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Ask Slashdot: How Would You Convince Someone To Give Up an Old System? 379

First time accepted submitter Vanderhoth writes "I'm currently serving as a new member of a board for a not for profit organization. The board currently has a few other members, and a couple of vacant positions. One of the issues I've noticed since joining the board is the method in which they conduct business is very out of date. The member that maintains our web presences (Bob) has developed a system over the last ten years to allow us to store documents, such as agendas and minutes on a website server.

Some of the big issues are:

1.) The system is very disorganized, there are documents from the late 90's that aren't relevant, but have to be sifted through to find more current stuff.
2.) Often documents are not where they should be and are difficult to find.
3.) No one except Bob really knows how the system works.
4.) No one really wants to use the system because of the monster it's become.

My concern is if Bob decided to leave the organization no one would be able to maintain the existing system and we would be scrambling to put something new in place. I feel, for what we want to do, Google Docs would be an excellent platform for collaborating and sharing documents. The other board members, except Bob, have agreed with me, but are worried that bringing the issues with the existing system may cause offense and ultimately cause Bob to leave. Other than being overly vested in a system he developed, Bob is an important part of our board and a very valuable member.

We're already having a difficult time finding members to serve on the board so it's very important that we don't lose any existing board members. I'm hoping that I can convince the Bob to start supporting some Google docs objects on the site and try to wean him off his existing system to something a bit more manageable and collaborative that can be passed on to new members and maintained easily.

I don't want this to turn into old dogs and new tricks. I'm not that far behind Bob in years and can appreciate the difficulty of being told it's time to give in to something more modern. I'm wondering how the situation could be approached tactfully so maybe Bob will see how much easier a new system could be for everyone, including him."
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Ask Slashdot: How Would You Convince Someone To Give Up an Old System?

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  • Smart Guy (Score:4, Insightful)

    by Seumas ( 6865 ) on Wednesday November 07, 2012 @08:48PM (#41914197)

    Sounds like Bob has found a way to ensure his continued employment and everyone around is too spineless to play that game of chicken with him.

    • Re: (Score:3, Insightful)

      by Anonymous Coward
      It sounds like the poster and Bob are fellow board members on a non-profit organization. Same result though. If political ego stroking is what the submitter's asking for then I would suggest putting Bob in charge of replacement. Just give him 2 or 3 options to choose from. If you have to resort to the ego, you should be able to get away with giving him the same kind of decision making power as a child.
    • by mrmeval ( 662166 ) <> on Wednesday November 07, 2012 @09:30PM (#41914575) Journal

      Always execute the indispensable person. The owner(s) are fools if the that person makes them the wagged tail. It will pay more in the long run to flush them.

      You do it this way. You give Bob an agenda and you send him off the most distant and obscure places to 'evaluate software' preferably somewhere he can play on the company dime using the very generous per diem you will give him. Make sure he does not have time to spend in house while you rip the system apart by hiring a team of energetic 20 somethings you'll discard with pockets full of cash at the end of the project. If Bob has a multiple moral indiscretions or is arrested that is just cake. Once you've had your Bobectomy you set up that system with a broader hierarchy where no one person will ever have such control again and take reasonable precautions to ensure it is well documented and also as secure as needed for the data contained in it.

      Well it worked at one place I was 'abused' at 20 something. ;) Pockets full of cash baby. :)

    • Problem is, he's not getting paid.

    • Bob IS ANGRY (Score:5, Interesting)

      by Anonymous Coward on Thursday November 08, 2012 @12:15AM (#41915549)

      Sounds like Bob has found a way to ensure his continued employment and everyone around is too spineless to play that game of chicken with him.


      My name is Bob. I am on the board of a small non-profit, and in my own time I built a document management system for our organization before you could buy such things off the shelf. We use it for records of board meetings and the like. Some idiot named Vanderhoth just joined the board. He is rubbishing my system which I've spent years maintaining. He complains about older documents being in the way of newer ones, but can't be bothered volunteering to help tidy the documents. He wants to throw away the whole system and go with something completely unproven. What's worse is he wants to put our documents on the cloud - at the mercy of a mega-corp that could pull their service at any time, or suffer a security breach. If this little punk had any clue he'd realize first step of moving our documents would have to be tidying them up. But he just moans to others behind my back instead. Now I hear he's posted to a large blog site called slashdot. Next time I see Vanderhoth I'm going to kick him in the nuts! If he thinks he's staying on the board for long he's got another thing coming.



      • Re:Bob IS ANGRY (Score:5, Informative)

        by drolli ( 522659 ) on Thursday November 08, 2012 @03:00AM (#41916117) Journal


        I was once maintaining a small political organizations website.

        OK my system (few hundred lines of perl, run offline) *was* minimalistic.

        OK my system did not have many features

        BUT my system did what was needed (define a navigation structure,insert ~100 text documents at the right place), my system froduce blazingly fast static webpages, delivered in a zip file, which ran on every client device and every webhoster. And my system was definitely low-maintainance (since there existen NO dependencies at all).

        Content was missing. People did not just mail me content (as i asked for). People did not just ask how to update the website. Content was outdated. *The ironic part is* as the guilty party for not updating (largely) static content my quite simple system was identified, which (seen from behind seems a little ironic).

        So some fucking greenhorn arrived (i was happily handing this over to him, since i had a lack of time) and decided that he

        a) does not understand enough perl to do this (he did not talk to me a single time)

        b) content which was completely static needed PHP - because that was the only thing he knew

        c) Taking an off the shelf CMS to magically solve all problems

        Reality check:

        a) The transition to the new web hoster (providing PHP) took so much time that the next election was nearly there before the website worked again

        b) The website did not contain more content, it did not even contain the old ported content. People who were not able to send mail before did not produce content afterwards (did i mention that he had problem to configure user access to the CMS)

        c) The guy left shortly later without a transition plan

        d) After that the website was scrapped again and set up by a professional web designer (which was payed for setting it up but not for maintainance). The website still had not more content than my first version

        Lessons learned:

        * If there is a running system and people complain about outdated content, changing the system along wont change much. The people conplaining loudest are usually the ones who write complain-emails instead of sending the fuckign article (or even just a decent self-intro) you ask them for 2 months. *Ignore them*

        * Running a website without getting payed has even worse ressource constraints than other websites. Every change of the underlying system is a ressource hog (oh yeah, you sure expect Bob to copy the few hundre documents in his spare time to google docs. You did the heavy lifting of settign up the google account)

        * Never ever touch a running system

      • by Barryke ( 772876 )


        OP is complaining the system is old, but in fact the system was a decade ahead of its time.

