Managing high-risk infrastructure projects without getting buried

Every contractor has a comfort zone. Then come the jobs that stretch you - $30M, $50M, $100M+. Multi-year, high-exposure, no-margin-for-error type work.

These jobs will define careers and companies.

I’ve learned more on big, tough jobs than any book or class ever taught me. I imagine many of you have had similar experiences.

Here’s how to run the big ones without losing your shirt - or your mind.

1. Staff It Like a Business, Not a Project

Big jobs demand real structure. You need a full-time PM, engineers, safety, schedulers, admin support, and enough bench to rotate tired staff when needed. When you roll up understaffed, it sends the message that you’re not serious.

Put the full-time safety lead in your bid. Don’t treat it as optional. On highway jobs, they’ll be managing claims as much as compliance.

Staff appropriately for day and night work - your people need rest to perform. Big jobs take a toll. Morale dips. Fatigue sets in. Plan for it. Rotate crews. Support recovery.

And remember: if you treat once-in-a-career projects as training grounds for future leaders, that’s exactly what they become. It’s a self-fulfilling prophecy.

2. Get Commitments Before You Bid

If you’re going into battle, everyone needs to know their role - and agree to show up. The PM, superintendent, and support teams should all be aligned before the estimate gets submitted. No surprises post-award. Who will build it? Know this going in.

3. Pre-Planning Is Not Optional

Once the clock starts, it’s too late to “figure it out.” Every person on the job should go through a job-specific orientation led by the PM and Superintendent. Every subcontractor should attend a preconstruction meeting on-site. All major operations should be pre-planned with the field team before work starts.

Time spent on the front end is always time well spent.

Don’t forget to celebrate the wins - especially the small ones. When a crew hits a major milestone or knocks it out of the park, make it a big deal. Shout out great performance. Throw a cookout, hand out gear, whatever fits your culture. Make it fun, make it visible.

What gets rewarded gets repeated.

4. Form a Committee - And Show Up

Big jobs should be reviewed in-person by senior management every 2-4 weeks. Zoom or Teams doesn’t count. You’ve got to get your boots in the dirt. I’ve seen them run as follows: PMs didn’t report into a division - instead they reported to a committee. It was our job to protect margin, stay ahead of risk, and keep the job moving forward.

The PM and team prepared a monthly packet ahead of each visit. It included:

• Job cost reports (JTD/YTD)

• Change order log

• Pending/approved CORs

• Safety and incidents

• Schedule risks and updates

• RFI Log

• Issue Resolution Log

• Idle Equipment Report

• Trucking Analysis

• Punch list progress

• Job Org Chart

• Key subcontractor issues

• Owner/inspector relationships

• Forecasted exposure

It was how we ran the job. If you’re not doing this, you’re not managing risk - you’re reacting to it.

We used to joke that the committee visits were “seagull management” - fly in, crap on everything, and fly out. But when you're the PM with 75 unread emails after 2 hours and stuff coming at you from 20 directions, knowing the company has your back means something. A well-run committee isn’t just oversight - it’s support. And that matters.

5. Cost Discipline Is Everything

Three Words: Know Your Cost. 

You cannot run a profitable big job without an obsessive focus on cost. Everyone - PM, superintendents, engineers - must know how we get paid, what things cost, and what’s in the budget.

Messaging to superintendents was simple:
“If we’re spending money that isn’t in the budget, I need to know beforehand. That’s the expectation. And it should be yours too.”

Every field decision has a financial impact. Act accordingly.

“The key to this joint, the key to staying on top of things, is treat everything like it's your first project”

- The Notorious B.I.G.

6. Plan for Claims. Build Contingency.

Big jobs are high-risk by nature. Something will go wrong. Design changes, quantity busts, utility surprises—you name it.

Put contingency in your bid. That’s table stakes. Offset your risk.

Maintain an issue resolution log. Track problems in real time. Keep a record. Assume the job will involve a claim. Prepare for the worst.

Build trust early with the people on the other side - inspectors, owners, third parties - because when things go sideways (and they will), those relationships matter. You need them, and they need you.

Follow the contract. Meet the notification requirements. Keep your documentation clean.

And above all: listen, follow through, and do what you say you’ll do. That alone goes a long way.

7. Do Not Bid Design-Build Like Bid-Build

In bid-build, the agency owns the quantity risk. In design-build, you do. Treating them the same is a fast way to lose millions. If you don’t have a clear strategy for dealing with scope gaps and quantity uncertainty, you’re not estimating - you’re gambling.

Don’t take my word for it - go read the earnings reports of publicly traded heavy civil contractors from 2010 to 2020. Design-build quantity risk (and other issues) wiped out years of profit. It ain’t pretty.

Price that risk. Protect your downside.

8. Finish Work in Sections. Punch As You Go.

Do not let punch list work pile up at the end. Work in tranches. Get sections complete and accepted before moving on. It’s the only way to maintain momentum and preserve margin during closeout.

Quality is a never ending journey. And I believe in sending your best crews to your biggest jobs and holding everyone to a high standard.

We once worked for Kiewit on a $40M subcontract. We thought we’d make 20% but we ended up around breakeven on the WIP with some “expensive education”. One major lesson: finish one area before you move to the next.

9. Sub Out Strategically

You can’t self-perform your way out of every problem. Use subcontractors to manage risk - traffic control, signals, striping, specialty scopes, and even portions of scope you typically self-perform.

But manage them hard. Ensure big contracts are bonded, no matter how good they are. Precon meetings are non-negotiable. Tell them you want the A-Team. Expectations should be clear before the first bucket hits the dirt.

10. Stay Tight in the Field

Clean site = tight operation. That includes the laydown yard, the foreman trucks, the signage, the trailer, the portalets. All the pieces matter. If the job looks like a mess, it is one. Don’t let disorder take root. Safety and quality are yours to own. Everyone must be held accountable. It’s your ship.

11. Beginner’s Mindset Until the Last Stake Gets Pulled

Big work is super fun to be a part of. But if you’ve seen enough of it, you know you’re never out of the woods on a big job. You could be 95% done and one bad shift, bad pour, or bad meeting away from a six or seven figure problem. Stay humble. Stay alert. Stay engaged.

Big jobs are never easy. But they’re where reputations are made. The right team, the right process, and a relentless focus on risk can turn them from landmines into legacy.

Don’t hope for luck. Build a system.

If you want a sample issue log, preconstruction checklist, or committee packet template, just ask - happy to share. And if there’s something you think I missed, I’d love to hear it.

Finally, credit where it’s due….

I was in South Carolina last week visiting the team at C.R. Jackson. On a $350M widening job, their team had written values right on the trailer walls. It was raw, clear, and honest - and it stuck with me.

That visit inspired the following post and this newsletter. A reminder that with the right mindset and discipline, we’re capable of more than we think.

Thank you for reading this week. See you next week!

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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]