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4 hours of work. Gone in 2 seconds.

My brain had a complete fade and I just… did it. I felt absolutely dumb. No autosave. No version history. Just a sinking stomach and a frantic Slack to the admin who, bless him, could do nothing.

(Side note: someone else had done the same thing a fortnight earlier. He’s now looking into backups. Better late than never.)

I was bracing for half a day of pain. Then my colleague said, “Honestly? It’ll take you an hour.”

He was right. Door to door, starting from scratch: 60 minutes.

Here’s what that little disaster taught me about digital transformation:

  1. Planning is the real work
    I’d already done the thinking. Redoing the execution was easy. If your digital projects feel slow, you’re probably skipping prep.
  2. Familiarity with your tools is an asset
    The more time you spend in a system, the faster you move when things go sideways. That “wasted” learning time? It pays back when it matters.
  3. Backups aren’t optional
    Yes, obvious. And yet. If your team doesn’t have a backup protocol, you’re one bad click away from a very bad afternoon.
  4. Repetition is a skill builder, not just recovery
    Doing something twice locks it in. My second attempt was faster AND better. There’s a lesson in that for onboarding and training design.
  5. Share the pain AND the wins
    My colleague’s calm response turned a crisis into a quick fix. That’s what psychological safety in a digital team looks like.
  6. One person’s mistake is the whole team’s learning
    Two people deleted work in the same system within two weeks. That’s a signal, not a coincidence. Build processes from patterns.

Digital transformation isn’t just about tools. It’s about the habits, safety nets, and culture you build around them.

It’s one of the reasons I do what I do at Digital Team Coach. The tools are the easy part. The habits around them are everything.

What’s one “oops” moment that taught you something you’ve never forgotten?

To learn more about how I can help you streamline your organisation:


1. Grab a free copy of the free 18 Epic Solutions guide

Identify the most common crappy tasks and ways to resolve them so that you can get the best out of your team and technology. Download here

2. Join our DIGITAL FORWARD PROGRAM and transformation your organisation

If you know you need to transform online: I'm working with a few leaders for the next 8 weeks to help them get clarity with their digital strategy to save thousands of hours over $50K in the next year. If you'd like to start this month, shoot me an email with the word FORWARD, and I'll get you all the details.

3. Book a strategy call

If you have outgrown your systems or they are not serving you anymore or they just feel painful, then book in for a free strategy call to get clarity on your goals and arrange your next steps.

4. Work with me and my team privately

If you'd like to work directly with me and my team to save thousands of hours of wasted time each year... just send me a message with the word PRIVATE... tell me a little about your organisation and what you'd like to work on together, and I'll get you all the details.