        And with this, there is no shame in realizing that it can still be, because if he'd work together with Bob on these issues, they have no need to reinvent the wheel they already have.

        And if OP trying to make clear that modern solutions are better, let him please setup his solution as full blown proof of concept and have Bob look at it, before arguing any further or taking down the old (proven) system before the ne

    • Old Legacy Systems are hard to remove. Even if the replacement is cheaper faster and better. Because people know how to use the old system.
      The best methods I have found is a slow removal process.
      Phase 1: Get a backup person trained on the system. In Case Bob gets hit by a train, there should be someone who knows how to maintain and upgrade the system.
      Now the "Bob" may resist this, that is why you will need to be strong and tell him it is just so your company has a backup, make sure the trainee has other j

  • What about Bob? (Score:4, Insightful)

    by Meshach ( 578918 ) on Wednesday November 07, 2012 @08:49PM (#41914203)
    Apologies to Bill Murary!

    Kidding aside, have you tried bringing it up with Bob?
    • Re:What about Bob? (Score:4, Informative)

      by Vanderhoth ( 1582661 ) on Thursday November 08, 2012 @08:01AM (#41917213)
      No, the other members of the board told me I needed to be sensitive about it. We had a nice little discussion going in the fire hose, unfortunately my substitution was posted while I was asleep.

      I plan on talking with Bob about his system and asking him to give me the tour, since one of the biggest complaints of the other board members is that no one would be able to maintain the system if/when Bob decides he has other things to do and doesn't have enough time to volunteer. It seems many posters took my request for suggestions as I'm a young whipper snapper trying to do away with the old guy. That's not the case. I like Bob and think he's brilliant, it's just everyone shudders when they have to go looking for something and it seems only Bob can create/sort/retrieve documents from his system. So if he leaves tomorrow we have no way of getting documents out of his system and into something we can access them from.

      We're not paid for our time on the board and don't work together. We don't really even live or work close together and only meet face-to-face a few times a year so the system has to be something we can all access from anywhere, which is why I was suggesting Google Docs, but I'm open to other suggestions. Even learning Bob's system and helping to improve it to make it more manageable for the other board members.
  • Tell him (Score:5, Informative)

    by s1d3track3D ( 1504503 ) on Wednesday November 07, 2012 @08:49PM (#41914205)
    Why don't you just tell him what you explained above
    • Re:Tell him (Score:4, Insightful)

      by Sfing_ter ( 99478 ) on Wednesday November 07, 2012 @09:27PM (#41914555) Homepage Journal

      Exactly, it is quite possible he has wanted to update, wanted to relenquish administration, but has not wanted to go through the process or speak up about making the change.

      • Re:Tell him (Score:5, Insightful)

        by NemosomeN ( 670035 ) on Wednesday November 07, 2012 @10:15PM (#41914909) Journal

        This. Except don't use Google Docs. I can't imagine using Google Docs to store 20+ years worth of documents. Google Docs is good for collaborating to create/modify a document, then allow you to take that out when you are done, and organize it how you want. Create a file server (probably what you currently have), and put things into folders in a sensible way. By year, by topic, by whatever will make it easier to sort through. I'm sure Bob realizes the mess that has been created. Just say "This has become disorganized over the years, let's make a conscious effort to organize it." It's not Bob's fault, it's everyone who didn't say something sooner that is to blame.

        • by skids ( 119237 )

          I can't imagine using Google Docs to store 20+ years worth of documents.

          Especially since Google could just decide to discontinue the service at their whim.

          Regardless of the system chosen, you really need to find someone with competent organizational and data entry hygeine skills, and have them serve as the person who manages content on the site. I don't care if you use a fileshare, wiki, or whatnot, if you let ordinary users choose the filenames/urls/directories where they upload content, it will end up a mess. Someone who knows such thing as not to name a file "minutes_2-2-1

          • Yeah, putting all of the organizational files on a 3rd party service where there's no guarantee that they will continue to offer that service, or that the service will be experiencing planned or unplanned downtime when you need access - that seems hardly well advised. Perhaps suggesting a document management system if there are really that many documents. If it's not an overwhelming number, even a couple hundred documents, since you're working free anyways, just invest a day on the weekend and organize the

    • by gaelfx ( 1111115 )

      If Bob has any geek in him at all, I think he just did.

  • Easy fix: (Score:2, Funny)

    by Anonymous Coward

    Lock Bob in the boot of a car. Come back in an hour and ask if he wants to migrate to Google docs. If he's recalcitrant, come back in another hour with a gun. Ask again. Sooner or later he'll come around.

  • Careful (Score:5, Insightful)

    by __aajwxe560 ( 779189 ) on Wednesday November 07, 2012 @08:53PM (#41914269)
    Bob probably is well aware of the chaotic disorganization of his system as well, where I suspect he devised something that worked well in small form, but simply is not scaling out beyond its original intent. If you approach it with educating him on understanding Google Docs, and what value it provides, he should start to learn for itself its advantages and how it actually makes it EASIER to manage the docs. He may well fully embrace the idea then on his own (the easier way to get want you want is he wants it as well). Be careful though... he may also finally have found the person he has been looking for all these years to take over the job and do whatever the hell they want with it, in which case he says congrats to you and its yours forever to maintain (until the next solid contributor comes along in 20 years).

    -A Jaded Board Member
  • by Anonymous Coward

    Bob has probably spent countless hours sweating and toiling on this in relative obscurity. The key to pulling this off in my opinion is to recognize his work and talk about the features you'd like to get added to the website. Constructing the right feature requests will help him come on board with an alternative solution.

