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Security Plans for When Your Senior Developer Leaves?

An anonymous reader asks: "Our CTO, responsible for all hardware and networking setup, who also coincidentally happens to be our senior (and only) developer, has just resigned to go work for the competition. We are not a software company, but he's written proprietary code that we use on a daily basis to work. What interim measures should we be taking to ensure a smooth transition to the next person hired to take over? What can we do about security, since this person designed and implemented all current security procedures? What about ensuring that we have all the intellectual property to which we're entitled? As one co-worker put it: 'His resignation was a surprise to us, but it definitely wasn't a surprise to him.' If he wanted to leave some hard-to-find malicious timed-release back-door-opening code running, it's certainly within his means. We don't expect any malicious action, and can rely on a reasonable level of co-operation and documentation before he goes, but I want to get a sense of what others have done in this situation."

90 comments

  1. Malicious action on his part would make your day. by Elwood+P+Dowd · · Score: 3, Insightful

    Get your lawyers lubed up and ready to go.

    --

    There are no trails. There are no trees out here.
  2. Too late! by Anonymous Coward · · Score: 5, Insightful

    You should phrase the question "what should we do the next time"

    1. Re:Too late! by renehollan · · Score: 2, Informative

      I was thinking the same thing... something about barn doors, horses, and bolting.

      --
      You could've hired me.
  3. This isn't a techological problem by MerlynEmrys67 · · Score: 3, Insightful

    This is a legal problem. I assume that you have all of the agreements in place (signed NDAs, Non-Competes, etc.). So from there just monitor what is going on. Frankly if you are loosing your CTO, only developer, etc.you are screwed as a company anyway, so maybe it is time to update your resume and get a head start on the new job search that is most likely coming your way

    --
    I have mod points and I am not afraid to use them
  4. Take care of it at hiring by rumpledstiltskin · · Score: 3, Informative

    When you hire the person, make them sign something saying that any proprietary code they develop for the company becomes the property of the company. also, insert clauses with penalties for intentional security breaches, etc. it's all a matter of planning. when you hire someone, you want to bring them on, but you should also look at it from the perspective that they can do real damage to your company. you should have them sign something to the effect that they shouldn't do that damage, and if they do, they will be held responsible for any intentional damage. NDA's while not always enforceable if they are unreasonable are a good deterrent as well.

    1. Re:Take care of it at hiring by stevenbdjr · · Score: 1

      When you hire the person, make them sign something saying that any proprietary code they develop for the company becomes the property of the company. This is unncessary. Any code developed by a company employee as paid work is automatically the property of the company. Not so with contractors, but definitly with employees. I just went to a conference on this.

  5. Old ways are best by NickFusion · · Score: 4, Funny

    I'd stick to gouging out his eyes and cutting out his tounge, lest he bring a plauge upon your house.

    Or, you know, change passwords, and stuff. I hear that works too.

    --
    What were you expecting?
    1. Re:Old ways are best by itwerx · · Score: 1

      I say shoot him, it's the only way to be sure... :)

  6. Two things by Charlton+Heston · · Score: 1

    Lawyers and insurance. At his exit interview make him sign another piece of paper asking him if he's aware that breaching security is a crime, that he has a responsibility to protect your secrets, and that you can and will send him to jail if he betrays that trust.

    Nothing else you can do, except do a code review of all the systems he had access to.

    --
    Get your stinking paws off me you damn dirty ape
    1. Re:Two things by Anonymous Coward · · Score: 0

      What if he refuses to sign it? What are they going to do, not let him quit?

    2. Re:Two things by Loosewire · · Score: 1

      i was just thinking that too. you cant force people to sign things especially if theyre leaving. Thats just likely to make him want to screw your company more.

      --
      Slashdot - The one stop shop for procrastination
    3. Re:Two things by Charlton+Heston · · Score: 1

      OK, forget about him signing it. Just hand him the piece of paper that says if you hack our systems, we'll send you to jail and we have the will to do it. If you give away our secrets, we'll nail your ass to the wall.

      Lots of people here are saying that you should kiss this guy's ass. I see no such need to do that. Tell him exactly what you will do to him if he screws you. Make him think twice about it.

      Then, if he screws you, take him to court.

      --
      Get your stinking paws off me you damn dirty ape
    4. Re:Two things by TheLink · · Score: 2, Insightful

      Yeah make him think twice about it. But what if he wasn't even about to think of it at all? Thought never occurred to him? "Don't think of the potato" sort of thing...

      If you're going to break up, why not remain friends if you can? Not go to "If you take my alarm clock, I'm going to sue you, and remember the time you left the toilet seat up etc". Doh.

      After all the questioner said: "We don't expect any malicious action, and can rely on a reasonable level of co-operation and documentation before he goes,"

      This pieces of paper should only appear when he first started working or during general policy updates.

