The Ai-Native Attempt

Do It 5 Times Manually

November 6, 2026

I got the opportunity to speak at MAICON 2026 a couple of weeks back. Absolute props to the SmarterX team for putting on a wonderful event, probably my favorite yet.

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When building a new presentation for this type of show, I never really know what will resonate. So I try to pack in as much practical stuff I'd find useful as I can. A win in my book is if at least one person quotes something they found helpful on LinkedIn. PRO TIP: Set the bar for success low enough and you'll win most of the time.

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This year, in a presentation about building automated systems to help complete different tasks, the slide that hit home most was one I wasn’t expecting …

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“Do it manually 5 times.”

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The recommendation is simple. Before automating a task, do it yourself five times.

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The first time, you’re paying attention to how you do it. By the fifth time, your brain is trying to figure out how to do it better.

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Each time, write down the steps, the decisions you have to make, the complications that come up, and the little tricks you’ve discovered that make the work easier.

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Once you’ve got all that documented, take a hard look at the process. What can you simplify? What's unnecessary? What are you doing just because you've always done it that way?

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Then, and only then, start thinking about AI and automation.

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So, in a presentation all about automating tasks with AI, what stood out most was remembering to do the job by hand first. Honestly, I did not see that coming.

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I’ve spent a bit of time thinking about why that one stuck, and here’s where I’ve landed.

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Most of us aren’t hellbent on spinning up dozens of agents to tackle everything we do every day. All we want is a way to do our jobs smarter. And sometimes that means taking the time to write down the steps and figure out how to make it better before automating it.

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So before you automate any task with AI, do it yourself five times.

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