I’ve been thinking a lot about two conversations I had about bosses. Both of women I talked to were experienced managers in a software organization.

The first woman, Susan, has a reputation as a solid manager who produces results. She’s spent the last 10 years building solid teams, mentoring the people in her group, and producing software that is considered top-of-the-line in her industry.

Susan described her boss as very smart, but personally cold and manipulative. During the year she reported to that executive, the executive changed directions frequently and ignored her results. His criteria for evaluating Susan’s performance were never very clear. Toward the end of their reporting relationship, the executive told Susan she was incompetent … and then within a week expanded Susan’s responsibilities.

Lois has held a series of management positions in the same organization over the last 10 years. She described her boss as the best manager she’s ever had. When I asked what made her manager a great boss, she told me that her boss left her alone when she was feeling strong, and gave her help when she asked for it. And her manager didn’t ask her to do anything he wasn’t also doing.

Lois feels like she’s at the top of her game and would willingly follow her boss to another company.

Susan feels that she suffered psychological damage during the time she reported to the cold, manipulative executive. She found a different job.

That’s the kind of difference having a good boss can make.

The funny thing is that Lois and Susan are describing the same person.

Now, I know Susan, and Lois, and the mutual boss. (And I have my own observations about all three, which I may go into at another time.)

Buckingham and Coffman state that the relationship between an employee and his direct supervisor is one of the most important factors job satisfaction and whether employees stick around (First, Break All the Rules).

There are some things that great bosses have in common, and the rest is about a good fit. A good boss for Lois was a disastrous boss for Susan.

When you start with a new boss – through an organizational shuffle or a new job — find out what your boss expects and how he/she views your role. Find out what you’re really being paid to do, and whether that fits with how you want to spend a big chunk of your life energy.

Here are some questions you can ask:

  • What are the major objectives for which you are responsible?
  • What are the two or three things I must accomplish to be successful in this job?
  • What is the work environment you want to create? (if you get a blank stare on this one, watch out…)
  • When do you look to your staff for input?

    What do you want to know when you start working for a new boss? What questions would you ask?

    (Also see Interviewing Your Next Boss.)