      I doubt people were talking about kissing the guy's ass. It's more of not burning bridges.

      Remember you MIGHT need to call the guy up for HELP.

      You're proposing a piece of paper that says if you do something bad we'll send you to jail.

      But that stupid piece of paper sure does not incline him to help if something bad happens for other reasons (nothing to do with him) OR you need to change things in your systems around - nothing wrong, business needs often change.

      He's less likely to help people who treat him as if he's the enemy. Goodwill often takes years to build up, and can vanish almost immediately with something like this.

      If you play nice, you are more likely to get free phone/email advice. People in my prev workplace have asked for advice a number of times after I left them, and I've given it free to them.

      I might have still given advice if they had given me such a piece of paper. But unfriendly and risky (threat of jail) environments might mean I'd charge or just hang up.

      Nowadays it's a small world. People are just a few seconds away. Whether for good or for bad.

      --
    5. Re:Two things by raju1kabir · · Score: 1
      OK, forget about him signing it. Just hand him the piece of paper that says if you hack our systems, we'll send you to jail and we have the will to do it. If you give away our secrets, we'll nail your ass to the wall.
      Lots of people here are saying that you should kiss this guy's ass. I see no such need to do that. Tell him exactly what you will do to him if he screws you. Make him think twice about it.

      Dumbest thing I ever heard.

      Fact is, this company needs a lot more from the person who's leaving than he needs from them.

      That's exactly the situation in which you kiss someone's ass.

      Consider the possibilities: Either he has good intentions, or he has bad intentions. Now, hypothetically, the company he's leaving shakes this impotent piece of threat-paper at him.

      If he had bad intentions, then any illegal acts were already illegal, and he could fairly assume he'd get in trouble if caught. However, now his bad intentions are magnified since he has been pissed off by clumsly handling by inept management. If he had the means to get away with something before, he still does now. The company has not gained any recourse or information source to help them punish or detect this.

      If he had good intentions, then he was potentially very useful - he would know which cable to wiggle next time the network went down, etc., and would in all likelihood have provided that information for free. Now, however, if they get it from him at all, they're going to have to pay for it.

      --
      "Patriotism is your conviction that this country is superior to all other countries because you were born in it." -- GBS
  7. Dot Bombs Are Perfect Model by mugnyte · · Score: 4, Informative


    In the heyday of the bubble, jumping ships was a practice that everyone knew about it, and often tried. So, relating from my experience of that...

    I think your requirements for a replacement CTO should start with securing the system. Hire consultants until the right guy is found to document what's going on - NOT for more development.

    Although I have no info about the politics, your lack of insight into managing your technology is stunningly poor. I hope you pick the best of those consultants and hire them to spread this risk in the future.

    Above all this, prepare for your competition to now exploit any weakness you have in your market. No more BusinessAsUsual. If you didn't care about what this guy until he left, perhaps you should re-evaluate what you use your technology for, and take it a bit more seriously.

    mug

    1. Re:Dot Bombs Are Perfect Model by JamMasterJGorilla · · Score: 2, Insightful

      You need to expand the depth of your paranoia. It was only deep enough to scare away your CTO. At little deeper and you would have had a backup CTO in a secure location in anticipation that the first would quit and take everything... The funny thing is you never had anything of value in the first place, well except the employees that left...

  8. Rats Leaving? Time to Go! by 4of12 · · Score: 5, Funny

    but I want to get a sense of what others have done in this situation."

    Ask him if you could go with him to the new corporation.

    --
    "Provided by the management for your protection."
  9. Don't put all your eggs in one basket by Violet+Null · · Score: 4, Informative

    You say you're not a software company, so obviously the code that he's written isn't your product. Is it utilities, or something that manages your workflow and process? If so, it doesn't seem like you've got that much of a problem. I guess a lot of it depends on what terms he left as -- going to the competition doesn't necessarily imply a bad breakup, but the tone of your posts seems to. Well, anyways...

    The easiest source of information is going to be him, himself. It doesn't sound like he's left on the worst terms, and, really, the truth of the matter is he's got all the cards now. If he wanted to screw you over with a malicious time bomb, he could, and there's very little you could do about it. So I would just take what he gives you in terms of documentation and all, and, unless evidence proves otherwise, assume that he's on the up and up. You have little choice, and the other options (like lawyers) are going to make him very uncooperative. Most programmers I know don't get malicious unless they feel that they've been royally screwed over. YMMY.

    But, to the future! The best way to avoid exactly this kind of thing is to not have a new guy, but two (or more) new guys. Even if its a senior-level and a junior-level, having someone who can be your backup is invaluable. At worst (depending upon the software), you could get an intern or other low-paid peon to serve as the backup on the cheap. Some of them are clods, but some can be quite smart. Code review reduces not only bugs, but logic bombs and backdoors, and it leaves someone who at least has a clue about the system if one of the two leaves.

