How do you handle clashing with upper management?
Posted by SpecialistTeach9302@reddit | sysadmin | View on Reddit | 56 comments
As IT, we are the stress ball in the office I feel, management lashes out since they are having technical issues or whatever the case may be.
i wanted to ask how do you deal with managers or higher ups who you don’t agree with or are hard headed when it comes to changing the culture and bringing the company into the 21st century tech wise?
bschmidt25@reddit
I’m only middle IT management, but you CYA. You email your concerns and let them be known. You keep the receipts just in case. But ultimately, upper management / executives can make the call on what to do and they should own their decisions.
ChronoZaga@reddit
I got shitcanned. So, don’t clash with leadership and keep your resume up to date.
No, but seriously. Let your Manager fight those battles, and if they can’t, you go somewhere where they can.
gandraw@reddit
I got laid off for clashing with upper management once too. On the next job I had a 30% higher salary, and an office presence rule of "when it's necessary". And they had to hire a service company to update 1500 thin clients from USB sticks because my replacement couldn't figure out how to do it from the device management software.
So if you are confident about your resumé, absolutely do not be afraid of picking a fight with stupid management people if it's not about something trivial.
TheBestMePlausible@reddit
What year was that?
Flip2Bside24@reddit
Document my suggestions and move on with my life. They're paid to make the decisions. No skin of my ass if they make stupid choices
Tall-Geologist-1452@reddit
Long as my paycheck hits the bank … I don’t care . I will make my recommendations if they don’t want to follow then let me know in writing… if it gets to bad I will find somewhere else to work.
ErrorID10T@reddit
If I'm being told to do something I disagree with, I just tell them I'm going to follow up on the conversation with a project plan for their approval, then give the specific risks and reasons why I recommend against it in that email, and now it's no longer my problem if things go wrong.
ImpossibleParfait@reddit
Yep. Bring up your objections via email, kick back and watch the shit hit the fan. Kick back and say I told ya so.
Rdavey228@reddit
“Drink”
ImpossibleParfait@reddit
I know what i said.
Rdavey228@reddit
I’m correcting the saying as it’s wrong.
“You can lead a horse to water but you can’t teach it to drink”.
ImpossibleParfait@reddit
I know what the saying is...
Rdavey228@reddit
Not sure why you said it the way you did then….
ImpossibleParfait@reddit
Its a joke brother
Rdavey228@reddit
👍🏻 I’m over here wetting myself with laughter at that one. 😒
alpha417@reddit
Can't tell, with all the doubling down you're doing...
alpha417@reddit
Was it over when the Germans bombed Pearl Harbor?
cleansheet25@reddit
Yes! They pay me for my time. My advice is free, and they can take it or not.
SknarfM@reddit
For me, at the stage of my career I'm at, I'm paid for my experience, wisdom and advice. If the company doesn't want to follow it, it will eventually impact me. Likely as in OPs anecdote, via the blame game. At that point it's a judgement whether to move on or stay the course.
cleansheet25@reddit
Yes - this is where people document the decision. It’s a pretty standard format: provide the facts, list the alternatives, document which was chosen and why, email to the team as a decision record.
When it boomerangs around, it isn’t even a blame game thing. “We made some assumptions, didn’t work out, we need to revisit it”
Even in the most toxic of environments, this at least builds credibility and a sense of history and direction.
Corgilicious@reddit
This is a very important thing that I learned. I will do my best to research, document an issue or decision very well, and deliver that to my boss in a way that is easily traceable. If they choose not to follow that advice, well, that’s their right to do. But no one‘s ever gonna come back and ask me why I didn’t tell them better.
Especially when you are in a job, and you put your sights on a better place in terms of culture and processes, you really need to focus on what you can do. Do what you can do, put it out there, and then deal with the reality that results.
Changing culture is very difficult and takes time and seems to grow at a snails pace. But it can be done.
bbqwatermelon@reddit
This is the way
ZealousidealState127@reddit
Not giving a fuck but remaining professional is the way.
