Lawn Care Blueprint w/Shawn Casemore: How Real Conversations Build Trust and Win Better Clients

Ezra McCarthy

Welcome back to the Lawn Care Blueprint. Today I am joined by Shawn Casemore, a global sales expert, consultant, and the author of The Unstoppable Sales Machine. Shawn has spent decades helping businesses learn how to sell better, build stronger sales cultures, and navigate today’s changing buyer behaviors.

And his journey actually from selling at age eleven to now advising lots of corporations, big businesses all over, actually a fellow Canuck.

So good to have you, Shawn, here with us today.

Shawn Casemore

Thanks, Ezra, for having me. It strikes me every time I do a podcast. I sometimes forget the basics. So it is no big deal. We will just, it is Casemore.

Ezra McCarthy

Oh, it is Casemore. Okay.

Shawn Casemore

I should always say that. I should always make sure I pronounce your name correctly. And I should also share the pronunciation.

Ezra McCarthy

You are good.

Shawn Casemore

Regardless, it does not matter. We are good. I have been called much worse in my life actually.

Ezra McCarthy

There is nothing worse than a pastor trying to read through those Bible names when you are preaching and you just know I am trying to get it right, but there is no way I am pronouncing this right.

Shawn Casemore

In a lot of the training I do, I will be doing some training tomorrow. I mentioned to you, I will be going down to Toronto. I meet on the average week, let’s say minimum twenty new people, maximum two hundred if I go to a conference and speak. I am not good with names to begin with. So trying to get names down and remember them is always my biggest challenge.

Ezra McCarthy

Yeah. So Shawn, at age eleven, from my research, I found that you were selling door to door. And actually, I had a similar experience. My brother and I were going to the Dominican Republic for a mission trip and we were selling chocolates door to door, at least hundreds.

Tell us about how this shapes your view of sales and kind of affects you today.

Shawn Casemore

Real briefly, the background there is that at about age ten or eleven, when you start to grow, as I was like anybody else would, my parents had bought me some clothes and said, there you go. There are your two or three pairs of jeans. Good luck. And so I did not want to wear the same jeans all the time. So I would start to say, look, I need new shirts, new jeans. I am growing. And they would say, well, we will wait and see. I think it was my dad that encouraged me, go get a job, cut some lawns, and stain some decks. They encouraged me to just go see our neighbors initially.

I did that the first summer and then the second summer I really wanted to make a go of it. So I made up some flyers, which back then was paper and a marker. There were no printers necessarily. I started delivering them door to door, knocking on doors, introducing myself. And that really came to benefit when I was in my early twenties.

The first official job I had in sales was selling cars. And back then it was very different from today. The dealer promoted the dealership so that people would show up and they had to show up if they wanted to see a car, test drive a car. The only way to figure out anything about the car other than what you read in the magazine.

My job was to go approach you in the parking lot when you showed up, strike up a conversation. How are you? What are you looking for today? How can I help? Try and build some trust. And if everything went well in the process, eventually you would buy a car.

So first off, I think it helped me there because I found that I was comfortable just talking to strangers and striking up a conversation. I still am today. That is probably why I speak professionally for a living. I enjoy it.

I enjoy that even though it is likely if you were to measure me psychologically, you would probably find I am more of an introvert than an extrovert. But anyways, that experience, I think, shaped my view of interacting with others. I find in the conversations I have, whether it is with business owners, such as those listening to this podcast or sales professionals.

One of the bigger challenges, and it seems to be bigger and bigger as you get younger and younger in the generations, is the idea of connecting with strangers. Everybody wants to launch an email or launch a social media message from a distance. And that can be effective if done correctly and in the right way and frequency and all that good stuff.

But I am more a fan of talking to people and having just conversations. And if I get the sense the conversation is not going anywhere, I do not drop the conversation. I can keep going.

So I think it really gave me the confidence to do so, to speak with strangers, but more importantly, the evidence to support why having a genuine conversation with people, which is the step to building trust, can actually form a relationship that in turn can lead to a sale when the time is right.

