Small business employee struggles with new AI-obsessed manager, considers quitting when job gets too confusing: ‘He does not want to spend the money on compliant software, so I’m at a loss’

Author image for Melissa Knudson
Melissa Knudson • Writer
Oct 2, 2026 7:45 PM EDT

Will AI solve most work problems or create new ones?

A change of management in a company can result in a change of business direction. Innovation at work can be good, and new people have new ideas that can be very useful at times. That said, it can also mean disorganization, losing the business's path, and a whole team not understanding what their job actually is. This is to say, new ideas are great and very important, but they must be given after proper research and understanding of the area of work itself. 

That's the core problem in this story. An employee seeks advice after new management takes over, and the company's know-how goes out the window. The new boss needs extra help with tech, but doesn't want to invest in new personnel for that area. He also wants to implement AI, even when not fully understanding how it works. In this case, technology can be of great help in day-to-day work responsibilities, but it is also important to know how and when to implement tech tools. 

This employee seems particularly frustrated because there is no open line of communication with the manager in question. Even though they have tried to raise some concerns to the new boss, apparently they have been dismissed repeatedly. This is also a very important thing to have at the office: if you cannot talk to your manager about any work-related problems, solutions will not come anytime soon.

This employee appreciates work conditions and hesitates about changing jobs because flexible hours accommodate their study schedule perfectly. However, the situation continues to escalate as another employee decided to leave the company, meaning the workload is about to get more intense. Can poor management break a team? 

AI tools can be very tricky. It might feel like you're saving money by using them, but not hiring actual people to keep track of them and make sure things are working smoothly can also be a very big mistake. 

Whose side are you on? Is the employee right to be upset? Is the new manager actually implementing smart ideas into the workflow? Keep scrolling to read the full story to decide what you would do if you were in this employee's situation.

Advertisement
  • Tired employee listening to boss.
    via pixelshot

    Tired employee listening to boss.

    Stock photo unrelated.

  • Small business problems, my boss wont take no for an answer about using AI..

    Hi all, i am trying to get advice on how to handle this situation. for a little bit of context, i am the admin assistant for a sdvosb and a wosb. my operations manager passed away about four or five months ago and it feels like the business has gone down hill from there. i began working here about
    via OkSchedule2670
  • there. i began working here about two months before he passed and to be honest i got this job on a whim with no real solid office experience. during my time here i
    via OkSchedule2670
  • experience. during my time here i have definitely expanded on my knowledge and i am pretty much confident in my position now but the dilemma is my new/current boss is a business man. he used
    via OkSchedule2670
  • boss is a business man. he used to be in the army and retired and then he worked for another 20ish years a chief financial advisor for edward jones. all of that to say he is a very money oriented man.
    via OkSchedule2670
  • this brings me to our problem. my operations manager who passed was also a money oriented man but he knew how the business worked and managed it properly.
    via OkSchedule2670
  • with his passing, my current boss has taken over and my current boss was still around and present during the time my operations manager was still with us but he was not constantly present because he was still working at edward jones which he has now retired from. but still, he is now
    via OkSchedule2670
  • Office meeting.
    via Via Pexels ( Via Yan Krukau )

    Office meeting.

    Models pictured are not representative.

  • retired from. but still, he is now essentially our operations manager as well but the issue is he doesn't know HOW to handle operations. he is very simple
    via OkSchedule2670
  • operations. he is very simple minded, very quick to get frustrated when he is told we cant do things the exact way he wants, hes very frugal, but wants things done right but doesn't want to spend the money to hire an actual professional to do some of the things he asks.
    via OkSchedule2670
  • i was hired as the administrative assistant for this business but ive been here for about 8 months now and i feel like i am constantly doing other tasks that are not in my job description. it ranges from
    via OkSchedule2670
  • my job description. it ranges from doing it tasks to teaching my boss how to use his phone... and its getting to the point where i am uncomfortable because i feel so confused with what my job here is supposed to be. for a little more
    via OkSchedule2670
  • is supposed to be. for a little more context i am also part time army and my army job is in the tech field which is why i think he asks. me about those kinds of things but the army does not teach me as much as id like so i cant always solve his IT problems and
    via OkSchedule2670
  • always solve his IT problems and it just makes me feel awkward because yes i do have some experience in it but it is simply not what i hired to do here. but to make matters worse, he can barely use his phone but he wants to integrate ai into everythingggg to mitigate paying professionals to do things for our business properly.
    via OkSchedule2670
  • Businessman talking.
    via Kzenon

    Businessman talking. 

    Image depicted solely for explanatory purposes.

  • i totally understand how innovative ai is and yes it is very helpful to do some things but he wants to use ai to keep a runnning track of our accounts receivables and payables. and
    via OkSchedule2670
  • receivables and payables. and ideally that would be great but we work with government contracts and there are regulations that need to be followed in regards to using ai for our expense tracking. but he
    via OkSchedule2670
  • our expense tracking. but he does not want to spend the money on compliant software to use so im just kind of at a lost. he also wanted me to try to build a compliant program using ai which is also out of my expertise range but he wouldnt really let me explain that to him. his
    via OkSchedule2670
  • me explain that to him. his response when i tried to tell him that was "youre just not confident in yourself, you can do it" which i interpreted as him essentially telling me to figure out a way to do it but again, not my job description.
    via OkSchedule2670
  • ideally i would quit but the job market is terrible and i am in college trying to get my degree and the hours at this job are flexible. this job certainly has its
    via OkSchedule2670
  • flexible. this job certainly has its perks but it also is still very disorganized and i simply do not have the experience to organize the entire business. i can only do
    via OkSchedule2670
  • the entire business. i can only do so much and my coworker is fantastic but she is about to leave so itll just be me and my current boss and i am terrified because not only will i have double the workload, ill also be the only one he can turn to for his tasks on top of daily operations.
    via OkSchedule2670
  • Exhausted employee.
    via Via Getty Images ( Via Boris Jovanovic )

    Exhausted employee. 

    Models for explanatory purposes only.  

  • any advice on ways to make the business operations more manangable or just how to help me deal with my boss's Al fixation would be great! thank you in advance!
    via OkSchedule2670
  • WallInside6758 At the end of the day, it's his business and his decision, not yours. You can give your opinion, but he doesn't have to follow it. If you can't handle that, move on to a company that operates the way you approve of.
    via OkSchedule2670
  • jsshapiro Document the issue in writing. When the contract issuers come after him, you won't be on the hook. Partly because you aren't in charge and partly because you documented.
    via OkSchedule2670
  • Using Al the way you describe him as wanting isn't so easy. When it fails, perhaps he will listen. Better still, perhaps you'll have landed a better job.
    via OkSchedule2670

Want More? Follow Us and Add Us as a Preferred Source on Google.

Tags

employee work place company policy work work life misunderstandings technology office life new manager new boss Office ai overworked-employees company
Scroll Down For The Next Article