There have been several kerfluffles around my office recently, all revolving around the same issue: What do you tell your boss and when? This would seem to be a simple question, but it’s not. First, it depends on the boss. Some guys (and in that category I, as always, include women guys) want to know nothing until it rears up and bites them in the butt, and then you should have told them. Others want to know what color tie or scarf you’re planning to wear next Thursday. And the target moves. On Monday, Chet may want to know everything. On Tuesday, you can’t rouse him from his slumber.

So what’s a poor employee to do? Take this quiz and see how sensitive you are. How you score may determine whether or not you have a future. 

1. You have a big party coming up and you’re trying to decide what canapes to serve. Do you tell the boss? 

a. No, that’s ridiculous. 

b. Of course! She likes to know every little detail! 

c. Not really, except I make sure to have those little empanadas she likes so much. 

2. You’re going on vacation next month. Do you tell the boss?

a. No. My life is my own! 

b. Of course. He likes to know every detail. 

c. I’m going to check the dates to make sure it coincides with his vacation as much as possible, but in the end I’m going to do what I have to do, making sure that he and his assistant know what my plans are. 

3. You’re going to have a meeting with a bunch of people about something that may or may not happen sometime in the future. Do you tell the boss? 

a. No! I’ll tell him about it when he needs to know. 

b. Of course. I don’t floss without telling him everything. 

c. Yeah, I’ll shoot him an e-mail, just an FYI. Some people are attending who may mention it to him and then he’ll feel like he’s out of the loop. He hates that. 

4. Your division is about to make a big deal with another company. It’s going to be announced next Tuesday. Do you tell the boss? 

a. I’ll tell her Tuesday morning. You know, give her a “heads-up.” 

b. I’ll tell her about the whole thing right now, before we even talk to Law and Public Relations. She’s going to want to go over this thing from top to bottom! 

c. I’ll get all the moving pieces started, and then dial her in, probably on Friday. That will give her the weekend to go over the paper and think about what we might have missed.

5. You’re getting a divorce. Your life is a shambles. Do you tell the boss?

a. Definitely! He’ll feel really sorry for me!

b. I’ll mope around until he asks me what’s wrong. Then I’ll tell him everything. For a LONG time. 

c. I’ll mention it. Since it’s not about him, he’ll have limited interest in it, but he ought to know in case I flake out a little bit in the coming months.

SCORING: Score yourself 1 point for every a. answer, which is a low score because you’re a really stinky communicator and a bad employee. Score yourself 2 points for every b. answer, because while you’re a suckup, you’re erring on the right side by reaching out and trying to make your boss aware of things. You’re likely to be a pretty big pain in the a**, though. Keep that in mind. Score yourself 3 points for every c. answer, because you’re clearly trying to address the issue with subtlety and modulation. You may not get it right every time, but you’re trying to play it a situation at a time and neither tell too much or too little. So good for you. 

As always, the higher you score, the higher your score. Give yourself a point for trying. Trying counts.

At this point, any optimism or upbeat thinking would be in the category of whistling past the graveyard, one where all the corpses have awakened and are bearing down on passers-by.

Looking at the events of the past few days, the question emerges: What kind of senior manager would you like to see in the corner office in the event of complete, life-destroying liquefaction? We’ve had a chance to see a number of styles on view: Paulson, Bernanke, the Congressmen attempting to satisfy Wall Street and Main Street concurrently, Obama, McCain, Bush… not to mention the host of gray-suited Commissars lining up from a variety of hobbled financial institutions to get a good pull at the bailout teat.

So… which kind of manager do you believe is best suited to confront such challenging seas and steer the corporate state back to some relatively safe port? Let’s choose:

Would you like a boss who gets very excited and angry, screams at people, and indulges in dramatic displays of bad temper? Or would you like a boss who is calm, thoughtful and spends a lot of time listening?

Would you like a boss who, when things grow dark, is full of threats and imprecations, scaring employees with vague prognostications of doom? Or a guy who puts his head down, studies the situation, and tries to see all the angles until he or she is convinced of what’s best for the greatest number of people possible?

Would you like a boss who hops all over the place like a Mexican jumping bean, hiding at times, then emerging with rage at people, cancelling appointments, rescheduling long-standing commitments, always trying to be all places at once? Or someone who seems to reside in the center of a hurricane, a safe place where people can go to give opinion, get counsel, and eventually direct orders? Whose strategic and moral center does not shift with the demands of the moment, even when they are, at least for the moment, insurmountable?

