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If the hiring manager asked this question during an interview "If there is something that would improve your productivity, but your manager disagrees with it, should you still do it?"
I replied that I will try to compromise, but the HM asked the same question again.
Can this question be considered as a red flag? or it depends?
This question isn't about productivity, it's about conflict and how you handle it. In fact it's a slight variation on the standard "how would you handle a disagreement" question. The question is intended to find out whether you handle disagreements in a reasonable and professional way. As you become more senior you can expect to be asked questions like this more frequently.
In order to get a good answer you should work out for yourself what constitutes a good way to disagree with you manager and/or colleagues. Once you have worked out this (and there are plenty of blogs training to help) you can give a good answer to the question.
Some hints to help you avoid traps:
Of course these hints are not just to give you a good interview result, but also to handle real conflict well. Make sure you actually do handle conflict professionally.
This question is not any kind of red flag. It's a good sign, since it means that the company cares that it's employees are reasonable people to work with, which means the most obnoxious candidates are filtered out.
Here's the thing. Experienced employees know that managers value their productivity, among other things. They rarely just arbitrarily insist you do something a less productive way. Most employees value their own productivity above everything else. So for example, let's say one person wants to use a different tool with files in a different format from us all, and is so much more productive with this tool that the time for that employee to convert to everyone else's format when projects are done is much less than the time saved by working with that tool. Sounds great, right?
Until the day that employee is sick or on vacation and stuff happens and no-one can get to their files, or read them or understand them because others don't have the tool or know how to do the conversion. The time lost then is often even more valuable than day to day time, because something has gone wrong and needs to be dealt with immediately.
Or, maybe you're more productive if you work 1am to 9am. But this means if anyone asks you a question, they'll have to wait until the next day to see an answer. This pulls down the productivity of the entire team. Your productivity increase may not be enough to balance this.
Or, maybe you're more productive if you never test anything you write, just toss it to QA to deal with. Never update tickets, just move on without the bureaucracy to deal with. Never fill out a timesheet, attend weekly meetings, provide status updates, help your teammates ... overly selfish focus on your own productivity can be truly awful (I know, I've employed people like that, for a while, anyway.)
A smart answer is aware of this. I might say:
It depends why the manager disagrees. For example, if the manager explains to me that this thing to speed me up a little slows everyone else down, and that on balance the team would be better if I was a little below my absolute optimum, then I would do as my manager asks. Sometimes, managers disagree for other reasons: maybe they don't believe I'll be more productive. In that case I might ask to try it for a short time to demonstrate the improvement. Sometimes it's even just that the manager wouldn't like doing that: in that case I need to explain that I do like it and it makes me more productive. Communicating about the reason for the disagreement is going to be crucial to settling it. And of course, bottom line, it's the manager's team and if there is a process or policy that must be followed, I'll follow it.
No, that is an opportunity to turn the question around. "What do you consider 'improving productivity'? Is it helping the whole group? Is it better meeting the needs of the customer? Is it about reducing the maintenance costs over the next few years? What types of things would help you improve your team's ability to meet the customer needs?"
From a manager's perspective, an individual using tools, languages, libraries, IDE's, etc. that nobody else is using may make that one individual "more productive" while adding a large technical debt to the group. One common problem in software development has been a single individual doing things that nobody else in the group is doing. (For example, writing comments in a language that nobody else knows.) Managers really don't want this type of problem. They also don't want someone to come in and right away try to change everything that has been done and how the group is operating.
So, turning the question around is an opportunity to show how well you can fit into an existing structure while offering ideas for improvement.
No.
The question is vague, you should have asked for more details or a more specific situation.
If the question was about using unlicensed software in order to accelerate productivity, then a compromise is not a good idea.
