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What is the most difficult conversation you have ever had with your boss?

I am looking at getting back into a corporate environment after running my own compnay, and it got me thinking about how different it will be to have a boss again. 

Answers

Chris Shumate
Title: Accounting Manager
Company: Dominion Development Group, LLC
LinkedIn Profile
(Accounting Manager, Dominion Development Group, LLC) |

One of the most difficult conversations I've had is when I told my boss that I would be in late, or that I needed to take a long lunch and he asked why. It's really hard to tell your boss "It's really none of your business". It is for me at least because of the relationship I have with him and the integrity I work to protect. Confessing that I have a job interview and the ensuing conversation surrounding why I'm interviewing always put me a difficult position.

As long as I protect my integrity I am confident that no matter what happens I'll be taken care of from an employment standpoint.

Randy Moore
Title: CFO
Company: SJB Bagel Makers
(CFO, SJB Bagel Makers) |

While I wouldn't recommend using "It's really none of your business", I would go with something like "personal business" or "Taking care of a personal matter". No further explanation would be necessary.

Chris Shumate
Title: Accounting Manager
Company: Dominion Development Group, LLC
LinkedIn Profile
(Accounting Manager, Dominion Development Group, LLC) |

Randy, thanks for replying. You're right, how one phrases that would make an impact on how well it's received- in most organizations.

I first tried to the personal business approach and my boss pushed and pushed, putting me in an uncomfortable position. I could just be a pushover though.

It would be nice to tell someone "it's personal" and that be that.

Anonymous User
Title: CFO
Company: Local Government Agency
(CFO, Local Government Agency) |

Good comeback Randy. But, I would argue as I so often do, that it "depends". There is no one size fits all answer here.

Bosses come in all flavors. And some are just damn nosy. They think they are entitled to know everything and anything about everyone.

And I say this not as much as someone who has been subjected to it, but as someone who is frequently a confidant of a boss and am informed by them of what they think about a particular employee's activities outside of work.

I work for a nosy CEO. So, I just lie. I don't like doing it. But, if I have accrued time off, I can take it as I please.

You wouldn't believe how many dentist appointments I have. :-)

Anonymous
(VP - FInancial Planning and Analysis) |

Having to admit I was unable to complete a task that had very high visibility in the company.

Anonymous
(financial controller) |

Having to tell my boss that we are not hitting the target for the month due to unexpected reason. No matter what reason is, it;s not easy to bring the bad news

Anonymous User
Title: CFO
Company: Local Government Agency
(CFO, Local Government Agency) |

The important question is, and every finance officer knows this experience: did they shoot the messenger?

Kathleen Busk Varas
Title: Consultant
Company: Varas Consulting
(Consultant, Varas Consulting) |

I actually went from running my own business to re-entering the corporate world. It has been quite a journey--interesting, challenging as well as just plain old hard at times.

As an entrepreneur, I had the luxury of being able to be much more transparent and authentic than is true in the corporate world. I loved my client relationships and being able to manage the levers that go with being responsible for the profitability and values of a self owned and operated business.

After returning to the corporate world, I had several challenging conversations with my bosses, where I was told that it was not my job to have an opinion or to make suggestions (sometimes they were just dismissed). I found it helpful to read some books about how to treat bosses and also to re-train myself on how to influence in the corporate world of finance. I continue to be awesome at working in cross-functional capacities...regardless of what particular area of finance am handling.

In addition, when preparing for this, I contacted several previous bosses and just asked them to help me out by sharing my strengths, areas (from their perspective) that I could have been better and some of their views on where I might fit in best. This was the best thing I could have done!

Anonymous
(Associate) |

I empathize with Kathleen. I went from a small company where I wore a lot of hats to a larger corporation where I was in charge of one department. If I didn't see something being done or done well in another department, I stepped in to help when I had to means to do so. I always tried to do this with respect and tact.
Like Kathleen, I was told to keep to my own department. I was written up by my direct supervisor at the demand of the Controller. They both called me in for the write-up. The tug of war in my soul was spirited that day. Should I sit there and take my lumps, or try to explain that all I was doing was trying to better the company? I'd be curious to know what books you read Kathleen.

Anonymous User
Title: CFO
Company: Local Government Agency
(CFO, Local Government Agency) |

More people need to be running their own businesses. It's a rewarding and viable alternative to subordinating oneself to idiots with egos and no self awareness.

Anonymous
(Fellow Chartered Accountant) |

I too went from running my own business back into the corporate world and have a supervisor who will not take - away for personal business as an answer. I now expect every request for time off to be met with interrogation and refusal.
On a helpful note - I would look for a mentor or coach who could help you transition from making your own decisions and being able to explain your vision to only being the transmitter of the plan. Learning how to support a decision you may not agree with would be very useful and having an ear where you can say why you are not supportive and work out a script for sounding supportive or deciding when you can no longer follow party line will be well worth the time and dollars for your own sanity.

David Dobrin
Title: President
Company: B2B Analysts, Inc.
(President, B2B Analysts, Inc.) |

I've been consulting with a single company for the last four years, so I've had a lot of opportunity to talk with people at many different layers. Before I went off on my own, I had my share of bad bosses, for sure. And these guys sound pretty bad. But I will say, too, that I now sympathize to some extent with the boss's desire not to have employees cowboying off and doing things their own way. This is particularly true when people are trying to "fix" the deficiencies of other departments. Most of the time, the farther off somebody is, the easier it appears to be to do their job and the more astonished you are when they do it this way, rather than the way that is "obviously" right. Almost always, this "obvious" perception is just wrong, and the time spent worrying about somebody else's work or somebody else's strategy is just time wasted.

Anonymous
(Accountant) |

Having to tell my boss that I believed he was stealing money from the company...talk about a difficult discussion!

Topic Expert
Christie Jahn
Title: CFO
Company: Prime Investments & Development
(CFO, Prime Investments & Development) |

I would say as many mention to expect it to be challenging to say the least. Will your employer allow you to work a flex schedule or is it a strict environment because that could make a huge difference. I think about things that really kept me up at night and they were not being able to meet a deadline, cash flow problems, and explaining we had a team member that was not contributing to the organizational goals and he was not doing anything about it, which was hurting morale. I wish you tons of luck and success.

Rich Robins
Title: Accountant
Company: Tec
(Accountant, Tec) |

I'll use direct language here. That I find them condescending. That I don't appreciate them complaining to me about their job. Giving me insight and FYI is fine. But I don't want to hear about the boss's problems. You complain up NOT down the chain. And of course, money.

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