Jon Bryant & Michael Murray use their combined 30+ years of experience in the painting industry to dig deep into finding the tools, tactics, and tricks to help you succeed.

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Podcast Episode

How Painting Sales Reps Can Sell When the Exterior Season Is Fully Booked

September 4, 2025
26 min

In this episode of Price. Sell. Paint., Michael Murray and Jon Bryant dive into one of the toughest challenges for painting sales reps: what to do when your exterior season is already packed. Learn how to shift your mindset, position scheduling as a strength, and use tactics like pre-booking, strategic pricing, and customer incentives to keep closing deals. Whether you’re up against weather deadlines or trying to sell for next spring, this episode shows you how to turn a “we’re full” calendar into more wins.

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Michael Murray: Hey everyone, welcome back to the Price Sell Paint podcast. I'm Michael Murray, joined by Jon Bryant. Today we're really excited to talk specifically to sales reps in the painting industry as we are headed into late summer, fall. What are we supposed to be doing if we're already pretty close to booked up for our exterior season? How do we handle maybe some of those challenges? That's what Jon Bryant and I are going to be talking about today. Good to see you as always. How are things going in your world?

Jon Bryant: Yeah, great, Michael. It's been an awesome day. I got up early today and I'm not a morning person. So we record the podcast at 11 a.m. and I feel like it's almost time for bed. I'm going to bring the energy, but I've been up in my mind way too long already today. But I do that to myself every Friday. I wake up early mostly because I told someone else I would do it. I play tennis Friday mornings with all of my retired friends and they can't sleep past 4 a.m. So they're up and ready to go. They're super excited to hit the day. They're in bed by 6 p.m. too, so it all works out. But that's what I'm doing. How are you doing, man?

Michael Murray: Don't make fun of people like me.

I'm doing great. Yeah, it's crazy that summer's kind of starting to head towards a conclusion here. The mindset that we're going to talk about is just so crazy. It's the hardest part about being a sales rep. There's times of year where it's complete famine, times of year where it's complete feast. There's times of year where we're selling a project today and painting it in a week or two. And there's times of year where we sell projects and we're booked out for two or three months. It's hard. Definitely is hard.

Jon Bryant: Yeah, absolutely. Today we're specifically talking about the period of time when the schedule is pretty booked at the end of the exterior season. You're getting those stragglers coming in being like, "I need the exterior of my 40,000 square foot warehouse painted before the snow flies." And it's like, dude, the snow flies on Tuesday and it's Sunday.

If you've done this long enough, you know that you're pretty booked up kind of August into the fall for exterior projects. If you're in the Northern Hemisphere like us. If you're in the South, we'd love to have your life. It sounds glorious, but it's just not the reality.

Michael Murray: I just want to become a small part owner of a painting company in the South. I just want to go down there and help them to be as successful as possible in January, February, March, and April. So if anybody's interested, send me a message. I want some write-offs for all the travel I want to do down to that part of the country that time of year.

Jon Bryant: Your emotional wellbeing would be a lot better, I bet.

So if you're a sales rep listening, you've got customers still calling you. You've got the 40,000 square foot person. You've got people who don't understand or know the cutoffs for temperature and that kind of stuff. You got that coming, but you've got this period of time where you feel like you can't sell.

We want to talk about some of the strategies that you can use to still sell, to always be selling, always be closing, and what you can do to make this so much better and more helpful for you and for customers. So Michael, I know you had a few ideas. Let's talk about them.

Michael Murray: I think the biggest one is just not accepting that as a sales rep as your excuse as to why you're not going to sell. The production team's booked out too far, whatever too far is in your world. This gets back to that money mindset. This one's going to be kind of almost like a schedule mindset. It really is made up in your own mind that nobody wants to wait more than blank. Six weeks, eight weeks, 10 weeks, 12 weeks, whatever, four weeks, I don't know. Maybe it's two weeks.

Yeah, okay, maybe that is a story that you are telling yourself and it will become your reality the more you try to tell yourself that. But I can also say that there are people in the home improvement industry at large and the painting industry more specifically that are selling work and customers are waiting six weeks, eight weeks, 10 weeks, 12 weeks, whatever that looks like. They're still out crushing it, they're still out doing well, and they're finding strategies to be successful.

So I think it starts with a mindset. And then we can talk about specific tactics. What would you say regarding the mindset that it takes to be successful here?

Jon Bryant: I think that the mindset is positivity and understanding that the customer is flexible more than they might give off. I think everybody wants it done now, but when now is impossible, now we're in a negotiation. It's like, "Hey, we'd love to help you, but let's talk about options to make this work for everybody."

