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#29 The Cost of Not Looking: problems that compound because nobody checked

#29 The Cost of Not Looking: problems that compound because nobody checked

Problems that grow quietly until you go looking: a field manager ratio that caps growth without anyone noticing, a price book that drifted off target with no bad actor involved, and a first 90 days that quietly decides whether a new hire sticks. We also cover what AI search means for how homeowners find a contractor, and why we'd rather lose a financing sale than let a customer get surprised by a bill.

Christopher Hoffmann
August 25, 2026 • Estimated Reading Time: 15 minutes

In Today’s Newsletter

The Manager Ratio Nobody Optimizes For
Things you should do…
The Price Book Audit We Should Have Done Two Years Earlier
The 90-Day Cliff
What LLMs Look for Before They Recommend a Contractor
What Every Homeowner Deserves to Know Before They Sign
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What’s on my mind?

The Manager Ratio Nobody Optimizes For

Every business owner I know can tell you their revenue per technician. Fewer can tell you their technician per field manager ratio, and almost none have ever asked whether that number is actually the right one.

I think that's a mistake. Headcount is not what caps how fast a service business can grow. Span of care is.

Here's what I mean. A field manager's job comes down to three things: conducting one on ones, completing ride alongs, and reviewing the summary of findings, options, and call details from the jobs their team ran that week. That's the whole job. Everything else is either coaching disguised as administration, or administration disguised as coaching.

The problem is that all three of those things take time, and time is the one resource a manager can't manufacture more of. Give a manager 25 technicians instead of 15, and something has to give. Usually it's the ride alongs, because they're the easiest thing to skip when the calendar gets tight. And ride alongs are exactly the thing that catches a bad habit before it becomes a customer complaint.

So what's the right ratio? We run our field teams around 1 field manager for every 12-15 technicians as a baseline. That number isn't magic, and I'd be careful about anyone who treats it as gospel. Lately I've started asking the underlying question differently, because the tools available to answer it have changed.

We now have AI tools, including a few MCP based ones, that can help a field manager prep for a one on one before they walk into it: pulling call scores, job history, and KPI trends so the manager isn't starting from a blank page. That changes the math. If prep time drops, a manager can carry more people without losing quality. If it doesn't, they can't. So the real question isn't "what ratio works." It's "what is the optimal ratio of field pros to field managers, given the tools your managers actually have today." Not the ratio that worked five years ago. Not the ratio a peer at another company uses. Yours, today, with your tools.

A few things move that number in either direction. Experience level matters separately from tenure, and both matter separately from technical skill. A five year tech who has only ever run routine service calls is a different case than a five year tech who has cross trained across three trades. Technical skill competence is its own factor again: some of your most tenured people still need the most coaching, and some of your newest hires need the least. And access to productivity enhancing tools and technology changes the equation for everyone, not just the manager. A field pro with good tools in their hands generates fewer of the small fires a manager has to put out in the first place.

None of that changes the goal, though. We want to minimize the time our field managers spend behind a screen and maximize the time they spend in the field, coaching and training their team. Every ratio decision should get judged against that standard. If a manager is buried in reports, the ratio is wrong, or the tools are wrong, or both.

The other half of this, and honestly the more important half, is who you put in that seat in the first place.

In our business, we've had the most success promoting field managers from within. When we have a field pro who's successful, who knows what it actually takes to be successful here, and who shows leadership potential, that's the safest and most reliable way to build our bench. They already understand the standard. They've earned the credibility that comes from having done the job themselves. A tech doesn't fully trust a manager's coaching until they know that manager has actually turned a wrench.

But promoting from within only works if you're honest about what the new job requires that the old one didn't. A great technician is not automatically a great manager, and assuming otherwise is how you lose a good tech and gain a bad manager in the same move. The foundational skills have to be taught deliberately: how to run a meeting so it doesn't turn into a status update, how to coach instead of just correct, how to have a difficult conversation without avoiding it or making it worse, how to actually read a KPI instead of just report it, and how to recognize great performance out loud instead of assuming people already know they're doing well.

Get the ratio right and give your new managers those skills, and you've built something that scales. Get either one wrong, and no amount of lead generation or marketing spend will fix the ceiling you've built for yourself.

After this visit to the amazing St Louis Zoo… my 3 year old would like a pet Polar Bear for her birthday.

Sunset in the Northern Cape area in South Africa.

