Here’s how you can turn awkward money conversations into smooth transactions 


Ever felt awkward reminding your clients about their due payments? You’re not alone. Many entrepreneurs, especially Online Business Managers (OBMs), have felt like they were begging for money at some point in their journey. But you don’t have to. Let’s dive into some practical strategies to change the way we perceive and handle money discussions in business. Whether you’re an OBM, a budding entrepreneur, or anyone dealing with clients, these tips can be a game-changer.


This episode shares:

  • Mindset shifts to confidently discuss pricing with clients.
  • Strategies for creating a solid pricing process.
  • Understanding your market positioning for effective pricing.
  • Recognising red flags to safeguard your financial interests.

Embracing the money talk

The first step to changing your relationship with money is to shift your mindset. Many of us feel apprehensive or uncomfortable when it comes to discussing pricing. But what if we could change that? What if we could transform our perception of money conversations from something daunting to something exciting? It’s important to remember that money is not a taboo subject. It’s a necessary part of doing business. By changing your mindset, you can approach money conversations with confidence and ease. Practice makes perfect. The more you engage in these conversations, the more comfortable you’ll become.

A few years ago, I decided to test this idea. I pretended that I loved talking about money. Not in a greedy way, but in a way that acknowledged the value of the services I was offering. I found that when I approached money conversations with enthusiasm and confidence, my clients responded in kind.

“I love talking about money”

This statement isn’t about greed; it’s about embracing the value of your services and the solutions you provide for your clients. It’s about changing the narrative around money and making it a normal part of business conversations. 

TIP: 💡Try flipping your mindset. Instead of dreading money conversations, look forward to them. Start to enjoy these discussions, because what you’re really discussing is solving a problem for your client. That’s something to be excited about! Remember, every time you get that icky feeling, flip it on its head. Say to yourself, “No, no. I love talking about money. They love talking about money. It’s going to be fun. It’s going to be great.” See what it does. I dare you.

Strategies for Creating a Solid Pricing Process


Having a clear, transparent pricing process can alleviate a lot of the awkwardness around money conversations. This process should include setting clear payment terms, offering various payment methods, and having a system in place for following up on late payments. A well-defined pricing process can eliminate confusion and misunderstandings. Be transparent about your pricing structure, payment terms, and what your service includes. This will help your clients understand the value they’re getting for their money.

When you have a well-defined process, it not only makes you look professional, but it also gives your clients a sense of security. It’s about decreasing the emotion around money and increasing clarity and confidence.


ACTION: 🎯Pretend you’re setting up this process for one of your clients. What would it look like? Now, apply that to your own business.

Knowing Your Place in the Market


Knowing where you stand in the market is crucial for setting the right price. Are you offering premium services that warrant a higher price, or are you aiming to serve a larger number of clients at a lower price point? Understanding your market positioning will help you set a price that aligns with the value you provide and the expectations of your target audience. Research your competitors, understand your target audience, and align your pricing with the value you provide. Don’t undervalue your services. Remember, you’re providing a solution to your client’s problem.


ACTION: 🎯Assess and determine your positioning in the OBM market. Remember, knowing where your price sits in the market means you can measure how much you’re going to have to coach the sale, how much anchoring you have to do of the price to explain the value of it.

Recognising Red Flags to Safeguard Your Financial Interests

It’s important to be vigilant and look out for potential financial risks when dealing with clients. If a client consistently delays payments or questions every charge, these could be red flags indicating potential payment issues in the future. In such cases, consider requiring upfront payment or setting stricter payment terms to safeguard your financial interests. Be vigilant and proactive. Don’t be afraid to set boundaries and protect your financial interests.


TIP:💡Not every job landing in your lap is worth taking. Safeguard your financial interests by implementing proper measures to prevent overdue, outstanding invoices. Remember, you don’t have to assume every person is in the most amazing financial position. Make sure you put in place some things to prevent there being overdue, outstanding invoices for people that potentially can never pay them.

The ‘Pricing for Pacifiers’ Theory

Here’s a principle to consider – people often pay more for solutions to urgent problems. This theory, which I’ve dubbed the ‘Pricing for Pacifiers’ theory, is based on the idea that the urgency of a problem can increase the perceived value of a solution.

Consider this scenario: imagine a parent with a crying baby in the middle of the night. The baby’s pacifier, the only thing that can soothe the child, is lost. In that moment, the parent would be willing to pay a premium for a new pacifier delivered immediately, rather than waiting until morning to buy one at a regular price. The urgency of the problem – the crying baby – increases the perceived value of the solution – the pacifier.

