Technology Health Checkup
10 questions every construction executive should be able to answer
Assessment
Nobody schedules a checkup for fun. But most contractors we work with have a sense that their technology situation could be better. Maybe the outsourced IT provider is fine but not great. Maybe the company has grown and IT hasn't kept up. Maybe nobody is quite sure what "good" even looks like for a company their size.
These 10 questions are drawn from the same diagnostic framework we use when working with contractors on their technology strategy. They're not technical questions. They're business questions with technology implications. The ones that make you pause are the ones worth paying attention to.
Here are 4 of the 10. Try answering honestly.
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Complete the form below to download this tool.1. Who is the person directly responsible for IT at your company? What's their title, and what else is on their plate?
Why this matters: This tells you whether IT has dedicated leadership or is a side responsibility someone inherited. A dedicated IT leader can plan ahead and align technology with business goals. Someone juggling IT alongside facilities, fleet, and office management will always be in reactive mode because IT gets whatever time is left over.
What your answer might be telling you: If the person responsible for IT "fell into it" because they're the most computer-savvy person in the office, that's not a criticism of them. It's a structural problem. The role outgrew the original assignment, and nobody adjusted.
2. Do you have a documented annual IT budget, or does technology spending come out of general overhead?
Why this matters: A budget is a plan expressed in dollars. If there's no IT budget, there's no IT plan. Technology spending becomes invisible at the executive level, and nobody can tell you what IT actually costs the company per year. That makes it impossible to evaluate whether you're spending too much, too little, or on the wrong things.
What your answer might be telling you: If you don't have a budget, every IT decision is being made ad hoc. Companies without IT budgets consistently underspend on prevention and overspend on emergencies.
3. Once your devices are deployed, how much control does IT have over them? Could IT tell you right now what software is installed on any given laptop in your company?
Why this matters: There's a difference between owning devices and managing them. If employees have full admin rights, every machine is a unique configuration within six months. That means higher support costs, bigger security exposure, and no ability to remotely wipe a lost or stolen device.
What your answer might be telling you: If you're not using an endpoint management platform, IT is flying blind on what's happening across your device fleet. Your software sprawl problem is worse than you think, your security posture has gaps you can't see, and a lost laptop is a data exposure event with no mitigation.
4. It's Friday at 3 PM. A superintendent's laptop dies at a jobsite 45 minutes from the office. He has a Monday morning owner meeting and his presentation is on that laptop. What happens?
Why this matters: This scenario tests several things at once: whether IT support reaches the field, whether files are backed up to the cloud or live only on local drives, and how quickly the company can respond to a technology failure with a direct business consequence. The situations that cost contractors real money rarely happen at the office during business hours.
What your answer might be telling you: Think about who actually solves this problem in your company. If the answer involves the super driving to Best Buy, IT has no field presence. If "he'd just log into another machine because everything's in the cloud," your infrastructure is more mature than most. But ask yourself whether that other machine actually exists at the jobsite.