Ezra McCarthy

So I am kind of curious about going back to your story there. Did people around you, because now if you tried to do that to your kid, tell him to go get a job at eleven, they might not be too impressed with you. Was that normal back then? Or did people look at your dad like a hard nose?

Shawn Casemore

Yeah. It was probably more normal. I think from my recollection, it was more normal, at least in the area where I grew up, for younger folks to go out and try and help out neighbors, especially those neighbors who are older.

But here is something interesting. So my son today, I have got two boys. My youngest just turned fourteen. And last summer, I helped him create a flyer.

I encouraged him to go hand it out. He did hand out a few. He has done work with our neighbors just like I did, because I am trying to instill the same combination of confidence and work ethic, which I agree with. I think kids these days do not necessarily get pushed in that direction. But I think long term, again, the skills that that helped me with have served me well and I assume can only do the same for him.

Ezra McCarthy

I am a huge fan myself. I did a lot of that. I was picking strawberries and I was like eight or nine, literally. And I think I spent more time eating them than picking them. But I did.

But people now, they have a hard time looking at you, looking you in the eye, shaking your hand. And it really is a forgotten skill just to try to connect with people.

One story I remember, I was selling chocolates one day and I was knocking on the door and the lady had this beautiful garden. And I knocked. They were two dollar chocolates and I forgot what we got for fundraising, like a dollar or something apiece. They were overpriced, but people knew that.

So we are knocking on the door. I asked her, and gave her a little spiel. This is why we are doing it. And I always learned you got to sell with a story. So I tell her this is why, because people would buy it. I was, well, I was a cute little kid then.

I knocked and said this is giving my spiel. And she is like, not today. And then I said, when she was leaving, you have got a beautiful flower bed. It looks so nice. And she turned around and she said, you know, I am going to buy one.

Most people, when you do not buy, they basically have a bad attitude, which, and I learned such a lesson there. And you would be surprised at what you learn just by putting yourself out there.

Shawn Casemore

You bring up a point. I think the other advantage to having had that experience at a young age is that not only do you have more confidence, but you are able to connect with different generations.

What I mean by that is that my fourteen year old son has lots of friends his age and he can use technology and communicate effectively just like any kid his age would. But he also has no problem holding a conversation with somebody in their sixties, seventies, or eighties because he understands the differences in generations.

So I think in sales, that is something that everybody must work on because you never know the age or demographic of your customer. And different demographics have different communication preferences. So our job is to be the effective user of different methods or means of communication so we can connect with different people of different ages. So I think it helps in that regard as well.

Ezra McCarthy

100 percent. Now your book, The Unstoppable Sales Machine, talks a lot about how selling has changed in today’s economy. Really, I think in general, that word sales, especially I hate to say it, you are a car salesman. Especially a car salesman. If you do one of those fill in the blank things, where you say salesman, the next word people are probably going to say is sleazy. Not that you are, Shawn.

But selling has such a bad reputation. In all reality, everything we are doing is selling. When we are trying to date someone, we are selling them on dating us. When we get married, et cetera. Life is about sales.

So what shifts do you see in the market right now in regards to sales. And what does your book cover?

Shawn Casemore

Yeah. Well first, something you mentioned, I will expand on. I think when it comes to selling, everybody has had a bad experience with a salesperson. And we tend to go back and attribute selling to that bad experience. No different than if you had a doctor who gave you bad advice or the wrong medication.

Selling is one of the most noble professions out there. It is one of the longest standing professions. Everything we do is based on sales, whether you are selling ideas internally, selling landscape services, or anything else.

Relative to what has changed, a big shift is the integration of technology. AI is the buzzword everywhere. When it comes to sales, even if you are selling something old school, like landscape services, technology can help you create flyers, structure messaging, and save time.

But there is an awful reliance on technology. I see ads saying our AI replaces your sales rep. That is dangerous. Selling is hard. Getting attention is hard. Keeping attention is harder.

Technology should support selling, not replace the human connection. Overreliance creates bad experiences.

I received an email this morning from someone trying to sell me a list. The follow up was blunt and ineffective. It pushed me away. That is what happens when you rely on automation without thinking about how messages land.