  • Bob's value (Score:5, Insightful)

    by jbeaupre ( 752124 ) on Wednesday November 07, 2012 @09:06PM (#41914389)

    From your description, Bob may have a vested interest in the old system. Security, self worth, whatever. Bob may feel that his value is tied with the old system. So going after the old system is going to feel like going after Bob, to him.

    So don't fight that battle. Turn it around and make it so that Bob has an interest in the new system. Ok, that's obviously easier said than done. But there are several ways it can be done. Here are two approaches:

    1) Let Bob be the hero. Talk to him privately about how he's managed miracles with what he's been given. Then ask him what he would do different if he could start over. Ask him what it would take. Offer to back him in his proposals. In short, put him in charge in a way that makes him indispensable and proud to do a good job.

    2) Let him be the mentor. Similar to letting him be the hero, but with the twist of having someone else do the grunt work under Bob's wise and benevolent guidance.

    3) Black box it. Ask Bob to come up with a new system, but don't get into the details. That requires a lot of trust, which may be what Bob is after anyways.

    You get the idea. Play to what Bob wants and make it work for you.

    • Re:Bob's value (Score:4, Insightful)

      by Psider ( 2734563 ) on Wednesday November 07, 2012 @09:29PM (#41914567)

      All good ideas. I think a lot of people are actually open to change as long as they feel their skill and experience is being valued. Suggest that it would be good to simplify and modernise the process and find out what ideas Bob has and the challenges he sees in implementing any changes.

      Also be clear on what you want to achieve, without dictating the route to go. Suggestions are fine, but don't make is sound like you've already decided - people generally take pride in what they do and want to have input into how changes proceed. And buy-in breeds better morale. :)

      Two problems I've encountered are top down dictators who ignore people's skills and experience; and unclear goals which make it extremely hard to move forward (e.g. "make is snazzy" is not clear enough. "Allow collaboration and make it easier to locate relevant information" is better.)

    • Re:Bob's value (Score:5, Interesting)

      by RedBear ( 207369 ) <redbear@r[ ] ['edb' in gap]> on Wednesday November 07, 2012 @10:24PM (#41914949) Homepage


      Read the ancient but still highly useful Dale Carnegie's How to Win Friends and Influence People. This is a textbook example of a situation that can be attacked using the advice in that excellent book. If you sidestep Bob when trying to bring this new system in there is about a 98% chance of significant strife and animosity resulting from such action. If you are able to get on Bob's good side and work with him to introduce a new system, things will go infinitely better. Especially if everyone including Bob thinks it's mostly his idea.

      Here's the catch though: You can't fake it. You must approach people with a real, genuine interest in getting to know them. If they are difficult to deal with you have to find some chink in their armor that will make them more approachable. If you fake it you will go down in flames and the Dale Carnegie approach will never work for you.

      Any other angle of attack in this situation usually will turn out very negatively for one or both parties.

  • Can you link to docs in the old system? If so, create Google docs that are organized links into the old system. You want to see the minutes from all the meetings over the last year? Here's that page of links. Budgets? Here it is.

    Over time you'll make the Google Docs the de factor standard. Once everyone is accustomed to using Google docs, you can start creating new docs in any system. Including Google docs.

    This will gradually wean people off the old system without any single, massive switch. And hopefully i

  • by phamlen ( 304054 ) <{phamlen} {at} {}> on Wednesday November 07, 2012 @09:10PM (#41914433) Homepage

    Just a few quick possibilities:

    1) You could try the 'duplicate, don't replace' strategy. For instance, minutes of the board meetings go in Google Docs (so they can be searched more easily) and then are copied over to Bob's system once approved. If you do it right, eventually Google docs will start to become the primary source system - simply because it's easier to use - but Bob will still be maintaining his system. The downside to this is that you'll have a lot of documents in two places but eventually you can drop the one that isn't working.

    2) You try to give Bob some kind of new, very cool project for him to work on - that is, give him a way cooler, more interesting bone and maybe he'll drop the one he's got. How's your donor database? Do you need some kind of app built for mobile or something? Once he's up and handling that (and gotten some real street cred for a good project), you might be able to obsolete the document management thing.

    3) Work on a Business Continuity Plan: an early step in all BCP's is to make sure that you can (a) recover the documents if disaster hits and (b) that no one person is a single point of failure. Use the recent 'Sandy' events to emphasize that this is not a slur against Bob but the organization has to be able to survive even if the current 'datacenter' (even if it's just a machine under a desk) is flooded/destroyed. Google Docs is far cheaper from a recovery point of view.

    4) Emphasize the shared document approach to Google Docs - if you have remote meetings, it's much easier to use Google docs to share/edit and remotely collaborate. Again, merging with approach #1 (use Google Docs until it's finalized, then it goes into the Bob system) might work well.

    Good luck.

  • by maynard ( 3337 ) <j DOT maynard DO ... AT gmail DOT com> on Wednesday November 07, 2012 @09:12PM (#41914451) Journal

    This is a political problem, not a systems problem.

    After over a decade in systems administration, I just a job where for six years I was an IT manager. There, I learned that the skills involved in managing projects and people are a vastly underrated skill among systems specialists. The belief is often that the right system - new hardware; new software - will somehow solve an organization problem that's inherently political in nature. By that I mean, a people problem. And I think you've got a people problem here. Which doesn't mean your documentation system isn't out of date, doesn't need a refresh, etc. It means that a core member of your team is out of step with the needs of the organization, as defined by a majority board vote.

    You have three choices:

    A) attempt to persuade this board member that his system needs a revamp, set a series of goals to achieve that he'll buy into, and give him the project to manage. Specify benchmarks and a timeline to achieve these goals and have the board review the project on a regular basis. Then the board must fulfill its obligation to the organization by grading project success on an honest but fair basis. If he honestly works toward these goals, then the issue will resolve itself in time. Otherwise, the board must consider the possibility of transitioning him off a leadership role in that project.

    B) Fire him. Do it now. Accept the fallout and hire someone else to clean up the mess.

    C) Do nothing.


    Option A: keeps someone in place who has shown himself to be an important team member who has strayed from the needs of the organization, but who recognizes this and shifts course as a result. This is the preferred course.

