E205: Why You're Actually Afraid to Ask for the Business and the Easy Way to Overcome it to Make More Sales
16 Apr 2026 · 10 min
Ben Wright identifies five reasons sales leaders avoid asking for the business: fear of rejection, damaging relationships, a final no, lack of training, and industry conditioning. He offers two fixes: reframe sales as service, and use a deal-setup checklist that walks customers through requirements before asking what they want to do next.
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In this episode, we're going to discover why you're actually afraid to ask for the business and the easy way to overcome it to make you more sales. Welcome to Sales Growth Made Simple, the show helping 7 to 8 figure trade, construction, and industry sales and business leaders finally end the stress of inconsistent sales by simplifying your sales systems so your team can close more deals and grow faster. I'm your host, Ben Wright, and over the last 15 years, I've helped hundreds of trade and sales leaders grow their businesses and generate over $200 million in additional revenue by simplifying their sales processes. Let's get started. Today we're going to unpack some of the key reasons that particularly trade sales leaders are afraid to ask for the business and what's getting in the way. And then I'm also gonna dive into something you can do about it to help reduce those nerves. And they're often nerves that come around with asking for the business. So I want you to put yourself in a situation. I've certainly been in these, but picture a time when you were working with a customer, you provided a great quote, you knew that they were ready to go, or you certainly knew that it was the right time to be asking them to move forward, but you didn't do it. And I want you to have a think for a moment if you can pinpoint exactly what it was that got in the way. And I'm going to go through some of the key reasons now as to what really does get in the way. And hopefully you can resonate with some of these because For me personally, I can probably resonate with all of them over my career, but I find it's really powerful sometimes that when you can hear some of the key reasons that stop salespeople and sales leaders asking for the business and to know that you're not on your own, to know that you're not different, right? Or unique. We're, we're all special in our own way, but to know that some of the challenges you have are ones that are shared by others. So, so when we talk about asking for the business, the key things that really get in the way across my 25 years in the industry, the first one is actually fear of rejection. And it's not so much rejection that they don't like you, but it's more fear that it's going to be a no and your pipeline's going to thin out, right? And we then need to move on to another deal, right? And our pipeline's a little bit smaller and we start to worry about how much work we have booked ahead for us. So that fear of rejection really drives people not wanting to risk burning a deal and let the deal just very slowly and softly move forward and hope that they don't alienate that customer to get that no. That certainly rolls into the second fear that I see people being afraid to ask for the business around, and that's around damaging the relationship. And that's around that you've built something with a customer along the journey, and that by then asking them to work with you, that if you get a no, that's the end of the relationship. And you might have been better to just let the deal again slowly plod forward and wait for the customer to come to their own devices, their own decisions, so you don't risk damaging the relationship. Now I can tell you both of those two I've had occurred myself multiple times across my career, and I've certainly seen it against so many salespeople. In fact, one of my best salespeople, when we had the largest of our businesses, the $40 million a year businesses, when he first started with us, it was his key issue. And he used to openly say to me, Ben, I'm afraid of upsetting someone if I ask them for the business. So I'd rather them come to their conclusion than risk upsetting them and them telling their friends who have also, you know, been recommended or have been recommended from and, you You know, and you thinking, I can't close a deal. And the list went on and on. By the end of this person's time with us, he'd become our best salesperson. And really interestingly, he was never afraid to ask for the business. And I'll give you some ideas around that in a moment. The next area is fear of hearing no. So it's not so much the rejection, but it's that it's a no and it's final and the relationship with the customer is over. I think that's a little bit of a blend of the first two, but I like throwing that in there because for some salespeople, just getting told the no can be quite daunting for them. Lack of training is definitely a big one. People don't know how to ask for the business. And I'll certainly in this camp say that it's not always about how you ask for the business, but how you set the deal up that helps you get that deal done and you move forward. And look, the last one here is I think there is certainly some cultural conditioning across trade industries that the quotes are done, you move on to the next one and the customer will get back to you when they're ready, right? It's we're so busy, we have so many other things to do, we just simply don't have time to follow up. And I can say unequivocally that sales and trade sales leaders who follow up do get more deals. There is no doubt about it. I have myself personally done deals with people who have bothered to follow up, who were neck and neck with someone else, and the deal got done because they were the ones who cared. They called, I had questions, they answered them. I was able to build some trust and away we went forward. So I'd say they're the main reasons that we find salespeople or sales leaders or business leaders can be afraid to ask for the business. And again, I'd encourage you to have a think back. Are there any of those where you think you got stuck? And then let's see if we can give you an an idea or two that's going to help you close more deals. So there's a couple of things for me here around, or one in particular, but we're going to go through two that I think are really impactful in helping you close more deals. So the first one is all around your mentality. And let's say this is the smaller of one. We'll start with this and move into the bigger one next, but it's all around your