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I make lesson plans for a small education business. It's small enough that my boss is the owner of the company and tends to directly contribute and make changes to these lessons. My problem is that a majority of the time, his changes significantly reduce the quality of the lessons and overall make things harder to teach. I'm really passionate about my work and he understands this to some degree and avoids working on projects that I'm currently in the process of creating.

At first he used to run any changes by me, but my opinion on them was almost always negative, so I think because of this he's just started working on things once I'm done with them. For example, I recently came back to a lesson plan I hadn't looked at in a few months, and it was awful. I wish I could show a comparison of before and after his changes as evidence, but that's definitely outside of my NDA, so just imagine slideshows that are intended for children covered in small, detailed text and you get the idea.

In the past, I've let him do these types of changes and just tried to let it go, since the amount of issues is usually so substantial that it would be hard for me to politely recommend more than just completely removing his work. The problem is, he now wants me to do some work based off these modified lessons, but they're so low quality that it's genuinely upsetting to try and work with them. I've truly been struggling to do any real work because every time I look at it I just get frustrated and want to fix it or quit.

I know he trusts me to some degree, it's why I'm in charge of this program, but at the end of the day he's my boss and I feel that I can only say so much before I push things too much, and I already have a ton to say.

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    Have you tried providing detailed and actionable feedback on the changes your boss makes? Perhaps you can share some of your knowledge and experience with them which will benefit both of you. – Egor Jul 29 at 22:05
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    @Egor The detailed feedback I give has been a part of the problem. He didn't really have any sort of disagreement with the issues I originally had been giving him with his contributions, but I think the constituency of always thinking negatively about his ideas has led him to no longer want to hear my opinion on things, even if I might have a point. Not that he's being stubborn or childish, I think it's a natural reaction to hearing so much criticism from a subordinate. I just think because of how he's going about it, I have to be really careful with how I provide any more feedback. – Vera Jul 30 at 2:38
  • Specifically, as a boss I think he wants to make these changes and move on. I think I need to find a way to communicate that these things really are significantly impacting things negatively, and that it's not just me nitpicking and being overly negative instead of focusing on the LOADS of other work I could also be doing, as he probably sees it. – Vera Jul 30 at 2:43
  • Does this answer your question? How to better provide technical pushback without appearing defiant? – gnat Jul 30 at 5:21
  • @gnat although that's very helpful, my situation more deals with pushing back against his own work, more so than his own decisions. – Vera Aug 1 at 0:32
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While it may be the case that your boss's versions of the slides seem worse to you, you have to clearly make that case to your boss. Teaching is hard mainly because many of the signals given off by students may not actually be indicative of better learning.

For example, you feel that the slides your boss produces appear visually worse to you, and you find them harder to teach with. So, prepare a couple case studies and collect some data from the lessons (i.e., average student retention with small text slides versus clearer/larger-text slides). That would make for a strong argument and a great conversation. You will probably learn that your boss has some previously unexplained reasons for making the slides a certain way, giving you and your boss the opportunity to move forward with a better plan. You may in fact discover that your boss has been busy with larger problems associated with running a small business and doesn't have time to make his changes to the slides visually appealing or clear for children.

As for the older, modified slides that your boss wants you to use, I would make your own revisions to the slides, then bring them to your boss before you begin using them. Take the feedback seriously, even if you disagree, and suggest trying to use both (in a sort of "A/B" test), and seeing which format works best for the students. However, take this strategy with a grain of salt. Not all bosses are open to trying new things, even if there's evidence behind them (it can be hard to let go of things, especially when you have a personal stake in them!). So, always approach these things patiently and diplomatically, so that with time, things can improve.

It's also worth mentioning that quitting might be a good option, but it depends highly on the context. This is harder to give general advice on, and there are many more factors at play. In my limited understanding of the context, I hardly see a reason to quit just because of a disagreement over slide formatting (even though it may in fact be a significant issue).

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