    Option B: cuts your losses now and takes the hit quickly, while the problem is fresh. This is a harsh course, but at least is a response to the problem at hand.

    Option C: 'do nothing' is a total loser. A problem recognized and yet not pursued to resolution festers until systems collapse, often at the worst time while leaving the organization unprepared for the consequences.

    But the first thing you've got to realize is that Google Docs is not your solution. Google Docs may be a fine system, and a worthy systems choice. But your problem is not 'the system'. Your problem is that one person in a leadership role in the organization has strayed from board consensus, and as a result has assumed command responsibilities he does not legitimately hold. That's what you and the board must address.

    • Your problem is that one person in a leadership role in the organization has strayed from board consensus, and as a result has assumed command responsibilities he does not legitimately hold. That's what you and the board must address.

      Just re-read the summary, it appears that Bob hasn't necessarily "strayed from board consensus", it's sounds more like this is an item that has been neglected, and the members aren't quite sure how Bob will react to change. Bob may respond with defensive anger, or with thankful cheer that someone is offering to help with his overgrown monster. To me the problem is how to broach the subject with the least chance of causing offense to a valued member of the board who's loss would be felt.

    • by pikine ( 771084 )

      I think option C would not be a bad choice. The system has worked and will continue to work until Bob leaves for any reason. The original poster already has an alternative. If he wants to, he can start using Google Docs today and benefit from the convenience of its search features immediately. He'll need to make some effort to sync with Bob's document system without Bob's help. This way, he and Bob can coexist. He will use Google Docs as a back up so that, if Bob's system collapses, the failover to Google D

  • by TopSpin ( 753 ) on Wednesday November 07, 2012 @09:12PM (#41914461) Journal

    new member

    Bob has it all over you. You can make a brilliant case and Bob will quietly pigeonhole enough support to get his way. In the meantime you'll squander whatever little political capital you have squabbling with Bob. Don't squabble with Bob.

    convince Bob

    Bzzt. Wrong. Bob is not the guy you need to convince. You need to convince everyone else. Here are some ideas on how to do that.

    First, demonstrate the weaknesses. Place legitimate demands on Bob's system that you know it can't handle (revision control, secure remote access, ACL, etc.) Make him squirm and come up with excuses. Don't offer an alternative because that just leads to squabbling. Don't squabble with Bob. Just make the system and Bob's advocacy of it look bad.

    Do something "new" in your prefered alternative system. It has to be something that does not require or even suggest that it belongs in Bob's baby, because otherwise you're back to squabbling. Don't squabble with Bob. This is where you show how inadequate Bob's system is. This has been how middle managers sneak solutions into institutions for decades; go around IT. If the system is really as bad as you say it is then this is already happening anyhow. Look carefully for those cases. You may be able to adopt them.

    Wait. Eventually some happy user of your alternative system, armed with knowledge and frustration with the inadequacies of Bob's system you carefully surfaced, will begin to argue for your solution. "XYZ can do it, why shouldn't we use that instead?"

    Wait. Eventually Bob's system will crumble a bit because Bob doesn't scale (medical problems, boredom, incompetence, whatever) and you're there ready to go with a proven solution, advocates and everything.

  • by xxxJonBoyxxx ( 565205 ) on Wednesday November 07, 2012 @09:13PM (#41914463)

    1.) The system is very disorganized, there are documents from the late 90's that aren't relevant, but have to be sifted through to find more current stuff.

    Google Docs won't fix that.

    2.) Often documents are not where they should be and are difficult to find.

    Google Docs won't fix that.

    3.) No one except Bob really knows how the system works.

    Google Docs will fix this.

    4.) No one really wants to use the system because of the monster it's become.

    Google Docs may not fix this. See #1 and #2.

    Besides the passive aggressiveness in this post, you might have bigger communication issues on your board than just the document collection system. If you want a more concrete suggestion: convert Bob's entire system into Google Docs, fix it up so it provides the same member benefits as Bob's system (no, one big "oldshit" folder won't cut it) and then give him a demo. And really dig into #1 and #2 - that's a problem with any document collection system ever built.

    • 3.) No one except Bob really knows how the system works.

      Google Docs will fix this.

      Umm, I think he means that nobody who uses the system knows how it works, not that nobody on the planet does.

      Simply using Google Docs won't fix the problem of nobody knowing how the system works when they don't know how to create systems in Google Docs or how this particular use has been set up. Google engineers might be able to wing it, but I, for one, would have no idea how things were done.

      We've got one Google Doc that I have to use to make some time reports. I have the URL bookmarked, I know how to

    • by Mabhatter ( 126906 ) on Wednesday November 07, 2012 @10:32PM (#41915001)

      Ultimately, nobody knows how Google Docs are stored either.... And his system has DONE THE JOB for longer than Google (has been around) his system has met the basic needs quite well if you still have docs from the 1990's.

      The FIRST thing you need is a GOOD reason to update the system. The SECOND thing you need is to get RESOURCES. Those resources need to come from the TOP and be given to Bob. If you don't have those, then you are just another person with a big idea and wants Bob to back it up.

      The goal should be to find a canned system Bob can build now but anybody else can also understand. My advice, call a local tech university and talk to a professor. You will either come up with something top-to-bottom like Microsoft Small Business Server with SharePoint running. It's trees blue and not geeky, but if the school TEACHES Microsoft, you got a steady stream of volunteers in the future. Alternately, find a web portal Bob would like in a language the school teaches. You don't want to TOUCH a single line of code, but you want a canned system like Wordpress (just an example) that any student can set up, and any ISP with hosting will have on their default setup.

      Ultimately you have to get Bob help with the grunt work. Bob has been nursing this baby for decades... Bob wants his baby to grow up. Bob doesn't want a NEW BABY .... You better offer serious help moving all these files over and building a new structure. This is where the Tech school comes in... Somebody always needs an internship credit... And you are non-profit... Just give good references!

  • by Bobfrankly1 ( 1043848 ) on Wednesday November 07, 2012 @09:13PM (#41914465)

    Google docs for board meetings? *facepalm*.