    As for security: Make sure you have a firewall, and the rules are set to the bare minimum allowed in (but you should have this already, right?) Change the root/administrator passwords. If you have a competent sysadmin, have him monitor for unusual activity...but these are all things that should be going on all the time. In other words, nothing out of the norm.

    1. Re:Don't put all your eggs in one basket by Loosewire · · Score: 1

      but two (or more) new guys. Even if its a senior-level and a junior-level,
      But then instead of just a BOFH you get a PFY too ;-)

      --
      Slashdot - The one stop shop for procrastination
  10. Trust by HRbnjR · · Score: 4, Insightful
    What can we do about security, since this person designed and implemented all current security procedures? If he wanted to leave some hard-to-find malicious timed-release back-door-opening code running, it's certainly within his means.

    If you think they are the type of person who may do something like that, you probably shouldn't have put them in charge of security.

  11. Is this a one-man company? by Radical+Rad · · Score: 2, Insightful

    Nah just kidding.

    I would suggest making two complete backups of all data on all machines. That way if there were a problem then the backups could be used for forensics. Second, monitor any connections to the network from remote access modems or internet connections using an intrusion detection system. Then just relax. If the guy is leaving on good terms then you probably have nothing to worry about.

    1. Re:Is this a one-man company? by voblia · · Score: 1

      2B || 2B == true !!!

    2. Re:Is this a one-man company? by Anonymous Coward · · Score: 0

      It's a good thing you didn't say:
      2B || 2B == !!! true
      because that would be not true.

    3. Re:Is this a one-man company? by Red+Warrior · · Score: 1

      And me w/o mod points.
      Of course, I don't know if you'd get funny, insightful, or redundant (as in blindingly obvious).
      LOL

      --
      "If, therefore, any be unhappy, let him remember that he is unhappy by reason of himself alone."
      ~Epictetus
  12. Give him stock by anthony_dipierro · · Score: 1

    lots of stock. Then he won't want to fuck you over, cause it's in his best interests not to.

  13. Care and feeding of developers. by eclectic_echidna · · Score: 3, Interesting
    Woody, is that you?

    We don't expect any malicious action

    Well then you shouldn't have made life so difficult for your CTO. I mean, everyone has their price, PAY IT!

    Oh wait, you want team players. Well then who's idea was it to cut his pay, deny funding to the latest project, or take photos at his last "business trip". Certainly not his...

    --
    Antiquated competence won't be a job skill forever.
    1. Re:Care and feeding of developers. by TomGroves · · Score: 1

      No, it's not me.

  14. Your best bet... by joto · · Score: 1
    Your best bet is to have planned for this, and made sure that there are always at least 2 programmers that have a good overall picture of each large product.

    Your next best bet, is to make sure he doesn't feel that you have a grudge against him, and that you are willing to let him go. At least then, you can probably ask him about something later, if a specific problem pops up.

  15. start from scratch! by Tumbleweed · · Score: 4, Informative

    First, hire a security team to secure your systems.

    Make sure they remove all existing accounts on all systems, and start with new ones, with very secure passwords. This is a good time to require a password rotation policy, and password length & strenght requirements as well.

    No non-secure connections to non-public systems from outside the company, period. Or at all, if you can get away with it. No connections from dynamic-IP connections to internal systems, either. (make sure all allowable connections to internal systems are from a list of known IPs)

    Make sure PHYSICAL access is secured! Lots of ex-employees keep security cards, keys, etc, and can often get back in after the fact.

    Make sure your people know about 'social engineering'!

    Don't use inherently-insecure technology from companies who don't give a rat's ass about your security. No bonus points for correctly guessing which company I'm talking about. This becomes stupendously more important if you're the sort of silly-ass company that only has one techie on staff at a time. Lots of updates are to be applied, no matter what platform you go with.

    Now's the time to separate systems if you host stuff. Hosting stuff should go in a co-lo facility (since you obviously don't have the staffing resources to handle your own data center), and you should have separate systems for business needs, like e-mail, etc., in case your website gets DOS'd, it won't impact your e-mail, etc.

    Have regular security reviews by external security companies. Rotate which company you use each time.

    Make sure your insurance covers all your computing infrastructure and eventualities (fire, flood, theft, cracking, etc.).

    Make regular backups.

    TEST your backups.

    Make sure you have off-site backups.

    Make sure you have a disaster preparedness plan and the appropriate people know how to implement it. What happens to your business if the building burns down? If the phones go out? If the Net connection goes down? What if there's a major terrorist attack in your city and noone can get to work? Welcome to the real world.

    Make sure you have onsite spare parts for your computers, at least for the critical ones.

