Questions to ask of a CEO.
September 27, 2011 8:31 AM   Subscribe

I've been selected to participate in a 'Leadership Pipeline' at the very big corporation I work for. I'll have a chance to participate in a one on one discussion with the CEO, COO etc. What questions should I ask of them in order to appear engaged and stand out while not seeming disingenuous or cloying?

Some questions that come close to what I might consider
-Tell me about your career path, what led you to your business focus?
-What skills does a good leader demonstrate?
-What advice would you give me, based on my background, to advance my career?
posted by BrodieShadeTree to Work & Money (18 answers total) 4 users marked this as a favorite
Ask them things you want to know to do your job better.
posted by Ironmouth at 8:38 AM on September 27, 2011 [1 favorite]

Response by poster: I don't come near reporting to these people, so they won't really have an answer to that. But you bring a good point about directness.
posted by BrodieShadeTree at 8:39 AM on September 27, 2011

Ask them -- politely and intelligently -- to explain the motivation behind decisions or programs that have come from on high that you hate or consider useless. They may be able to open your eyes to a bigger picture that includes a compelling reason for those things, or you may find that continuing to climb the ladder would necessitate altering your values in ways you find unattractive. Don't vocalize negative opinions. Never badmouth co-workers or bosses, however subtly, no matter how hateful or incompetent they are.

The impression you make will be made most strongly by being attentive, intelligent, well-spoken, and eager. Don't bother trying to pimp yourself; however subtly you think you're doing it, it will show. Don't worry about doing something memorable to make an impression; they may or may not remember you, but will probably have a more favorable lasting impression if you don't try to force the issue. So take the event at face-value and get everything you can out of it without agonizing over how you come across.
posted by kitarra at 8:49 AM on September 27, 2011 [1 favorite]

Have you done any research? Perhaps their administrative assistants can give you a canned bio or you can find one online / on intranet so that you can ask more focused questions.

On preview, ditto kitarra. There are always reasons for decisions you don't understand, and this is a prime chance to find out what they are. Also consider any answers your boss has given you that didn't sound quite right and ask for another perspective. Your boss might not have been wrong, but you might be missing part of the answer.
posted by momus_window at 8:52 AM on September 27, 2011

It's a bullshit fauxtivational ploy though, you know that. Leadership Pipeline - they imagine a bunch of underlings lining up to suck their cocks. Do what kitarra says: be yourself, be honest, and ask about their mistakes.
posted by fraac at 8:52 AM on September 27, 2011 [1 favorite]

I think fraac is on to something, actually. But you might phrase the question more like, "When the Leadership Pipeline was conceived of, what did you envision this program being? How has it changed our company?" or "What were the original goals of the Leadership Pipeline program, and have they changed over time?" Someone came up with the idea of this program because they thought it would be good for your company. Like posters above, it sounds like some kind of touchy-feely motivational horseshit to me, but if you play along, it'll be good for you and might even result in some insight.

If I could as a corporate CEO and COO some questions, mine would be along the lines of:
"Given the benefit of hindsight, what do you wish you'd known about the business of widget-making ten years ago?"
"What kinds of things do you do on a daily basis for work that no one realizes you do?"
"At the end of the day, is there anything you won't compromise on?"
posted by juniperesque at 8:55 AM on September 27, 2011 [1 favorite]

I'd personally get at the following: you - Brodie - presumably work in a department that handles a specific focus within the company. The senior level executives meanwhile are looking at the bigger strategic picture, such as long term corporate goals, how your industry is evolving over the next decade or whatever, new opportunities that currently aren't on people's radar screens, etc. So ask them about that stuff, and how your department can help the company achieve those goals.

That way, you'll be able to anticipate what will be happening in your department and make moves accordingly.
posted by Spacelegoman at 8:55 AM on September 27, 2011 [3 favorites]

I'd personally ask them what they wish people would ask them.

fraac is on point in that neither you nor us have any idea what your execs would like to see happen with this program. Do they want their egos stroked, or do they want truth to power? I'd feel them out and see what they want. If they want truth (hint: they won't) then just be you. If they want warm fuzzies (likely), then start practicing your company dogma now.