    I work for an school district that employs a web based product that manages board meetings. It handles agendas, attachments, motions and voting, as well as keeping a measure of the minutes. I would suggest examining the options available and getting some demos. Once you've seen something that grabs your interest, involve Bob. Tell him you just found this think that you think would make everyone's job easier. But don't involve Bob alone, introduce it as "something you saw" to the whole board. This will make it so you aren't pointing out how horrible Bob's system is, you're pointing out how wonderful the new system is. Perhaps Bob is buried and doesn't know a way out, or perhaps he's clutching onto this thing as his personal feeling of self-worth(which would be sad).

    1) Identify a new possible(needs to be MUCH better then the current) solution
    2) Bring it to the attention of the board as a whole
    3) Let the whole board carry the conversation, and let Bob make his defense if he really wants to. If he's shut out of the decision making process, he'll probably want to leave. If he makes an obviously stupid defense in the face of overwhelming benefit, then thats on him, and he'll see it at some point (even if he never admits it).

    • Care share that web-based product for board meetings? I belong to some groups that could utilize a formalized system instead of ad-hocing it with Word via a projector.

    • Re: (Score:2, Insightful)

      by Anonymous Coward

      What is wrong with geeks...

      DO NOT bring the alternative straight into a board meeting - that's a really dumb idea. If he identifies with the system you are effectively publicly pointing out his failings. At best he will likely be crestfallen and his resignation will follow shortly. At worst there will be shouting and old grievances long put to bed will be brought out for another run up the flagpole.

      You have two options, and given your description it seems you want to keep Bob onside, so you really only h

    • by laird ( 2705 )

      Good point. The problem may not be documents at all, but running the meetings and recording them efficiently. You can do that in Google Docs (or any other document based system) with a little discipline. But if what you really need is a system that helps plan meeting agendas, record decisions, track action items, etc., you need more than document management, you need something more like LessMeeting.

  • This is a common scenario. Basically not one organisation should depend on a single person. To deal with such a scenario, I would suggest you approach Bob and ask him "what if you get hit by a bus tomorrow?". His response will reveal his personality. Either he depends on the power he has accumulated, or he will understand the problem. In the former case you are in a big deal of trouble, in the latter case you might brainstorm together and find a practical solution.

  • by Osgeld ( 1900440 ) on Wednesday November 07, 2012 @09:14PM (#41914471)

    Google docs will be the exact same mess in 10 years that your current system is now ...if it lasts that long. Just have Bob tidy shit up and fix the band-aids come back in another 10 years

    • by hodet ( 620484 )
      So many responses about getting Bob to be part of the solution and "tip toe'ing" around his fragile ego. This response right here is the best one. Presumably you are involved with this non profit to make a difference in relation to the goals of the organization. Who wants to muck around with document tracking systems. As Osgeld says, "Tidy shit up!".
  • Show them how the new system will save them money

    Money talks and bull shit walks

  • by SuperBanana ( 662181 ) on Wednesday November 07, 2012 @09:21PM (#41914519)

    Learn how to be a proper board member.

    In short: submit an agenda item to discuss resolving issues to the document management system. Either ask Bob if he'd like to present a plan of his own to resolve the problems along with your own, or let the board discuss the problems and request plans of action from you, Bob, and anyone else. At the next meeting, the plans are presented and one is selected by the board.

    Everything is above board, he's given a completely legitimate/fair shot at fixing the problems, and if the board fairly discusses and votes against him, he at least should feel he was treated fairly, and it won't impact his desire to help the organization.

    IF and ONLY IF he's treated fairly and he goes off in a huff about the whole thing, then so be it. He's toxic.

    If you go sneaking around trying to build support for switching to google docs (which you've kind of already done - you need to buy a copy of Robert's Rules of Order and read up about polling, and why you don't do it), then ambush Bob at a meeting and throw up a motion to switch to Google Docs - he's rightfully going to be angry and defensive, and it will definitely impact his contributions or cause him to leave.

  • by tftp ( 111690 ) on Wednesday November 07, 2012 @09:26PM (#41914549) Homepage

    I'm wondering how the situation could be approached tactfully so maybe Bob will see how much easier a new system could be for everyone, including him."

    If the situation is as bad as you describe then there is a person (Bob) who holds the entire company hostage, and nobody is willing to defy Bob's will - not even the CEO or whoever there is.

    If the CEO is not willing to cross Bob then why should you? Is there a reason why you'd sacrifice yourself for the common good? Your fellow board members aren't willing to deal with Bob, they want to sit it out while you and Bob are fighting. Do you want that role? What is the upside for you?

    The company in such a shape is already in trouble. It cannot govern itself; instead of being governed by rational decisions that are based on facts the company is governed by personal opinions of strongmen who refuse to consider alternatives no matter what. This is not a healthy company to work for. Bob can flip his lid at any time, for any reason. If he, being omnipotent, wants you gone then you will be gone. If that describes the company well enough then I would quit - there is no future for the company, and there is no future for you as a part of it. The only alternative is to seize control of the company. I don't think this is what you are thinking toward because in that case Bob and his problems would be discarded as a bad dream, and you wouldn't need to ask Slashdot how to deal with a generally simple management problem (a rogue employee, a.k.a. a loose cannon.)

  • Seems you have summed up a very typical problem. Not just with computer guys, but with all sorts of professions. So the question really is how can you lead Bob to make changes in how he does things so everybody can find what they need, without making him feel threatened or defensive about how things are now. Apparently you don't think the direct approach is a good because you fear that Bob might be offended and leave, dropping the whole thing in your lap. So how about some indirect approaches?

    Start ask

  • ...and it's a sticky situation. The easiest thing to do might be to initiate a cost/benefit analysis of the current system vs another one, entirely based around the idea of cost (running the servers, maintenance costs if any, storage upgrades). Time spent on the system should only be included in the analysis if anyone is being paid. Make sure to include Bob (or even better, ask if he'd volunteer as the "systems expert"), and have him help choose alternatives for the comparison. If you do have an existing so

  • Are you crazy?

    Why would you go to anything entirely controlled by an outside entity which could decide to change interfaces or deprecate your entire workflow for no particular reason?