Would you like a boss whose ultimate solution seems to gravitate always toward the dynamic expression of his personal ego? Who picks odd moments to rush in like the cavalry, superceding line operators who have been working hard to attend to the details, who view their own exercise of Self as an important element of success? Or the guy who not only leads, but has respect for the management structure he seeks to guide?

Do you prefer a boss who surrounds himself with sycophants and attendants who defer all power and glory to their master? Or one who prefers to operate as the center of a nexus of smart people, all dedicated not so much to his person but to the strategic goals of the organization?

How about a boss who works each crisis for the greatest possible strategic advantage against the competition? Who employs a ton of PR tricks to manage the situation? Who seems often to make decisions based on how they will position him in the press and the public eye? Is that the kind of boss you like to work for? Some people do. Guys like that have actually run the world for several millennia, in fact.

I’ve worked for all kinds of bosses. And like I said: we’ve had a good look at the current crop in both the public and the private sector. An old senior officer of mine once said, and I think it’s generally true, that you can’t choose your boss. But let’s just say that in certain very important cases, you could. Which kind of boss would you choose?

Hidey ho, neighbors. It’s Monday morning and I’m back in New York with several thoughts in my head. One: Domestic Coach class really stinks. I mean, low-cost seating is one thing, but I don’t expect a piece of cheese to be wedged in my headrest.And yes, there WAS cheese. Old cheese. Seat hadn’t been vacuumed for weeks. My ancestors came over on a boat from Europe about a hundred years ago. The part of the boat they were on must have pretty much felt like I did before I got my very late, unexpected upgrade to the last seat in Business yesterday. Come on, dudes. Guys who fly on their own dime are people too. Attention must be paid! Thanks.

Two: Be it ever so mired in tension, politics and tedium, there’s no place like your office. As you know, I’ve been away for a bit. I got back to find a desktop (the real one) full of mail and my computer crashed from some incident that happened over the last few days. I rebooted and threw away a bunch of analog paper. It’s amazing how — now that everything of value is done electronically — there is not one single piece of snail mail that’s anything but useless. What a pile of mung! Note to Chase Bank: Stop sending me solicitations! I have enough credit cards! Haven’t you guys gotten tired of supplying credit to people? Save a tree!

Anyhow, here we are. In a few minutes, I’ll have some coffee. If I’m very lucky, nothing at all will happen in the next several hours before lunch. All of this while a beehive of activity goes on around me. Know why I can crank my yanker this way? Because I’m the boss.

This brings me to my request of you today. That’s right. Because my brain is almost utterly empty at this moment, I thought I would shift the work to you and ask you to do something. Know why I am allowed to gather wool in this particular fashion? Right again. Because… I’m the boss.

In case you haven’t noticed, bosses get away with a huge raft of behavior that normal people can’t. The bigger the boss, the greater latitude the individual has for work stoppage, labor shifting, on-the-job snoozage, feeding on company time, vague perambulation, digital invisibility, inexplicable vacuity, manipulation of time as a solid/liquid object that retains the properties of both a particle and a wave, that kind of thing.

I’m doing some research on the subject and would like anybody within the sound of my voice to consider the matter and then send along something bosses actually do to 1) have more fun, 2) do less “work” and 3) enjoy the “work” they do more, than the average person. I want real stories about real people. Bosses, send in your tactics and strategems. Employees, report on the ones you’ve personally experienced or even heard about. How does being a boss replicate the experience of actually being a retired person? Lots of golf? Mentoring the young? Sleeping during the day? Think about it. And lemme know.

Oh, and one last thing, vis-a-vis a certain recent controversy in this space: I write this blog. Nobody else does. There are no interns. There are no mini-Bings. What there are, of course, are people who are doing all the things I should be doing while I write this blog. Thanks to them. And to you guys, of course.

And hey, don’t get me wrong. If you want to toss a Bing Blog over the transom for my use, please feel free to do so, as long as it doesn’t get in the way of today’s real assignment. I’ll use it if I feel like it and ignore it if I don’t. I’ll take the credit if I like it and forget to say thank you. After a while, I’ll convince myself I actually thought it up in the first place. Know why I can do all these things?

Correctamundo!