We've always had a theory that towards the end of the exterior season, we want to be selling work for next year. We want May and June to be as full as possible in September and October. So we're actively having that discussion with customers and it has to do with rushing before the end of the year. It has to do with potentially a discount for waiting, but we want these areas of the year to be stacked so that we can bring on a lot of staff. That was always the theory.

That mindset is that we need to always have an option available for every customer that contacts us. And timing, although they say they want it done tomorrow, there is a lot of flexibility that they might not even realize they had until we start talking about it. So I think as a sales rep, you need to stay positive and understand that you're delivering solutions that meet the customer's needs. That's what I believe. Does that resonate with you, Michael?

Michael Murray: Yeah, I think it comes back to understanding your job as a sales rep is to solve a problem. Sometimes that problem is "Why should a customer pay more?" and you need to be able to answer that question for them. In this scenario, what we're describing is "Why should a customer wait?" What is the reason that you're going to give them to wait for you versus maybe go with somebody else who can get it done sooner?

That makes your job as a sales rep a little bit harder, just like maybe having a higher price can, but it doesn't make it impossible. It just means you've got to up your game a little bit as a sales rep to be able to better understand the customer's ultimate goals. Maybe their goal is to have the highest quality, longest lasting paint job. And they'd be willing to wait a little bit to accomplish that goal.

Maybe to your point just mentioned a minute ago in terms of discounting, maybe their goal is to have this awesome quality job and experience and to save a few bucks if they can, in which case schedule isn't the most important thing. I think that just like every other sales conversation we ever had, it really comes back to asking great questions and really getting to the bottom of what is it ultimately that the customer wants.

There are times that we meet with people where schedule is the most pressing concern. "I'm about to put my house on the market. It has to go up in this time because we have to move and I need this thing done." Or maybe to your commercial example, "I have to get this painted this year for tax purposes. I've got to get this invoice taken care of this year so that we can get this off our books." Zero chance I'm waiting until next year. "I'll get this painted literally when it's snowing out and I don't care if the paint job lasts."

That's crazy, but people do that because I'll see people out painting in 35 degree weather at the end of the season. I'm like, what are we doing?

There's all sorts of things that we can pretend that people might be thinking about as prospects and clients, but until we go in and have these really in-depth conversations, we're making assumptions and projections as to what might be going on.

Jon Bryant: Absolutely. So I want to add to that just slightly. I think there's also an opportunity here and a lot of us—there's a mindset around selling, around money mindset and schedule mindset is just as prevalent, I think. A lot of us see schedule, having to wait, as a negative.

There's a way to position all of this that's actually very positive and fits in well with human nature, which is that you're in high demand. And when you're in high demand, there must be something really good about you. So it comes off in the way that we present these things, these options to customers. If you feel bad about the schedule, like "I'm really sorry, we can't help you in the two weeks that I think is reasonable," then you run the risk of setting that up in their minds as it's not reasonable.

Whereas if you come at it as, "We are the best option out there. Customers know that. The community knows that. We have incredible demand for our services because of X, Y, Z. And you know what? Waiting until the spring is going to be great for you. It's a great time of year to paint. We're going to have time to really figure out the colors and really set that experience up for you." That's a great way of positioning that delay so that you're not down. You're not setting it up in their mind as a negative. It's actually a positive.

I think that's really critical in these discussions. Even if you are offering a discount, there's so many great reasons to work with our company. And here's why.

Michael Murray: Yeah. I've said this a few times, but until as a sales rep you've framed it in your own mind as a positive, you can't frame it in the client's mind as a positive. You can't. When you're not talking from a genuine perspective to a prospective client, it is obvious in the way that your tone is, your body language, all of the things.

Versus somebody who's confident that, yeah, it's October we're booked up for the season. We'd love to get you on our schedule and let's talk about what that looks like come April or May, or whenever you guys start based on where you live. As opposed to: "Well, I'm sure you wanted it done this year, but sorry. Our production team, we just can't handle any more work because we just don't have enough painters. So probably not going to be able to help you on this one." We're already defeated.

I think I just keep going back to that mental side of things, because nothing that happens afterwards is going to work if you don't actually believe that it's in their best interest, perhaps.

Jon Bryant: Now let's maybe talk about how to position this as well from the discounting point of view. I know we've talked about this in a number of other episodes. Discount, no discount. Does it matter? Does it not matter?

I think anytime you're asking someone to wait, you give good reasons, whether like we just talked about—the value of waiting, the value of your company—but there's also an opportunity, at least we've seen, to give some further incentive. Do you use this?