    Make sure noone saves important documents ONLY on their own machine - either make them start saving to shared drives which get backed up daily, or have each machine backed up daily. Say you lose the business plan you're showing to investors tomorrow? What do you do? WHAT DO YOU DO?!

    Don't get locked into proprietary file formats, or you may never be able to switch. Plus you may get hit with 'requests' (ie threats) to inventory every piece of software on your site.

    Definitely have more than one techie & programmer (2 of each, at least) at your company. That's flat-out ridiculous, as you are probably aware by now.

    Okay, that's all I can think of off the top of my head right now. Have a day.

    1. Re:start from scratch! by metacosm · · Score: 4, Insightful
      God -- comments like this make me a bit crazy -- this is a company, unlike you, they don't live in fantasy land.

      Any company with one developer is going to be a small business -- small businesses have budgets, just like REAL people -- believe it or not, companies don't want to spend every penny of budget on IT, since -- without sales -- there is no damn IT department. Making a bunch of silly recommendations that are beyond the means of this company is silly.

      Some or your recommendations are valid
      • Secure core machines (possibly with a consultant)
      • Make sure that you have backups and do test restores, move backups off-site every once in awhile


      The rest of your recommendations were intelligent assuming a magical world with no budgets, no deadlines and no need to be realistic. But -- if you take into account the real world -- they were moronic.
    2. Re:start from scratch! by Eneff · · Score: 2, Insightful

      Something tells me you've never worked for a small company before.

      The cost of such an action may be more than the company makes all year, if the company is a microbusiness.

      Fast, cheap, good. Pick any two. I'd suggest hiring a CS college student now and have him be the intermediatry between the old worker and the new. Keep him on as an intern, and have him in charge of documenting everything.

    3. Re:start from scratch! by Anonymous Coward · · Score: 0

      Something tells me you've never worked for a small company before.

      Or that he does work for a security consulting firm... :-P

    4. Re:start from scratch! by scheme · · Score: 1

      Actually some of his suggestions wouldn't fly even in larger companies that have money to spare. Especially the one about removing all existing accounts on all systems and then adding them back in. I'm curious as to what the people who use those accounts are supposed to do while the accounts are being removed and then added back in.

      The comment about not using Microsoft software at all is pretty humorous. I wonder what happens when an important customer sends a document that Abiword or OpenOffice can't read.

      --
      "When you sit with a nice girl for two hours, it seems like two minutes. When you sit on a hot stove for two minutes, it
    5. Re:start from scratch! by Anonymous Coward · · Score: 0


      Let me see. I work for a company with only one developer / sysadmin / support guy / dataprocessing guy, ie me.
      If I was hit by a bus tomorrow the company would hit serious problems within a week. No question about it, despite the fact that everything's well documented - there's a lot of things that take time to learn.

      Sensible business practice should suggest hiring a second IT person to learn the ropes and increase throughput at the same time, rather than spending 100k+ a year on two sales staff who've managed to bring in <50k of business in the last year. In the same period the billable work I've done has brought in far more than the costs of the IT dept.



      In short - it's the real world that's moronic a lot of the time...

    6. Re:start from scratch! by duffbeer703 · · Score: 1

      You're a clever one...

      The only problem is, after the entire new team of 75 IT people is finished making off-site backups with amanda, deleted and recreated all accounts, eliminated all Microsoft products, replaced Word with vi and excel with an abacus paid your $2.5 million insurance bill, and shipped your systems to a colo facility... all your real employees will have quit and you'll be out of cash.

      Get a clue, fucktard.

      --
      Conformity is the jailer of freedom and enemy of growth. -JFK
    7. Re:start from scratch! by Anonymous Coward · · Score: 0

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    8. Re:start from scratch! by aaraar · · Score: 1

      I agree with your views that a small company has constraints related to budgets and theory will not work. In addition to what you have written, one practical act would be to hire the same senior developer ( i.e. the guy who has resigned ) as an unofficial week-end consultant for about six months to an year, till you get control of all things. You may not take his help unless desperately required, but it will keep him cool( and away from any thought of creating problems for you) and you still have him in an emergency; and paying him may be more effective than paying legal fees !!! This has worked in many places before. It is a win-win situation for all !! Good Luck.

  16. Actually, what I've seen before by immanis · · Score: 1

    I've seen this handled in a draconian sort of way in the past - take his stuff and send him home now, pay his salary for the rest of the two weeks.

    It's not always the best way to handle it, especially when dealing with a C$_O, but it would get the job done.

    1. Re:Actually, what I've seen before by raju1kabir · · Score: 2, Insightful
      I've seen this handled in a draconian sort of way in the past - take his stuff and send him home now, pay his salary for the rest of the two weeks. It's not always the best way to handle it, especially when dealing with a C$_O, but it would get the job done.