ContributionFit1243@reddit
Yup.
I do “real engineering” at home, because they pay me at work to do it their way.
ukulele87@reddit
Just get your recommendations and rejections on mail, cover your ass and continue with your life.
Dont try to be a shitty evengalist when its not needed, its not your company, if they want to stay on the stone age less work for you.
Muted_Image_9900@reddit
Culture change has to come from the top down.
JustAnEngineer2025@reddit
But the world revolves around IT (and cybersecurity)...
dhardyuk@reddit
No.
You are the fuel. A mere comestible.
norcalscan@reddit
I’m IT so obviously I know everything right? Yet…I learned a new word today.
JustAnEngineer2025@reddit
Anyone with any experience working in or with would know that is both a joke and also truth. There are way too many people in IT and cybersecurity that wrongly believe that businesses exist solely for their benefit and they know best how all businesses should be ran.
rickroepke@reddit
I love reminding my management that if they quit/leave, people will say “oh well”, but if I leave, people will say “oh crap”.
I remind them we’re all on the same team, and they have a job to do, just like me. Which is why I don’t “work for them” but either I work with them, or better, they work for me to get job done
spezisagiantdouche@reddit
that "oh crap" doesn't last nearly as long as you think. everyone, from ceo down to a l1 tech, is very much replaceable.
2_Spicy_2_Impeach@reddit
I quit/move on.
Unless you’re in senior leadership or someone wants to affect change that can, it’s not going to change. Your mental health is going to suffer because it’s not going to change.
Sometimes there’s a catalyst event that wakes folks up. Most of the time there’s not. The good folks leave, the good managers leave, and morale continues to tank.
But as others have said document everything. No hallway convos or lunch discussions. Everything with a written record, your concerns, and them saying “just do it.”
Won’t protect you 100% but it’s better than nothing depending on company/leadership. Also keep emotions/frustrations in check. Even if you’re right, it’s not worth it. Keep opinions to yourself with your team unless directly asked about something.
Might find a sympathetic ear higher up. But some managers resent someone going outside direct chain so that’s risky as well. It boils down to folks trusting your expertise and recommendations. If they don’t, time to start looking.
I had our C-level deny a product implementation for a team that was struggling. It’d fix a lot of their current pain and took six months to document/trial/shadow to make sure it was a good fit. At the last minute this exec said “no.” Not because we didn’t do what we needed but so it looked like he was doing his due diligence.
We had another team spend $150M on a product that wasn’t implemented after 18 months. And another $200M on a suite of products that didn’t work like they claimed. Exec didn’t want to get in trouble even though this was $500K — total.
I left about two months later for a new role.
1401_autocoder@reddit
I wasn't in IT, I was in the R&D division of an IT supplier. When all the "old guard" management had left - the engineers who originally built all the products, and been replaced by non-engineers - I retired. Boom. Took a few years to get to that point, but the disgust with management finally was too much to ignore. So many others had left that by the time I left, there wasn't anyone left that I knew well enough to hear how things were going.
2005 revenue - $6B ($10B adjusted), 2025 revenue $1.8B says it all, I think.
FarToe1@reddit
Work around them.
Don't bite back and don't correct them (unless you're in a meeting where it's appropriate and then do so with soft methods), always remain professional. Most C-levels are very sensitive to being undermined, and if you point out they're wrong, especially publically, they'll rarely forget, and forgive even less often.
Sometimes you'll turn one of them into an ally with this method - folk, even C-levels, can get embarrassed by their own behaviour in hindsight and will feel guilt. Sometimes they're just an arsehole and nobody can fix that.
If you flare up and push back, you won't appear strong, you'll appear problematic. Remember most of these people don't know or care how critical you are (or think you are), and if you're even mildly annoying then you're the first name they'll reach for when they need to cut costs.