One of our relocated “tower clocks” that we moved here to our new facility. A cool reminder of my great grandfather’s entrepreneurial journey.

Things you should…

1. Look up how many technicians you hired this year are still with you at 90 days. If you don't already know that number without checking, that's the finding.

2. Ask a LLM to recommend a contractor in your own market and see if you show up. If you don't, that's not a marketing problem you'll notice slowly. It's one you'll notice all at once, in a quarter you didn't expect.

3. Pull the price on your three most common jobs and put it next to a competitor's. If you can't explain the difference in plain language, your customers can't feel it either.

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Technology Corner with ServiceTitan

The Price Book Audit We Should Have Done Two Years Earlier

We got our price book wrong last year, and it wasn't for the reason I would have guessed going in.

The pricing guidance itself was good. We'd built a genuinely structured framework for how our teams should think about pricing decisions. The problem was that we let execution of that framework stay decentralized. Different managers, in different markets, applying the same good guidance in slightly different ways, drifting a little further apart from each other and from our actual targets every month, with nobody positioned to notice the drift until it had compounded. By the time we went looking, one of our brands had been significantly underpriced for months.

That's an uncomfortable sentence to write, but it's the honest one. Nobody made a bad decision on purpose. A lot of good people made a lot of individually reasonable calls that, in aggregate, added up to a real margin problem. That's actually a more common failure mode than the one people assume, which is some single manager quietly cutting corners. Decentralized execution of a genuinely good policy will drift on its own, with no villain required.

The fix isn't better guidance. We already had good guidance. The fix is centralizing how that guidance gets executed, so pricing decisions run through a consistent structure instead of a dozen individually reasonable interpretations of the same rules. We're in the middle of working through exactly what that looks like now, and the goal isn't to strip judgment away from the field. It's to make sure the judgment being applied is the judgment we actually intended, everywhere, consistently, not just wherever someone happened to read the guidance the way we meant it.

Underneath that structural fix is a pricing model we've gotten a lot more disciplined about. Pricing, for us, is a function of four inputs: overhead, target margin, billable hour efficiency, and billable hour rate. Billable hour efficiency is the one most operators underweight. It's simply how much of a field pro's total time worked actually goes toward revenue generating tasks, as opposed to drive time, admin, callbacks, and everything else that eats a workday. Get that number wrong and your billable hour rate is built on a fiction, no matter how carefully you calculated everything else.

The other piece we've gotten more deliberate about is recognizing that not every job should be priced the same way, even at the same billable hour rate on paper. We now sort tasks into three tiers, high perceived value, medium perceived value, and low perceived value, and we apply different billable hour rates depending on which tier a task falls into.

A full electrical panel and service entrance replacement is high perceived value. Customers understand intuitively that it's a serious job, and they're willing to pay a rate that reflects that. Installing a customer supplied ceiling fan is low perceived value. It looks simple from the customer's side of the wall, whether or not it actually is, and a customer will push back hard on a premium hourly rate for a job that reads as small, even if the technician's actual cost to deliver it is similar.

That distinction matters because it changes where you extract margin, instead of assuming you have to extract it evenly across everything you sell. As long as your blended margin across the whole book hits target, you don't need every individual job to hit that same number. You can be surgical: price the high perceived value work at what the market will actually bear, stay competitive on the low perceived value work where customers are watching the number closely, and let the two halves of the book balance each other out.

That's the part of this I'd tell any operator to steal before they even touch the centralization piece. Ask whether your price book is treating every task like it deserves the same margin. Ours wasn't. Once we started applying rates by perceived value instead of a flat formula, the underpricing we'd been carrying for months got a lot easier to see, and a lot easier to fix.

#grateful to have ServiceTitan sponsoring this section of TPLT

CEO: Growth Mindset

The 90-Day Cliff

Most of the technician turnover we see happens early. We see the bulk of it within an employee's first 13 months, and a meaningful share of that within the first 90 days. That's not an accident of scheduling. It's the most useful data point we have, because it tells us where the actual leverage is. A tech who leaves after seven years might be leaving for reasons that have nothing to do with us. A tech who leaves after seven weeks is telling us something about a hire we made, or a first 90 days we ran, or both.

Every time it happens, we ask the same question: what can we learn from this?

Was it a bad hire?

Did we fail to communicate expectations clearly before they ever signed on?

Did we not actually onboard them, meaning give them the training and tools they needed to do the job well?