      It would probably sink the company.

      The reason you have someone escorted out is because you believe they may cause some sort of damage.

      If he wanted to do any damage, he would have done the dirty work in the period between deciding to leave, and telling everyone else that he was leaving.

      At this point, the most damaging thing he could do is leave the building and not share any of the business-critical information inside his head about how the IT infrastructure works. Why would you want to force him to do that? You'd be shooting yourself in the foot.

      --
      "Patriotism is your conviction that this country is superior to all other countries because you were born in it." -- GBS
    2. Re:Actually, what I've seen before by Anonymous Coward · · Score: 0
      Perhaps if he is being fired. But if he is quitting, he is the one who was in control of the timing and his activities. He already had opportunity to cause any intended problems.

      Rather than send him home, don't assign him new tasks so he will have more "free" time. Have him teach others anything which he has forgotten to document. Have someone else supervise and learn what he does during this time -- he can be a teacher, and if he did security then he understands why supervision is a good idea.

  17. First Step by mike_lynn · · Score: 2, Interesting

    I'm guessing you've already hired someone to take over at this point. I say this because hopefully anything technical that may need to be done to insure a smooth transition won't be performed by your former CTO. This also leads to a less hostile work environment where the CTO doesn't feel you're worried about him doing something damaging.

    Assuming that you already have some sort of data backup performed on a semi-regular basis, my first step would be to keep a static copy somewhere in storage. A snapshot like that might prove useful later should something be 'waiting' for him to leave.

    As for the proprietary code, if you haven't already worked out the legal ownership issues involved with it, you're a bit late. The less you have in writing already regarding that, the more you should be considering a replacement setup. At the least, you should be requesting documentation for everything that doesn't have it already.

  18. Re:Malicious action on his part would make your da by NegativeK · · Score: 4, Funny

    Get your lawyers lubed up and ready to go.

    I think what you meant to say was "Get lubed up and get your lawyers ready to go." They are lawyers, after all. >.>

    --
    This statement is false.
  19. It happened here by Anonymous Coward · · Score: 4, Interesting

    We make DSL equipment. Shortly after a layoff last year, all of our test stations at several contract manufacturers stopped working almost simultaneously. It seems one of our test engineers had programmed them to phone home to his PC at headquarters to make sure everything was ok. Thank goodness it wasn't one of the linecard software guys or we could have had thousands of lines out of service.

    Trouble? Yes, we've had our Phil.

  20. Get him first! by KDan · · Score: 1

    Kidnap him and lock him in the basement, then torture him until he tells you where he put the backdoors. If he dies before he tells you, he probably was innocent.

    You live in Iraq, right?

    Daniel

    --
    Carpe Diem
  21. He is probably more worried than you... by (H)elix1 · · Score: 3, Insightful

    For the most part, if they were really malicious, you are boned anyhow.... The good news is development is really a small community - even if they don't get the book thrown at them, I know folks that were more or less excommunicated because of bridge burning and other stupid departure tricks. More than ever, jobs are had by personal recommendation rather than some recruiter pushing your resume. You may not like your job, your peers, etc - but I've seen prospects burned before they got in the door because of what they did a company or three back. Odds are, if this guy was a senior level developer, he has more at stake than you. I know I made sure everything was checked in, documented where possible, and asked IT to change my passwords - I also never checked to see if they did...

    1. Re:He is probably more worried than you... by metacosm · · Score: 1

      If I had not already made a comment I would have moderated the parent post up. Dead on.

  22. audit the code by falsification · · Score: 4, Insightful
    First and most obviously, get him to document his code fully and properly before he leaves. It's the honorable thing to do. In addition to writing up documentation, the code should be fully commented. He should walk people in your company how to compile the code. Maybe there's a trick to it.

    Then, once he's gone, audit the code. Maybe you'll need to hire an outside consultant to do it. Anyway, once the source code is audited, you still aren't in the clear. It could be that he put a backdoor in the binaries, leaving the backdoor out of the copy of the source code he pointed you toward. Thus, once you are done auditing the code, compile it. Do a file compare of the current binaries and the newly compiled binaries.

    In Windows, the command line is fc /b filename1 filename2.

    If there are any differences, that doesn't necessarily mean anything significant. Move the current binaries to a temp directory or someplace out of the way. Don't delete them, as they could be important later. Copy the newly compiled binaries in. Test the whole system to make sure it works.

    As for ensuring your intellectual property is protected, I don't know how you can truly do that from a technical standpoint. You should notify your corporate legal counsel of your concern. If you don't know who that is, bring it to your CEO's attention.

    Good luck.

  23. "make him sign another piece of paper" by HotNeedleOfInquiry · · Score: 1
    How the fsk are you going to do that? You can't just make him sign a piece of paper? Hold a gun to his head? How many hours have you worked in HR? Besides, a contract isn't valid unless there's an exchange of value.