The old saw about managers "not wanting to hear about problems, only solutions" is mostly true of bad managers. Figure out what kind you've got sitting in front of you, first.
posted by NoRelationToLea at 9:10 AM on September 27, 2011

Best answer: Man, questioning past decisions is not a good idea if you're looking to score points. Asking them about themselves and their career paths are going to be cloying. Asking about the leadership program is a waste of their time and will show them that you can't expand your vision. If you want to stand out, ask about the future of the company and their strategic visioning, how the company can be positioned to take advantage of upcoming change, and how they think the organization needs to grow or change to get there. If this is a speaking truth to power moment for you, be prepared for that angle to end your opportunity with the company. If you're looking to advance in this organization over time, demonstrate to them that you can think about the future of the company from a "30,000 ft" level, and express confidence in their ability to get there. You'll always learn more by asking a leader to talk about what they lead rather than why or how they lead.
posted by ulotrichous at 9:15 AM on September 27, 2011 [4 favorites]

My favorite question to ask:

-What do you like about your job? What do you dislike about your job?

This also reveals the higher ups on a more human level, no one likes 100% of everything about their job - thats why they give the secretaries the uninteresting paperwork.
posted by amazingstill at 9:16 AM on September 27, 2011

Best answer: Listen to Spacegoelman. I've had the opportunity to speak to and ask questions of a number of senior management at various places I've worked at in the past. Execs hate questions like "what do you like or dislike about your job", because, well, that's prying, and they're as uncomfortable as you would be if you were asked that question. Asking about mistakes, ditto.

Your best bet is to ask questions like - what challenges to you see our company facing in the next (period of time)? Soften your language here - don't call them problems or issues, call them challenges or opportunities for growth. You don't want to suck up, so keep the discussion about business, and the fawning to a minimum. But questions like that show strategic thinking - you show them you want to be ahead of the game when something comes down the pipes.

Even if this Leadership Pipeline thing really is a load of crap, it's also an opportunity for executives to get a bead on some of the up and comers, and I think showing a strategic mindset is the best way to put your best foot forward.

Good luck!
posted by LN at 9:28 AM on September 27, 2011

Response by poster: As a senior myself, I can't really think that this whole exercise is one of time wasting. I see it as a really big org wherein it is tough for the highest leaders to 'get to learn about' others who would generally fall out of their view. The org is top-heavy age wise, so they know they need to grow a crop of new younger (I am 40) people to step into these roles soon. Given that, I can assume its not Fauxtivational (awesome word btw!). I go into this with the single motivation to raise my visibility to these leaders. Having said that, I don't think it is a good call to ask for 'mistakes made' sorts of questions. Targeting questions in this case on the principles of leadership and career building seems the right choice. Some very good ideas so far and certainly food for thought.
posted by BrodieShadeTree at 9:29 AM on September 27, 2011

I wouldn't be so skeptical about this opportunity. It may not be a direct pipeline to leadership, but it is a great chance to have a conversation with some really powerful people in your world.
posted by yarly at 9:45 AM on September 27, 2011

Nth'ing the be yourself advice. In most of these contexts, CxOs tend to act human.

However, just in case, I would not talk too much about myself, interrupt the CxO, contradict the CxO unless you are invited, or give an indication that you think the opportunity is a waste of your time.

If you want to prepare something beforehand, read the last quarterly report for you company - not all of the numbers, just the summary and possible business impacts. See if anything resonates with you, where you have something intelligent to say, or if something is directly related to your job.
posted by NoDef at 11:16 AM on September 27, 2011

Ask them about the biggest risks the industry faces in the coming decade. If you have a clear notion of what it may be, then expound on it with a question, such as: "It seems that foo is the biggest risk to our industry in the coming decade. How do you envision our company managing it?"

Similarly, ask about the biggest opportunities. The answers could be surprising.
posted by dgran at 1:26 PM on September 27, 2011

"What keeps you up at night?" - this is a more personal approach to the "tell me about the biggest challenges we face" question.
posted by crazycanuck at 1:57 PM on September 27, 2011

I wouldn't ask any questions at all. I'd make interesting small talk, because being grilled by an underling is a hassle. As shallow as it may sound, this is about making them like you. Likable people don't cross-examine.
posted by Short Attention Sp at 5:25 PM on September 27, 2011 [1 favorite]

Best answer: * "Who in our organization do you think would make a good mentor for me?"
* "What other companies do you think could be most disruptive to our business/industry?"
posted by anildash at 9:20 PM on September 27, 2011 [1 favorite]

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