A frustrated IT technician sitting at a desk, holding their head in their hands while looking at a computer screen filled with technical data and error messages, symbolizing project delays and client dissatisfaction in MSP operations.

I woke up in a cold sweat this morning. 

Nightmare? Not exactly. Just the aftermath of a conversation that stuck with me. Over dinner last night, one of our partners hit me with something every MSP knows too well but never says out loud: 

In IT, perfection isn’t optional—your clients expect it. 

Screw up a LinkedIn post? No big deal. Miss a deadline on a marketing campaign? Nobody’s coming for your head. 

But in IT? One wrong move, and suddenly your client is ready to burn down your five-star reviews and threaten your dog. 

Where IT Projects Really Fail (And It’s Not Where You Think) 

Here’s the truth: Most IT failures don’t happen during day-to-day support. 

They happen during projects. 

Migrations, software rollouts, major upgrades—this is where the stress levels hit DEFCON 1. Imagine showing up late to the airport only to find your gate’s changed, the signs are in Japanese, and now you’re sprinting to make your flight. 

That’s how your clients feel during every major project. 

Two Steps to Stop Your Projects From Turning Into Client-Killing Disasters 

I don’t have a bunch of options for you here, instead two simple steps will fix this. 

Step 1: Set the right expectations from the start. 

Be honest: “This is going to get bumpy.” We always warned clients upfront before kicking off any major project—especially if it hit the 5-5-5 rule: 

  • Affects more than five people
  • Involves more than five tasks
  • Takes longer than five hours

Once a project crosses those lines, expect turbulence—and let your clients know it’s coming. 

Step 2: Move fast, or pay the price. 

The longer a project drags out, the more likely you are to: 

  • Mess something up
  • Get stuck in the dreaded “in-between”
  • Lose your client’s trust

The fix? Break large projects into one-week sprints. 

Why does this work? 

  • It keeps momentum high
  • It shows constant progress
  • It lets clients see movement, fast

Small wins every week are better than one big win after six months of silence. 

What Does This Look Like in Real Life? 

Let’s take client onboarding—an MSP’s worst nightmare. 

Instead of trying to tackle everything at once: 

  1. Warn your client: This will be the hardest part of working together.
  2. Limit the scope:
    • Document users
    • Set up access portals
    • Train on ticket submissions
    • Deploy agents and security tools (EDR, MDX)
  1. Get it done in 7 days.

That’s it. No huge server migrations. No tenant hardening. Not yet. 

Once the basics are done, start chipping away at the bigger projects—one week at a time. 

Does This Work? 

Yes. I’ve done it. 

If you want to stop your projects from killing client relationships, this process will save you time, money, and sanity. 

And if you’re serious about taking your MSP operations to the next level, grab my best-selling book on running and securing MSPs: Level Up. 

Because your clients aren’t going to lower their expectations. It’s time to raise your game.