Nine Things to Ask Your Future Boss, the CEO

Since knowledge is power, know all you can about your prospective superior's habits, history, likes, and dislikes.

How to find that great next CFO job? Here is one tactic that you might overlook but should not: Interview your future boss, the CEO, as if he or she were the job applicant, not you.

Because when it comes to your career, knowing as much as possible up front about the company and person you might work for is probably more important than dazzling them with your résumé, presentation skills, and personal charm. Nobody, most of all you, wants that supposed dream job to turn into a nightmare, and one that ends with a rude awakening — another job search, and a lot sooner than you’d thought.

Besides, CFOs can rightly feel emboldened to question the CEO, who probably needs you as much as or more than you need the job, according to Eric Rehmann, co-managing director of the financial officers practice for recruiting firm Korn/Ferry International. (Rigorous due diligence, albeit on your own behalf, should impress any savvy CEO, anyway.)

“There aren’t enough good CFO candidates to go around,” says Rehmann. “The best ones have multiple choices.”

While a few straight-forward questions are obligatory and possibly useful, you’ll probably discover the most revealing information about your prospective CEO and organization through indirect questions — that is, those that appear to be about one topic but really are meant to elicit information about another.

And rather than ask questions that invite abstract, non-specific answers, get down to cases. Whenever you can, ask for examples of how the CEO and organization dealt with real-life situations.

“When they tell stories, they tell you a lot,” says executive coach C.J. Liu, principal of My Whole Life, and a former CFO herself.

To fully understand the meaning of those stories, and other answers, a CFO job candidate needs “two antennae: one to process the facts and the other to process feelings and impressions. Both are critical to get a complete picture,” says Jonathan Schiff, a Fairleigh Dickinson University accounting professor and founder of the Finance Development and Training Institute, an alliance of 15 global companies dedicated to deepening the bench strength of their finance organizations.

In other words, listen carefully for the subtext, or unspoken message, in the CEO’s responses.

And last but not least, a CEO’s answers probably won’t do you much good, Schiff points out, unless you first ask yourself a few tough questions. “The first step,” he says, “is to know yourself; then find the right match. Sometimes that understanding of one’s self is lacking.”

To help find the best fit for that next job, here are nine questions to ask the CEO:

1. What were the strengths and weaknesses, or what did you like and not like, about the former CFO, both in your working and personal relationships, and what are you hoping to change with a new hire?

Some CEOs can’t adequately articulate what attributes they’re looking for in a new CFO or what kind of relationship they want with a new finance chief, according to Rehmann. This question probes that issue for details. “You’re on more neutral ground talking about a third party, but you’re still getting granular detail about the CEO’s day-to-day relationship with the CFO,” he says.


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