these in person, then i'm gonna have you do the next best thing. Which is go ahead and practice the pitch on video. I'm usually an advocate of role play with a colleague on stuff like this, but in this case, I don't want you to do that. In this case, I want you to grab your laptop or your phone or whatever. If you're using your phone, set it up on a stand or something so that you're not having to hold it. And go ahead and practice your whole thing. The whole conversation you would do with the decision maker. That would be the lead up to your ask. And then go ahead and make the ask. And do it all on video in one take. Don't be doing a bunch of retakes, just do it all in one. And then number one. Watch it back and see what you do when you get to the ask. When you make that pivot, what's happening? Are filler words starting to creep in? Are a bunch of qualifying and diminishing words happening? What's going on there with the actual words you're saying? And then what's going on with your voice and your energy? And just observe all of that. The other thing that can be really useful, and I just did this for a client the other day, was we looked at the transcript. And wow. It really jumped off the page. We were both aware that they were using a lot of filler words and some qualifying language, but neither one of us realized just how much till we printed a transcript and looked at it. And it was shocking how many filler words suddenly appeared around the ask. It was stark. At a minimum, make a video of yourself doing the lead up and the pitch in one take. If you're not used to doing video on a regular basis, you're gonna feel weird about it. Don't worry about that. If you're feeling weird about doing video, that baseline weirdness will show up in the whole video. Don't worry about it. You'll get better at it. But in the meantime, what you're gonna notice is what are the shifts that happen when you pivot to the ask? That's what you're looking for. So that's how you tell if it's happening. Then the next thing is you gotta investigate and identify the beliefs and stories that are running in the background in your subconscious that are causing those behaviors. So some things to look at. This is not an exhaustive list, but this is a good place to start. The biggest one right away is, what about this ask feels like too much to me, and why? Write down all the answers to that. It might be things like, I've never asked for anything that big before, i'm kind of scared to ask for that much. What will the reaction be? Maybe it's, whoa, that's a lot of money. I don't think any decision maker would be comfortable with a number that big. Whatever it is, write it down. And it's probably a bunch of things that are making you feel like it's too much. Write it all down. And then here's some other questions to take a look at. If the subject is you're asking for a dollar amount, then it is very relevant to ask, What beliefs about money were you raised with? Money's hard to come by. Money doesn't grow on trees. Money's the root of all evil. Money can't buy happiness. All the things that might be lurking in there, that may be influencing how you view a really big number when you are asking someone to give it to you. Now a layer deeper, and this is very broad. There are any number of more specific ways to ask this question. But a general area of inquiry is what beliefs about deservedness or worthiness are running in your subconscious? What beliefs were you raised with about that? And then ask yourself, do those beliefs align with your desire to get those big investments? Probably not is probably gonna be the answer. So then the next thing to ask yourself is, well, what new beliefs would serve me better? If my goal is to get these big investments, or these big policy changes. Whatever big thing you're going after that constitutes that big scary ask. What would be some beliefs that would align with my getting that? And identify those. And then a very simple next step is to pick the two or three that resonate most powerfully, the new beliefs, and write them into a short paragraph. It could be, for example, there is more than enough money in the world to address the needs of everyone who needs help. We just gotta get that money flowing to the right people the right way, and I'm the conduit for that. It could be, I have big ambitious goals and a vision and ideas, and I want people who can see that vision to jump in with both feet and invest everything they've got because it is a hundred percent worth it. The outcomes that we'll get from this will be transformative, and anybody who doesn't get on board is gonna be missing the boat. And they need to commit every last dollar they've got. Craft that for yourself, whatever it looks like. It needs to be an affirmative counter to the beliefs you've identified that are keeping you from being comfortable with that big ask. And then what you have to do is tell that to yourself daily, multiple times a day. For at least a month. Two months is better because it takes that long. It takes roughly two months and a few days to set a new program in the subconscious. Once you've done that, once you have taught your subconscious, your reticular activating system, whose job it is to keep you safe. Once you've taught it a new belief, then it will automate the rest of your behavior to fit that belief. Because whatever the subconscious believes is safe and good because you've told it that, is what it will automate to bring to you. And it will shift your behavior. You'll start to let go of those filler words and the qualifiers and the diminishers and all that. That will go away because it's not aligned with that new belief. It doesn't serve that new belief. The subconscious is your best ally, once you train it into the belief set that aligns with the thing that you actually want. But when there's competition running in the background, when your subconscious is sitting there going, oh, you think you want that? But no, we know better. We know,'cause we were told since we were age four that money's the root of all evil Any number of beliefs that may be running in the background. Big, powerful people don't invest in people like me, or in nonprofits in general. or people like me aren't the kind of people who go and get big investments. All the things. Those are some that I hear every single day. There's a million more and whatever's going on in your subconscious are the ones that you have to go after. It doesn't matter what's in somebody else's brain, it only matters what's in yours. We absolutely can program the subconscious to align and serve us well in pursuing really big asks. But we have to work the process. That's a super quick nutshell of how you begin to get out of this problem. And rewrite your story and rewrite your results. Because if you can deliver that big ask with the same amazing energy and power, and vocal integrity that you deliver all the rest of your messaging around how brilliant your stuff is. You're golden. You're gonna find that decision makers are excited to invest and they are not scared by your big numbers. Thanks for listening and I'll see you in the next episode right here on the Nonprofit Power Podcast.