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How to Test Automations: The "Try to Break It" Method That Catches Disasters Early
Alyssa Schaefer (aka The Business Cowgirl)
Saturday, September 20, 2025
If You Can Break Your Automation During Testing, It's Not Ready. Yet If It Doesn't Break During Testing, It's Not Ready. Here's the Approach That Catches Disasters Before They Cost You.
Last Updated January 25, 2026
Read Time: 8 Minutes
The Short Version
The secret to bulletproof automation is deceptively simple: test it thoroughly, try to break it, and have someone other than the builder do the testing. Test in a sandbox environment before touching live data.
If you can break it, it's not ready. A builder has preconceived bias about how things should work; a separate tester thinks through what you're not expecting. One client learned this the hard way and their automation quietly deleted contacts for an entire year because no one tested the edge cases.
Key Takeaways
- Test in a sandbox environment before testing in production (live data)
- The goal of testing: try to break it, if you can, it's not ready yet
- The builder should NOT be the tester; they're too close and carry preconceived bias
- Separate testing reveals how intuitive your designs actually are
- Test for what you expect to happen AND what you're not expecting
- You cannot automate a process you haven't first done manually
If you’re tired of “set it and pray” automations that might be breaking things behind the scenes, start with my free 3‑part mini‑course on building bulletproof automations inside the Winning Business Vault. It walks you through how to design, scope, and test automations properly so they save time instead of creating fires.
The Simple Secret Nobody Follows
We've covered the components of automation (trigger, criteria, outcome) and the rules for defining requirements (95/5 rule, thinking forwards and backwards, building with the end in mind).
Now for the part that actually prevents disasters...testing.
The secret is embarrassingly simple. And almost nobody does it properly.
Try to break it. If you can break it, it's not ready yet.
Best Practices For Testing Automations
Testing Rule #1: Try to Break It
This is the mindset shift most people miss. Testing isn't about confirming your automation works. Testing is about trying to make it fail.
When you test with the goal of breaking things, you uncover:
- Edge cases you didn't anticipate
- Criteria gaps that let the wrong records through
- Scenarios where the outcome is technically correct but operationally wrong
- Dependencies on data that might not always exist
If you can break your automation in testing, you've just saved yourself from a production disaster. If you can't break it despite genuinely trying, that's when you know it's ready.
Here's my honest take: if you test your automation and don't find at least one problem, I'd be a little worried about it. Either the automation is genuinely bulletproof (rare), or your testing wasn't aggressive enough (common).
Testing Rule #2: The Builder Should Not Be the Tester
This is crucial, and it's where most teams cut corners.
The person who built the automation comes in with preconceived bias about how it's supposed to work. They designed the happy path. They know which buttons to click in what order. They unconsciously avoid the edge cases because they built around them.
A separate tester thinks differently. They...
- Don't know the "right" way to use it, so they try things the builder wouldn't
- Ask questions the builder assumed were obvious
- Test for what they're NOT expecting to happen
- Reveal how intuitive (or not) the design actually is
When the tester breaks something, it's not a failure, it's the system working. You found the problem before your customers did.
Think of it this way: the builder is too close to see things they don't expect. The tester catches what familiarity blinds you to.
Not sure if your current tech setup is helping or hurting? Get your Tech Health Scorecard: 10 minutes, 25 questions, and you'll know exactly which part of your systems is draining the most time and money.
The Horror Story: Deleting Contacts for a Year (Whoops)
I promised a horror story. Here it is...names changed, lesson preserved.
I worked with Company X. They prided themselves on being tech savvy, so they built two automations both related to automatically updating contact records.
The first automation was designed to automatically associate contacts with accounts. Simple enough. The trigger was: when a new contact is created, match it to the right account based on email domain.
The second automation was attempting to sense duplicates and automatically delete records they didn't want...
Long story short...they had been accidentally deleting contacts for about a year.
The root of the problem was the exact same trigger activated these two contact automations, so sometimes they wanted to associate records together and sometimes they wanted to delete. Unfortunately, their automations weren't specific enough so they weren't in control of the outcome.
This is the risk you run when...
- Requirements aren't clearly defined (which email field is the source of truth?)
- Edge cases aren't tested (what happens with personal emails?)
- Testing doesn't involve trying to break things (does it handle non-business domains?)
A consulting bill would have been small potatoes compared to a year of lost leads!
Join the Winning Business Vault to get instant access to the full Building Bulletproof Automations mini‑course.
Pro Tip: Start Manual. Document It. Then Automate.
Before you automate anything, make sure you have a manual process that works. If you don't know exactly how to do something manually, step by step, you cannot automate it successfully.
I find everybody wants automation before they have a process. But how are you going to tell the computer what to do if you don't know what the process is?
Wrap-Up: The Cost of Not Testing
Automation is complicated. That's not a bug...it's the nature of telling a computer to make decisions on your behalf across thousands of scenarios.