If you're seriously annoying, that's unprofessional and they'll get rid of you quickly.
By calm. Learn the right way to say things. Phrasing is key.
You mention non-technicals, so learn and PRACTICE explaining technical things clearly, without being patronising. It's hard.
If they're unprofessional to the point of bullying, talk to HR. Reddit loves to say "but HR works for the company" as if that means they're always going to side against you, but that's not the case if someone is being unprofessional. They're damaging the company's reputation and potentially making it liable. In that situation, they are your ally. (Assuming they're worth a damn, and you work in a country with employee laws that are worth a damn)
Hierarchy is inevitable and important, chain of command critical in most businesses. Learn your place and how to use that to your advantage.
(Source: Personal. I was a CEO. I'm now a bob. I enjoy being a bob much more and am a much less angry person)
jason9045@reddit
I don't. Not my company, not my rules, not my culture. I'm happy to present information and to offer opinions when those are sought, but I'm not arguing about it.
OneSeaworthiness7768@reddit
This is really the only way to look at it IMO. You do your best to inform them of your recommendations. If they don’t want to implement it, it’s on them. I’m not losing sleep over their choices. If that environment caused too much strain interpersonally, then I’d be looking for another job. But I’m not arguing with anyone over their decisions.
Prepped-n-Ready@reddit
I just do the consulting thing where you offer three options with the pros and cons, but really theres only one good option. Sometimes you have to deal more with the psychologies of whoever it is. It can be helpful to have other people express your opinions or agree with them publicly. It can also be helpful to associate the decision with strong brands. With risk adverse people, you might have to address risk directly with some kind of mitigation plan. If you do SOC stuff or other risk stuff, you might have had to do the "Incident Management" process where they raise a risk to the board and all that. That kind of framework is great for risk adverse people. You need "Champions" to help you really influence people, people who talk about how smart and right you are all the time so when it comes to this conversation, theyre entering it feeling like they are talking to someone who is smart and right all the time. You have to market yourself better, improve your personal brand. Especially if you bump with them a lot.
One thing to consider is if they even have the same objective as you. Its easy for a sales guy to do this, because they want to capture the revenue and its not their fault if the cost to deliver is high. You really need to be in a position to negotiate how the billing will be arranged to internal cost centers. If you don't have that influence, its not really fair to expect you to clash with them and win. Because ultimately, they own the risks, and most people are risk adverse.
bjc1960@reddit
CEO calls me directly for help. He trusts us, takes care of us. People complain to him about us, but we always help him. He understands it is a 'thankless job."
SemicolonMIA@reddit
I clash
ninjaluvr@reddit
Don't let them stress you out? If management asks you to do something you disagree with, explain the risks to them and then do as they direct you. It's only stressful if you let it be.
harrywwc@reddit
The risks hit "best" if you can couch them in (big) dollar terms, or potential gaol time ;)
Or both :D
ProfessionalEven296@reddit
Use their language.
Bring every proposal down to money. "Doing x will cost $y. If we don't do it, the cost will be $z, plus damage to our reputation", etc.
Even more effective, "Our biggest rival, BlueWidget, is investing $xx into this technology. We can't be left behind"
Get a copy of the companies business plan (or last set of reports), and link your proposals back to line items there.
Get your proposals in writing, and keep a record of the rejections. Then, go home and sleep soundly knowing that the future issues are not going to be because you didn't do due diligence.
Sure-Assignment3892@reddit
You don't get emotionally invested in the job.
As long as I get paid, if the CEO says open Any/Any, sure. Sign here that I warned you not to do it.
Elensea@reddit
Documentation is a great cover your ass. I require a ticket for everything.
