I spend a lot of time with estimators and the people who manage them. The good ones share specific habits. The bad ones make the same mistakes over and over.

James Clear nailed it in Atomic Habits: "You do not rise to the level of your goals. You fall to the level of your systems." The best estimators don't succeed because they're smarter or work harder. They succeed because they've built better systems.

Here's what separates the best from the rest - and none of it requires working longer hours.

1. Spend Half a Day in the Field Every Week

I can already hear the excuses: "I don't have time." "I'm buried in takeoffs." "The bid's due tomorrow."

Make the time anyway.

You have to see the work progressing and evolving. Does it match what you pictured when you were doing the estimate? When you watch crews in action, it plants seeds that will sharpen your future bids.

Get out of your truck. Shake hands. Ask questions. You'll learn more in 30 minutes on-site than in 4 hours at your desk.

Pro tip: Leave your phone in the vehicle. Be present. Then write a summary of what you saw (good, bad, lessons learned) and send it to the project team. They'll appreciate that someone took the time to understand their reality.

2. Build a Monthly Look-Back Habit

After accounting close each month, gather the reports for jobs you've estimated:

• WIP reports

• Field cost reports (HeavyJob, B2W Track, whatever you use)

• Monthly ERP accounting cost reports showing budget vs. actual

• Cost to completes

• P&L statements if you have access

Study them. Where were you right? Where were you wrong? What patterns emerge?

Great estimators don't just submit bids and forget about them. They track performance and learn from every job.

Pro tip: Run quantity over-under reports on every completed job! You will learn a lot about whether the takeoff assumptions you made were right or wrong.

3. Plan Your Week on Sundays

Sunday planning eliminates Monday morning panic. It gives you time to process the previous week and prepare for what's coming.

This is what James Clear calls "habit stacking" - linking a new behavior to an existing routine. Sundays are naturally reflective. Use that existing pattern to build your planning habit.

Don't need anything fancy - a simple notebook works fine. But having a plan beats winging it every time.

4. If You Lead a Team, Keep Bidding Work Yourself

Even if it's just a few jobs per year, roll up your sleeves and estimate something. This keeps you sharp, builds credibility with your team, and reminds you what they deal with daily.

The best estimating managers never completely stop estimating. They stay in the game.

5. Conduct Post-Build Reviews at Project Milestones

Don't wait until a job is complete to see how your estimate performed. Set up reviews at 25%, 50%, and 75% completion.

Include the PM, superintendent, and original estimator. Ask three questions:

• What did we learn?

• Where were we off?

• How do we apply this to future bids?

Most contractors skip this step. That's a mistake that costs money.

6. Explore Technology Constantly

AI, drones, new software platforms - the technology landscape changes monthly. Set aside time to explore what's new.

You don't have to adopt everything. But you need to know what's possible. Your competitors are already experimenting.

7. Meet With Key Subs and Suppliers Quarterly

Let them buy you lunch. Ask what they're seeing in the market. What projects are coming up? What challenges are they facing?

These conversations often reveal opportunities or problems you'd never spot from your office. Plus, staying connected matters in a relationship business.

Get involved with trade associations too - AGC, local road builders/site contractors, peer groups. The intelligence and connections you gather are worth the membership fees.

8. Take Daily Walks

You're at your desk for hours analyzing plans and running numbers. Your brain needs breaks.

Great creators and authors throughout history shared one habit: daily walks. Ten minutes outside on office days can unlock solutions you'd never find staring at a screen.

Here's the Atomic Habits approach: Make it obvious. Put your walking shoes by your desk. Make it attractive - pick a route you enjoy. Make it easy - start with just 5 minutes. Make it satisfying - track your walks on a simple calendar.

Fresh air and movement aren't luxuries - they're productivity tools.

9. Ask for Help Early

Mature estimator: "I need help with the drainage and retaining walls on this one."

Immature estimator: Tries to handle everything alone, realizes they're in over their head at 4 PM the day before the bid.

Don't be the hero who needs to be rescued. Ask for help when you first get the bid package, not when you're drowning.

10. Schedule Every Meeting Immediately

The second you receive a bid package, schedule every required meeting - site visits, sub meetings, internal reviews, everything.

Work backward from the bid deadline. Never show up unprepared. If something changes, reschedule in advance rather than scrambling at the last minute.

Great estimators are never surprised by deadlines because they planned for them from day one.

11. Find Your Peak Hours

One advantage of estimating: you often control your schedule. Some people are sharp at 6 AM. Others hit their stride at 8 PM.

Figure out when you do your best work and protect those hours for your most complex tasks. Use your low-energy times for administrative work.

The Bottom Line

None of these habits require working more hours. They require working smarter.

The estimators who consistently win profitable work aren't necessarily the most technical or experienced. They're the ones who understand that estimating is about more than just counting quantities and pricing items.

As Clear writes: "Every action you take is a vote for the type of person you wish to become." Each time you visit a jobsite, review a completed project, or ask for help early, you're voting to become a better estimator.

Start small. Pick one habit from this list. Make it so easy you can't say no. Build momentum. Stack new habits on top of existing ones.

It's about staying connected to the work, learning from every job, and building systems that compound over time.

Which of these habits will you implement first?

Thanks for reading this week!

Want to share your estimating habits? Reply and tell us what works for your team. We read every response and feature the best insights in future newsletters.

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About the Author

Tristan Wilson is the CEO and Founder of Edgevanta. We make AI agents for civil estimating. 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]