Technology is powerful, but be careful how you use it. You cannot turn over selling to technology.

Ezra McCarthy

I am a huge proponent of technology, but I could not agree more. Especially people, when I get AI on the phone, it is not there yet. I use ChatGPT every day, but I do not want to talk to it on the phone. And those website chats are annoying. I think it will get there, but right now there is a lot of hype. Those emails are the worst.

Shawn Casemore

You see automation everywhere. LinkedIn is full of it. You accept a connection and instantly get a sales message.

There are efficiencies to technology, absolutely. But do not lose the personal touch. Do not lose who you are. That is what people want to buy from. As soon as you turn that over to technology, you blend into the crowd and become the salesperson nobody wants to talk to.

Ezra McCarthy

So Shawn, for local service based businesses, most people listening are lawn and landscape businesses looking to grow. How can we integrate that human touch while using time effectively?

Shawn Casemore

Here is a simple example. If you are doing a project in a neighborhood and you want to touch base with people nearby, and you get their email address, instead of blasting a flyer, you can send a short personalized video using tools like Vidyard.

You can say you wrapped up a project, ask for feedback, and invite questions. They get to meet you, not just read papers.

Use technology to open conversations and personalize the experience, not depersonalize it. People buy from you. If customers only buy on price, that is because that is what you are leading with.

Ezra McCarthy

A lot of people struggle with follow up. What is a good follow up regiment for a medium sized lawn and landscape business. How many touch points should you have?

Shawn Casemore

You need a process. If you only follow up when you have time, it will not happen.

Follow up directly a couple of times. After that, continue following up by adding value. Share insights, information, or resources that are useful.

If you add value, you can stay in touch without being annoying. People have not forgotten you. They just need reminders.

Use different channels to find their preferred way to communicate. Once you know it, stick with it.

Ezra McCarthy

You talk a lot about sales culture. How do you bring that into a business so every team member has a sales mindset?

Shawn Casemore

It starts with leadership. Culture follows the focus of the leader.

In small companies, take employees with you to meetings so they understand the customer connection. In larger companies, expose everyone to customers.

When people understand how their job impacts customer satisfaction, you build a sales culture.

Ezra McCarthy

I really like what you said there. Sales is about satisfying the customer, not taking money from their wallet.

Shawn Casemore

Exactly. Lead by helping. That builds credibility.

I once offered free interviews with a potential client’s team before deciding if I could help. It built trust.

Helping others is the best way to sell, as long as you manage your time.

Ezra McCarthy

How important is having an ideal customer profile?

Shawn Casemore

It is important to know who you want to work with. Focus on clients who value your services and can pay their bills.

You do not sell to everyone. Focus your prospecting on ideal clients. Marketing will bring others to you.

Ezra McCarthy

Can you really separate sales and marketing?

Shawn Casemore

It depends on what you sell. Some sales require face to face relationships more than marketing.

But the lines have blurred. Salespeople must understand marketing tools like LinkedIn. If your online presence is outdated, it hurts credibility.

Ezra McCarthy

What do you say to someone who says I do not like selling, I am just good at service?

Shawn Casemore

Everyone is a trusted advisor. Service supports sales through repeat business, referrals, and reviews.

You may not see yourself in sales, but you are contributing to it. That mindset builds alignment.

Ezra McCarthy

If a business is stagnant in sales, what shifts would you encourage them to make?

Shawn Casemore

First, understand why sales slowed. Then decide whether to adjust pricing, niche, or market.

Second, never stop connecting with people. Set aside fifteen minutes a day to follow up.

Third, get out and see people. Knock on doors. Have conversations. That is where sales come from.

Ezra McCarthy

If people want to learn more about your book or your work, where can they find you?

Shawn Casemore

My website is shawncasemore.com. My books are available on Amazon. My new book is called The Unstoppable Sales Prospecting System.

Ezra McCarthy

Thanks Shawn. This was great. For those listening, be sure to subscribe, leave a rating and review, and we will catch you on the next one.