    You obviously have access to a server, and you have a lot of legacy files. Look into a document management system that has a search function built in, and call it a day. For bonus points, create a folder structure which you find relevant and suggest everyone abide by it.

  • by Hotawa Hawk-eye ( 976755 ) on Wednesday November 07, 2012 @09:35PM (#41914609)

    "I've heard about a lot of stories recently about big companies getting hacked or their documents being held hostage by hackers that encrypt them. Do we have a backup for the documents on this server? If not, I'd like you to work on coming up with a backup system -- maybe something like Google Docs or something similar."

    If that doesn't work, let him go on vacation for a couple days. Call him repeatedly asking for help locating documents during that vacation. You want to annoy him just a little bit. When he returns, apologize for disturbing him so much then suggest that you had trouble navigating the system. If the documents were organized a little better, or if there was less old cruft, you wouldn't have had to disturb his vacation so often. Offer to help him if he wants to spend a little time reorganizing or exploring alternate solutions that may have features to make his task of document maintenance and your task of document location easier.

  • by dtmos ( 447842 ) * on Wednesday November 07, 2012 @09:36PM (#41914619)

    In my experience (speaking as someone old enough to remember watching the coverage of President Kennedy's assassination on television), the odds are not good, since the existing people are typically happy with the existing system -- otherwise, they would have changed it by now. However, one hope is to find a value of your organization -- and it'll be specific to each organization -- that would be improved by the change you desire.

    Note that this is not your value, but a stated value of the "old guard" that could be improved by the new system -- and, usually, avoiding the mortality of the old guard itself is not an acceptable value. Extra credit if you can arrange a discussion of the old guard value in such a way that Bob can take credit for the improved performance of the new system.

    Often, like so much in life, people with existing beliefs have to pass on before new ideas are accepted; ask yourself if you will be open to replacing your Google Docs system by something you don't know and have never heard of, in ten or twenty years' time.

    Recognize that you will have to do all the work to install the new system, just as Bob did to install his own system years ago.

  • 3 suggestions from someone who has worked for many nonprofits.

    1) If you have any staff members, make technology a staff responsibility. More than just passing the buck, this puts control of tech decisions in the hands of the folks who work with it most often.

    2) Ask Bob to chair the Board's nominating committee. This committee is responsible for finding new Board members (which you seem to need) and for monitoring Board terms and committee assignments. Hopefully, this will lead Bob to recognize that Board

  • Once you can answer the WIIFM question, then you are ready to talk to Bob. Bob will be asked to do work - to change the way he works, to learn a new system. In the short term, this will cause hassle, frustration, delay and extra work. Those are all negative things. Change _itself_ can be perceived as a negative thing.

    To be worth it, it needs to either save Bob time, or remove one of his pain points. The board doesn't matter, no one else matters. Only Bob's pain points matter.

    So, look at the existing s

    • Once you can answer the WIIFM question, then you are ready to talk to Bob. Bob will be asked to do work - to change the way he works, to learn a new system. In the short term, this will cause hassle, frustration, delay and extra work. Those are all negative things. Change _itself_ can be perceived as a negative thing.

      To be worth it, it needs to either save Bob time, or remove one of his pain points. The board doesn't matter, no one else matters. Only Bob's pain points matter.

      So, look at the existing system from Bob's point of view. What does he spend most of his time doing? How can you make that faster and less error prone? If you can do that, then you have the hook to pull in changes that benefit everyone else.

      Agreed - I'd have asked Bob what he sees as the problem, and how he'd cure it. Get Bob's buy-in. Could be a case for De Bono's 'Six thinking hats' and get everyone (including Bob) saying what's good about the current system, then everyone (including Bob) saying what's bad. And finally everyone to say how to fix it.

      As for offending Bob - offence is only ever taken, not given. If Bob's going to take offence, that's his call. And it'll happen sooner or later if it will happen. Better to face it now.

  • Make copies of everything into google docs or whatever new system you want, then "accidentally" erase his software. Bonus points if you can make it look like a hardware failure.

  • Do not ever put any critical system, such as board records, in such a precarious situation as there being a single point of failure. Because it *will* eventually fail, and then you're screwed. By all means, use Google Docs, but as a *backup*. Encrypt everything you upload on there. This is for the security of the data, not to prevent the right people from accessing it - so you could safely write the decryption keys on post-its for the purpose. Your working directories should be local and duplicated, not run

  • by westlake ( 615356 ) on Wednesday November 07, 2012 @09:54PM (#41914749)

    i want to see if I understand this clearly:

    Bob's experience and competence in other areas are regarded as indispensable to a board that is struggling to fill at least two critical vacancies .

    Bob built this system on his own time for an NPO that appears to have no IT staff or competence whatever and a board which seems almost too eager to embrace an alternative solution --- any solution --- proposed off-stage by its most junior member.

    How you avoid the blow-up to come, I can't even begin to guess.

  • Add a function that automatically uploads the docs to Google docs when they are uploaded to the old system, and a small button to view them using Google docs. People, including Bob, can then try out the new "G Docs" in the context of the old. Then two months later ask Bob how he thinjs G Docs might be more integrated into the UI.
  • I'm a trainer and implementer for a an accounting application customized for a particular industry. We are a global company with about 1500 active customer installations and a user base of about 25000 with our software managing labor and payroll for about 250,000 workers. Our accounting software is used by many publicly traded corporations, a few of which are on Nasdaq and other world exchanges. That is my background. What I do is go into a company that has bought our software and teach them how to
    • by Lokni ( 531043 )
      Hmm, thats lame. I put in paragraphs but when it submitted it stripped out all of the spacing. Cliff notes: 1. I do this professionally as a software trainer and implementation manager. 2. Key thing is to make the change relevant to their lives. 3. Understand what the existing system is and what their issues with that system are. 4. Explain the new system and how that relates to what they did in the old system. 5. Explain how the issues with old system are taken care of in the new system. Not just
  • Ask Bob (Score:4, Insightful)

    by dbIII ( 701233 ) on Wednesday November 07, 2012 @10:00PM (#41914809)
    Maybe it started off with a simple system like you are proposing and then edge cases created the complexity. You really need to understand the current system or work with somebody who does before you can effectively replace it with something else.
  • by Kaz Kylheku ( 1484 ) on Wednesday November 07, 2012 @10:01PM (#41914819) Homepage

    I support Bob's opposition to Google docs.