Did they have a bad experience with their manager in those first few weeks, before they'd built up any goodwill toward the company to offset it?

I won't pretend we always know the answer. The honest diagnosis is never 100 percent certain. A departing employee oftentimes does not tell you the real reason, and even when they do, it's usually only part of the story. But uncertainty isn't a reason to stop asking. It's a reason to keep narrowing the possibilities, one hire at a time, until you can see the pattern instead of just the exit.

Here's what we've focused on to try to get it right before someone ever puts on the uniform.

Behavior based interviewing. We train our hiring managers specifically on how to run an interview that actually tests for organizational fit, not just technical competence. Anyone can ask "tell me about a time you solved a hard problem." Getting a useful answer out of that question, and knowing what to do with it, is a skill we teach on purpose rather than assume people already have.

Clear expectation setting at the interview stage. If someone accepts an offer without a real understanding of what the job actually demands day to day, you haven't hired them. You've deferred the moment they find out, usually to somewhere around week three, which is exactly when the early attrition starts.

Technical skill testing. We confirm skills and abilities before day one, not after. It's a small thing that removes a huge source of early frustration on both sides: the new hire who's in over their head, and the team that assumed they weren't.

And an onboarding program built to actually equip someone, not just process them. That means the information, tools, and training a new hire needs to do the job well, delivered in a sequence that makes sense, instead of whatever happened to be available that week.

The improvised version of onboarding and the structured version look similar from the outside. Both have a first day. Both have some paperwork and some training. The difference shows up three weeks in, in whether a new hire feels like they know what's expected of them and have what they need to meet it, or feels like they're guessing.

One piece of our onboarding I care about personally is the first hour. I spend it with every new hire on their first day. We talk about the company's history, how we actually got to where we are, not the polished version. We talk about our values and what they look like in practice, not just on a wall. And we talk about what's expected of them as part of a team that's trying to deliver wins for our employees, our customers, and the company, in that order, because I don't think you get the second two without the first.

It's an hour. It doesn't fix a bad hire, and it doesn't replace real training. But it's the clearest signal I can send on day one that this isn't a job where you show up and figure it out alone.

Onboarding isn't a compliance checkbox. It's the highest leverage retention tool most operators already have and mostly waste. The first 90 days aren't just where you find out if someone's going to make it. They're where you decide it.

CyberNetic Labs - bringing powerful Agentic AI tools to the trades

What LLMs Look for Before They Recommend a Contractor

For most of the history of local search, the audience for your website was a person and an algorithm working on that person's behalf. Optimize for both, understand what makes a person trust you, and you were in reasonable shape.

That's no longer the whole audience. A growing share of homeowners are now asking a model directly who they should hire for a given job. A model doesn't browse your site the way a person does. It reads it, weighs it, and decides whether it has enough to actually recommend you by name. That's a different game, and most operators, including us until recently, have been playing the old one.

We spent a working session with our team at Netic mapping out exactly where the two games diverge, and the gap was bigger than I expected.

Start with reviews, since they're the single biggest lever either way. A person skims your reviews and gets a feeling. A model needs something closer to a citation. If your reviews aren't marked up as structured data, meaning the rating, the author, and the body of the review are actually readable as data instead of just text on a page, a model has to guess at what it's looking at, and it will trust a competitor's clearly structured reviews over your unstructured ones every time. Recency matters more to a model than it does to a person, too. A human doesn't check the date on a five star review before deciding it counts. A model weighs recency as a real signal, which means a review widget without visible dates is quietly working against you. And breaking reviews out by location gives a model something concrete to cite when a homeowner asks about a specific city, instead of forcing it to guess whether your reputation in one market applies to another.

The second gap is credentials. A person walking through your homepage might glance past a manufacturer certification badge without really registering it. A model can't glance past anything. It either has the fact or it doesn't. If your manufacturer tier status, your licensing, your technician training, and your warranty terms aren't spelled out in actual words on the page, a model has nothing to point to when a homeowner asks it to compare you against another contractor. A missing credential isn't a missing decoration anymore. It's a missing citation, and the model will cite the competitor who bothered to write theirs down.

The third gap is pricing, and this is the one that surprised me most. For years, "call us for a quote" was a perfectly reasonable answer, because a person calling you is a person you can talk to, build trust with, and close. A model can't call you. If your pricing philosophy, how it works, what drives the range, what's included, isn't written out in plain language on the page, a model has nothing to reference when it's asked whether you're transparent about cost. It will simply prefer the competitor who said it out loud, even if your actual pricing is perfectly fair.