    --
    "Eve of Destruction", it's not just for old hippies anymore...
  24. don't be an idiot and learn... by kevin+lyda · · Score: 4, Insightful

    first, treat the person leaving with respect. if this person is mature then they won't burn bridges - neither should you.

    don't accuse him of things he might not have done. don't screw around with his career. shake hands, wish him well and generally be professional. it's business. cope.

    second, solve your problems. the person who is leaving has his own issues - poor communication, poor loyalty, excessive greed, whatever. those are his problems. let him work on those, they're not your problem.

    the main reason for your discomfort is that you put all your eggs in one basket. and now your basket has left. so in the future hire two people, not just one.

    and when you have these two people on board, talk to them more often. find out how they feel. you were taken by surprise by this person leaving, that suggests poor communication - on his part or your part.

    finally, you seem to have no idea what code this person wrote even though your business seems to depend on it. does the code go in a source code control system? do you have a release procedure? can you get the previous releases?

    you need to answer yes to all three of those. if you don't answer yes to all of those now, make sure you can in the future.

    --
    US Citizen living abroad? Register to vote!
    1. Re:don't be an idiot and learn... by Kris_J · · Score: 1

      Thank you. Having worked in some places that treat any competent computer officer like an evil voodoo witch doctor, I'm really grateful for your comments.

    2. Re:don't be an idiot and learn... by no_mayl · · Score: 1

      Also look at Europe's working contract model.
      The trickier the job, the longer the leave-notice period.
      Normally people have 30days leave notice for most technical jobs. Engineers have 90days.
      If the job requires more hand-over time, then make it required in the contract.
      If he wants to quit but does not help the new guy during those 90 days, then he becomes sueable.

      I hope this teaches all you "at-will"-contract-touting companies a lesson.

      --
      jpa

  25. You need a registered bad-ass by Glonoinha · · Score: 4, Insightful

    Quite honestly, your company needs to get their ducks in a row. Here is what you are up against :

    Your company sounds small enough that they had very few 'computer guys' but big enough that the computer infrastructure is fairly complex.

    The guy in charge (your soon to be ex-CTO) probably designed and built the existing systems from the ground up. As he didn't have anybody watching over his back, do not be surprised if there is some jury-rigging in there. He probably shared some of the quirks with some of the other computer guys, but not all.

    He may be an important part of the wet-ware in your system. An easy to understand example would be a bowling alley - if your company has to bowl a strike every time the ball gets thrown, he was the guy that walked down the alley continually making minor adjustments to the path of the ball. This could be custom reporting on your data, swapping out the backup tapes, deleting temporary files, cleaning out the log files so they don't fill the hard drive, or booting the servers in a particular order so as not to overload the UPS. It has become routine that he takes for granted and probably doesn't even think about them any more so when he doesn't mention it (and they don't get done) ...

    You have some pretty important apps that he may be the only guy that understands how they work.

    Today is the day of truth, you are on the cusp of finding out if he is disgruntled or not. If he is disgruntled, the LAST people you want talking to him is HR. They will either piss him off more than he is, or try to bully him - you need to get his favorite tech to take him off-site, dinner or to a strip club, and off the record find out why he is leaving, what his primary concerns are, what he would honestly have changed given the chance, what he anticipates the hot-spots being after he is gone, and most importantly : does he have any recommendations for a good replacement.

    This last one is key. There are lots of paper tigers out there (MCS* certs), lots of guys that are good at network administration, lots of guys that can code language A or B or C++, lots of guys that can diagnose and maintain an SQL Server, and lots of guys that can operate in the role of CTO to work as manager and liason between the IT department and upper manglement. You are going to find precious few people that can do ALL of the above(*), and unfortunately that is exactly what you need to do - and find a guy that enjoys doing it because the first few months are going to be rough. Doubly rough if your CTO is disgruntled, so if one of trusted colleages was in there he might hesitate before setting off some time bombs that his pal is going to have to clean up.

    The penalty for getting this wrong is going to be pretty severe.

    (*) I would be perfect for the job, but I am pretty happy where I am.

    --
    Glonoinha the MebiByte Slayer
    1. Re:You need a registered bad-ass by Ieshan · · Score: 4, Funny

      "...you need to get his favorite tech to take him off-site, dinner or to a strip club, and off the record find out why he is leaving..."

      Or - you could lock him away on some Island someplace after gassing him just as he arrives at his Apartment and give him the number six as a code-name.

      Why did you resign?

  26. Position by limekiller4 · · Score: 1

    You know, when I first read the description of your problem, the first thing I thought of was that poor, poor goatse.cx gent. Because if everything you say is true, you're in pretty much the same position.

