How to Hire a Contractor - What They’re Really Thinking

[: 00:00

Bill Reid: All right, everybody. Bill Reid here with The Awakened Homeowner. I'm continuing on my mission this year to bring guests onto the show, and I've been fortunate to reconnect with one of my colleagues from my general contracting past. I'm going to introduce him in a moment, but we are about to get into some really valuable details that are going to help you become a better homeowner when it comes to dealing with contractors.

But first, let me ask you something. Have you ever gotten three bids on a project, picked the lowest one, and then watched the whole thing unravel? Maybe that's happened to you, but I'd bet it's happened to at least one of your friends.

Here's the reality — that's not a coincidence. And here's something nobody tells you when you start getting bids on a project: every contractor who walks through your door, before they've said a single word to you, is already reading you. They're picking up signals from how you talk, what you ask, how prepared you are, and how you treat the process. And based on what they observe, they're making decisions.

They're deciding how seriously to take your project, whether they even want the job, and how much effort to put into that proposal. That may sound backwards, but that's really what's going through our minds as contractors — because we have to invest a tremendous amount of time into a project before we see a single dime.

Most homeowners approach hiring a contractor completely backwards: gathering as many bids as possible, guarding their budget like it's classified information, and shopping ideas from every firm they talk to. They think that's being smart. But from where a contractor sits, those behaviors are big red flags. They signal a difficult client, a low-value project — and honestly, they make great contractors walk away.

Today we're flipping the script and going inside the contractor's mind. We're going to talk about the bidding trap, what your behavior is signaling without you even realizing it, and what you can do — starting with your very first conversation — to attract great contractors and get their absolute best work. I know this sounds a little unconventional, but this is what's happening behind the scenes. And I promised you when I wrote this book, and when I began this podcast, that I'm going to pull back the curtain on all of it so you truly understand what's happening when you're standing in front of a contractor.

My guest today is Enrique Guzman, principal designer and owner of Contexto Landscape Design Build, based right here on the California Central Coast. Enrique is a Cal Poly San Luis Obispo graduate who has built his firm around a design-build model — meaning he doesn't just hand you a set of drawings and wish you luck. He leads projects from the very first concept conversations all the way through construction completion. His specialty is modern, sustainable outdoor spaces that feel like they genuinely belong to the land and the people who live there — rooted in the local environment, the architecture, and the life happening inside that home.

What makes Enrique the perfect guest for this conversation is that he brings both sides of the table. Although he offers design services as a major part of his business, and even when he does design work exclusively, he still keeps his eye on the ball throughout the project — he also offers construction services. That brings us back to the design-build business model we've discussed recently: the different paths available to you as a homeowner — whether you go the conventional route and hire separate designers and contractors, or engage one entity to handle everything. Enrique does both, so we're going to get some great perspective.

He's had thousands of contractor-client conversations, and today he's going to tell you the truth about what contractors are really thinking. I'll probably chime in too. Welcome to The Awakened Homeowner, Enrique. Take it away.

═══════════════════════════════════════════════

[: 04:09

Enrique Guzman: Thank you, Bill, for having me. It's been a pleasure working with you over the last few years, and working with you was truly a privilege. I always looked to you as a teacher, and even now, years later, I look back on all those projects we worked on together and appreciate the opportunity to lean on your expertise. I want to thank you for that. I'm very excited about being transparent and speaking from a place of humility, because this profession is a beautiful and wonderful one. To be selected to design a project is such an honor — to go on that journey with the homeowner, to design it and build it. I'm very excited to discuss the topics we have in mind today.

Bill Reid: That's great. We worked together on projects in Northern California — the Silicon Valley area — and I remember you starting your own business and asking a lot of questions about the design and construction process. Now, many years later, you have an active practice in San Luis Obispo. You've gone down all kinds of paths with different clients, and I think that's a great segue into our first question.

═══════════════════════════════════════════════

[: 05:48

Bill Reid: Remember, everybody, much of what we're going to discuss revolves around how you as a homeowner approach a contractor — whether you're hiring a designer only, a contractor only, or one company to do both. Our questions will touch on both design and construction.

Homeowners often start with the misconception that they need to gather as many bids as possible to get the best deal. What I want everyone to understand is: what is the real cost of excessive bidding to a project's quality? What does the number of bids have to do with quality? And how does a quality contractor react when they find out they're one of five or six bidders? Let's get inside both of our heads on this one.

Enrique Guzman: Absolutely — excellent topic. I think a lot of homeowners operate under the assumption that getting as many bids as possible is the smart move. They want to be educated, they want competitive pricing, and the logic is that more bids give you a better understanding of the actual cost of a project.

