In a small business with a flat organizational structure, where every exec performs 10-15 jobs, there is always a possibility of timeline conflicts. It's like cooking ten dishes on a four-ring range: eventually you run into a point when the same burner is needed for two pots. Which one to put on? There is really no such a thing as a right decision at times like that - you must simply follow your instincts.
Let's say your are in the final stages of negotiating a Credit Agreement renewal with your main institutional lender. It's Thursday, 03/13. You have scheduled a meeting with the bankers, their attorneys, and your own esteemed corporate lawyers for tomorrow afternoon to press on with a few remaining crucial changes before the deal is released for the approval by the bank's Credit Committee on Monday, 03/17.
At 5 pm your phone rings: It's your tax attorney hesitantly letting you know that his team must meet with you urgently tomorrow, because they just figured out that the company may have tax exposures in Illinois and Wisconsin; the extensions are due on Monday, 03/17 (somewhat hysterically); and, he is very sorry to tell you, but he is not quite sure about this and that's why they need to seat down and read you into the details of the Code, so that you can express your opinion, because nobody understands the business better than you do. No, it cannot be in the morning, because it's tax season and everybody's schedule is full as is; only the afternoon is workable for everyone who needs to be there (except you, of course, but who cares).
By the time you hung up, it's too late to reschedule the bank - most bankers leave at 5 pm, just like the government. Now, you've got a dilemma. Bank or taxes? Of course, you can tell the tax lawyers to suck it up and do their well-compensated jobs without getting you involved. Yet, you cannot - that's not how you do. But the bank is incredibly important: the last stages of negotiations are the hardest, because nobody wants to give up the last frontiers. On the other hand, you are literally the only person in the company who can express taxation opinions. At least the owner has been in a tandem with you on the contest of wills with the bank. However, he is easily mauled by financial predators if he is left on his own.
But what are you going to do? It's the balancing act - you have to optimize. You cannot be in two places at the same time. So you decide that the tax meeting is the one you must attend and send your boss to the other one alone. And, of course, you prep him on Friday morning. You go over all important points of the agenda with him and outline your position on every issue (in writing, for better retention). Then you silently pray to Hermes/Mercury, the patron god of all CFOs, and go on to your appointment.
You don't disturb him during the weekend, but as soon as he shows up at work on Monday (around 1 pm) you pull him into your office. "Well, tell me," you inquire. He beams at you: "Oh, it went very well. They practically accepted all the conditions on the list you gave me. You should have the amended Term Sheet by tomorrow morning." You are cautious: "Practically?" And he clarifies, "There is one item. They said they couldn't do anything about migrating from weekly reporting to monthly. But I figured that was okay, right? Just this one thing? And what? It's like a nine-line report, or something? Probably a few buttons on your system, right?"
Well, it's actually a 52-line statement with 5 supplemental schedules. It takes two of your staff accountants several hours to update all raw data and 2.5 hours of your valuable time every Friday to compile the reports. This was one of the top 10 most important items you've introduced into the negotiations right from the start. Of all items that's what he decided to let go? And what is it with bosses? Why do they always assume that everything you do is effortless - fast and easy? Just because you are toiling away without making any fuss?!
You feel like Zorg from The Fifth Element. "I am very disappointed!!!" growls Gary Oldman inside you. If you want something done correctly, you'd better do it yourself! Unfortunately, you don't have his powerful ZF-1 under your desk. So, instead of simultaneously throwing flames and blasting freeze-rays, you grab your phone like a weapon and calmly explain, "These weekly reports end up costing you a lot of salaried hours that can be used more productively otherwise. So, let me call and talk to them about it again."