When do you tell your boss?

Telling the Boss

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.

16 Comments Add Comment

Thanks for telling me that.


I agree with you on this one..communication is essential. But even when u tell the higher ups and they don't act on it, where should the finger point? There have been situations where I have informed VPs of pending MAJOR issues and they slept, and slept and slept; and all of a sudden they woke up and started screaming "The Sky is Falling", to which I replied "No worries chicken little, everything is under control"

Honest Bing, I made a perfect 16 points (including that point for trying). It's funny that we only get good at this sort of thing after 30 years of practice. Now I'm retired and don't need it anymore.


Scary - 3 out of 5 hit home at one point or another in my work life. More scary than that according to the Bing (no not Bing.com for you new comers) rating systems I have a serious future... Business is all about communication and Organizational Behavior based with in the culture, politics and last but not least covering your A#$. Smiles, positive reviews sprinkled with a small negative to keep you in line and all other methods of manipulation to attain objectives, and expectations are all link to one crazy boss's desire to succeed. If you play it right you can too.

I'm with Winston Salem Jim on this one with a couple of caveats.

Much easier to know than do and I'm only approaching retirement.

I still don't know which is more difficult, being a good boss or a good subordinate?

Very nice, Bing...I always enjoy your BizZen advice and tutorials...

I laughed out loud on option 5b (FOR A LONG TIME) so much that the cranky lady across the hall had to stick her head in my office and flash me a dirty look, as if to say "they should send you down to medical for a wizz-quiz...you gotta be smokin' something"

Thanks for the advice.

Sometimes the question comes down to...
"Who's Driving Your Plane?"

As teenager in the Marine Corps I learned a solid organizational truth; you can't be a good leader without being a good follower. And by 'good follower' I don't mean a brown-noser...I mean somebody who tries to get the job done, cares about the organization (which is really only rational if the organization gives a damn about you...something in short supply in today's world), and feels a sense of responsibility to subordinates as well those above.

In the many decades since, I have not been impressed with what passes for leadership in the business world. Most managers are focused 'up', and not particularly concerned about anything but their own careers and survival. They desire the rewards without accountabiliy...nothing is ever their fault.

They ignore timely warnings and valuable information from those lower in the organization, often in the hope that by the time trouble comes home to roost they'll be long gone (mostly because they have mastered the art of transmitting only good news to the toadies above...who are also structuring their work life on the same sh*tty principles). On occasion I've had the opportunity (and sweet satisfaction)to watch such managerial turds swing in the wind, reaping what they've sowed.

Your subordinates may not be powerful, but they are not powerless. A foolish manager confuses authority with knowledge. Disrespect and abuse does get repaid. A manager is much more dependent upon their good graces than one might expect.

Of course, in the business world such a managerial attitude is not really dangerous..(maybe Buffy won't get to go to a really good school)...but in the Marine Corps a young officer who treats enlisted marines with disrespect (all of which he outranks from the top of the payscale to the bottom) may well find himself not receiving the kind of information that will keep him alive. His disdain for knowledge and reliance on nominal authority endangers everyone. Grunts need somebody who can help them stay alive.

Anybody who scored anything on that quizz needs immediate attention to correct their heads,,, real people don't give a dam about canapes, confused vacation schedules and the rest of it.....okay the divorce thing might be juicey over coffee,,,,but lets face it....A Boss who needs information about company take overs from a subordinate is out of the loop and shouldn't be boss in the first place....best let the dummy wander around picking his nose until you replace him....

Want to know what happening in the corporate world ask the gal who makes the coffee.....they know everything and could probably run the whole shee bang better than the so called brains of the outfit...Want a good secretary pick a chubby one they work the hardest, are the smartest and are in tune with the world not their nails and hairdo...also they have the best sense of hummor....

Interesting choices. In each you completely left off "I'm a marrionette dancing on a string. I don't have to tell him anything because he doesn't let go of the ropes for an instant." I'm not sure what the score is. I only know how many aspirin it rates.

I thought the general rule of thumb was to tell your boss anything/everything that might get you in trouble had you not informed them. Everything else is discretionary.

Austin Mike, you have just articulated the upward management strategy that would get you a swift rap on the noggin if you worked for me.

Mike, Spokane, WA - NICE! That is called being responsible... not many managers know what it means to feel responsible for their grunts...back in the day they did but not anymore, disposable is probably the clearest way I could state the REAL connotation of the thought being written here. When in Rome...

Bing, I suspect you're a good boss, but don't like to be blind-sided by information (good or bad) that your subordinates should let you know about? Nothing like the deer in the headlights look that no manager can suppress when a peer brings up something everybody (including your trusted team) but you knows about. I hope you don't give a damn about which empanadas will be served, but maybe that stuff makes or breaks careers in NYC. Your obvious concern about a certain aged spaniel indicates otherwise.

Bing, to be fair to Austin Mike (and I think basic human decency requires that anyone dealing with a 'Mike'....the noblest of names, be unfailingly equitable....though I admit a certain bias); I don't think he was advocating keeping the boss totally out of the loop. By your own definition...a 'swift rap on the noggin' from the boss, I believe he would have included withholding said information as a violation of the precepts mentioned. Perhaps you were experiencing a cranky low sugar afternoon?. I hope you've not neglected the body's basic minimum daily martini requirement. Alcohol deprivation can wreak havoc upon our sense of humanity.

Even this Mike, in his more juvenile life-stages, enjoyed giving a bad boss bad (but quite accurate) news, particularly when the bad boss was ill equipped to handle the information.

Bing - if you were my boss I'm sure things would be very different. I adjust to the environment. I have had the same boss for a long time and she made it clear that if I am comfortable making the decision, I have complete authority to act. While this is an honor for me, there is a downside. She might not have picked up on the fact that I invented e-mail.