Michael Murray: I think yes. The first, the biggest thing to me is before we get to the situation. So I'm going to back up just half a step. You can see, let's just call it maybe July, August, you see kind of "Hey, I see where this is going." Let's just say on August 1st, you're normally booked out for two months. So let's call that end of September. And let's just pretend end of October is kind of the end of your season. So you have about a month's worth of work left to book.

At this point, if you haven't raised your price from whatever you were selling it at in May and June, that's a problem.

First and foremost, start there. I would say the way that I've always thought about it is if you book a project with us after August 1st, 15th, somewhere in that range, depending on how the year's going, you're paying next year's rate. We all know paint prices go up, labor prices go up, cost of benefits go up, insurance goes up. All those things typically happen sometime in that winter as the calendar changes, things like that. So as we get to next season, my price is going to be something higher, typically, I don't know, 5 to 10% or whatever, just inflation and all the things that are happening.

I just try to get ahead of that before we have booked up this entire season because I have only a handful of slots left in this year. If you want one of those slots, you're going to pay a premium, at least and maybe more, than what it would cost to just do it next year if you called me next spring. So that's first and foremost. I think it sounds like you agree with that.

Jon Bryant: Absolutely. Yeah, that's our theory as well.

Michael Murray: And so then from there, I'm now discounting potentially for next year. So let's just pretend it's August 1st. I'm out doing an estimate and I would say to somebody, "Here's your price. It's 10,000 bucks or whatever, $20,000 to paint the outside of your house or whatever that looks like for you. And we can get it done. I've got two options. I can get that done for you this year in August. I can still get you in. Or if you're willing to wait until the spring, I might be able to take a few bucks off for you and save you a little bit of money here." Is that kind of how you would think about that?

Jon Bryant: Absolutely, yeah, it's exactly the same. That's proven to be very helpful to give customers options. I think we've talked about this in other episodes as well, just allowing the customer to have control and understand what's available to them is really helpful.

If you're more price sensitive and you say, "These guys are really high demand and I get a discount. I get two of my values met because they seem like quality trustworthy contractors and the price is lower. I'll go with them next year." Then you're still getting that customer who may be a good customer, but they have different values.

Anytime you can offer benefits to the customer that also benefit you and have that positive exchange, I see as positive. Now, the counterpoint here is "Don't ever discount. Don't ever do that stuff. You're doing a disservice to everybody." And I don't believe that, but I know people who are listening may have that perspective.

Michael Murray: They're wrong. Okay, what else?

Jon Bryant: They're just simply wrong. Moving on.

Michael Murray: I don't know. Find me a Fortune 500 company that doesn't discount as part of an intentional strategy. It's good enough for all the biggest and best companies in every other industry.

Jon Bryant: What was the—there was a company that did straightforward pricing one time. I think it was maybe JC Penney, I want to say. And they rounded off all of their prices to just be like $5, $10. It wasn't like 99 cents, 98 cents, whatever. And it was like no sales. It was just straight like 20 bucks. Here's the item. We're going to give you the best price. And what do you think happened?

Michael Murray: I'm guessing people didn't buy because it wasn't $19.99.

Jon Bryant: There you go. Yep. People didn't buy because people—as much as we say we understand the game—we still love being able to get a deal.

When you understand that mindset, it's like, okay, well, how do we allow our customers to still get that joy? And we've talked about it before, but it's a "never give without getting" type situation. Pricing is different at different times of year. There's a few things you have to understand, because if you're just saying one price throughout the year, discount off it, yeah, you're going to be giving away way too much. You got to understand your numbers to do that.

Michael Murray: I was going to say, most people don't have any idea how much they're supposed to charge. So if I don't have any idea how I'm supposed to charge, how would I ever know if I should give a discount? Because yeah, you probably shouldn't discount. If you aren't confident that you're charging at a premium rate to afford to run the business that you want to run and handle the risk that comes with running a business like this and all that, then sure, yes, I can see that.

But I think if you've got all those things nailed in, then discounting can and should be a part of your strategy. It's a tool in the tool belt. I wouldn't use the hammer to put the screw in. I wouldn't use a screwdriver to put the hammer in. And I don't think discounting solves for everything. But it is a tool that, when used correctly, can help to run a better, more profitable, faster growing, whatever the goals are, kind of a business.

Jon Bryant: Happier customers as well, right?

Michael Murray: Yeah, for sure. Yeah. That's a good point.

Jon Bryant: So yeah, obviously this episode really is geared towards sales reps. That's probably too much background on pricing, but I think whether you have the option to discount or not, it still holds true that mindset really plays a major factor in how we deliver information and how when it comes down at these times of year where you feel like there's no options, you need to check yourself and realize there's actually lots of options for the customer. There's lots of things that can benefit them.

