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Success doesn't always breed more success, sometimes it causes more harm later on and a small bit of skepticism is always welcome

This has been baking in the back of my head for quite a while now and it happened to me and the team that I am part of, at work, in the last couple of months. I think it is worth analyzing what actually happened and worth keeping the lessons learned in the back of your head all the time, especially during estimations.

Now on with the story. Initially when I joined the company I currently work at, we started slowly doing work and getting to know the application with its business logic. We had a lot of doubts in the beginning. So during the estimation meetings at the beginning of a sprint, we were constantly unsure of the tasks that we had to estimate. At first glance this seems like something bad but it actually had a silver linning. That doubt kept us analyzing the tasks that we had to do more in depth. We also looked into existing code more often which helped us too.

And quite often we would discover hidden issues that at first glance were not so obvious, issues like hidden dependencies between tasks, more required changes that were not so obvious at first glance, special edge cases which had to be covered or incompatibilities between newly designed features which had to be implemented and the existing ones or even between the newly designed features themselves.

Eventually we were lucky or unlucky, depends on how you see things, and we got pretty successful. After a while we learned the application pretty well and we didn't have to waste so much time learning the application when starting a new task. We delivered a lot more features and effort with each consecutive sprint. Everyone was really impressed by our progress, including us.

But we weren't aware of the fact that we were becomming more cocky and full of ourselves. This led us to stop analyzing the tasks so deeply during the estimation meetings. Which caused to underestimate quite a few tasks, which in turn made us seem like we were delivering less and working less when actually things were much more complicated than we initially anticipated. We only superficially analyzed them and didn't look inside the code as often to get a sense of what changes they might imply.

We also became more friendly with one another. This caused us to agree with each others opinions and ideas without scrutinizing them enough. It's good if everyone gets long, actually it is crucial, but should try to look for faults and downsides in your colleagues idea even if you get along really well.

It took a while to get things back on track and this is where the sprint reviews and retrospectives really came in handy. It was our chance to explain to the customer that things were much more complicated than initially anticipated and come up with a proper explanation with sound arguments as to why things turned out badly.

Now thinking back, there should always be a healthy dose of skepticism during estimations. In small doses, skepticism makes us think things properly and in depth. On the other hand, too much of it makes us get lost in details so much that we forget the bigger picture.

It can be really slippery and it can happen slowly enough for people not to notice it. I actually read about this on the internet and it's actually a phenomenon that happens in other fields such as the army. In the israelian army they have a technique especially dedicated to situations like this. In any group of people when making a decision, at least one person is designated by default to disagree with everyone to force the entire team to analyze things thoroughly. To be honest, during meetings I am the guy that kind of guy that disagrees with everyone just a bit to make sure that they thought things through.

This doesn't happen at a small scale like it happened to me and the team that I am part of. There are quite a few big companies that fell in this trap, companies like Microsoft, Nokia and so on. Not all of them managed to recover from this. I will leave the talk about big companies here because it has already been talked enough everywhere on the internet and many people are sick of this.

Another place that this can happen is during interviews. It actually happened to me quite a lot of times when the interviewer asked me to solved a very well known problem, I became full of myself and after I finished implementing the algorithm/solution I didn't test it properly. Speaking of testing, a healthy dose of doubt and skepticism forces you to think of every possible edge case to test after you have implemented something at work. Too much of those can cripple you and force you to test every redundant case.

So in the end, a little bit doubt and skepticism should always be present, they are healthy up to a point. And everyone should have this reflex properly embedded in their behavior to analyze when the are becoming way too sure of themselves before it causes any damage.





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