Most projects don’t fail because the team lacked technical ability. They fail because pressure exposed weak leadership.
I learned this the hard way. After a nine-year NFL career, I transitioned into construction and business development. The parallels between football and construction became clear quickly. Execution is never tested when things are easy. It’s tested under pressure.
When you’re sitting across from a contractor who looks great on paper, credentials alone won’t tell you whether they’ll actually deliver. Nearly 60% of contractor failures are caused by one catastrophic project, often stemming from poor estimates or inexperience in a specific project type.
The real question is: how do they think, plan, and respond when adversity shows up?
Ask About a Project That Went Wrong
One question I always ask is this:
“Tell me about a time a project started going wrong—schedule pressure, manpower issues, unforeseen conditions, safety concerns—and walk me through exactly how your team responded.”
Anybody can talk about the projects that went perfectly. The real separator is how a contractor performs when adversity shows up. This shows me they are solution oriented and understand what project excellence actually requires.
Great contractors don’t just build projects. They communicate clearly, solve problems early, protect the schedule, maintain safety standards, and keep teams aligned when challenges arise.
I pay attention to whether they speak about:
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Planning and preconstruction
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Accountability
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Safety culture
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Communication with ownership and trades
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Workforce development
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How they handled people, not just the problem
The contractors who can execute professionally usually answer with specifics. What happened. What decisions were made. Who was involved. What they learned. And how they prevented it from happening again.
The ones who only sound good usually stay general and talk more about blame than solutions.
Listen for How They Talk About People
That’s usually the moment where you can tell whether someone truly leads projects or just manages paperwork.
When a contractor gets it right, they talk about people with ownership, respect, and awareness of how decisions affect the entire team. You’ll hear things like:
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“We pulled the trades together early.”
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“We slowed the schedule down for a day because the crew was getting stacked.”
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“We communicated directly with ownership before it became a bigger issue.”
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“We reassigned manpower to protect safety and avoid burnout.”
That tells me they understand construction is a people business first. Good execution comes from alignment, communication, trust, and accountability across the field, office, subs, ownership, and design teams.
The contractors who are just checking a box usually answer differently. They focus only on the technical issue, who was at fault, the paperwork, or how quickly they “pushed through it.”
You’ll hear a lot of “We handled it” or “We made schedule.” But very little about team coordination, safety culture, workforce management, communication, or protecting relationships.
To me, that matters because projects are rarely lost from one technical issue alone. They usually break down because communication fails, pressure builds, people stop speaking up, or leadership disappears when things get difficult.
Test Whether Leadership Stays Visible Under Pressure
When leadership disappears on a job site, it usually doesn’t happen all at once. It happens in moments.
It looks like:
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Problems getting ignored instead of addressed
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Field teams not getting answers
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Trades blaming each other
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Safety concerns getting pushed aside because “we need to make schedule”
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Superintendents carrying everything alone without support
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Ownership hearing bad news too late
You can feel it on a site. Communication gets shorter. Frustration rises. Small issues become expensive issues because nobody wants to make a decision or take accountability.
Before hiring a contractor, I think one of the best ways to spot this tendency is to ask questions around pressure and conflict, not just success.
For example:
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“Tell me about a project where the schedule started slipping.”
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“Describe a disagreement between trades or ownership and how your team handled it.”
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“What happens internally when unexpected conditions impact budget or schedule?”
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“Who communicates difficult news to the client?”
Then pay attention to how they answer.
Strong leaders usually speak specifically, take ownership, talk about collaboration, mention communication and planning, and explain how they protected people, safety, and relationships while solving the issue.
Weak leadership usually reveals itself through blaming others immediately, overemphasizing “pushing through,” avoiding details, talking only about paperwork and contracts, and never mentioning field teams, communication, or accountability.
One thing I’ve learned in construction is this: Anybody can lead when things are smooth. The real question is whether they stay visible, decisive, and accountable when things get hard.
Ask How Safety Collides With Schedule Pressure
Every contractor will say “safety is our priority.” The real test is what happens when safety collides with schedule pressure, manpower shortages, or financial pressure.
I recently had the opportunity to speak during Safety Week with CPG Beyond the Cloud, a company deeply involved in AI and data center infrastructure. One of the biggest points we discussed was how construction is becoming faster, more technical, and more complex, especially in mission-critical environments with high-voltage systems, advanced cooling systems, heavy logistics, and accelerated schedules.
Pressure exposes culture.
Anybody can talk safety during orientation. The real question is: What happens when the project falls behind two weeks? What happens when multiple trades are stacked in one area? What happens when overtime increases and fatigue sets in?
That’s where you find out whether safety is truly embedded into leadership or just written into a proposal.
One of the best ways to test this before hiring a contractor is to ask very specific pressure-based questions:
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“Tell me about a time safety impacted your schedule. What decision did you make?”
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“Have you ever stopped work on a critical activity?”
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“How do your supers handle schedule pressure from ownership?”
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“What happens internally when a safety concern delays production?”