Michael Murray: Well, yeah. And I just want to put one more little point on the discounting thing. One of the reasons to discount is, let's just say, let's go with this exterior. We're selling exterior in late summer fall and maybe somebody waits until next spring, either because they got a discount or just because we're booked for the year and you're that good of a sales rep and you're just like, "Yeah, don't go with a competitor who can come and paint this in 35 degree weather in November or December, but actually just wait until the spring and we're going to give you a better end result."

What that does now from a company-wide perspective is it gives you confidence going into January, February, March, April, that we can go hire additional staff because we've got work coming up on the schedule. Once we get outside, it also gives us confidence that we can maybe raise our price, which with a higher price, maybe I can pay my sales reps more and all the things.

We can bring this all back to the sales rep. But part of this is really just being in a position of strength when you have work on your calendar that is booked. It's a good thing. I think it comes back to that psychology of: is it good to be booked out or not? And there is a perfect sweet spot. It definitely does affect your ability to sell jobs when you're booked out too far, but in our industry, because most people don't have any tight deadlines, it's not too big of a deal.

I've had these conversations with a buddy of mine who owns a moving company and it is wild because in the moving industry, people have very specific dates. "We have to be out of our house on September 21st and on September 22nd, we're moving into the new house." The title is transferring, the keys are transferring. It's gotta happen. And if you don't have that available date, I'm calling somebody else.

There's no "Yeah, but we're booked that day, but if you can wait until the following week, I could give you a better price." I can't even imagine. I would much rather deal with our problem than with that problem personally.

Jon Bryant: Yeah, we have so much flexibility. We've talked about this before, but the idea of taking advantage of demand while demand's available and trying to convert that demand into something, whether that's winter work or something for next spring—I think as a salesperson in this industry, every opportunity to bid is an opportunity to make a deal because of that flexibility.

If our businesses are running correctly, we are setting ourselves up to give opportunities to our team to actually win that work and give options to our customers and be the best solution. A lot of that happens in summer. The best time I think to try to make a deal with the customer is when you're feeling like you have a lot of power in the negotiation. It's like, "I don't need the work."

Then it can be the most honest, helpful, transparent. I'm not pressured into trying to sell it. And there's a lot of freedom to that once you get to that point of "I don't need this work, but here's what we can do." It's amazing how people are drawn to that feeling of not selling, just being helpful. And it's very different from the other experience you're getting where it's someone coming in being like, "Well, here's your price, you want to do it?" Or not getting the callbacks, chasing people around. At least if we're professional and we go in and do that, provide them the service, give them the options, I think there's still a high likelihood they might want to work with us.

Michael Murray: Yeah, I think the one last little thing, it's probably more for the business owners, but it's try to increase our capacity by really maybe incentivizing overtime, incentivizing our crews to work more in the fall. If you work with subcontractors, perhaps it's finding additional subcontractors in the fall and things like that. But that's not maybe the reality. And as a sales rep, you can only control what you can control. I think it's finding ways to build lifelong relationships where we can, like you just said, come at it from a consultative approach. And even if you can't book this project, you've done such a good job of building that good relationship that they're going to want to talk to you again for whatever that next project might be.

Jon Bryant: You create so much fear, uncertainty and doubt that they can't not wait two years for your services. What kind of discount would you give someone who waited two years?

Michael Murray: Two years is a long time. I don't recommend. And probably none because at that point you're probably already getting a 20% discount or whatever the heck with inflation lately.

Jon Bryant: It's a funny concept though, to go in and be like, "So you want to do this today, but how about we do this in 2030?"

Michael Murray: We had a customer who pushed our project off for more than a year though. We just held onto a deposit for more than a year because she was like, "I'm just not ready yet. I'm not ready." We're like, "Do you want your deposit back? This is silly." She's like, "No, no, you guys will definitely do the work." Our accountants were loving this right now. This isn't good.

Jon Bryant: I hope you bought Bitcoin with it.

Michael Murray: Yeah, I'm not that smart.

Jon Bryant: Fantastic. Well, I think that probably covers it on my end.

Michael Murray: Yeah, we had said, "Hey, let's make this for reps." And I hope we focused there. We wanted to keep it short. I think it is: do what you can do to the best of your ability, controlling what you can control. You can't control all the outcomes, but you can absolutely go sell stuff for next year or whatever that might look like, even when you're booked out for way too long. And just making sure that whatever you are booking is booking at the highest rate possible, that you're not gouging anybody, but you're not undercutting anything. So you've given your production team really good opportunities to win.

Jon Bryant: Love it. Thanks, Michael. Talk to you soon.