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      Asking “why” at my previous job caused a lot friction for me. Also the first time it happened for me, because other companies did not seem to mind as much.

      But at the last, most people did not know why something was that way because the decisions were made by people before them, who had quit before they came along. Nothing was documented. Some took it as criticism and thought I questioned their abilities. After I told them that it is just to understand, they relaxed a bit. But still, the team mantra seemed to be: tomorrow we can do things to make it better, now we need to add this feature without many changes (also due to a very minimal test suite and a tech lead who was adverse to testing).

      As can be expected, the mountain of tech debt was enormous and it was expected to quietly agree that the “organic” growth to the current state was acceptable and preferred.

      I was fired after 6 months when I complained about being micro-managed by the manager (not tech-lead) who started a heated argument with me and insisted I kept adding features by adding rows into a Single Table Inheritance schema.

      In the end they offered to pay me for another 2.5 months, without having to do any work, so I was glad it ended this way.

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        Asking “why” at my previous job caused a lot friction for me. Also the first time it happened for me, because other companies did not seem to mind as much.

        Yeah this one is tricky. I very much agree with the author’s sentiment (or as I understand it) of being cognizant of just because something is in place, doesn’t mean it’s the best way, it may have just been entrenched and calcified over the years. Being new doesn’t mean just accepting the status quo in the absence of evidence.

        However, asking “Why” is hard because there are IMO two problematic cases:

        • Sometimes people ask why incessantly on every detail that eats time and energy from the team. Sometimes this points to a lack of documentation, others its because the one asking failed to look at the documentation and prefers to be told “why” or even uses it as a nervous conversation starter. This can be draining if prolonged.
        • Some people ask “why” as a leading question, or as a “gotcha” because they know a better way. This is also draining on the team and IMO not a great communication strategy.

        It’s usually easy to tell an honest “why” versus other forms, but it’s hard to articulate the difference. Honest “why”s are usually also OK with and can accept or improve answers such as, “Because X. Yeah we know it’s not great, but due to constraint Y it’s all we’ve had time to implement thus far.” or even, “Because no one has had the cycles to change it.” or “No idea? A better way didn’t exist at the time, and the effort to update it isn’t worth the cost at the moment.” Not that these are great answers, but they’re realistic and happen all the time.

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          You both raise good points. The context and sentiment of the “why” question is made more difficult to convey over text communication. It becomes even more important for the asker to ensure they provide context and a reason for asking the question to avoid negative feelings.

          I also realized I need to circulate the notes amongst the current team when new hires join so they are reminded to exercise more empathy toward new team members and assume more positive intent when being asked questions about their work.

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            Agreed that it can be problematic when the question is used in the ways you describe. Sometimes it helps to frame the answer by providing a possible answer like: “was it a business requirement?”. Maybe I should have grouped my questions and asked them during a scheduled meeting.

            “No idea” answer seemed to be the hardest answer to give.

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              “I don’t know,” is a fine answer. At a some stage of the company’s life, I feel there should be strong support to encourage folks to turn “I don’t know” to an actual answer, and write it down.

              Not sure what that stage is. Startups have a relatively smaller system that should be easier to document, but don’t have the time. Larger orgs may have the resources, but the system has grown too large and the original builders may have moved on.

              All that said, I do want to incorporate the idea of making it safe for new hires to answer, “I don’t know, but I can help figure it out.”

      🇬🇧 The UK geoblock is lifted, hopefully permanently.