    And that's what you company is gonna look like if you don't have NDAs in spades signed by this guy.

    --
    My .02,
    Limekiller
  27. Piss him off by Glonoinha · · Score: 3, Funny

    This is -exactly- what I was talking about when I said the last people you want dealing with this guy is the HR department.

    Might as well steal the toys off his desk, decline the steak dinner on his expense report, deduct some personal long distance calls from his paycheck, and key his car while you are at it.

    --
    Glonoinha the MebiByte Slayer
  28. two words... by tongue · · Score: 1

    non-compete clause...

    1. Re:two words... by TheLink · · Score: 2, Funny

      1) Proprietary code written, but wasn't a software company.

      2) Non-compete clauses are dumb ideas. You don't want a skilled baker to work in a rival bakery? What's he going to do then? Work as a beautician? You going to pay him to do nothing? Same for programmers.

      In fact some companies do pay key people to do a year or so of "gardening".

      BTW if someone is really crap... e.g. Mr Anderson, you suck, we'll help your CV look good, just go work for the competition. And if you sign this "do compete clause", you'd get a USD5K bonus. j/k.

      --
  29. Run, run competent staff! by coyote-san · · Score: 2, Insightful

    Yeah, the lawyers and HR would love that but anyone worth their pay would run the instant yuo suggested it.

    "Intentional security breaches," for instance. Okay, no problem, none of us want intentional security breaches and since Outlook and MSIE are both responsible for a large number of breaches they're history. What, I can't do that - you're telling me that you're holding my feet to the fire yet denying me the authority to do anything about it? See ya!

    Ditto all of your other suggestions. Of course any code written for the job, at work, for pay, etc., belongs to the company. It may or may not be proprietary, in the sense that I may extend GPL code to fix a problem. It's perfectly legal unless the company wants to distribute the code to others (which doesn't sound like the case here), in which case you need to say so upfront so I can budget about 10x as much resources to duplicate the prior work. But the stuff I do at home, on my own time, is mine.

    I could go on, but it shouldn't be necessary. Anyone with real experience has been burned by somebody with such a list, or had a friend burned, and no matter how bad the economy is they know that unemployment is better than being the target of a lawyer trying to prove that their client's incompetence is really your fault.

    --
    For every complex problem there is an answer that is clear, simple, and wrong. -- H L Mencken
  30. Make him eager to help out ... by Glonoinha · · Score: 2, Interesting

    Another suggestion - depends on how important your uptime is, but ... as you walk him out the building the last time hand him his bonus - if the systems maintain their existing uptime percentages (nobody is 100% uptime, but pretty close) for one year - with his occasional cooperation if necessary (assistance via phone or VPN access or whatever) - then give him his usual bonus for that year, or some arbitary amount of cash ($5,000? $10,000?)

    Consider it a very important support contract with a limited lifespan (a year should suffice.) Unless he is really, really pissed or his new company is paying him double what he was making with your company - he will go for it and be a pretty eager helper when the chips are down.

    If he declines that offer you guys are hosed, because he declined it for a reason.

    --
    Glonoinha the MebiByte Slayer
  31. Be nice to him. by clambake · · Score: 2

    Seriously, it doesn't hurt you and maybe then you won't have to worry about him...

  32. Anything he wanted he already has... by thecampbeln · · Score: 1

    Any proprietary code/internal documents/emails/etc he wanted are already safely in his possession. Why bother breaking in later when he has full access now? The only real reason would be to disrupt your business, but being as that is *highly illegal* (i.e.- goodbye BMW, hello federal prison) I would doubt that as a possibility. Anything he wanted or anything he thought he just might possibly need in the future has already been copied. This was probably the first thing he did once he knew there was a possibility that he would be leaving. Having him stay throughout his 2 weeks is a good and bad idea... Good in the fact that you can pick his brain and help in the transition, but bad in the fact that if there was anything he forgot to copy before, he can get at it now.

    --
    "1984" was ment to be a warning, not a guidebook. You hear that Kim Jong-il!? BushCo?!
  33. Enter, stage right... by Hard_Code · · Score: 1

    Documentation Documentation Documentation Documentation Documentation Documentation
    Documentation Documentation Documentation

    [image insane person running around the stage clapping his hands]

    --

    It's 10 PM. Do you know if you're un-American?
  34. When I was your boss... by Anonymous Coward · · Score: 2, Informative

    I have been the guy in charge of everything technical, and left to go work for a competitor. (by that I mean in charge of IT, in charge of engineering, for a sick period of time, in charge of the web site, answering to the board, and oh by the way writing mission critical software.)

    Where's about what I told them. (I wish I could find the original letter, but I can't.)

    Disable all accounts listed on attachment (a). Better yet, monitor activity on them. Look for ones I've forgotten/failed to list. (We had a horribly fragmented pile of crap for authentication/authorization.)

