TL;DR:

I was once the world's worst procrastinating estimator. I missed a $6.5 million bid by 19 seconds because I waited until the last minute to submit, costing my company the win. This failure forced me to change, teaching me the value of preparation and discipline, which led to my improvement and inspired this post on the differences between good and bad estimators.

Good estimators are prepared

They dig into the details - plans, specs, competitors, suppliers, and the job site - before anyone even asks. Their bids are clean, polished, and backed by research. They make sense of hundreds of pages of contracts and drawings and turn that chaos into a clear plan. Good estimators learn from mistakes and rarely repeat them. Their takeoffs are tight and consistent. They tell a story with their numbers. Even when the bid review is after lunch on a Thursday, you’ve been looking forward to it since yesterday because you want to hear about their creative approach to the job. They’re open to new ideas and always push for better.

Bad estimators are unprepared

You know before you ask the question that they don’t know the answer. And it’s not because they’re not smart. They’re bad because they haven’t put in the time. Their bids feel rushed and incomplete. The good news? The gap between good and bad is simple preparation. It’s not about intelligence; it’s about doing the work.

Good estimators think like business people

They understand that an estimate is more than just costs. It’s about pricing strategy, market position, and competitive analysis. They know the balance between cost, profit, and price. They don’t mix cost and profit. A good estimator doesn’t just give you a number - they explain how that number fits into your overall business strategy.

Bad estimators only think about cost

They think their job ends when the estimate is done.

Good estimators are detailed

They manage to process massive amounts of data - drawings, schedules, subcontractor quotes - and turn it around quickly. It’s incredible to think that someone can break down the costs of a $100 million project, lasting four years, down to the penny - in just 30 days. The complexity they navigate is wild. They balance accuracy with speed and hit deadlines. Good estimators know when to dive deep into details and when to step back and look at the big picture.

Did we plug in sub numbers?

Did we double check the mix costs with the plant team?

Did we call the Engineer about the manhole adjustments?

Did we actually speak with the guy who owns the dirt pit?

Did we round up on the trucks?

Yes, yes, yes, yes, yes…………

Bad estimators are overwhelmed

They get bogged down in the details, missing deadlines or overlooking critical elements. Their bids are often rushed at the last minute, leading to errors or gaps. They procrastinate like I used to.

Good estimators ask the right questions

They think ahead, identifying potential issues with resources, scheduling, or execution before they happen. They communicate effectively with everyone - owners, suppliers, subs - making sure the work is understood beforehand. They even pick up the phone and call people to talk about a job!

Bad estimators assume everything will work itself out

They don’t ask the right questions, leading to costly mistakes down the road. Instead of owning the process, they wait for issues to arise. And they didn’t read the sub quote for clarifications. An argument for Project Manager/Estimators is owning the whole cycle. There’s nobody else to point a finger at.

Good estimators are appreciated

Their work is the backbone of a successful contractor. They make sense of complex projects. Then, they pay attention as the jobs progress and get feedback from the field: how did we do? how’s the job going? what did we miss? where are we a little heavy? They never stop learning and are fun to work with.

Bad estimators are a headache

You’re constantly double-checking their work and dealing with unexpected problems. They make things harder, not easier.

Some KPI’s

Jobs Bid

Jobs Won

Dollars Bid

Dollars Won (single & multi bidder separated)

Dollars Left on Table (multi bidder only)

Gain and Fade on jobs estimated (use the WIP)

Gross Profit Acquired

Job site visits

* All separated by estimator

* Trailing Twelve Months (TTM) and Year Over Year Comparisons

Qualitative: How comfortable would you feel if their bids went in before you reviewed them?

The takeaway?

Good estimators do the work, ask the right questions, and think beyond costs. Bad estimators don’t.

I was once a last minute person and it took a major mistake for me to correct my ways.

So if you’re reading this and recognize the qualities of an excellent estimator in someone you work with, take a moment to acknowledge them.

Estimating is often a thankless job, but great ones deserve recognition for turning chaos into clarity. A simple thank you goes a long way in showing appreciation for the role they play!

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About the Author

Tristan Wilson is the CEO and Founder of Edgevanta. We make software that helps contractors win more work at the right price. He is a 4th Generation Contractor, construction enthusiast, ultra runner, and bidding nerd. He worked his way up the ladder at Allan Myers in the Mid-Atlantic and his family’s former business Barriere Construction before starting Edgevanta in Nashville, where the company is based. Reach out to him at [email protected]