4 Mistakes Contractors Make Running Multiple Jobs

Ever tried juggling 10 or 15 projects at once?

Yeah, me too.

Mostly spec homes, with a couple of custom jobs thrown in. It’s like riding a unicycle while juggling flaming chainsaws — and, of course, the wind’s picking up.

At first, it all seems manageable, until suddenly, it’s not. Deadlines slip, subs disappear, and clients start asking questions you don’t have answers to. But don’t worry—I’ve made the mistakes so you don’t have to. Let’s break down the four most common screw-ups that happen when managing multiple projects, and more importantly, how to avoid them.

Poor Communication Across Teams

There was this one time I figured my crew knew what was happening on each site. We had check-ins, texts — the works. Then I show up at a jobsite and it’s a ghost town. Subs? At the wrong house. Materials? MIA. Client? About to blow a gasket.

When you’re running multiple projects, clear communication is non-negotiable. If you’re not on top of it, things go sideways fast. Assuming people know what’s going on without clear, centralized communication? That’s a rookie move I won’t make again.

Resource Mismanagement

Ever tried moving 35-foot trusses that were delivered to the wrong site? Yeah, I have. And no, you’re not throwing those back on the truck like a box of screws. We had to drag those beasts two blocks with a Lull while the crane just sat there, running up the tab.

If your materials and crews aren’t where they need to be, when they need to be there, your whole project grinds to a halt. And trust me, the crane operator won’t be thrilled about sitting idle while you scramble to fix it.

No Centralized Project Tracking

Here’s a killer—thinking you can track everything in your head. I tried that (too many times). Next thing I know, I hadn’t checked on that one pain-in-the-ass project for a week. Showed up, and of course—deadlines blown, materials missing, and the client’s ready to send me packing.

Trying to keep track of multiple jobs from memory? That’s like herding cats. You’ll lose track of the details, and pretty soon, stuff starts falling through the cracks.

Overcommitting (and Then Under-Delivering)

I’ll admit it—I’ve overcommitted more times than I can count. It’s easy when clients are ready to sign checks, and you think, “I can handle this.” Next thing you know, you’re running from site to site, putting out fires, and telling clients, “It’s almost done,” while praying the subs actually show up.

Overcommit, and you’ll end up delivering half-finished projects and dealing with clients who are less than thrilled. It’s a hit to your reputation, and trust me, it takes time to recover.

Wrapping It Up

Managing multiple projects doesn’t have to feel like juggling chainsaws. If you can dodge these four mistakes—communication, resource management, tracking, and overcommitting—you’ll keep things on track (and keep your sanity).

Here's the good news…

I've been working on something that'll change the way you manage projects. It's called ContractorOS — a customizable tool designed to keep everything organized, no matter how many jobs you've got going.

We're still building it (literally adding a couple of automations right now), and we're looking for a few more beta testers.

Why ContractorOS?

• Streamlined Communication: Keep your team on the same page with easy to access updates.

• Efficient Resource Management: Make sure materials and crews are where they need to be, when they need to be there.

• Centralized Project Tracking: Stay on top of every project without relying on memory or scattered notes.

• Prevent Overcommitment: Get a clear view of your workload to make informed decisions.

Interested in giving it a spin?

We're offering early access to a select few who want to simplify their project management and provide us with valuable feedback.

Here's how to apply:

1. Click the link below:

   »»»»» Apply for ContractorOS Beta Testing

2. Fill out the quick application: It'll only take a few minutes.

3. Wait to hear from us: We'll reach out if it's a good fit.

If you do plan on taking ContractorOS for a spin, you will need to Download Notion Here

That way I can invite you in and help get you up and running.

If you're ready to stop juggling flaming chainsaws and start taking control of your projects, I'd love to have you onboard.

Looking forward to hearing from you.

Cheers,

Keith

P.S: Do you currently use any project management software, or are you still flying by the seat of your pants? Either way, ContractorOS might be just what you need. Apply now and let's make your life a whole lot easier.