Price. Sell. Paint. podcast cover featuring hosts Jon Bryant and Michael Murray discussing estimating and sales strategies for painting contractors

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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Episode 64

The Real Reason You’re Not Winning Painting Jobs

April 29, 2026
45 min
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Most painting contractors lose jobs before the estimate even begins. In this episode of Price. Sell. Paint., Jon and Michael break down how to start estimate appointments the right way, from the first call to showing up at the door.

If you’re struggling to close painting estimates, this episode will show you how to build trust early, set the right expectations, and win more of the jobs you’re already bidding.

Episode Transcript

Episode transcripts are machine generated and may contain errors.

Michael Murray: Hey everyone, welcome back to the Price Sell Paint Podcast. I'm Michael Murray, owner of Textbook Painting, joined as always by John Bryant, owner of Paint Scout. John, excited for today's topic. How are you?

Jon Bryant: Doing pretty good. It's mid-end of March, and living in Canada, we just had a foot of snow. Someone in Oregon was sending me pictures of flowers they'd picked from their own garden — a few emojis came to mind. I'm great, but I could use some warmer weather.

Michael Murray: Yeah, here in Cleveland we've experienced every season this week — 75 and sunny, then snow, and today it's chilly, hence the vest. We get a lot of fake spring. Anyway, it's the busy selling season. We've just hired three new sales reps and are deep in training. I've spent the last few weeks doing detailed sessions, and one thing I always emphasize is how important it is to start estimate appointments well. If we're having trouble closing, we probably had trouble opening.

Jon Bryant: That's a deep thought. I'm trying to get my head around it.

Michael Murray: If you're not winning enough jobs, you can talk about handling objections and asking for the sale the right way — but the true problem probably happened before you got to the house or when you first arrived. It's hard to make up at the end for mistakes made at the beginning.

Jon Bryant: First impressions are a big deal. There's a lot of mental work involved — setting yourself up with the right mindset. But it all flows into how we start. Customers are probably a little anxious about having someone in their home. They start from a place of distrust. Showing up well and doing these things right is really important. I take a lot of this for granted now, so it'll be fun to share today. Where do you want to start?

Michael Murray: It all starts before you arrive. A very practical thing we teach is a phone call beforehand — reps introduce themselves. We have automated emails and texts, but automation often lacks personality and human connection. If our sales reps make a quick call before they go, chances of a successful outcome are much better.

Jon Bryant: Yeah, absolutely. The office books the call, then you're confirming day-of. Is that how you do it, or day before?

Michael Murray: My philosophy is the sooner the better. Instead of thinking about how soon before the appointment, think about how long after the original call or form fill. If someone calls Monday, I want to call them Monday or Tuesday — capture that excitement. Most people aren't calling just one company, so I want to lock them in and get them excited about our appointment before someone else gets there first.

Jon Bryant: Are you using something like Calendly or GoBookMe to book appointments?

Michael Murray: We actually built our own estimate scheduling software last year — a customized version of something like Calendly. We'd used both in the past. I'm a big fan of giving homeowners the ability to schedule estimates themselves on our website.

Jon Bryant: When you talk about that call — is it from the office or the sales rep?

Michael Murray: The sales rep. Once we've assigned the appointment to a rep, that's the trigger — hey, you have an estimate with Mrs. Smith in two days, please call to introduce yourself. That's the when. From there, we confirm all the details. Every sales rep knows the worst outcome is showing up and nobody's home. We never do an estimate without someone present — you have to be there so we can talk. We confirm you'll be home, that you have 45 minutes to an hour, and that we'll give you a price on the spot. If the prospect is willing to chat, I'll ask one or two questions: any scheduling concerns, timeline, or tell me more about the project. Sometimes the call is 10–15 minutes, but most of the time it's done in four or five.

Jon Bryant: It's also a great time to reiterate some of your unique selling points. In our world, color is a big one — how do you feel about color, should I bring anything? We've even asked what type of experience they're hoping to have. People need to hear things a few times before it sticks. They're getting multiple estimates and will mix things up. So reiterating early is valuable. Anything else important on that call?

Michael Murray: One other thing — confirm the right people will be at the appointment. We don't take a hard stance like some companies do, but we will ask. One way we handle it ties back to color: "Are you planning on changing colors? Is anyone else going to be involved in deciding? Is that person available for the appointment, or should we look at a better day?" That kind of flow can get you to a better spot and avoid some landmines.

Jon Bryant: Some verbal jujitsu — they don't even see it coming. I like that a lot.

Michael Murray: It really is in their best interest. If I can talk to both of you at once, the other spouse doesn't have to try to remember and relay everything from an hour-long appointment. We've all been there.

Jon Bryant: It's a nuanced question though — you can really offend someone if you do it wrong. "Is your husband going to be there?" — don't do that. I've seen that play out badly in person. The rep showed up and the husband wasn't there, and he basically said he shouldn't be. You think you're getting that job?

Michael Murray: Oh my gosh. All right — so you've made the call, you show up to the house. Quick recap on appearance: we sell a premium product, and you need to show up in a way that reflects that. Collared shirt, khakis, not covered in paint. But don't show up in Gucci driving a Lambo either — they'll think you're too expensive. We've had sales reps show up with mustard stains on their shirts. I kept deodorant, mouthwash, and an extra shirt in my car — if a dog jumps on you before your second and third appointments, you need to be ready. A branded polo shirt with your logo for 30–40 bucks makes a big difference. If we can improve win rate by even half a percentage point just by investing in branded gear, it's worth it.