Then listen carefully to how they answer.
Contractors who truly prioritize safety usually talk about planning and sequencing, preconstruction coordination, protecting people first, leadership accountability, communication between field and management, slowing work down when necessary, and learning from near misses and incidents.
The ones who are just checking a box usually answer with generic statements like “Safety is our culture” or “We’ve got a great EMR” or “We do toolbox talks.”
Those things matter, but they don’t tell me how leadership behaves under pressure.
Research shows that a strong safety culture correlates with reduced workplace incidents, increased employee engagement, and improved operational efficiency, with leadership commitment emerging as a critical element.
Real safety culture shows up in scheduling, in manpower planning, in constructability reviews, in lift planning, in trade coordination, and in whether field teams feel empowered to stop work without fear.
Because at the end of the day, the best projects are not the ones that simply finish fast. They’re the ones where every person goes home safe while still delivering quality execution.
Evaluate Their Understanding of Specialized Environments
A lot of contractors can list healthcare or data centers in a portfolio. What I listen for is whether they understand what makes those environments operationally sensitive and high consequence.
For example, through conversations and alignment with CPG Beyond the Cloud, one thing that stands out is how deeply their teams understand mission-critical infrastructure. They don’t just talk about “building data centers.” They talk specifically about high-voltage electrical systems, UPS redundancy, cooling infrastructure, white space integration, commissioning, sequencing around uptime, and QA/QC processes.
That tells you they understand that data centers are not normal construction projects. They’re operational ecosystems where failure has major consequences.
At The McDonnel Group, you see a similar mindset in healthcare construction. Strong healthcare builders don’t just say “we build hospitals.” They understand infection control risk assessments (ICRA), interim life safety measures, phased occupancy, working adjacent to active patients and staff, MEP redundancy, noise and vibration control, and shutdown coordination.
The connection between healthcare facility construction work activities and increased patient infection risks is well documented, with ICRA serving as a critical process that must be carefully planned and implemented.
That’s the difference between technical experience and operational understanding.
The contractors who truly understand specialized environments usually speak in terms of sequencing, risk mitigation, coordination, constructability, communication with operations teams, preconstruction planning, safety integration, long-lead equipment strategy, and commissioning and turnover.
The ones who don’t typically stay surface level. “We’ve done hospitals before.” “We’ve built data centers.” “We can handle fast-track schedules.”
But they can’t explain what actually creates risk, how they coordinate shutdowns, how they protect active operations, how they manage trade stacking, or how they integrate safety into planning before work starts.
Specialized construction is less about the building itself and more about understanding the environment you’re building around.
Ask What Preconstruction Actually Means to Them
That’s usually where you separate contractors who truly understand preconstruction from the ones who simply know the terminology.
Anybody can say “We’re collaborative” or “We focus on planning” or “We bring value early.”
What matters is whether they can explain exactly what they are doing during preconstruction to reduce risk before the field ever mobilizes.
Most schedule disruptions, cost overruns, and coordination issues in commercial construction can be traced back to decisions made before construction begins.
When a contractor genuinely understands preconstruction, the conversation becomes very concrete and operational. They should be talking about things like:
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Sequencing critical path activities
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Identifying long-lead procurement items early
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Evaluating trade stacking risks
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Coordinating shutdowns and phasing plans
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Constructability reviews with field teams
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MEP coordination before installation
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Logistics and crane planning
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Safety integration into scheduling
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QA/QC and commissioning planning
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Procurement timelines tied directly to schedule milestones
For example, in healthcare construction at The McDonnel Group, real preconstruction conversations involve “How do we maintain patient operations during this shutdown?” and “How do we sequence noisy work around active procedures?” and “How do we protect infection control barriers?”
In mission-critical environments like data centers, especially in discussions aligned with companies like CPG Beyond the Cloud, the conversation shifts toward “How do we coordinate commissioning with construction turnover?” and “What equipment has the longest procurement risk?” and “How do we prevent overlap between energized systems and active trade work?”
That’s when you know people are actually doing the work.
Another major sign is whether field leadership is involved in preconstruction. Strong contractors bring supers, safety teams, MEP leaders, and operations-minded people into planning early. Weak preconstruction usually stays trapped in conference rooms without field input.
The biggest giveaway, though, is whether they talk proactively or reactively.
Real preconstruction teams sound like “Here are the risks we see before construction starts” and “Here’s how we’d sequence this differently” and “Here’s where schedule compression could create safety exposure.”
The weaker teams usually sound like “We’ll figure it out in the field” or “We’ve built projects like this before” or “We’ll handle it when we get there.”
And honestly, that’s often where projects begin losing schedule, money, and trust.
To me, the best preconstruction teams are not just estimating projects. They’re actively removing uncertainty before uncertainty becomes expensive.
I say all the time: Trust is gained in drops and lost in gallons.
In construction, just like in football, discipline, preparation, teamwork, and the ability to adjust under pressure are what separate good teams from winning organizations.