I'm a mid level manager at a financial firm. I have a handful of supervisors that report to me. I recently got the news that one of my supervisors was going to another division in the company. My boss suggests we all have a meal with him and the rest of the supervisors to celebrate his achievement and his service over the last 3+ years. I ask this supervisor to put together a list of a couple ideas on where he wants to go for lunch downtown. Asian bistro, steakhouse, and upscale American place. Fantastic suggestions, I forward them to my boss. You guys pick it, I'll pick up the tab was the reply. So I sent the email back to my supervisor getting the promotion and told him to make the final pick. Steakhouse it is. I send out the meeting invite to all the supervisors and my boss for the agreed upon date and time. The day before we go, my boss gives notice that he has a meeting conflict, tells me to take care of the tab and he'll reimburse me. The day of, the 5 of us meet at the steakhouse for our reservation, are seated and look over the lunch menu. I encourage the guest of honor to order whatever he wants. His is around $100 and the rest of us order from the lunch menu. We all have a grand time and celebrate this supervisors promotion. Tab comes and I sign for it. $280 + $75 tip (they did a great job taking care of us). The next day, I send over a copy of the reciept in an email. Almost immediately I get a phonecall and berated for being highly irresponsible and spending so much money on a guy who isn't even leaving the company. He then proceeds to tell me how he had a similar circumstance with another division where they tried to spend too much money on a lunch. He then proceeded to ask me how he was supposed to submit this for expense. I told him since it became such an issue, not to worry about it, and I would be the one to cover the bill and that I would be a blessing to these folks (that our company allows us to do nothing for).
Now, hindsight being 20/20, I should have asked if there was a budget he had in mind and I'll be doing that moving forward. But, if you're going to admit you've run into this before, don't blindly approve something that comes across your desk, and also, for everyone's sanity, tell us not to go over a certain amount.