Now, let’s apply this theory to your business. Understand the urgent problems your clients are facing. What keeps them awake at night? What solutions are they desperately seeking? Once you’ve identified these problems, tailor your services to provide the solutions.

When you solve a significant problem for your client, they will see the value in your service and will be willing to pay a premium for it. This is the essence of the ‘Pricing for Pacifiers’ theory. It’s not about arbitrarily raising your prices, but about aligning your pricing with the value you provide, especially when that value involves solving an urgent problem for your client.


TIP:💡If your service is solving a significant problem for your client, they will happily pay more for it. Remember the pacifier story? That’s the kind of value you want to provide.

Deliver What You Promise

Trust is the cornerstone of any successful business relationship, and the surest way to build trust is to consistently deliver on your promises. When you promise a service to your clients, ensure that you meet or exceed their expectations. This principle goes beyond merely completing tasks on time; it encompasses the quality of your work, your responsiveness to client inquiries, and your ability to anticipate and address your clients’ needs.

When you consistently deliver what you promise, you demonstrate your reliability and professionalism. This not only reassures your clients of your competence but also shows them that you value their business. In turn, this can lead to stronger, more enduring business relationships. Clients who trust you and value your services are more likely to pay their invoices promptly. In situations where cash flow is tight, they are more likely to prioritise your invoices.

Moreover, consistently delivering on your promises can enhance your reputation in your industry, leading to more business opportunities. Word of mouth is a powerful marketing tool, and satisfied clients are likely to recommend your services to others.



TIP: 💡Doing what you say you will is the surest way to build trust, ensuring you are one of the first people to get paid when cash flows in. Remember, your actions speak louder than words. By delivering on your promises, you’re not just completing a transaction; you’re building a relationship based on trust and mutual respect.


And there you have it! All the nuts and bolts to tighten up your pricing game. Remember, money talks shouldn’t give you the heebie-jeebies. Instead, think of it as just another feather in your business cap, another way you get to showcase your OBM prowess.

“You’ve built a cycle where the bills get paid themselves, and that’s what we want to happen.”

By implementing these strategies, you can transform awkward money conversations into smooth transactions. Instead of feeling like you’re begging for money, you’re establishing a healthy, reciprocal financial relationship with your clients.

Want to dive deeper into perfecting your OBM pricing strategy?

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Follow along with the transcript

Here’s how you can turn awkward money conversations into smooth transactions 


Dear OBM client – please pay me. How to stop feeling like you’re begging for money

Hello. Hello. Welcome to the next episode of The Audacious OBM. Alright, today is our last episode in my mini-series on pricing. And yes, I realized that I just, context switched between we and my, please forgive me. All right, so this episode is called. Dear OBM client, please pay me how to stop feeling like you are begging for money.

Now, you might be thinking, what does this mean, Leanne? And essentially it means how do we set our business up so that we don’t run into situations where we feel like we’re a charity? Or we are scared to talk about pricing or to follow up on unpaid bills, we don’t ever wanna be in a position where we’ve delivered our service.

“Hey, I’ve been your OBM for a month and I noticed that you haven’t paid your bill yet.” “Hey, I’ve been your OBM for two months and I noticed that you haven’t paid any of your bills yet.” “Hey, it’s been three months and now I’m starting to get really worried” and now I’ve got people chasing me to pay my bills cos you haven’t paid me and it’s getting really awkward.

From the get go, how can we put an end to that cycle? Let’s stop the cycle before it even starts. Now, a lot of this will have to do with money mindset and how we feel about money and our money stories, and there are so many different people you can go to to learn about the mindset behind money. But I just wanna give you a few tips.

And hopefully some things that you can put in place that will quickly, change your trajectory with money. So the first one is the thought. So when we come to talking about pricing and money and how much we’re going to charge in our business, our thought usually, not for everyone, but a lot of the time is something like, “uh”, or apprehension or, “ah, I’m gonna have to talk about money next.”

Or how do I tell them how much it’s gonna cost? So how can we move away from that? Because with that thought becomes more thoughts and comes feelings. And feelings of being uncomfortable. Or avoidance. So we just, we wanna change that. And I noticed that that’s how I felt talking about pricing a few years ago.

And then I thought, but what if I loved pricing? What if I loved talking about money? And that’s what I tested. I pretended that I loved talking about money. Now, not in a conceited way, but I remember having a conversation with a new lead and we chatted about all the things we were gonna do and I was really excited about it.

And then I thought, okay, we’re gonna have to talk about money. And so I said to this client, Hey, I guess we should have the money conversation. And they replied with, oh, I love talking about money. And all of a sudden I went, oh, and I felt relief. Let’s just talk about money like it’s a thing.