It's challenging from a contractor's perspective. It doesn't happen all the time, but there are occasions where a client will mention upfront that you're the third person they've met with and there are four or five more competitors coming. That immediately raises a flag for me — not necessarily that this client will be difficult to work with, but from the perspective of time investment. A typical project, depending on the scope, can take me two to three hours to bid. I need to review the project, do some research, and budget about an hour to meet with the client. So there's a real time commitment involved.

If I know a client is getting two or three bids, I know my chances of closing the project are reasonable, and I'm happy to invest that time. But if there are five or six competitors, my chances of closing the project are significantly reduced — and that affects how I prioritize that opportunity.

Bill Reid: That's right. For landscaping, you might spend two to three hours bidding. For a complex custom home, I could easily spend a hundred hours or more. Contractors don't get paid to bid projects, so my first objective is to understand who this client is — and frankly, what type of client they are.

If someone is genuinely getting six bids, that immediately tells me price is probably their top priority. And it's human nature — when six bids come in and one is significantly lower, a kind of fog starts to settle over that homeowner. Suddenly they're thinking, "Wow, this is a great price. Maybe I can overlook the fact that he's not licensed. Maybe I've heard a few things, but I can manage him." I've seen prospective clients actually talk themselves into selecting the least expensive contractor while knowing there might be an issue from the start. And here's the thing — I don't think people even realize they're doing it.

As a homeowner, you really have to think about what's most important to you. And what excessive bidding does, when the goal is finding the cheapest price, is diminish the quality of the project — because the cheapest contractor is probably not the highest quality.

Enrique Guzman: Absolutely. Before I started my own practice, I worked at other design-build firms. I remember conversations with my former bosses about clients who took them down that road — bidding against four or five contractors, ultimately choosing the lowest bidder. And colleagues of mine would share that those same clients would eventually come back and say, "I wish I had hired your company. The contractor I chose didn't install the project correctly, and now it's costing me even more to fix it." These things genuinely happen when you don't properly vet a contractor and when price is the only filter.

═══════════════════════════════════════════════

[: 11:30

Bill Reid: As a homeowner, you really need to think about what's important to you before you start calling ten different people to come bid your project. There's a certain amount of reciprocity here. Yes, a contractor is trying to earn your business — but you're also trying to find the right person to meet your expectations. You have high hopes. You have inspiration images. You've shared your vision with multiple people. And one of the things you have to decide is: how much do you value having those expectations met?

The question I'd pose to both of us is: what does it mean for a homeowner to define their own type? And why is it a contractor's mission to understand a client's type — in order to avoid the frustration of delivering Mercedes-Benz quality expectations on a Toyota Corolla budget?

Enrique Guzman: A lot of that comes down to pre-qualifying questions and genuinely understanding a client's needs from the very beginning. We work with clients of all types and have been fortunate to work on projects at every scale — from someone who wants to add a couple of potted plants in their front yard, to major remodels and new construction.

Having a solid understanding of the process — and even just a basic familiarity with the constraints of construction — is important. There are so many variables. If we're talking about a simple planting design, most landscape companies could handle that installation. But if we're discussing a modern steel pergola, a built-in fireplace with a gas burner, or a barbecue setup — things that are far more complex — you're working with more constraints and more time requirements. In those cases, you really should be engaging a licensed, insured, bonded contractor with a great reputation who is going to focus on those details to deliver a higher-quality project.

Bill Reid: Absolutely. What you just described is what contractors are doing in those first few minutes with a homeowner — we're trying to figure out what you value. Are you just focused on price? Is that why you're getting six bids? We're asking questions about your project, about the details, to gauge how invested you actually are in the outcome.

Suppose you already have a design and you're handing a contractor a set of plans. If you just hand them the documents and say "give me a price" without any desire to have a conversation, that's a big red flag. It signals that you're shopping, not engaging — and frankly, this is why a lot of contractors never call you back.

I know homeowners get frustrated by that, but if what you're doing is flooding contractors with bid requests, that's the signal you're sending. On the other hand, if you take the time to convey what you want, what you love, what you don't like — if you've made extra effort to express your hopes, your wishes, and your expectations — then a contractor sees that you care about the outcome. And they recognize that a client like you will likely place value on an established, licensed firm with a portfolio that backs up what they say.

The bottom line: if you truly are only looking for the cheapest price, don't call the most reputable companies in your area. You're wasting their time, and they will be higher.

Enrique Guzman: One of the most challenging things when I meet a new client is determining whether their vision aligns with the work we do. Before I even go out to meet a client, I'll get on what I call a discovery call — pretty standard — and ask some basic questions. One of the most telling is: have you ever worked with a designer or contractor before?