There's a longer list of smaller things underneath all of this. Naming your core services directly in your homepage headline instead of a clever tagline, so both a crawler and a model see the service list immediately. Making sure every location page is actually listed somewhere a model can find it, instead of buried three clicks deep. Cleaning up leftover code from one market that's quietly showing up on another market's homepage, which happens more often than anyone wants to admit once you actually go look. There's also a newer category worth taking seriously: niche directories that used to matter mainly for backlinks now function as citation sources a model pulls from directly, so a listing carries more weight than it did two years ago. None of these are new SEO tactics. They're old SEO tactics that used to be optional and are becoming mandatory, because the audience reading your page now includes something that can't extend you the benefit of the doubt a person naturally would.

The uncomfortable version of all this is that you can have a genuinely excellent local reputation, decades of trust, real credentials, and fair pricing, and still be functionally invisible to a homeowner who asks a model for a recommendation, simply because none of that trust ever made it onto the page in a form the model could actually use. Being good isn't the same as being legible. Right now, most of our industry is good and illegible, and that gap is only going to matter more.

#grateful to have Cybernetic Labs sponsor this section of TPLT

Consumer Financing¹

What Every Homeowner Deserves to Know Before They Sign

Financing has become part of how we sell large jobs, the same way it has for most of the industry. HVAC replacements, roofing, big plumbing jobs, the ticket sizes are large enough that financing is often the difference between a customer saying yes today and a customer saying they'll think about it. I'm fine with that.

What I'm not fine with is treating the explanation of that financing as a formality to get through on the way to a signature.

Most deferred interest plans, including the ones we offer through GreenSky, work like this. If you pay off the full balance within the promotional period, you owe zero interest. That's the pitch, and it's true. What's less often said out loud is what happens if you don't pay it off in time. It's not that you start owing interest going forward from that point. You owe all the interest that accrued from the day you signed, calculated at the plan's full rate, added back onto your balance all at once. A homeowner who thought they were carrying a low monthly payment on a mostly interest free loan can suddenly find themselves owing far more than they expected, not because anyone lied to them, but because nobody made sure they actually understood the mechanism before they signed.

That's a solvable problem, and solving it is a choice, not a legal requirement. The paperwork discloses the terms. The paperwork always discloses the terms. But disclosure and understanding are not the same thing, and the gap between them is exactly where trust gets built or destroyed. Our position is that the person selling the job, standing in the customer's kitchen, needs to explain deferred interest in plain language before a signature ever happens, not point at a document and let the fine print do the explaining after the fact.

That means walking through it simply. This is the promotional window. This is what happens if you pay it off inside that window. This is what happens if you don't. Here's roughly what that would look like in dollars if it went the second way. If a customer's eyes widen a little when they hear that second scenario, good. That's the reaction we want them to have before they sign, not fourteen months later when the statement arrives.

Sometimes that conversation ends with a customer deciding financing isn't right for them, or that a shorter promotional plan makes more sense than the longer one with the bigger monthly savings, or that they'd rather wait a month and pay cash. I'd genuinely rather lose the sale in that moment than win it on an explanation that was technically accurate but functionally misleading. A sale you win because a customer didn't fully understand what they agreed to isn't a sale. It's a complaint with a delay on it, and the delay doesn't make it cheaper to fix. It just means the damage to the relationship shows up later, after the work is done, when there's nothing left to negotiate and nothing left to fix except the customer's opinion of you.

We built our reputation on transparency long before financing was part of the conversation. Honest advice, pricing you can see, options explained instead of assumed. Financing terms are just the newest place that value has to show up, and it's an easy one to get wrong quietly, because nobody's standing over your shoulder checking whether you actually explained the deferred interest risk or just handed over a tablet and pointed at the signature line.

Most contractors treat the financing conversation as the fastest part of the sale, something to get through so the real conversation, the one about the job, can end. I think that's backwards. The financing conversation is part of the job. Get it right, and a customer walks away from a five figure decision feeling like they understood exactly what they signed. Get it wrong, and it doesn't matter how good the installation is. The bill is what they'll remember.

#grateful to have GreenSky® Home Improvement sponsor this section of TPLT

¹ The views and opinions expressed here are owned by The Path Less Traveled and its author and may not reflect the views of GreenSky®

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