How to Choose an IT Company for Your Construction Business: 10 Questions Most Owners Never Think to Ask

If you run a construction company with 5 to 25 people, you probably already have an IT guy. And he probably does a good job at the thing you hired him for. The printer dies, he fixes it. New hire needs a laptop, he sets it up. Somebody locks himself out of his email, he handles it. That is real work and it matters. If you are still looking for the right fit, our guide on how to choose an IT company in Oregon covers the basics: after-hours response, what is in the monthly fee, contract length, and whether they know your industry.

Something I run into a lot, though. Nobody ever told you there was a second half of that job.

So you do the second half yourself. You pick the project software. You watch demos on your phone at nine at night. You decide whether the guys get tablets. You build the folder system, or you decide not to have one. And when it does not work the way you hoped, you figure that is just how it goes in this business.

It does not have to go that way. You would have no reason to know that, though, because you never had a reason to ask.

The questions below are that reason.

The part nobody explains

There are two different kinds of technology help out there and they get called the same thing.

One kind fixes what broke. You call, he comes, it works again. That is good service and there is nothing wrong with it.

The other kind starts somewhere else entirely. He asks how the work moves through your company. Where the hours come from. Where the photos go. What your office manager does twice that she should only do once. Then he builds around what he finds and keeps it running.

That second kind is what a managed service provider is supposed to be. Support is included, but support is not the point. The point is that somebody besides you is thinking about how your company runs.

Both are real jobs. Most owners have only ever been offered the first one. So take these ten questions to whoever you already have. You might be surprised what he says yes to.

1. Do you know what a change order is?

Start soft. This one is not a trick.

Most IT people have never once been asked about the actual business. They get asked about wifi. So this question is more of an invitation than a test.

A change order is money. It is also an argument waiting to happen if nobody wrote it down. Ask where yours should live. Email? A text? A photo on somebody's phone? If the answer is "I don't know much about that, walk me through it," that is a great answer. Curiosity is the thing you are looking for here, not a construction resume.

2. Can we walk through how a job makes money here?

Trace it out loud together. Bid, to job, to hours, to material, to invoice, to paid.

He will not know your numbers. He does not need to. He needs to see the path.

Every computer in your company exists to move that money from the field into your bank account. Once somebody can see the whole path, he can see where it leaks. It usually leaks in the same two or three spots, and those spots are usually fixable. Most owners have never drawn this out for anybody. Drawing it once is worth the meeting all by itself.

3. What happens to the photo my foreman just took?

Your crews take photos all day. Progress shots. Damage. The wall before the drywall covered it up.

Ask where those end up.

Almost always the answer is that they sit on his phone. Then he takes a job somewhere else and your proof goes with him. Nobody planned it that way. It just never came up.

Photos can land in the right job folder on their own, without your foreman thinking about it at all. That is a normal thing to set up. Most owners have no idea it is even on the table, so they never ask for it.

If you have ever had a crew that just would not use the app you set up for them, the problem is almost never the crew. Read why field crews skip the app and what actually works instead.

4. How many of my programs talk to each other?

Your office manager probably types the same information into two or three different places. She may have stopped mentioning it years ago.

Ask which of your programs already pass information back and forth. Then ask which two could be connected next.

This question gets the biggest reaction of the ten, because most owners assume double entry is just the cost of doing business. A lot of the time it is not. You usually do not need another app. You need the ones you already pay for to start talking.

5. Who does my field guy call?

Most IT support is built for offices. Desks, chairs, printers, wifi.

Your people are not at desks. Your guy is in a crawl space in Lebanon with one bar of signal and a tablet that will not open the plans.

Ask whether your lead guys can call directly. Ask if there is a limit on how often.

Right now that call probably comes to you, in the truck, while you are in the middle of something else. It does not have to.

This is the gap between your office and your jobsite that construction IT support in Oregon is supposed to close. Most companies are still carrying it themselves.

6. What would you tell me not to buy?

Ask it, then be quiet and give the man room to answer.

This is a kind question, not a trap. You are handing somebody permission to talk you out of spending money, and almost nobody ever gets that permission.

A good answer might be that the tool everyone is pushing right now is too big for a nine person crew. Or that you should clean up your files this year and buy the fancy software next year. Anybody willing to save you money right in front of you is worth listening to later.

7. What happens when I hire somebody in March and lose him in November?

Construction runs in seasons. You add people when the work shows up and you let some go when it slows back down.

Ask what that looks like on the technology side. Email, phone, the job folders, the login for your project software. Then ask what happens to all of it the week after he leaves.

Most companies handle this by hand and it goes fine, right up until it does not. Somebody still has a live login eight months after his last day. Nobody meant for that to happen. It just never got written down. This can be a ten minute checklist instead of an afternoon of hunting. Hardly anybody thinks to ask for it.

8. Will you get on the phone with my software company?

Your project software has a support line. So does your accounting software. When the two of them stop talking, each one will point at the other.

Ask if he will take that call for you.

A lot of owners assume vendor phone calls are their own job forever. Sitting on hold with a software company is not a good use of a business owner's Tuesday. This is one of the easiest things to hand off, and hardly anybody thinks to ask for it.

9. What does my next year look like?

Ask for a plan, not a fix.

The answer you want sounds like a schedule. Here is what we do in month three. Here is what we leave alone until fall, because you are slammed all summer.

That second part matters more than people expect. Good planning works around your season. Nobody should be moving your email over in July. If nobody has ever handed you a twelve month plan for your technology, that is not a knock on anyone. It just means the conversation never got started.

10. What happens to my files if I ever leave?

Ask this early and ask it of everybody, including me.

You want to hear three things. Your data is yours. Your passwords are yours. Everything gets handed over cleanly if you ever move on.

Ask for it in writing. A good provider will be glad you asked, because it is the same protection he wants for his own business. This is the cheapest insurance you will ever buy and it takes one sentence.

Take these to the person you already have

I mean that.

Start with your current IT guy. Some of them will light right up. A lot of good technicians have been waiting years for a client to ask them a real business question instead of a printer question.

Some will tell you plainly that this is not what they do. That is an honest answer and it is worth knowing. Then you get to decide whether you want to add that piece or keep carrying it yourself.

Go easy on yourself while you are at it. Closing the gap between your office and your jobsite is not a weekend project. It is usually a year of small changes that each hand your office manager twenty minutes back. Anybody promising to fix all of it in thirty days is selling you a feeling.