If the answer is yes, I know they understand the process. They value what designers do and they're familiar with the journey. In my experience, those projects tend to go very smoothly. If the answer is no, then I know I need to educate — humbly and transparently, not from an egocentric place. I ask questions: What is the scope? What does the project entail? What's your timeline? Are you looking to start right away, or is this something for later in the year? Those simple questions give me a much clearer picture of the constraints and the opportunity.

═══════════════════════════════════════════════

[: 18:38

Bill Reid: One thing homeowners often don't realize is how much work happens behind the scenes on a professional project. You see the pictures in the magazines, but ten, twenty, thirty people may have been involved in pulling that off. As a homeowner, you need to make sure you're talking to the right people who have the resources to achieve your expectations.

That brings me to what I call "decoding the client's hidden signals." This is where we expose some client behaviors that can actually undermine a project — and a homeowner's ability to find a qualified contractor — without them even realizing it.

Here's the scenario: a highly organized homeowner walks in with a fifty-page document — a fully detailed scope of work. Now, on the surface that looks like preparation. But as a designer — whether you're an architect, a landscape architect, or a designer — what is your internal reaction when you see that level of detail? Is it a double-edged sword? And how could this homeowner actually be handcuffing their designer with an overly rigid plan?

Enrique Guzman: Absolutely. I've encountered clients of all types. Some are very well prepared — they'll send me a clean, well-organized document, and as a designer, I genuinely appreciate the time and thought they put into it. To me, it signals they're ready. They really want to move forward. It's just a matter of finding the right designer or contractor who aligns with their vision and values.

But on the polar opposite end, there's the client who is overly prepared — the one with a forty-three-page document, like one we recently received. When I work with a client like that, I find myself wondering whether I'm being asked to design or simply to draft. There's an important distinction. Being hired as a designer means the client is placing their trust in you to take their ideas and shape them into a vision. That creative freedom is what excites us — we want to design, we want to be creative, we want to bring that beautiful vision to life.

When a client comes in with too many rigid constraints, it essentially handcuffs the designer. I've learned to ask the question directly: "Do you want me to design the project exactly as you've outlined in this document?" Some clients say yes — and at least then you know. But many of them don't even realize they've created such a rigid framework. You'll only find out when you present the design and they say, "That's not what I told you to do."

e that to a contractor with a: 1990

Second, and this is important: if you're going to handcuff your designer and effectively ask them to regurgitate what you've already created, you need to be prepared to take ownership of that design. As a homeowner, you haven't done the hard part. You haven't translated that long list of bullet points into the creative process — the actual design planning, the form and function. It's easy to list "I want this plant, this plant, and this plant." It's something else entirely to understand how to artfully combine all those elements. So if a designer is just executing your prescribed list, and something doesn't work, that's on you.

I still want to see a lot of detail from clients — but like you said, it's critical to establish upfront: are you giving me this as creative inspiration and freedom, or are you asking me to follow it verbatim? Because depending on the answer, a high-value designer may not be interested in the project at all.

Enrique Guzman: Exactly. A high-value contractor or architect — someone like a Bill Reid of Remodel West, with a strong company and a backlog of ideal clients — is going to think carefully before taking on a project with a very regimented brief. And if you couple that with getting multiple bids, you've created a scenario where most quality professionals are going to step back.

I want to be clear: it's not ego. At Contexto, we work on projects of all scales — small to large. We're a yes company. But when I encounter a client with that kind of document, I'm genuinely less excited, because I want the creative freedom to design portfolio-caliber work that I can showcase. On the other hand, when a client says, "Enrique, I've heard great things about your work, I've seen your website and your social media, and I want you to take our ideas and create a vision" — that's my ideal client. I will invest everything I have into that project.

═══════════════════════════════════════════════

[: 29:05

Bill Reid: People need to understand that in a designer's or contractor's career, you only have so many projects you're going to build. As we mature and gain more experience, we're genuinely interested in the right projects and the right clients — not just volume. That leads me to something I want to ask you directly: have you ever felt like clients were just trying to extract ideas from you without any real intention of hiring you?

Enrique Guzman: Absolutely — and it happens more than you might think, especially in initial client meetings. I've had this conversation with interior designers, architects, landscape architects, and landscape designers alike. It's a common topic in our field, because our ideas are essentially everything we have. Our entire business is built on our creativity. Giving that away is a real risk.