mentality. And I remember I was taught about two-thirds of the way through my sales career to date. So I was probably mid-30s by the time I learned this. Right? So hopefully if you're younger than that, you're hearing this sooner and it's going to help you more. But one of the things I heard was for us, when we're selling our business or our services and whatever we're doing, a mindset that lands really well with all of us is that we are there to help someone. And if we run a business that isn't built on greed, that isn't built on selling more and more and more to our customers, i.e., unnecessary upsells and unnecessary pricing levels, then We should be able to stand by the services that we offer. I know I certainly do. I know the programs that I run for my students in sales training move the dial. They make a difference. And I've just, I've seen it happen with so many customers that I have full confidence in that. So for me, when I'm meeting with customers, and this is an extension of this definition here, is that I know I'm here to help. And for me, I'd love to help you and help you as quickly as I can. But if I'm not the right person for you, or if you don't need that help right now, or you don't recognize you need it, I'm more than happy to ask you, and then if you say no, move on to someone else that does need my help. So by saying that I'm here to help you, it's your choice if you want it or not, but if you say no, it then allows me to move on to someone else who does. It really softens the blow for me around any edge or any anxiety around asking for the business. So that mindset point of view works really, really well for me. We're here to help. I would love to help you. If you're not interested, let me know, and then I can move on to help someone else. Now that doesn't mean we're verbalizing it, but certainly internally I really love having that as a bit of a guiding star for me. Okay, so the second one here is much more tactical, and this comes down to how we're setting deals up. And for me, when we can set deals up really effectively, it actually removes the need for the hard close, that hard sell that says, right, are you ready to go? Right, do you want me to book it in? I had that used on me today with a service. You know, when would you like me to get that booked in for you? Right? It feels forced. It feels a bit mechanical. Sure, it works sometimes. But the piece for me that I've seen most trade sales leaders roll out that works for them is by getting really clear with the customer at the start, what are the key things they need to tick off before they can make a decision? So if we stick with the windows example for today, the key things for me would have been, I want all my windows done except louvers. I'd like a separate price for the windows at height. And I'd like to know how you're going to deal with the pool windows or the pool glass that has some deeper stains on it. So if the first provider had asked me that, I would have said they're the 3 things. And then what they're able to do is walk around my site, go through each of those with me, and then at the end say, hey, here are the 3 things you wanted to talk through, right? External windows, everything except louvers, and your pool glass, your pool fence windows. Here are my solutions. Boom, boom, boom. 1, 2, 3. Have I covered everything? Yep. Fantastic. Great. What would you like to do now? It's the most brilliant question when we can set ourselves up that we're really clear on what the customer wants. We methodically tick it off. And then at the end we ask them, hey, right, fantastic. What would you like to do next? What would you like to do now? What can I do for you from here? And what we're actually doing is a little bit more subtly, a little bit more softly asking for the business. We're also giving full control to the customer around what they want to do next. Right? So in this instance, I think the fear of damaging the relationship, super low. I think the fear of no. Less likely because our customers are allowed to verbalize what they want to look at. Lack of training's ticked off because we are moving the deal forward. Cultural conditioning, well, we're hopefully reducing the amount of follow-up we need to do post-sale because we're asking the customer then and there. And then the last piece around fear of rejection, that's always going to sit there. But I think this is covered off a little bit neater than a straight out ask because we are actually giving the customer the power, which they always have, but we're giving the customer the explicit verbalized power, right? What would you like to do next? To work through with them in a structured manner where they want to go to from here. Great, I'd like to book it in. I just want to check with my wife first. I'm not sure about this. I need to get some other quotes. I need to do some research here. Yep, I'm ready to go. Whatever it may be, by not only having the mindset that we're here to help, and if they're not ready, we'll go and help others, but also by having a checklist that we can then decide or define, tick off, and then move on from there, it really softens the blow of asking for the business. So out of today, one thing I'd like you to think about is certainly, are you someone that's afraid of asking for the business? And maybe afraid's the wrong word, right? But do you have moments in time when you're a little bit reluctant to ask for the business? And how could you adjust your mentality or your processes, right? Getting clear on what customers want to help solve that. And if you're not clear on how you do that with customers, so if you're someone that's spending a lot of time quoting but not winning enough of those quotes, what I'd say is that you probably do need to change something. And if you don't do that, you'll keep getting those same results and it's really going to annoy you and irritate you and sometimes cause stress and it'll happen over and over again. So what we've done for podcast listeners is we have a free quote audit that will pinpoint exactly why you're not winning more of these jobs, why you're spinning your wheels quoting and what you need to do to increase your close rates quickly. Really easy to do. There's a free quote audit link in the show notes. You can jump into it. It's near the top. Book it in, spend some time with us. I guarantee we'll be able to find something. That will move the dial for you. If that's not your go today, I thank you for listening. Really look forward to the next episode. Bye for now.
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