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In many places, bosses are notorious for not understanding the details of what's happening. This leads to many very silly and frustrating questions and requests. But from time to time the opposite occurs.

What is the most insightful or useful question your superior asked you? These can be questions that revealed a big problem, or it can simply be a question that showed a deep understanding of the subject matter. Ideally, they should be questions that led to better software.

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13 Answers

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What's preventing you from finishing this?

Not followed by "Why the heck isn't it done yet!?!?",

but by "What can I do to take those obstacles out of your way?"

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+1 Cherish such a boss. They are a rare, invaluable kind. – Aaron Digulla Oct 4 '10 at 9:41
+1 I had one of these, it was nice – Jon Oct 4 '10 at 17:21
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I decree that management-as-a-service (MAAS) should be "The Next Big Acronym" that business folk latch on to and adhere to. – Steve Evers Sep 6 '11 at 16:40
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On one occasion my boss (actually my boss' boss) asked me to implement a particular feature and my immediate response was "that can't be done, there's no way to do it."

He smiled and said "OK, right, I've heard what you said, and I understood it. Now let's just pretend for a moment that I'm saying it will be done, how would you go about it?"

He was damn right, as well, and I did find a way to do it. Just re-phrasing the question in that way really helped (even though it was not a technical comment).

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+1: This is an incredibly powerful technique you could take into other areas of your life. Commit to yourself that you will cause X to happen even if you have no idea how. Then figure out how. There's no room to doubt yourself when you put it that way. – Jonathan Hobbs Dec 21 '10 at 5:45
I've had this same question put another way that helped: "Assume that I'm telling you that someone else has already done it. How do you think they did it?" – Steve Evers Sep 6 '11 at 16:41
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"What does that do?"

Probably the best question I've ever been asked. It shows that they are interested enough to be willing to learn. If I'm working for someone who even only understands 10% of the code that's better then someone who will promise the moon and the stars to someone without realizing what it actually takes to package and ship those suckers.

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up vote 15 down vote

Why do we need that?

The question wasn't about the technology or what we were doing. It was intended to get us thinking about why we were doing it. What benefit did it bring now, or later, for the organization? His idea was to get us focusing on the business of IT and not on the immediate technology concern.

And before anybody bring it up, no, this was not a way to get us to stop doing things that were necessary even if the only benefit was within IT. The objective was to get us to stop doing things that didn't lead to benefits for the company, either directly or indirectly.

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up vote 7 down vote

Why can't this be done "the other" way?

This really shows that your boss has command and experience over the task assigned to you. This makes his team members brainstorm the ideas before they bring them to him.

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I can count on one hand the number of bosses who knew "the other" way. They also all knew tradeoffs with doing it the other way and why it was being done "this" way. – Josh K Oct 4 '10 at 13:14
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What the @#$& is a GUID?

Edit

While it might seem like just a funny question; at the time it showed me that the Boss, in this case the CEO, was really trying to understand what a room full of technical people took for granted. As a result we re-evaluated our needs and changed the GUID to an Int.

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Is that best as in useful, or best as in hilarious? :) – JoshD Oct 5 '10 at 18:42
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It is powerful because it takes humility (much more than curiosity) for someone in a very senior position to admit they don't know, rather than bluff, in a roomful of people. This is essential role-modeling to all the other managers present, as much as it is technical Q&A. Context is everything. – smci Jul 16 '11 at 21:11
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That should have took you a month to do. How did you do it in 2 days?

Many years ago working for someone that didn't know what you can achieve with a little bit of programming.

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up vote 5 down vote

What obstacle can I remove to help you get your work done?

Bar none, best question that has ever been asked of me. I can't quantify how great it was, except to say that until that point all of my bosses, non-programmers the lot of them, hadn't a clue that there could be impediments to progress or that code didn't just magically appear.

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I dream of the day... – JoshD Oct 5 '10 at 18:42
up vote 4 down vote

"How do you build computers, really?"

"You design logic and make circuits from it..."

"But how did they make the first computer?"

"The hard way..." (I goes to the white board...)

I actually had to draw a complete-ish mini-CPU with ALU, registers, memory and an example instruction stream with bits.. but I think he got it. :)

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Did you take a photo of the drawing? I'd be interested in seeing it – Slokun Oct 4 '10 at 14:45
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One of my personal favorites. I have an EE degree, so I start with how to dope silicone to make P and N material, and gradually get up to the rudimentary parts of a processor, machine language, computer architecture & hardware, high level languages & compilers... but very few stick around that long. Most of them bail before flip flops. :) – JoshD Oct 4 '10 at 17:08
@Slokun: It was a watered down version of a basic CPU schematic that you can find in most textbooks on computer architecture. Not really complete though (i.e. one integer op only, two registers, etc etc..) but the gist of the thing was there. – Macke Oct 4 '10 at 17:19
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"What do you want to do?"

Granted this is a rather generic question, but there is something about having the power of choice at times in my job that it can be rather cool to feel that kind of power.... He-man theme music plays

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Only if it is actually followed by a discussion of how to get there from here (specific, with timelines). Some managers do did this as a token 1-minute ritual to Show They Really Care about your development, although they're not able to deliver on your request. – smci Jul 16 '11 at 21:13
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What are you?

After I had somewhat miraculously pulled the answer to a problem out of nowhere.

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up vote 2 down vote

Boss discusses a lot of things ,plans and probably new projects then asks:

When will you get this thing done? give me a timeline.

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up vote 2 down vote

In his autobiography, a naval cadet (and future President) named Jimmy Carter relates being asked by his "big boss" Admiral Hyman Rickover, "Did you always do your best? If not, why not?"

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