Why My Best Clients Are the Ones Who Argue With My Automations
Picture this: Two clients walk into my office. The first one practically throws confetti, declaring me their automation savior before I've even finished explaining my proposal. The second? They squint at my presentation, cross their arms, and say, "Hold up. I'm not sold."
Guess which one ends up with the better system?
Spoiler alert: It's the skeptic. Every. Single. Time.
Here's the thing about pushback—it's not resistance, it's revelation. When a client challenges my automation suggestions, they're not being difficult. They're being brilliant. They're telling me things I didn't know I needed to know.
"But what about when Emily from accounting is on vacation?"
"This won't work during our busy season."
"You clearly haven't met our nightmare client, Bob."
These aren't roadblocks. They're treasure maps to a better solution.
Every argument unveils another layer of how their business actually works—not the sanitized flowchart version, but the messy, beautiful reality. That "annoying" edge case they bring up? It happens twice a week. That workflow exception they insist on discussing? It's actually their secret sauce.
The magic really kicks in when we stop seeing these conversations as me versus them and start seeing them as us versus the problem. Suddenly, we're not debating—we're building something together. They bring the deep business knowledge. I bring the tech expertise. Mix them together with some healthy friction, and boom: automation that actually fits like a glove instead of a mitten.
And here's something wild: The systems learn from your stubbornness too. Every time you push back, every time you say "but in our case..."—you're teaching the automation to handle real-world complexity, not textbook scenarios. Your quirks become features, not bugs.
The clients who question everything? They end up with:
- Systems that handle their actual workflows (including Bob)
- Fewer "oh crap" moments when edge cases pop up
- Automation that feels like a natural extension of their business
- Way less time fixing things that should've worked from day one
Meanwhile, my confetti-throwing friends? They're usually back in six months wondering why the "perfect" solution keeps breaking.
So if you're working with someone on automation (or honestly, any major business change) and you feel that urge to push back? Don't bite your tongue. Speak up. Question everything. Be the client who says, "Yeah, but..."
Because the best systems aren't built in echo chambers. They're forged in friendly fire.
Just remember: When I argue back, I'm not being defensive. I'm getting excited. Because I know we're about to build something incredible together—something way better than what either of us imagined walking in.
The path to an exceptional system is paved with productive arguments. And honestly? I wouldn't have it any other way.
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