  • You sound like you need to gather a little more information on the problem. The most important things concern Bob. Bob being a possible flight risk makes finding out exactly why he would leave very important. It probably won't be 100% one specific reason, but figure out the split. Ego? Job security? (even if not gainful) Pride in his "child" project? Worries for the organization's welfare if his masterpiece is replaced with a bad system? There are many other possibilities, and better understanding h

  • Make sure you have a full, offsite, verified backup that ISN'T under the control of Bob, just in case he takes the news badly. ;)
  • Honestly. Breaking it now once and for all is the best and easiest for all concerned.
    But first get all the stuff out that you can.
  • by roc97007 ( 608802 ) on Wednesday November 07, 2012 @10:47PM (#41915105) Journal

    I'd start with having the board agree to purge all the old docs from the old system. You'll have to do this anyway whether you stay put or move to a different product.

    Get agreement and set Bob to work on that. If he doesn't get frustrated and give up, move on to the next step, which is to decide a document hierarchy and have him implement it. If Bob doesn't get sick of that, proceed to the next step, always making the steps reasonable and never losing sight of the ultimate goal -- to have a robust system that people actually want to use.

    At some point, one of the following will happen: (a) Bob will quit. While not ideal, this gives you the opportunity to bring someone in to dump the content out of his code, sort it, drop old documents, and move it to Google Docs. (b) Bob will whip his system into shape and make it more useable. This is not a bad solution, as your goal is (or should be) to have a usable system, not specifically to migrate to Google docs. Bob might even surprise you, given the proper motivation. (c) Bob will suggest that we move the content to Google docs to save him work.

    Alternately, you could just live with the way things are. But if you're genuine in improving the system, not just cutting Bob out of the deal, you'll have to involve him in the solution. It's not an easy thing to do, but management never is.

    Personally, I wouldn't want to have a career maintaining some clunky system I had cobbled together, because (a) it's boring, and (b) it's a lot of work for not much reward. In the past I have jumped at the chance to move on to something that was maintained by someone else so I could build something new.

    Years and years ago, I built a content management system from scratch in PHP. The actual content was in text files, (not even HTML) and the code took care of formatting and presentation, on the fly. It included a dynamic gallery that would build an index on the fly from a hierarchy of folders containing images. It was fun to build and worked fairly well. I had four websites using it at one time.

    A year or two later, I realized that there were a bunch of free CMS packages out there that looked better than mine and did more things, so rather than compete with that, I audited them, selected the best fit, and converted. I'm proud of my code, but it's not about the code, it's about the content, and it was time to move on to other projects. Hopefully, Bob will see the wisdom in that.

    • Full stop. (Score:4, Insightful)

      by westlake ( 615356 ) on Thursday November 08, 2012 @02:34AM (#41916021)

      At some point, one of the following will happen: (a) Bob will quit. While not ideal, this gives you the opportunity to bring someone in to dump the content out of his code, sort it, drop old documents, and move it to Google Docs.

      Bob isn't a staffer you can fire and forget.

      He is a senior member of the board, an advocate and fund-raiser, a very familiar face, representing an important constituency of his own among the agency's clients and financial backers,

      • At some point, one of the following will happen: (a) Bob will quit. While not ideal, this gives you the opportunity to bring someone in to dump the content out of his code, sort it, drop old documents, and move it to Google Docs.

        Bob isn't a staffer you can fire and forget.

        He is a senior member of the board, an advocate and fund-raiser, a very familiar face, representing an important constituency of his own among the agency's clients and financial backers,

        I did not mean to imply that Bob was a staffer that you could fire and forget. I've been the president of my homeowner's association board -- I know about having unpaid, volunteer members of a group who have skills that the group would really suffer to be without. But are you really prepared to be held hostage by that? How important is the application? If it's not as important as Bob's participation in the group, and you can't see a way to win Bob over to your side, then you don't have a problem. At be

  • by Xeno man ( 1614779 ) on Wednesday November 07, 2012 @10:58PM (#41915169)
    Too many people are treating this like a business or office problem. Every suggestion to get rid of Bob, build a new system behind Bobs back or go over his head is just wrong. For a small board of not for profit members, you all need to be working together to get anything done.

    Right now everyone but Bob agrees that the system needs to be updated. The system build and run by Bob is Bobs baby. Insulting the system is insulting Bob. At the same time, Bob is probably aware of what is in the system and how much work it would be to reorganize and move all the information, which might be overwhelming for Bob. When you talk to Bob about the system, you don't want to be listing every fault and everything that is doesn't do. Instead, talk to Bob about things that you and the other members would like to add to their computer systems. Features that would help improve daily business. Ask Bob for his opinion on something that he thinks might be a good solution. Ask him if Google Docs would work and if not, why not? Involve Bob in creating something new and not hot to get rid of his hard work.

    Working together, design a system layout for how information should be separated and organized. How will information be accessed and by who? What security measures need to be taken and information backup. Only once the layout is designed do you start putting any information in it.

    Transition slowly, start with something small and simple like meeting minuets. Start using the system and get everyone involved that needs to be so everyone knows how to access information, how to input new information and document everything so when anyone new joins, they have something to read to get caught up quickly. When people get familiar with the new system, start bringing more data over and use the new system for imputing that data as well.

    The key is not to fight Bob or exclude Bob but to involve him. Offer your help with any and all parts of the project but at the same time, make sure there is something for Bob to be in charge of and responsible for. Holding his hand the whole time will be just as insulting as telling him the failures of his system.
  • by mattr ( 78516 ) <mattr@t e l e b> on Wednesday November 07, 2012 @11:19PM (#41915275) Homepage Journal

    As others have said, I would not recommend Google Docs since they keep discontinuing products.
    It also would seem difficult to organize a lot of files there.
    Follow the advice of other poster recommending running the board professionally and not sneaking around or preconceiving you need a certain product. Sounds like Bob has done good work for you all, give him a chance to discuss it with you.
    Frankly you could get a cheap hosting service (just throwing out a name, hostgator for $6 a month..) which will let Bob or someone else build a content management system for you.
    Start with outlining the current problems, and what the goals of the new system would be. For example a CMS could let multiple people in your organization contribute regularly to the website or CMS.

