You keep trotting out this excuse, but the responsibility is on the people conducting the drill to plan for that possibility and you're letting them off the hook.
If you're on a group hike/bike/ride/run, the group goes at the speed of the slowest person.
It may be that you didn't sleep well last night, or that your stomach is bugging you, but the reason it's going to take an extra hour today is because Tim has a blister.
Whatever is holding up that server is what's holding up the entire train of communication. If that is where $5000 will fix the problem, don't talk about any other problems, you'll just confuse management.
The next place to stop if that doesn't work is, if you can't fix "Tim's foot" can you offload some things "he" is dealing with? Dump some of his load, work steal, etc. But these are just mitigations.
Prove that you can do something about their problems
Explaining problems to vendors is work. If you can't give a reasonable assurance that the meeting will be productive, the people who have to take that meeting will naturally assume it will be a waste of time. No matter what my problems are, I'm not going to waste time talking about them with some company that's never done anything for me.
Just say, "It's a practical problem for us and if you don't fix it, I'll take our business elsewhere." If you can't take your business elsewhere, then you or your org dug itself a hole and is thus partly responsible. Never depend on one lone idiot. (Remember Jurassic Park 1?)
My point is Every single item on your list is fixable, don’t attempt to fix every one, start small and create a roadmap, and timeline. Hold people accountable especially contractors. You’d be amazed how quickly things get better when you hold people accountable.
Personally I want this kind of attitude on my team. We should not be cargo-culting stupid stuff. We should be clear about the problem and the solutions should be simple and direct.
I would add: overcommunicate everything you plan before you do and give others plenty of time to react to even simplest operations.
The company may have failed but when the proverbial truckload of shit hits the proverbial supersonic fan there will be tremendous pressure to find a culprit. A small peon might find himself/herself outnumbered and outgunned.
Take a proper holiday and give your team the space they need to show you that you're not a single point of failure. Give them a phobne number that is only to be called in dire emergency. Turn off data and Wifi on your phone.
Don't call it 'bullshit.md', call it 'challenges and opportunities.md', s/fuck|shit|cunt// inside and organize a series of coaching sessions about how you fixed one of these and how can they help themselves fix these.
or, channel your inner complainer into your promo-seeking behaviors.
If a problem bites you on the ass enough times, you'll either correct it yourself or run out of ass.
That is, it sounds like you've only suffered mild inconvenience so far, not any real consequence (failure to meet deadline, being reprimanded by boss for not making progress, etc.). Once that happens, it is a powerful motivator not to make the same mistake again.
Oh absolutely, I've got a lot of respect for that team. I'm just saying even if you're wiling to really go the extra mile this can still happen. I think the only way to really address it is to put the blame squarely where it actually lies, with the people doing it. Holding manufacturers to account does play a role in flushing these problems out into the open, but we need to be realistic about the limits of what we can expect from them.
"Down time is still on you" - well put. And it is actually great when you can only blame yourself because then you can fix the issue right away. If someone other is to blame, you need to a) convince that person that there is a problem and b) wait for the issue to rise to the top of their queue. Which can be painful.
You can ask customer service for help politely and constructively, without disingenuously (or passive-aggressively) stating that the problem is your fault.
If you want, you can acknowledge how you tried to fix it and failed (if that's accurate). But don't say that the problem is your fault unless it is.
(There are situations in which taking blame for a situation not necessarily yours might be a convention, but mistakes of vendors when talking with the vendor aren't one of them, IMHO. For example, you might take a little heat for colleagues, when appropriate, and all the CEO you're talking with needs to hear right then is, "Sorry, I don't have that for you yet; let me get that to you later today." Not "I've been pestering Bob since Monday for the dependency." Then you can go tell Bob that you two really need to solve this in the next couple hours. And if there's a larger problem, like Bob has been overextended by a family problem, or tasking has been unclear since a tentative pivot, then work it with management in the appropriate vertices of the org chart.)
The only thing you're doing wrong is pointing out that you mentioned it two months ago. That's the last thing an organization faced with a problem wants to hear. What they want is for everyone to act like the problem was entirely unpredictable and have everyone make 'heroic efforts' to make the fix.
Your professional laziness clearly has you in the wrong, and all you can muster is a snide, defensive "are you ok?"
I'd really advise you to work on that. There's a world of difference between "This is impossible" and "I can't be bothered to figure out how this useful thing others successfully do while managing billions of dollars of risk is possible." Otherwise, you risk professional stagnation.
Coming from the small business/startup world, to a giant enterprise, this is what I struggle with the most. I'm used to digging in the dirt to figure out an issue, and get it done as quickly as possible.
Having zero control over the infrastructure and having to work with various teams can be a pain whenever you want to make a change, but they have a silver lining in that production issues are usually not your responsibility.
But with their response times, you would think it's not their responsibility either...
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