Anyone have good questions you have asked upper managers?
February 4, 2008 8:10 PM   Subscribe

Anyone have good questions you have asked to upper management in a similar situation?

I have a big meeting I will be attending. One unwritten rule is that when you are with "upper managers" in our organization you "ask questions". The tough thing is asking something that seems insightful, but doesn't come off disrespectful or put them in awkward positions. Recently having botched a similar opportunity with my boss' boss at dinner, I don't want to make the same mistake again.

Anyone ever have to dance this dance before? I truly do like what I do and the company I work for, it is just tough for me to "ask questions" when I'm told "be sure to ask so and so some questions tonight"

The sitting will likely be a group setting and range from conference rooms to dinner.

Anyone have good questions you have asked to upper management in a similar situation?

Thank you.
posted by jseven to Work & Money (15 answers total) 3 users marked this as a favorite
Read up on the company (if it is big enough to be covered in the news) and if you find something that interests you, ask them about it. The best questions are ones that you are interested in the hearing the answers to.
posted by zippy at 8:31 PM on February 4, 2008

"What do you perceive to be our greatest weaknesses going into next year? How are we going to address them?" other questions along those lines that allow them to address the difficult issues facing the business in positive ways. trust me, they have considered them if they are even partially competent, and probably will by happy to talk about the wonderful plans they have to address them. that is a huge part of management and you want to play into it, plus it is interesting for the rank and file to hear.
posted by caddis at 8:36 PM on February 4, 2008

One good approach is to ask them questions that allow them to display their expertise and insight. These are the questions you'd ask this person if you found their job fascinating and you wanted to know more about it (rather than the ones you'd ask as someone with concerns about the company and where it's going).]
posted by winston at 8:44 PM on February 4, 2008

Ask an opinion question that deals with your industry, not your specific company. "Company X and Y are merging, is this a smart move?"

It's sometimes difficult to answer questions about your own company in a big meeting on some topics. You'll get a bland and stock answer.
posted by Argyle at 8:46 PM on February 4, 2008

One question that I think shows ambition and interest in the industry is, "What do you think we can do to distinguish us from the competition this year?" or "What are we doing to position us for changes in the economy over the next year?"
posted by slavlin at 9:11 PM on February 4, 2008

"Upper managers" are just people, so first off I would make sure that you aren't obviously kissing ass. In fact, don't ask a question unless you genuinely want to know the answer to something. Brown nosing is easily detected.

Who is instructing you to ask questions anyways? Its not the "upper managers" I assume, so why is their advice so necessary to follow? Absolutely no need to stress out about this.
posted by pwally at 9:17 PM on February 4, 2008

The good questions I have asked upper management in similar situations have always been geared towards them as individuals; hobbies, achievements, past history with the company. Get someone talking about themselves and like magic they'll start thinking you're the most interesting person they've ever met.

I avoid work-related or industry-related issues that I don't have a deep knowledge of; I'm not a good enough actor to pick a few random things out of the annual prospectus and then try to spin that into a conversation. Talk about asking to look like a complete tool. You would most likely be better off asking them questions honestly geared toward YOU... suggestions for committees you could help with, career-development paths they personally benefited from, industry groups and/or publications that could move you along, etc. If it was me, I'd have no problem with someone junior clearly asking ideas for how they could kick more ass.
posted by TheManChild2000 at 9:53 PM on February 4, 2008

"Upper managers" are just people
Not any more. Most of us are now bio-engineered robot hybrids.

I tend to have a much more informal style and may be less of an "upper manager" than the folks you are dealing with, but in these situations I most enjoy questions that ask me to analyze or predict the future with regard to either internal corporate events or external industry trends. I most dislike questions like "Susie in accounts receivable is really annoying, what are you going to do about it?" A lot of questions from people are clearly designed to show off the knowledge of the questioner which usually go "It seems to me that .... what do you think?" They are fine too, in that the expected answer from me is pretty easy (Gee, that's an interesting insight and I agree with your penetrating analysis) and sometimes the people really do have an interesting take on something that is fun to think about.
posted by Lame_username at 10:06 PM on February 4, 2008

I work for the world's largest Management Consulting firm. About 2 years ago I was at a conference in Orlando for the management / senior management of *just* my operating group, and that was a few thousand people, in and of itself.

We had a guest keynote speaker on the last day of the conference, D. Michael Abrashoff, author of It's Your Ship: Management Techniques from the Best Damn Ship in the Navy. It wasn't any joke, either, this guy took one of the most under-performing ships in the entire US Navy and completely turned it around to make the leading model of performance, by modern Navy standards.