And we did. We set the price, we moved on, did the job, it went fantastic. And so from then on, I’ve made that my premise. I love talking about money. They love talking about money. It’s just a conversation, a box we have to tick. And so it gives me all of the exciting emotions instead of all the scary ones.

So we wanna change our perception a little bit, and we wanna change the feel of conversations to joy. Let’s have some joy when we’re talking about money because what we’re talking about is solving a problem for someone and hey, I really wanna do that for you. So I know creating this podcast now, I was so nervous, I’m still nervous, but if I compare my nerves to, but what if something I say actually helps someone else?

It trumps it every time. I like to help people. And if I have to get over my insecurities to do that, then that’s what I have to do. It’s the same with money. Let’s bring that “I love money”. Money brings joy because money helps people. And so see if you can change that emotion a little bit just by flipping it on its head every time we get that icky feeling.

“No, no. I love talking about money. They love talking about money. It’s gonna be fun. It’s gonna be great.” See what it does. I dare you. 

The next thing is the process. So when we were talking about bringing joy into the conversation, we were talking about increasing the emotion around that, increasing the feeling with the process.

The aim here is actually to do the opposite. It’s to decrease the emotion. So sometimes we feel safer when we have a process in place and we know exactly what’s coming and what we have to do. It makes us feel safe and secure and confident. So to help with stop feeling like you are begging. Let’s put a process in place so we know when, how, what increases are going to look like and start having those conversations.

Okay. When I get a new lead, it’s at this point that we start to talk about money. This is how my pricing works. This is when you’ll get charged. This is when we’ll start looking at increasing that price or decreasing that price if it’s, you know, based on scope. And just explain it. Do the work beforehand so that you have a process, because then it’s just a matter of moving through that and we’re OBMs, right?

So we’re good at this. Pretend that you are doing this for one of your clients. What would it look like? Now? Go and do it for you. You can totally do it. You’ve got this. And then see, how that impacts the experience you have with leads and clients when talking about money. And just by being prepared, you’re going to eliminate a lot of that, hesitancy or people not paying their bills and having to chase people and feel like you’re begging.

The more prepared you are and the more straight up you are with people about what to expect and how it works. They can be prepared and that’s how we get ahead of that cycle of we’re three months in and I haven’t seen a dollar, let’s just stop it before it starts. 

Okay. Then let’s look at knowing where your pricing sits in the market.

And what that means. There are people who structure themselves as, I’m gonna charge a really low amount and I’m gonna sell a lot of them, and then it’s gonna be really easy. I can sell that easily because it’s cheap and because I don’t feel like I have to justify the amount that this is gonna cost someone.

You know, if you were selling a house for $2, I’m sure you would have millions of people wanting to buy that, but unfortunately you don’t have a million houses to sell for $2. You would just be broke and have a lot of angry customers. Then the opposite is to price really high and have less customers and really show the value that you are giving them.

So you’re gonna sit somewhere between the bottom and the top. We all do. And it’s important that you know where in the market you are because you can start to measure how much you’re gonna have to coach this sale. How much anchoring do you have to do of this price to explain the value of it?

Because something that. We look at when we are, when we’re looking at sales pages, for example, if you have something that is quite cheap and you have a sales page that’s a thousand miles long and talks about hundreds and hundreds of different benefits that this offer has, by the time we’re in the third paragraph, we’re going, okay, you’re telling me it’s $4, but it’s got a thousand benefits.

What’s the catch? All of a sudden I’m thinking, this is too good to be true, and what are you hiding from me? So it’s really knowing where you sit and what the expectation is of people and how they’re going to perceive that offer to how much information you give them and when you give them the information, simply knowing that your price is in the premium range or the high end range means that, you know, that type of client is probably gonna wanna know a little bit more detail on how it all works. Cos they wanna make sure they’re making a good decision, a wise decision, and that’s a great thing. Whereas if you were selling, a downloadable, that was a no-brainer.

You don’t have to do all of that. And people don’t really want you to, they just wanna give you the money quickly. It’s a quick transaction. Otherwise you end up undoing the sale, which is not what we want either. So another way to move away from begging people to pay you is to give them the information they need at the level that they need it from the get go.

Another thing we need to do, is look for red flags if we’re having conversations that are too pointed or asking if there are late fees or talking about how they haven’t launched anything yet, but they’re sure it’s going to be really successful. And how long till they see ROI and are you going to help them increase sales as an OBM

if I was sitting there hearing these kinds of things, I would think, okay, what kind of person am I talking to? Because different people require different, questions answered, detail, the way they think is different. But if it sounded like a little bit of an alarm, I would automatically put in place things to prevent this being a risk to me.

