Alright, let’s talk about often overlooked failures that trip us up as when driving change, more specifically in the context of digital transformations. Sometimes, those things don’t wave red flags; they’re more like tiny loose threads on your favorite sweater that, when ignored, eventually unravel the whole thin
We often hear that failing is learning’s best friend. Indeed true! But what about those failures that whisper instead of shout? The ones so subtle we don’t notice them until they’ve start building up and caused some good damage? It’s like grabbing that innocent ice cream after lunch, seems harmless once or twice, but fast forward a few months, and suddenly your favorite pants are staging a protest.
Well, I’ve learned when working with teams and organizations towards business agility, that these “ice cream” habits can lead to some pretty messy outcomes down the road.
Let’s go over two of those learnings!
Do It and They Will Follow
Oh, back in 2012 this one felt so right at the time! I was still a full-time software developer consultant and “transformation” was pretty much the side effect of the work I did with the client developer teams. I was convinced that if I just poured all my energy into coaching the teams, getting them buzzing with Agile goodness practices like shift-left, TDD, BDD and delivering value like rockstars, then surely the higher-ups, the senior leadership would see the magic, jump right on board, and pamper us with support. Makes sense, doesn’t it? Plant the seeds, watch them grow, and the whole garden thrives.
The Hard Truth: Turns out, those seeds often hit a concrete ceiling before they even are allowed to sprout. Teams would get fired up, ready to change the world (or at least their workflow), only to smack right into organizational roadblocks, budget freezes, outdated policies, managers who didn't get the memo. The teams would get stuck, frustrated, sometimes even before they could showcase that “meaningful value” I was constantly preaching on.
The Ice Cream Lesson: Don’t start with deep team coaching until you’ve got real, visible commitment from top management. You need leaders who aren’t just nodding along but are ready to roll up their sleeves, clear roadblocks, and champion the changes needed across the whole system. Without that cover, your work with the teams are just running into a brick wall.
The Speed VS Technical Debt Dilemma
Getting developers excited about Scrum, Kanban, daily stand-ups? Easy. Talking about the beauty of clean code, CI/CD, TDD, and all those technical practices? Even easier! I get genuinely giddy about it. I love this stuff!!!
Whether the teams were happily working on a greenfield initiative or dreading nightmares maintaining legacy systems, my mistake was thinking: “Right, let’s run some coding dojos! Give them a safe space to practice these tech skills, and they’ll naturally start using them every single day.” It was easy, as I figured that passion plus practice equals perfection.
The Hard Truth: The teams might be nailing Scrum, having sprint goals nicely crafted and often achieved, retrospectives getting insightful and concrete actions, demo-ing working software regularly. Good energy all around! But then… a subtle shift happens a couple of months later. Regression bugs started creeping up more often. User stories taking longer to finish. Velocity charts, which had gone upwards so proudly, started to dip, then plateau, then sadly trending downwards. It was like building a super-fast race car but forgetting to improve the engine, it looked great from the outside but clearly couldn’t keep with other cars.
The Ice Cream Lesson: The buzz and intensity of working in an Agile way are fantastic, truly energizing. But it can never be an excuse to cut corners on technical quality. Software craftsmanship isn’t a “nice-to-have” add-on; it’s the bedrock foundation. Continuous training, mentoring, and embedding practices like TDD and CI/CD need to be front-and-center priorities for every development team, right from the start, no matter how Agile they seem on the surface. Otherwise, you’re just contributing to build more technical debt even faster.
It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all — in which case, you fail by default.
I truly hope this week's episode comes as reminder that as coaches or anyone involved in driving a transformation, we need to keep our eyes open not just for the obvious storms, but for those tiny leaks that can eventually sink the ship.
What failures have taught you the most? Let me know!