MyPhotographyReddit@reddit
I enjoy it.
bit0n@reddit
Everywhere I have worked the people who can’t deal with Upper Management have all been super arrogant do what I tell you types. But my first boss told me if you go to management and tell them something you fail. If you go and say we have this problem costing x amount. We have option a that will fix it or option b that fixes but costs 10 times more they agree much sooner as they get to make the choice. Our job is presenting the choice in the right way.
sardonic_balls@reddit
IT does not exist for culture change or pushing some kind of agenda. You're there to support the staff and company's technology related needs.
If managers don't want you to change process [x] in their department, that's their perogative, and you should defer. I've worked for so many IT directors who try to proseletyze/push change that execs or managers don't want and it ends up backfiring most of the time.
corruptboomerang@reddit
Outline the options in writing, outline the consequences of each in writing, outline what you believe they're planning to do and the consequences in writing... If they do a stupid they are doing a stupid, you've done all you can. That way, when shit hits the fan, you can be protected.
BootlegBabyJsus@reddit
I have started saying "I told you so, or this was an outcome I mentioned in the risk meeting."
I am close enough to retirement that a decent severance package would not break my heart.
JustAnEngineer2025@reddit
Do your job and let them do their job.
Give your valid recommendations and move on. Folks love to talk about which hill they will die on; but in corporate the answer is "none" unless there is a direct threat to you of prison and/or fines.
Want to increase your odds of persuasion? Learn to convey your message in in a language they understand; this is a major failing of most people in IT and cybersecurity.
iceph03nix@reddit
Give them the options available to fix what they want and what it will cost. They run the company, it's their call. If they're making your life hell in an unreasonable way, job hunt.
13Krytical@reddit
Document everything. Research thoroughly. Ask their perspective, reasoning, and motivations.
Make sure you understand the full picture, and push back professionally on the parts that matter for the business and moving forward.
Don’t try to make examples of them or get apologies. Be humble, they are the boss, you are trying to save them from themselves.
If they won’t listen, you try to save the business from themselves by following the proper chain.
If you’re doing things right, HR protects the business, which should be you over the boss, if you’re actually doing things correctly and pointing out business risks.
Helpjuice@reddit
You set hard boundaries and force accountability. They want something you get that request in writing. You don't like it, you put that in writing professionally while still getting the request moving forward and completed. When things hit the fan they can stare at their executive coworker that made the call and bash them behind closed doors. Enough bashing ends up with them leaving with the tradition "To spend more time with family" line but in actuality they were too much of a risk to the company. Exception is if they are a family member or C -Exec.
Other than that, not your problem and it makes no sense to get worked up about things outside of your control. Do your 40 and get out of there. If they are wanting OnCall you make them pay for it in some form of additional compensation equal or greater than the amount of time you have to work. As every hour worked uncompensated decreases your compensation per hour below what your agreed upon base salary was supposed to be.
Also be sure to keep your options open and stay very employable. If one job is approaching your limits send out that resume and get out of there before you reach your breaking point.
We are not the stress ball of anything, send them to the helpdesk if they need to complain.
ChaoticSalmon@reddit
Make whatever you want to do their idea. "If we don't upgrade/change this, and that thing breaks or otherwise goes down, that will result in a minimum down time of X and will cost Y to repair and will take Z long before it's all back up again. What we could do instead is n now or soon to avoid all of that." Then that's it. You've planted the seed. Let them think on it and come back once they've decided that it's a good idea (meaning they already told their buddies and higher ups that they're going to do it, pats on the back, great job, so on).
Document that you had this conversation - date, time, specifics, even if it's just in a personal log (I put everything in a personal OneNote doc organized by year and month) - so if what you want to do DOESN'T happen and then something breaks because of it, you have specific ammo to say well, I fought to fix this earlier, but I got told "no."
tc982@reddit
There is no one solution that works. It is about the type of management you have.
I always make a business case, describes why why need it. The return (not always monetary) and how it aligns with our set goals for us.
But again, it depends. Generally speaking you should talk about business outcomes (risk reduction, business continuity, etc) instead of technical details. But it starts with a strategy for IT.