  • by lucm ( 889690 ) on Wednesday November 07, 2012 @11:20PM (#41915279)

    What you need is to work out a good taxonomy, and that can be done easily with a whiteboard. Once everyone is clear on the classification and processes, then you can decide if "Bob's system" is the right implementation or not.

    Technology can be an enabler for business (or non-profit) but selecting the tool should be the last step in any IT project, not the first one (unless you believe in SAP but then it's a whole different problem).

  • by rueger ( 210566 ) * on Wednesday November 07, 2012 @11:42PM (#41915377) Homepage
    I'm coming at this after twenty+ years on non-profits, including time as a consultant, and time working with technology.

    Your'e new. Too new to be suggesting anything dramatic unless you have been explicitly drafted to do so. If you're not 100% sure that is the case, then it's not. All that you'll do is piss people off.

    You're new. It will take you at least 18 to 24 months to really understand how the organization works. And that much longer until you know the history behind the way things work. Now's the time to sit tight, keep your mouth shut, and listen and watch.

    Ignore Bob's stuff. Almost certainly 95% of anything really important exists on paper - primarily minutes and budget docs. The rest is historical stuff that's nice to have, but not mission critical. I once stepped into a non-profit which, after twenty years, had exactly one banker's box of records. Someone had purged everything else in the place. We survived.

    Start from scratch. Seriously, just start creating records in a new organised format. Leave the old stuff on the (virtual) shelf. If you really need it, there will be a back-up somewhere, or someone will have printed a copy.

    Finally, You're brand new. Two seats are open. Records are in a mess. I'll wager that there a lot more pressing problems than just record-keeping.

    Finally again, the stuff that really, really matters - minutes, budgets, grant and funding documents - should exist on paper, in a file cabinet. As much as a I love e-docs, some things are just better in a permanent, uneditable form.
    • by Cyrano de Maniac ( 60961 ) on Thursday November 08, 2012 @04:07AM (#41916371)

      What rueger said.

      I've been there before as a new board member of a non-profit, and rueger is completely correct that it takes at least a year to understand how an organization works and why things are the way they are. More importantly in your case, it takes that long to suss out the nature of the personalities involved, and know what is important or not to each director so that you know how best to advance your goals and make it a positive thing for everyone involved, but most importantly the organization itself.

      More than any of that though, you really need to study what the appropriate and necessary roles of a director are. Start Googling and reading on the subject -- there's lots of good stuff out there. As a director you are entrusted with serious legal responsibility for governance and oversight of the organization and accomplishing its stated mission. Everything you do must serve those ends and must be evaluated in light of them. This is your primary role and duty -- everything else is secondary.

      Your legal duty and responsibility is to the organization. Not to the board. Certainly not to Bob. So first you need to identify how the current situation is holding back the board from any or all of its responsibilities for governance, oversight, or accomplishing the organization's mission. Once you understand that you can use it as a basis of a discussion with the board so that the board can decide whether they want to solve the problem. If they decide as an entire board through an adopted motion that they want to solve the problem, then you can work with the stakeholders such as Bob to figure out the "how" part of solving the problem (unless Bob already agrees that it needs fixing, in which case the two of you may be able to work together to approach the board together with a presentation of the problem and a proposed solution). See how that works? Identify the core duty/responsibility, address the problem in achieving that duty/responsibility, determine a course of action through the board's official decisions, then implement that decision while maneuvering in the zone of the personalities involved.

      How does this then apply to your situation? In order for the board to perform its oversight and governance functions, as well as preserve business continuity in achieving it's mission, it is important that they have reliable access to all documents which they need. The degree to which it is easy to locate those documents impacts how effective the board members can be at carrying out those duties. And for the important documents reuger mentioned (minutes, budgets, etc), it is extremely critical to have a solid paper trail, particularly if for some reason your secretary of state, the IRS, or J. Random Attorney With Aggrieved Client comes knocking. Maintaining these records is part of your legal "duty of care", and you need to make sure it is done, and done wetech.slashdot.orgt SuperBanana mentioned further above: Once you've identified the weakness that your board is responsible for fixing, operate within the correct procedures of the board to address the issue. Get the item on the agenda. Let Bob present on how he would like to fix it, or have the board discuss how they would like it fixed. As part of this the board should create and vote on motions that direct the next steps that should be taken (e.g. further research, funding for implementing a solution, etc). At this point it doesn't matter any longer if Bob is on board with the approved motions or not -- though hopefully he is and a plan that he's happy with has been adopted. In any case at this point the board's decision is as good as law for the organization: if any director cannot faithfully support and help execute the adopted motion, whether or not they were in favor of the motion in the first place, that director needs to resign. If the director works to undermine the board's decision and doesn't resign, the board needs to remove them post-haste.

      This doesn't have to be as heartless in practice as it sounds

  • Not the answer (Score:3, Interesting)

    by SuperDre ( 982372 ) on Thursday November 08, 2012 @04:55AM (#41916523) Homepage

    Well, because you like Google Docs and some other members doesn't mean it's the best solution.. Yes I understand bob's system isn't the best either, but in the end, it's all in the eye of the beholder.. If you're really into wanting to replace the system you look beyond your own shallow view of 'google docs' before deciding on that one.
    Personally I would ask bob to look into fixing the problems if he can and if he can check out other systems (for inspiration). With him having to check out other systems might actually convince him his own system is in need for a change.. Trust me, Google docs is NOT the answer, and is mostly suggested by people who have not looked further (as their own gmail/google account).
    You also have to remember that you're still in need to convert/transfer all the old documents to the 'new' system..
    Yes Google docs can be handy, but it certainly also has it's flaws (but then every system has flaws)..
    To me it seems more like you want to impose your work-habbit on others..

"You can have my Unix system when you pry it from my cold, dead fingers." -- Cal Keegan