Jon Bryant: A wrapped vehicle is more of an investment, but it matters too. Alright — so where do we park?

Michael Murray: Never in the driveway. Park on the street. A couple reasons: some people's first thought when you pull in is whether you'll leave an oil stain. That little moment of concern is not how we want to start. I want their first impression to be, "How courteous." Also practically — I hate getting interrupted mid-conversation because I need to move my car.

Jon Bryant: Parking on the street is hard to get wrong. We'll even say when we arrive, "I parked out front on the street — is that okay?" It ties into showing you care about them first. Parking in the driveway subconsciously signals you're putting yourself first. People already assume contractors are doing what's best for themselves — these small gestures show that's not the case.

Michael Murray: The more you look and sound like the negative perception of a contractor, the more it works against you. Customers' perception of contractors is not good — right there with lawyers and politicians. You've got to work against that. Alright — you go up to the house. Don't ring the doorbell.

Jon Bryant: Obviously. Ring the doorbell and you're done.

Michael Murray: You're an invited guest with a scheduled appointment. You've called, you've texted. So many homes have babies sleeping. A doorbell is a stress-inducing sound. You knock. And after you knock, back away from the door — a lot. If there's a front porch, back to the steps. Even step down. It's about body language. Standing face to face, shoulders squared, close to someone is an intimidating posture — it triggers a fight-or-flight response. So I back away, turn slightly sideways, so when they open the door, that first impression is calm and non-threatening.

Jon Bryant: Alright, so you knock, they answer — sometimes I shake hands, sometimes I just say hey. And then this is where setting the table comes in. I learned this from Nolan Consulting, it's part of the Sandler system. Without a system, you show up and ask "what are we doing?" — and now you're in their system. They're not trained in sales. So here's what I say: Thanks for having me. I parked just down the street — is that okay? Great. This is going to take about 45 minutes. Does that still work for your schedule? I ask a lot of questions because I want to learn what's important to you — is that okay? Before we start, what are two or three things you're hoping to learn today? Then I explain the process: I'd love for you to show me around, I'll spend some time on my own, then come back with pricing and cover what's important to you. And finally: if at any point this isn't a good fit — whether something I say doesn't sit right or the price doesn't work — just let me know. No is totally fine. Does that work? Great, let's get started.

Michael Murray: Yeah, I agree with all of that. We put a slightly different spin on it. There are two pieces — the intro and the connect step. The intro can be brief or longer depending on the homeowner's personality. We'll have some small talk first to warm up the conversation. Then we want to sit down if possible. Even on exteriors, when the homeowner just walks out and wants to start walking around, we'll say: "I'd love to walk around, but before we do, I have some questions and want to tell you a little about the company. Is there anywhere we can sit for five or ten minutes?" Sometimes they say no — baby sleeping, whatever — and we'll stand on the front porch. But sitting down is ideal. We want to slow things down and not look like every other home improvement sales rep.

Most homeowners expect to just show you what needs painting and get a price. We want to slow that down. Be consultative — a price on what, for what? Do they want it to last a long time? Not every customer is looking for the same thing. We'll ask how long they've lived there and how long they plan on staying — that tells us a lot. It helps us understand what paints and warranties to recommend, what experiences they've had with contractors before. We'll ask about schedule, colors, and whether our interior designer for color consultation is something valuable to them.

We also do a brief company presentation using Paint Scout — who we are, history, BBB ratings, Google reviews, community involvement. And we think of the whole estimate as crossing three bridges. The first bridge: are we a company you could see yourself working with? Once we've covered the intro and company overview, we ask that directly. Most say yes. The second bridge is scope — is the prep work, paint, and process aligned with your expectations? The third is price. You can't cross that price bridge without crossing the first two. If you skip them, you get price objections — and no wonder.

Jon Bryant: Love that framing. To qualify what I said earlier — my version can be a bit aggressive jumping straight in. What you described about slowing down and connecting is right. The four things I mentioned — confirm the time, make sure questions are okay, confirm no is okay, ask what they're hoping to learn — those work best woven naturally into the conversation alongside genuine rapport building. The heart of it is making the person feel comfortable and understanding there's a process.

Michael Murray: A lot of it comes down to emotional intelligence. With a high-D personality type, they're not going to give you time for all of this up front — so you read them, get to it, and circle back later. This whole intro and connect piece takes somewhere between five and fifteen minutes before you get into what you're actually painting.

Jon Bryant: Which we're covering in the next episode. Consider this part one of three — we'll be going through how to get into the nitty gritty and price on the spot, which is vital for increasing your win rate. Stay tuned for parts two and three.

Michael Murray: Sales is fun because you get to constantly refine and learn. There are so many little things — word choices, body language, what you're wearing — that go into whether homeowners trust you with their project. Have a system, and think of it as constantly refining. That's how you reach your potential.

Jon Bryant: Absolutely. Great place to end part one of the in-home sales process series. Leave your comments — business card or no business card, any other questions — and we'll answer them. Give us a like and subscribe if this is valuable. We'll see you on the next episode of Price Sell Paint. Thanks, Michael. Catch you later.

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