With Lillie Maximo at the ASPE Summit 2026 on September 25, 2026.
Long before Lillie Maximo knew what an estimator was, she knew what one sounded like.
Not from the estimator themselves, though. From the superintendents.
And this last week, live at the ASPE Summit 2026 in Orlando, Florida, she sat down to share the stories.
Starting her career in the field, Lillie worked alongside supers who were, as she puts it, extremely expressive. And there was this one mysterious figure they would curse more than anyone else. The almighty estimator.
“How could the estimator do me like this?”
“What on Earth am I supposed to do with that?”
So while she didn't have a name for the role yet, Lillie saw the consequences of it every day.
And it’s because of those first-hand lessons that once Lillie eventually became an estimator herself, those voices came with her. Every assumption. Every line item. Every challenge. Somewhere in the back of her mind was a superintendent she knew would have to live with her decision.
That right there is the root of any good superpower, real-world living with the consequences. So for Lillie, now a cost estimating consultant working with owners, developers, designers, contractors, forensic experts and even attorneys, that power is put to use for good by taking the complex information of a project and finding the real story behind the number.
Because it’s that story where most estimates can easily go wrong.
Every Number Has a Backstory
When you boil it down, an estimate is really two things stapled together.
A number. And the story of how that number came to exist.
For most people, it’s that first part that matters. The total. The bottom line. The figure that goes into the budget and gets held up against the engineer's estimate.
But it’s that second part where the real risk lives. The methodology. The assumptions. Where the work starts and where it stops. What got included because someone looked closely, and what got left out because nobody did.
Lillie is blunt about where that story is written. The qualifications. And the phone calls with whoever submitted the number to begin with.
You see, a number can be technically right and still be wrong for the job. It might match the market rate. It might even match the last three projects. But if the methodology behind it doesn't fit the work at hand, being right on paper just means being wrong later in the field. Most likely in front of that cursing superintendent who never saw it coming.
Market rate is not a plan.
The Smallest Detail Test
So how do you quickly assess the detail of a story when someone hands you a number? For Lillie, her favorite move is actually quite simple.
“Find the smallest little detail buried in the drawings and ask about that.”
Not the big-ticket items. Everyone double checks those. The tiny one. The detail buried on that sheet most people flip right past. The answer to that question tells her everything she needs to know about how closely the bidder actually read the documents. If they know that detail, she knows they put in the work. If they don't, the number was built on a skim.
And she’ll even run the same test on new tech. Every time someone pitches her an AI takeoff tool, she asks that same simple question: if it sees a detail on sheet seven, can it apply what it learned to the floor plan on sheet three?
So far, nobody has said yes.
Now let’s be fair, this is coming from someone whose conference session was titled "Long Live the Spreadsheet." Lillie certainly will defend Excel as the engineer's best friend all day. I mean, how do you improve on a blank sheet of graph paper? But that’s more so because she's clear-eyed about where the real work of estimating happens. Not in the tech, but in the connections between details. The story is written across pages, never on just one.
And when every detail checks out, the backup is complete, the number looks reasonable, and something still feels off?
Listen to your gut. Every time.
If there is still a question in the back of her mind, Lillie goes back through the documents one more time. She digs back into the estimate, her notes, her texts with vendors and even her call log. Something she saw triggered that feeling. Scroll past it one more time, and it jumps out.
Simply put, the gut is just pattern recognition that hasn't finished its paperwork yet.
Qualifications Are Relationship Builders
What was most interesting though, is Lillie took a minute to drive the conversation one level deeper. All too often, estimators seem to under-qualify and keep it lean. All to one, simplify the story, but also to give the other side less to argue with.
Lillie, though, goes the other way. She over-explains. Over-qualifies. Shows her thinking.
To her, every qualification is an invitation. A chance for the person across the table to challenge an assumption, ask a question, and start a real conversation about the job. In other words, qualifications are a low-pressure relationship builder.
It’s an instinct she learned from living in nearly every seat a construction project has to offer. Field, GC, sub, owner-side and yup, even forensic claims. The lesson from all of them is the same. Everyone has headwinds they can't always say out loud. Once you've felt those headwinds yourself, you start hearing what the other side isn't saying. Nothing in construction is obvious. Case after case, the lessons learned seem to land in the same place. Communication. Relationships. Asking the question before it became an assumption, and later a dispute.
When everybody wants the project to succeed, the estimate is the first place that intention shows up in writing.
Build a Feedback Cycle
If estimators owe the field the story behind the number, the field owes estimators something in return. That something is the ending.
“Come tell us how it went last time.”
Estimators make dozens of assumptions on every job. Then the job gets awarded, disappears into the field and the next bid lands on the desk. Almost nobody circles back. Lillie begs for the results. Were the assumptions good? Did the crew find a smarter way to solve a problem that should show up in the next estimate?
Without that loop, estimators keep writing the first chapter of stories they never get to finish. And the superintendent keeps cursing at a number that was built without the lessons from his last project.
It’s a quick win with loads of benefit on the back end.
The Relationship is the Payback
If you were to walk up to Lillie today and ask, "What's the number?" she would grill you right back.
“The number for what?”
At the end of the day, before any figure gets spoken, get on the same page. What's the scope? Where does the work start and stop? What's the methodology? What does this person actually need?
The number has to meet the need. And nobody can price a need they don't understand.
Strangely enough, the volatility since COVID has made these conversations easier. The other side of the table expects things to move. Show up with your facts straight, with case studies, database history and vendor quotes, and a hard number becomes a conversation instead of a fight.
The number is the headline. The qualifications are the story. The relationship is what makes anyone believe it.
So the next time someone asks for a number, don't start with the number.
Start with the story.
Construction is cool, tell your friends!