One of the things I've learned over the years is not to give all your ideas away in that first meeting. Share enough to get them excited about the potential of working with you — but no more. The pitfall is oversharing. You start to recognize the warning signs: certain questions like, "What do you think about this area?" or "What would you do on this side?" If you answer everything fully, you could be providing a creative roadmap that another contractor ends up building — without you ever getting paid for it.

Bill Reid: And this is almost the perfect storm of a problematic client: someone getting six bids, asking detailed design questions of every designer they meet, and then hiring the cheapest contractor to execute the best ideas. That combination is exactly what it sounds like — and I know that's hard to hear, but it's what's happening.

Contractors and designers think of their ideas as intellectual property. It's not ego — it's experience. If you've been in the business long enough, you can spot that client a mile away. So don't take it personally if a contractor or designer seems to be holding back a little in that first meeting. They're gauging how serious you are. As you build a relationship and mutual trust develops, the ideas will naturally surface. That process is actually how you discover whether you're a good fit for each other.

Whatever you do, don't be the client who collects six bids, gathers everyone's best ideas, and then matches them with the cheapest contractor. That's where things completely fall apart. Build a healthy relationship. Respect their time. Respect their knowledge. Some of my client relationships are nearly thirty years old — because that's what this business, done right, is really about.

═══════════════════════════════════════════════

[: 34:48

Bill Reid: All right — budget, budget, budget. We could do an entire separate episode on this, but let's hit the highlights. When you first meet a client, what's looming in the back of your mind? I think I know. It's: can they afford this?

Enrique Guzman: It's a challenging question, and I've been thinking about it a lot recently. A lot of clients come into a project guarding their budget — not wanting to disclose it — often because they're afraid of being taken advantage of. There are plenty of stories online about homeowners getting burned by unlicensed contractors, and I think that wariness carries over even to legitimate professionals.

But here's the thing: as a designer-contractor, when we're vetting a project to determine whether the scope and the budget are aligned, we need some information to work with. Going back to your earlier phrase — do they want a Mercedes-Benz on a Toyota budget? I think homeowners should have that conversation among themselves, even before they pick up the phone to call anyone. How much do you want to allocate for this project? What's a realistic number?

Now, I understand that a lot of homeowners genuinely don't know what things cost — what artificial turf runs per square foot, what a built-in fireplace costs to install. That's understandable. But there is a tremendous amount of data available today, and with AI tools, you can get a reasonably solid ballpark figure for most projects. The important thing is to at least arrive at a range.

I always ask a client: do you have a range in mind? Is it $20,000 to $30,000? $40,000 to $50,000? Even a rough range gives me enough to gauge whether we're in the same ballpark. And frankly, it protects both of us from wasting months of time and significant investment, only to present a proposal that's three times what they had in mind.

Bill Reid: Let me ask you this — for a complex, one-acre project with fountains, custom features, 3D renderings, the works — how long does it take from your first meeting with a client to a completed design that everyone is excited to build?

Enrique Guzman: From the time of that initial meeting, if the client already has a site plan, we can move quickly. If not, my team needs to go out and measure the property and document site conditions first. From there, the fun begins — conceptual design takes about a week to a week and a half. 3D modeling takes a bit longer if you want it to look really polished. All in, from first meeting to presenting the initial concept, you're typically looking at two to four weeks, depending on the complexity of the project. We take our time with code compliance, site constraints, and design details — the due diligence takes real effort.

Bill Reid: And in your case, you also do the construction. For comparison, a landscape design might take three to four weeks; a full custom home design can take six months to a year before it's ready to build. The point is — it's a significant investment of time on everyone's part. Have you ever completed a full design, or taken on someone else's design, presented a proposal — and completely blown the client away with the price?

Enrique Guzman: It's happened. And what I've learned is to ask the budget question early and not be afraid of it. A lot of contractors — and even designers and business owners just starting out — aren't trained to talk about money. But money is important. If you're not having that conversation during the initial consultation — even just priming the client with something like, "Based on past projects of this scale, you're likely looking at a range of X" — you're setting yourself up for a very hard conversation when you present that final proposal. Priming the budget expectation early is critical.

Bill Reid: Listen carefully to this, everybody, because there's a distinction worth making: budget versus investment. It's not just "how much does this cost?" It's "how much do I want to invest in my home?" That's a private conversation you should be having with yourself — and your partner — before you ever pick up the phone.

The investment could range from a few thousand dollars on the low end to $100,000 or more for a full estate landscape build. You're going to spend a lot of time, and so will the entire team. The chronic problem in this industry is that a client goes through four to six months of design — landscape or home — gets genuinely excited, and then receives a proposal that's three times their original number. Empower your design team with at least a range. It lets them make informed decisions throughout the process — steering away from elements that will blow the budget and toward alternatives that meet both your vision and your financial reality.

