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Ask Slashdot: How Would You Convince Someone To Give Up an Old System?
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 One of the issues I've noticed since joining the board is the method in which they conduct business is very out of date.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."
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."
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.
Apologies to Bill Murary!
Kidding aside, have you tried bringing it up with Bob?
"Maybe this world is another planet's hell"
Aldous Huxley
Why don't you just tell him what you explained above
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.
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
Usually there's a "click the read more link below to learn about Vanderhoth's amazing investment opportunities!" link. Bad samzenpus!
Bio questions? Ask me to start a Q&A journal. Computer analogies available for most topics!
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.
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.
The world is made by those who show up for the job.
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.
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.
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.
Lurking at the bottom of the gravity well, getting old
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.
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).
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
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.
Please help metamoderate.
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.)
"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.
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.
Not knowing what system Bob currently has in place, Google Docs may (or may not) be an improvement.
However, there is no such thing as a document management system that can't be screwed up for it's effectiveness by poor data hygiene processes.
Any system needs to have a high level plan for how the data will be structured and organised. Meta data needs to be agreed upon and used. The information architecture needs to scale and be flexible to be restructured if something changes in how you want to access it (say in response to mandatory reporting requirements being changed).
The tool in most cases is the least important part. It's how intuitive the navigation is and how well everyone sticks to using the agreed (and published) naming conventions and saving files in the agreed locations. Even simple things like naming your files YYYYMMDD_Agenda.doc can help make things easier to find and simpler to sort.
Sara
Designer, Gamer, Macgrrl in an XP World
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.
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.
I support Bob's opposition to Google docs.
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.
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.
Oliver's law of assumed responsibility: If you're seen fixing it, you will be blamed for breaking it.
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.
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.
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).
lucm, indeed.
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.
Three Squirrels
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.
Hi,
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.
Sincerely,
Bob
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 best you have an irritation that you'll just have to get used to. Or quit.
Oliver's law of assumed responsibility: If you're seen fixing it, you will be blamed for breaking it.
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..
While the OP did say "old dog new tricks" and all that. I'd also consider maybe asking Bob, as the creator of the system, to maybe learn a new technology, and compare it to his own, to make a side-by-side comparison of the features and possiblities of a new vs old system. Maybe even ask him to port a few of the documents to show feasibility of doing this. Then have him present his findings to the rest of the team. If he's a professional, he'll either come up with a whole new set of changes he wants on the old system (because I'll bet any new system has a lot fo smart features his hasn't being 10 years old and all), or he'll see that the new system is a good way to store stuff, and clean up the old documents at the same time.
If Bob has the gatekeeper syndrome, then putting him in charge of the transition, will simply make him the gatekeeper of a new and improoved system. Which if he can see the benefits of the transition, would make him feel even more appreciated.
In my view: The important part is to not criticise his system, but let him do it himself. He KNOWS the flaws of the old system. Getting him to admit them will make it easier for him to see why the system needs to be updated.
--- To err is human... Am I more human than most ?
Good points, but I'm not into selling BS. Bob's a good guy and I really believe no one has approached him with the issues yet, at least not in a "your system is great and we want to keep it. How about someone helps you reorganize the files to make it more efficient"
I don't think he's a "gatekeeper" as some have said and he's just a guy that did something good that got out of hand. I've definitely reconsidered my original idea that putting things in Google Docs is the way to go. I can do somethings with Google Docs, but ultimately Bob's system is really just disorganized files. I think if I offer to learn his system and help reorganize things he'll be receptive.