• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

When do you tell your boss?

By
Stanley Bing
Stanley Bing
Down Arrow Button Icon
By
Stanley Bing
Stanley Bing
Down Arrow Button Icon
June 16, 2009, 11:48 AM ET

chimpsThere 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.

About the Author
By Stanley Bing
See full bioRight Arrow Button Icon

Latest in blogging

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Most Popular

‘This is the way’: Elon Musk endorses Warren Buffett’s famed 5-minute plan to fix the national debt
Economy
‘This is the way’: Elon Musk endorses Warren Buffett’s famed 5-minute plan to fix the national debt
By Jacqueline MunisMay 10, 2026
18 hours ago
OpenAI CEO Sam Altman says Gen Z and millennials are using ChatGPT like a 'life advisor'—but college students might be one step ahead
Tech
OpenAI CEO Sam Altman says Gen Z and millennials are using ChatGPT like a 'life advisor'—but college students might be one step ahead
By Sydney LakeMay 10, 2026
19 hours ago
'Employers are increasingly turning to degree and GPA' in hiring: Recruiters retreat from ‘talent is everywhere,’ double down on top colleges
Future of Work
'Employers are increasingly turning to degree and GPA' in hiring: Recruiters retreat from ‘talent is everywhere,’ double down on top colleges
By Jake AngeloMay 9, 2026
2 days ago
Red flag test: former CEO explains why he rejects job candidates who say they can start right away
Success
Red flag test: former CEO explains why he rejects job candidates who say they can start right away
By Orianna Rosa RoyleMay 9, 2026
2 days ago
Trump thinks he's flying to Beijing with leverage. China spent 6 years making sure he doesn't have any
Commentary
Trump thinks he's flying to Beijing with leverage. China spent 6 years making sure he doesn't have any
By Steve H. HankeMay 10, 2026
21 hours ago
Ted Cruz says the quiet part out loud: Trump accounts are Social Security personal accounts as GOP senator reveals 'dirty little secret'
Politics
Ted Cruz says the quiet part out loud: Trump accounts are Social Security personal accounts as GOP senator reveals 'dirty little secret'
By Jason MaMay 9, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.