My job takes hours of thinking to ensure the outcome is right the first time. Because the cost of not thinking it through? It's lost leads, broken data, angry customers, and that sinking feeling when you realize the computer was just following the terrible instructions you gave it.
If you've followed this three-part series, you now have:
- The framework: Trigger, criteria, outcome
- The rules: 95/5 rule, think forwards and backwards, build with the end in mind
- The testing approach: Try to break it, separate the builder from the tester
When you work with someone who's seen these solutions applied across industries, you build better designs in the first place. I've seen solutions for real estate agents work just as well for health and wellness businesses. It's about thinking outside the box to find the simplest, fastest solution that won't bite you later.
Ready to Build Your Automation the Right Way?
If you've got a workflow that needs to be automated or an existing automation that's causing more problems than it solves - the Automation Blueprint Intensive is designed exactly for this.
What it is: A 2-call, done-with-you consulting sprint where we:
- Map your current manual process step by step
- Identify Scenarios A, B, C—and the scary Scenario D you're worried will blow things up
- Design clear trigger → criteria → outcome flows
- Apply the 95.5 Rule so you know what should NOT be automated
- Deliver two build options (the Prius and the Tesla) with pros and cons
- Give you a visual map, written spec, and test checklist your team can build from
What you walk away with:
- One critical workflow mapped, de-risked, and designed properly
- A blueprint any implementer can build from without guessing
- A test checklist so you know exactly how to "try to break it" before it touches live data
This is the same process I use to prevent the horror stories, deleted contacts, double billing, broken handoffs, so your automations finally save time instead of creating fires.
→ Get the Automation Blueprint Intensive
This is Part 3 of the Build Bulletproof Automations series.
← Part 1: What an Automation Actually Is (Trigger, Criteria, Outcome)
← Part 2: How to Define Requirements (The 95/5 Rule)
Whenever You’re Ready, Here’s How I Can Help:
- Free 3‑Part Automation Mini‑Course – Inside the Winning Business Vault, learn how to design, scope, and test automations properly so they save time instead of breaking things behind the scenes.
- Automation Blueprint Intensive (Paid Working Session) – A focused 2‑call sprint where we map one critical workflow, design a bulletproof automation blueprint, and give you a clear spec your team can implement with confidence.
Prefer to watch? Catch the Quick Demo here:
FAQs
Q: How do I find someone to test if I'm a solo operator?
A: Ask a friend, VA, or colleague to spend 30 minutes trying to break your automation. Give them minimal instructions—just "here's what this is supposed to do, try to make it fail." Their fresh eyes will catch things you can't see.
Q: What if I inherited an automation I didn't build and don't fully understand?
A: Document what you can observe (trigger, visible criteria, outcomes), then test it with the breaking mindset. You'll learn how it actually works by seeing where it fails. This is often faster than trying to reverse-engineer the original builder's logic.
Q: How long should testing take?
A: For a simple automation (one trigger, straightforward criteria, single outcome), allocate 1-2 hours. For complex automations with multiple paths, budget a full day. The time investment is nothing compared to the cost of a broken automation in production.
Q: Should I automate everything that feels repetitive?
A: No. Some processes have too many exceptions (failing the 95/5 rule), some aren't worth the build time, and some are better handled by humans because judgment is required. Automation is a tool, not a mandate.
Whenever you're ready, there are 3 ways I can help you:
- Quick Content System — 30 days of content in 90 minutes. A content creation system that uses AI as a teammate (ethically) and sounds like you, not a robot.
- Winning Business Vault — A free member area for service businesses, consultancies, and agencies. You get all my scorecards, guides, video trainings, and future resources in one place, plus optional paid deep‑dives when you’re ready.
- Ecosystem Audit & Roadmap — We go under the hood of your entire tech stack, identify what's actually broken, and build your personalized roadmap to stop bleeding time and money on manual work.
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Howdy, I'm The Business Cowgirl
(aka Alyssa Schaefer 🤠)
Online Business Digital Architect and AI Strategist
- 10+ years building businesses online and developing backend workflows
- Senior-level experience in business process automation and CRM optimization for 8+ years
- AI integration specialist with 3+ years focused on practical business applications
- Unique combination of technical expertise and marketing creativity
- Proprietary methodology that leverages both developer-level tech skills and marketer intuition
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Customized Tech Solutions
- Quick Content System — 30 days of content in 90 minutes. A content creation system that uses AI as a teammate (ethically) and sounds like you, not a robot.
- Winning Business Vault — A free member area for service businesses, consultancies, and agencies. You get all my scorecards, guides, video trainings, and future resources in one place, plus optional paid deep‑dives when you’re ready.
- Ecosystem Audit & Roadmap — We go under the hood of your entire tech stack, identify what's actually broken, and build your personalized roadmap to stop bleeding time and money on manual work.
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