Are Your Estimators Pricing Work They Don't Understand?

I've met some really sharp young estimators over the years. They know their software, can read drawings, put together takeoffs, get subcontractor quotes, and turn around bids under some pretty crazy deadlines.

But I've also met estimators who struggle when you start asking questions about how the work they're pricing is actually going to get built.

And I don't necessarily blame them.

A lot of contractors spend plenty of time teaching estimators how to put bids together, but not nearly enough time helping them understand the construction behind those numbers.

There's a big difference, and it can become pretty expensive when those estimates turn into actual projects.

Experience Doesn't Always Mean Someone Is Getting Better

Think about how most estimators are developed. They start with takeoffs, learn the software, review old estimates, and eventually begin pricing their own work.

A few years go by, they're handling bigger bids, and everyone assumes they're becoming better estimators because they've gained experience.

But are they really?

I've spent years estimating billions of dollars of construction work, and one advantage I had was spending a good portion of my career managing projects in the field before moving into estimating.

I could picture the crews, equipment, sequencing, and challenges behind the numbers I was putting together.

Not every estimator gets that opportunity, which is exactly why I believe training needs to go well beyond the technical side of estimating.

Five Areas I'd Be Paying Attention To

1. Are they understanding historical costs or just reusing them?

There's nothing wrong with using historical production and cost data. But just because something worked on the last project doesn't mean it'll work on the next one. Does the estimator understand what drove those costs, or are they simply carrying numbers forward because that's what the company has always used?

2. Do they understand how construction sequencing affects cost?

Think about installing 1,000 linear feet of underground storm drainage. An estimator might carry 150 feet of pipe installation per day based on previous projects.

But what happens when the crew encounters existing utilities every 100 feet, needs trench boxes, has limited room to stockpile material, or has to work around other trades?

That 150 feet a day could quickly become 75 feet, and now you've potentially doubled your installation duration.

Does the estimator understand what it takes to achieve that production, or did they just carry a number from the last bid?

3. Are they comfortable challenging assumptions?

This is a big one for me. Just because a production rate came from a senior estimator, superintendent, or previous bid doesn't automatically make it right. Young estimators need enough understanding and confidence to question what they're being told. Otherwise, they could spend years repeating assumptions that nobody has bothered to challenge.

4. Do they understand what happens after the bid is won?

I've seen estimates built around one construction approach while the operations team had something completely different in mind. Sometimes nobody realizes the disconnect until the project is already underway. An estimator needs to understand how their decisions affect the project manager, superintendent, and crews who eventually have to deliver the work.

5. Are they actually learning from completed projects?

Here's one I'd really challenge contractors on. When a project finishes with significantly more or less profit than estimated, does anyone sit down with the estimator to understand why?

And I'm not just talking about reviewing a cost report.

Was the original estimate accurate? Did operations outperform expectations? Were there conditions nobody anticipated? Or did the company simply get lucky?

If estimators aren't learning from completed projects, how much better are they really getting?

What Are We Actually Developing?

I don't expect a young estimator to have the same construction knowledge as a superintendent who's been building projects for 25 years.

But I do expect their development to include more than learning software, improving takeoff speed, and getting bids out the door.

I want estimators who understand what drives costs, recognize risks, ask good questions, and appreciate what happens when their numbers get handed over to operations.

Because eventually, that young estimator could be responsible for pricing $10 million, $50 million, or even multi billion worth of work as I did.

And at that level, there's a lot more at stake than getting the quantities right. A company can get crushed! 

Here's What I'd Ask Every Chief Estimator

If you looked back at the last 12 months, could you point to specific ways your estimators have improved their construction knowledge and judgment?

Or have they just gotten faster at putting bids together like a robot?

That's a pretty important distinction.

At Pro-Accel, a big part of my estimating training focuses on developing the construction knowledge and judgment behind the numbers, not just the technical skills needed to assemble a bid.

With the end of the year approaching, it's a great time to start thinking about what your estimating team needs to get better at next year.

Gerard Aliberti
Pro-Accel, Owner

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Ways We Can Work Together

Employee Performance Training. Role-specific training for PMs, Estimators, Superintendents, Field Engineers, and emerging leaders. The focus is practical. Better decision-making, stronger ownership, greater accountability, and employees who understand how their role impacts project and company performance.

Operational Performance Advising. For contractors who know things could run better but need an experienced outside perspective to identify where performance is breaking down. We work through leadership, accountability, communication, project controls, team structure, and the operational issues affecting profit and growth.

Fractional Operations Leadership. Senior-level operational support without adding another full time executive. I work alongside ownership and leadership to strengthen how the company operates, develop the people already in place, clarify responsibilities, and reduce how much has to find its way back to the owner.

Leadership and Organizational Development. As contractors grow, the people and structure that got them here may not be enough to get them where they want to go. I help develop stronger leaders, clarify who owns what, and build a team capable of taking on more responsibility as the company grows.

The goal across all of it is pretty simple. Better people. Better decisions. Better operations. Better results.

If any of this sounds like something your company is working through, reply to this email and let’s talk.