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Because of a change in technologies, we are doing a major version change in our in-house enterprise software. I am going to be doing the usual of interviews, observations and brainstorming sessions.

What general (and fun!) questions do you recommend/use in a first pass to elicit the discovery or remembrance of new functionality or changes to existing functionality? (Too much literature on requirements gathering tells you the easy part: how to get details on functionality. Nobody seems to have much on actually eliciting the function at first!)


  1. You have a magic wand. You can wave it and change one thing about General Software v1.0. What would you change, how and why?
  2. Have you used any software where you wished something in it was also in General Software v2.0?
  3. What functionality is too complicated in General Software v1.0?
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What? You don't have a room full of whiteboards or a wiki or bug tracking software or scribbles on a napkin or something that has already captured this information? – Robert Harvey Aug 4 '11 at 19:13
@Robert Harvey: Maybe OP will have whiteboards and wikis full of this stuff after all the interviews are done. – FrustratedWithFormsDesigner Aug 4 '11 at 19:14
Alright, but once this is done, make sure you have something in place that captures these ideas as you go. You can't possibly commit all of them to memory over the long term. – Robert Harvey Aug 4 '11 at 19:15
We do. But, we are making a bigger push than a passive wiki. We're doing a deep session of observing huddles, shadowing users in specific processes, interviews, etc. – alphadogg Aug 4 '11 at 19:31
After all is said and done, more is said than done, and even more is forgotten. BUILD DEMOWARE. – Job Aug 5 '11 at 1:53
up vote 1 down vote accepted

I have found that a lot of (user) suggestions bubble out of support calls. Either from chit chatting while working out their problem or just because they wanted it to work differently than designed. Make sure support (assuming it's not you) captures this in a fashion that is brought to the dev team's notice.

Update Ok that didn't really answer the question although I think it's a valid suggestion.

As far as questions try to ask open ended questions rather than questions that a user can answer yes/no to.

General Questions:

  1. What do you do outside of the application with the data from the app?
  2. What do you wish it did? (Be prepared to reject ~75% of these responses)
  3. What does it do differently than you think it should?
  4. What do you do that is related to this app but the app doesn't help you do?
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"What are customers saying about our product? How do they want us to change or improve the software? What are their ideas?"

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Design the Box

Pretend the software is finished and it's being boxed for shipping. What features, functions, and improvements should be advertised on the outside of the box? These are the high priority, big request features.

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Usually you get too many requests from users and someone has to say no. Maybe this has happened so often, since you've forgetten everything they've been asking that they gave up? They're already having these discussions, but probably behind IT's back.

The tough problem is getting people to work 'on' their job and not 'in' their job all the time. They accept inefficiency and for cash-flow purposes no one wants to speed up employee reimbursements. Manual data entry, repeated ad hoc reports in spreadsheets continue because people don't mind doing this. It's why some people see no need to learn programming. Ever met anyone who prints every email? Talk about a time waster.

Hang out in their areas. Pay attention. Watch them work. Ask them why. Get copies of their notes, instructions, documentation, cheat sheets on the wall, put a recorder behind the coffee machine (kidding). It seems like you care or you wouldn't have asked this question. Let your users know that.

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