And that would be a “we don’t start anything until we’re paid first”, then we do it. There’s all different ways you can approach it, but what I’m saying is you don’t have to take every job that lands in your lap, and you don’t have to assume every person is in the most amazing financial position.

So just make sure you put in place some things to prevent there being overdue, outstanding invoices for people that potentially can never pay them. Then you won’t have to beg for money. It’ll always be paid at start. It’s a good feeling. Right? 

Okay. Then two more things to go. 

One, use the pricing for pacifiers theory.

Now, yes, I 100% made up this theory, and it’s something that I just started saying. And you might be kind of going, okay, Leanne, what the heck? So I know now I have had many, many little people in my time, which means I have had many, many little people awake and crying in the middle of the night. And then, I’ve also been awake and crying in the middle of the night cos I’m tired or begging them to go back to sleep.

It’s awful when you’re half asleep and all you wanna do is go back to sleep and you can’t because you have to soothe this poor little cute child. Now I have always been a fan of the pacifier, so my kids all had dummies and. One of them in particular had many, many dumps. She had a box full of pacifiers, and the reason for that is we kept losing them.

And very quickly did I decide that not being able to find a pacifier was certainly not a problem that I wanted in my life. And. It got to the point where one night, in the middle of the night, she’s crying and I can’t find a pacifier, and I’m running around and I’m turning all the lights on, and I’m looking everywhere for this pacifier like it is gold.

And then thinking, all right, maybe I’m gonna have to find a shop that’s open 24 hours a day. And. I wish there was someone that would just come to my house and give me a dummy. That’s all I want from life. And you go to the shop and you pay $4 for a pacifier. But in that moment, man, I would’ve paid hundreds, and I’m not even joking.

If someone would bring me a pacifier and I could go to sleep and she could go to sleep and life would be better again. It’s worth so much money to me, more than the $4 of waiting until morning and going to the shop. So how can we apply this to business? Essentially, it’s more about knowing who you are selling to, knowing what it is that is really, really important to your clients and pricing based on that, including THAT in your service because I tell you someone who said to me, if you just wait until morning, you can get it for $4, or you can pay me $200 right now and I’ll bring it to you. I’m skipping the $4 thing. I did not want a cheap thing right then. And I wouldn’t have felt ripped off. I wouldn’t have been complaining.

I just would’ve been so happy that someone could actually help me when I needed help. And if we can set up our services so that whatever we are doing is providing that level of value and that level of benefit, you can charge more and it’s totally worth it and people will happily, happily pay you instead of you constantly asking, it’ll just be, please, please take my money.

I need help. And that’s absolutely where we wanna be. Win-win for everybody. 

And then the last thing, now this is really crucial for if you wanna stop feeling like a beggar. And if you wanna stop chasing money or chasing invoices or feeling concerned about having money conversations. The key here is to do what you said you were going to do.

Now, it seems obvious, but a lot of the time we say one thing and what we do is another, or something happens and the outcome gets a little bit skewed, and that’s not nice for anybody. But if we can know what we’re selling and then deliver what we’re selling every time or above expectation, you’ll find clients are happy to pay their invoices, they’re happy to be contributing to you like you contribute to them.

And if there is, a cash flow situation, which that just happens in life and in business, sometimes there’s lots of cash, sometimes there’s not. And then you wait a week and all of a sudden there’s lots Again, it’s just the way cash flow works. But if you find we’re in one of the decreases in cash flow situation and you are consistently doing what you say you are going to do and delivering over and above, you’re going to be one of the first people that gets their invoices paid.

Because that’s the way that your clients can honor you back. And if that’s what’s happening, you’ve got people who are happy to pay you and people who know that the second that the funds land in their account, you are who they’re going to. Then you’re not going to be begging for any money.

You’ve built a cycle where the bills get paid themselves, and that’s what we want to happen. And just to be clear, I’m not saying to let client invoices pile up and to just keep working in hope that someone’s going to pay them. That’s not really wise. But I’m saying if you can create a really great experience and show that you’re trustworthy and keep giving your clients the benefit that you’ve said you’re going to give them, you’re going to have happier clients who want to pay you.

And for there to be less defaults and overdue invoices. So that’s my little thought on how to stop being a beggar for money. And to feel confident when talking about money and pricing instead of feeling scared or icky. We want a win-win for everybody every time. If you found any of this helpful, if you are going to go and implement any of this, please, please let us know.

I would love for this to be a two-way conversation. Have a great week, guys. See you next week.