In talking to us about how he did it, he mentioned one of his key tactics that he used to get in touch with the pulse of the men and women that ran his ship. He would ask everyone, from his XO down to the lowest enlisted man, three questions:

What do you like best about the ship?
What do you like least about the ship?
What's the one thing you would change about the ship if you could?

He took their answers to heart and used them (along with a whole lot of other techniques / approaches) to manage a US ship arguably as well as anybody ever has.

So, time came after his speech for some Q&A. In one of my exceedingly rare strokes of genius, I walked to the mike and told him I had a 3 part question: What he liked best about the Navy, what he liked least, and what one thing about it he would change if he could.

That got a big response from the audience before he could even answer - I had trumped the Q&A.

The lesson I took from it was this: listen attentively to people (be they speakers, girlfriends, senior management, or the guy who makes your morning coffee), and then ask them questions based on what they just said. When people talk, they are giving you openings to ask them the deeper, probing questions. You just have to be actively listening and thinking about the consequences and natural conclusions of what it is that they are saying. Its all about turning the subject at hand back on them with the opportunity for them to go into deeper detail and give you more of their expertise on it.

And, last, don't sweat it - just try to remain confident. If they're good managers, they're going to be interested in what their people have to say, and what their people want to know about, in which case you can't really go wrong.
posted by allkindsoftime at 12:23 AM on February 5, 2008 [8 favorites]

I've had to do this question game. It's annoyingly frequent in (yes) the Navy. I've found that trying to ask "good" questions always sounds lame or like you're brown-nosing. What works really well is to think about the last time you asked a question of someone you work with, and the answer was something to the effect of "I know it's stupid. That's just the way it's done."

In my experience, High Level Guys tend to like it when the peons bring up something simple they can change for an obvious benefit, however small (though big is better). Silly example: "Why do we still fill out a paper form for X? This is 2008. Couldn't we use the LAN for that somehow?" Even better if you can tie a bunch of examples together - "I don't think we're getting all we can out of the LAN. Examples: we still fill out paper forms for X, Y and Z. I still have to call Dept. W to find out when Event T is. Couldn't we have some sort of central interweb-site-thingy to handle that kind of stuff?"

I use that as an example because in the Navy as a whole, we still haven't figured out this whole computer thing, even though most of us individually have. It's very easy to identify how backward we do things, but it's just accepted that that's how it is. That's probably not your problem, but there's something you do that just seems asinine and nobody at the "appropriate" level is willing to fix it, I'll bet. That's what you ask about. (If not, can I get a contact number to send my resume?)
posted by ctmf at 12:59 AM on February 5, 2008 [1 favorite]

Be careful that you're not asking questions for question's sake. If you haven't a good question stay away from the question thing all together.

A good strategy and a little sneaky is to latch on to someone else's question- if it is a qood question.

After they have asked the question (and presuming it's in a converstional setting) fold your arms, stand close to the questioner and cock your head toward the respondent, umm and ahhh suitably as if you were asking a joint question, you might even get enough crumbs for a half decent follow up yourself.

If the question is a dud, move away quickly witha suitably disparaging look.
posted by mattoxic at 3:29 AM on February 5, 2008

Make it relevant. To the market, the economy, the company vision. Muckety mucks love to talk about the company vision, hard to go wrong there--of course, you might be expected to already know the vision, so modify it to dove tail with something that might impact the vision, like lack of trained workers, changing marketplace, global expansion, etc.

Also-- I recently asked the president of a college about her half time dance routine that was announced in a press release. It addressed her fun side and she loved talking about it. Don't be afraid to comment on something a little lighter if you think it would be well received.
posted by 45moore45 at 6:16 AM on February 5, 2008

Another angle for the making conversation aspect of this is to ask about how things were done or worked in the past. It can be tough getting a handle on institutional memory if you're relatively new to an organization, but it can also be a real advantage, and often it's the higher-ups who have been around long enough to tell the war stories that get you that insight. So if the credit crunch is affecting your business now, ask about how things went down during the S&L crisis - that kind of thing.
posted by yarrow at 10:46 AM on February 5, 2008

How did we end up going in ____ direction? (Back in history, at what point did X become a core part of our mission / product line / our key market?)
posted by salvia at 2:09 PM on February 5, 2008

Oh, but be careful not to ask in a way that makes it sound like "...because I think that decision was bad."
posted by salvia at 2:10 PM on February 5, 2008

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