Designers aren't necessarily accountable for budget management, but they can absolutely guide the process if you give them the information to work with. If you don't, you're going to waste time and money.

Enrique Guzman: I want to share a real example. We recently had a client who had just relocated from the Los Angeles area. Right from the start, they said: "Enrique, our budget is about $80,000. We want a built-in fire pit, a seat wall, vegetable boxes, new landscaping, irrigation, new lighting, a complete front entry remodel, new walls, and a driveway."

My honest response was: you're roughly in the ballpark. We can probably work with this, and there are some knobs we can turn. Are you open to concrete in place of pavers in certain areas, if it achieves the same function and saves you some money? That's the kind of collaborative conversation a design-build firm can have because we have real cost data from past projects. We can design with a budget in mind and flag issues before the final proposal. I've called clients in advance to say: "I've been running some numbers and it looks like we're trending a little over your target — not because we're trying to exceed it, but because of the cost of materials and the complexity of certain elements. Let's talk about options."

Some clients hold firm at $80,000 — fine, we get creative. Others say, "We actually have a little wiggle room if we love the design." Either way, that conversation is only possible if the client has been honest with us upfront.

Bill Reid: And hear this, everybody: use that as a way to qualify your designer or contractor. Ask them directly — "How do you help a client stay on budget?" Listen for the answer. A truly professional designer or contractor is genuinely engaged by that question. If they're not — if they seem dismissive or uninterested — that's your cue to run. And if you sense enthusiasm, curiosity, real problem-solving energy — someone who says, "Let's do this, skip that, and really invest over here" — you want that person on your team. They're going to be looking out for you.

═══════════════════════════════════════════════

[: 48:57

Bill Reid: We're getting close to wrapping up. I know homeowners struggle with this question: how do I actually know if a designer or a contractor has real integrity and genuine skill? Can you give us a few subtle but observable clues — what I call hot spots — that a homeowner should be looking for?

Enrique Guzman: Great question. With today's technology, there are excellent resources available, and I think the first place most people look — rightfully — is reviews. Yelp, Google, wherever. Does this contractor have excellent reviews? To me, reviews are a reflection of quality, integrity, and craftsmanship as seen by the community. That should absolutely be your starting point.

The second thing I'd say is this: high-quality contractors don't mind losing a project to another highly vetted, equally reputable firm. Apples-to-apples competition among professionals who have great reviews, strong reputations, and do quality work is healthy. Honestly, many of us are friends. We went to school together, we've worked on projects together, we talk regularly about the industry and how to raise the bar collectively.

What we don't want is to lose a project to an unlicensed operator with no reviews and no track record — often the ones who come in lowest on a bid because they're no longer getting referral business and are relying on paid advertising to stay visible.

So: check reviews first. Then check web presence. It doesn't take much to build a solid website today, and a quality professional should have one — with a bio, team information, a portfolio, and project images. Check social media as well. Are they active? Are they showcasing recent work? Does the work align with your vision? Is it exciting? Is it the caliber of craftsmanship you're hoping for?

Those three areas — reviews, web presence, and portfolio — are your key starting points.

Bill Reid: I'd add one more layer to the referral piece. Reviews matter, but dig deeper. When you're speaking with a finalist — and hopefully it's only two or three, not six — ask for referrals that are a bit more targeted. Ask for a client who is currently under construction. Ask for a client whose project just finished last month. Ask for a client who is currently in the design phase. Ask for projects you can drive by. The more layers you peel back, the clearer the picture becomes. Any company that's been around for twenty years can make three people happy. Go deeper than that.

═══════════════════════════════════════════════

[: 54:25

Bill Reid: We're running short on time, but I want to end with this: if you could give one final piece of advice to a homeowner who is about to select a designer or contractor — one non-price factor they should absolutely prioritize — what would it be?

Enrique Guzman: Are they a good listener?

Do they truly listen? Do they fully understand your project? And do they have a genuine interest in working with you? You want to work with someone who is excited about your project — because this is a long journey, and you want a partner who is positive, invested, and happy to be on it with you.

There are plenty of architects and contractors who want to do it their way. What I always tell our clients is: you're not hiring Contexto to do it our way. We want to go on this journey with you. We want to listen to your ideas. This is a collaboration, and we take that seriously — from that very first meeting all the way through the end of construction. Work with someone who is genuinely collaborative-minded. That's my best advice.

Bill Reid: That's exactly right. As a homeowner, you've communicated everything — through your design brief, your conversations, maybe that forty-three-page document — you've conveyed everything you want, hope for, and love. Now look at how th