Are You Insane to Become an Estimator?

The Challenge

It was the height of COVID. I was one of multiple senior estimators leading the estimating effort on a $1.25 billion project in New York City. My scope alone was $450 million — concrete, utilities, an esplanade over the East River, bridges, abutments, foundations, and more. In the middle of all of it, I was getting vendor quotes worth well over $20 Million each. Here’s where it got crazy, the majority said “Price good for seven days” AND it was a four year project! O’Boy did we learn a lot about ourselves and limitations. 

I have also managed and led hundreds of millions of dollars worth of work in the field. I speak both languages. And what I can tell you is that estimating and field execution are two sides of the same coin BUT unfortunately many companies treat them like they are on opposite teams.

You know the lines that come with being an estimator…

“We made a ton of money on that job -> what a great field team” 

OR

“We lost money -> the estimators messed up the bid.” 

That stigma is real, it is toxic, and it is exactly why nobody is raising their hand to become an estimator.

The Impact

The field gets months, sometimes years, to think through how a project unfolds. An estimator gets plans, thousands of spec pages, and a deadline in a few days or weeks. They make consistent educated guesses on how production will play out and they have to back every single one of those numbers. Not everyone has what it takes. The ones who do are rare.

When you find one of those people, understand what you actually have. They carry institutional knowledge that touches every project you run, productivity rates, vendor relationships, past mistakes, real margins. That knowledge does not live in your software. It lives in their head. And when they walk, it walks with them.

Most contractors have no pipeline, no mentorship structure, and no culture that makes estimating feel like a career worth building. The bid your estimator puts together is the check you are writing for the next few months or years. AND that handoff between the bid and the field better be mastered, or your days of growing profitably are numbered.

The Shift

Changing this starts with changing the culture around estimating. Whether you have a formal training program or not, development has to be intentional.

Senior estimators need a defined responsibility to train the next person up. Not just software. Not just unit prices. How to read a project. How to think through logistics, sequencing, and risk before a single dollar goes on paper. How to build a realistic crew from the ground up based on actual field conditions, not only assumptions carried over from the last job. That knowledge only transfers through deliberate mentorship and structured process. If you do not build that system and culture, you are always one resignation away from starting over.

And here is what most owners do not realize. Your field and your estimating team are sitting on a goldmine of shared knowledge that almost nobody is capturing. Productivities, means and methods, lessons learned, that data exists in your company right now and it is walking out the door every time a project closes out. You must figure out how to collect it, organize it, and put it back in front of your estimators so you can stop guessing and start building bids with real conviction.

Training also has to address the mental side of this role. Estimating under pressure, making high stakes decisions with incomplete information, managing the weight of knowing that your numbers become someone else's reality in the field, that is NOT something you can throw a new hire into and hope for the best. It requires coaching, repetition, and a culture that treats mistakes as part of the development process rather than a reason to point fingers.

The companies that build this infrastructure stop bleeding knowledge, stop buying bad work, and stop losing their best people to competitors who make them feel valued.

The Closing

Your estimating team is laying the financial foundation of your business every single time they put a bid together. The freedom you want as an owner, the margins, the predictability, the ability to grow without chaos, all of it traces back to how well you develop, protect, and invest in the people building your numbers. That starts now.

P.S. — Pro-Accel has launched training workshops specifically designed for Estimators, PMs, Superintendents, and Field Engineers. We cut straight to accountability, decision-making, and getting crystal clear on what each role must deliver for the company to win. If that sounds like something your team needs, reply and let's talk. More info here https://www.pro-accel.com/training-bootcamp

Gerard Aliberti
Pro-Accel, Owner

Ways We Can Work Together

Role Specific Training Bootcamps - Pro-Accel now offers role-specific training workshops for Estimators, PMs, Superintendents, and Field Engineers — focused on accountability, decision-making, and ownership. Reply if you want to talk about your team.

Organizational Assessment — A deep look at how your company operates, where breakdowns happen, and what is keeping your team from stepping up

Bid Handoff Accelerator Process — A structured handoff system that closes the gap between estimating and field execution, dramatically improving project success

Strategic Planning and Leadership Development — Tailored consulting to align your team, clarify roles, and build systems that improve profitability and efficiency

Builder to CEO Mastering Cash Flow Summit — Tampa, FL, May 13 and 14, alongside Patrick Shurney, owner of 3P Consulting. An exclusive in person experience for construction owners. Limited seats. More details here: https://go.3pcllc.com/from-builder-to-ceo-summit-tampa-2026