    Review all changes I have made or have caused to be made by others on externally facing systems for the last N months, where N is something I obviously cannot recommend. (I was a nazi about change logging.)

    Review all executive reports I've made for accuracy.

    Randomly interview my employees and fish for things I might have done, might have wanted to do, etc.

    Review this list of important things I've done over the last while, and think of how I could go about damaging you with underhanded techniques.

    Review your infrastructure. Hire outside people if needed.

    Review your trade secrets. Hire outside people if needed.

    Note problems with either of the above. Wait for signs that I'm exploiting them.

    Think about my tenure here, what I've done, and what I'm legitimately taking to my next workplace. If you believe I've been underhanded, please call me to task. I'd prefer a non-judicial approach first, obviously.

    Don't trust me, think of how, in my shoes and with malicious intent, I'd be sneaky. Please assume I'm not doing so (because I'm not), but verify.

    ***

    There was more, some of it company specific, some of it items I've forgotten. My approach was to put myself beyond reproach. I don't do underhanded things. There was concern that I could, and I wanted to explain the tools they could use to convince themselves of that. Of course, I could have done all of that just to try to trick them... I was hoping (and have been proven correct) that my prior track record reinforced faith in me, even when I was moving to a competitor. Sometimes, being a good person makes sense.

    I also had some heated sessions with a corporate attorney at my new role over that letter. It came down to, "well, then I already fucked up. Fire me." They didn't.

    (Afterseveral years: the two companies have moved in different directions in the same general field, there haven't been any problems between them, and we still trade employees from time to time. And I'm back to having dinner with my former CEO.)

    -obviously, anonymous

    1. Re:When I was your boss... by Clover_Kicker · · Score: 1

      >My approach was to put myself beyond reproach.

      Great advice, mod this guy up!

  35. Procedures by mattsouthworth · · Score: 2, Interesting

    Just follow the termination procedure. You do have one, right?

    This isn't a termination, of course, but should be handled the same way.

    1. Re:Procedures by KyleCordes · · Score: 1

      A while back a resigned from a company. I got a big chuckle out of the HR people handing the "termination". The wording of all the documents was as though they were doing the terminating, which was far from the case (the management and I had and still have a good relationship).

      There are of course some similarities between firing someone and them leaving to move on in their career, but treating the latter too much like the former, just makes you look silly.

    2. Re:Procedures by Anonymous Coward · · Score: 0

      In many cases it looks better for you if the termination was a downsizing initiated by the company and not a firing due to incompetancy or "bad attitude"....

  36. One word in response... by mr_death · · Score: 2, Informative

    non-compete clause...

    California, where no-competes are unenforceable. Note that you could still get the soon-to-be-ex-CTO with inevitable disclose of company secrets, but you have to go to court for that one.

    --
    It's Linux, damnit! Pay no attention to renaming attempts by self-aggrandizing blowhards.
  37. Too little too late. by Mr.+Piddle · · Score: 1

    What interim measures should we be taking to ensure a smooth transition to the next person hired to take over?

    If you are worrying about these things now, then you are screwed. It's too late. If that senior developer didn't have appropriate clauses in his employment contract...well, you just had it coming, didn't you?

    All you can do now is disable his login account. That doesn't buy much.

    If there isn't enough documentation to make his replacment straight-forward, well, you might as well offer him a 50% higher salary and get that loser back.

    --
    Vote in November. You won't regret it.
  38. get root's password and some source code now by bluGill · · Score: 1

    More than one person fell into the sysadmin job because the old guy left and only one person remembered to ask for root. The old guy didn't care cause he was leaving, the people who remember to ask care because they are staying. Of course if there are junior guys to this person you don't need to get the password (assuming the juniors are smart enough to get it, maybe you should check...).

    As for source code: if you ahve the source code you can audit it. I'm willing to audit it if you need someone. (I have no special expirence in this area, but I'll do it. I won't feel bad if you find someone better qualified though) Make sure someone audits that code. And make sure you re-compile it with a clean compiler, remember the old login hack?

    1. Re:get root's password and some source code now by Anonymous Coward · · Score: 0

      I have some source code to audit, may you assist?

      i do not know what it is, but its code i think and and I am but i'm willing to send it to you for audits.

  39. A problem to be solved long before a resignation by KyleCordes · · Score: 2, Insightful

    The way to address this is to hire good people, and treat them well, especially for key positions like this one. That way when the person leaves to move on in their career, it will be with regret and good wishes. They will be eager to help you in way they can help you recover from their departure, rather than looking for ways to harm you.

  40. We had something simliar by Anonymous Coward · · Score: 1, Interesting

    A contract manager stole her NDA/NC out of a cabinet she had a key to. She also stole a few developers' NDA/NCs and hired them. She's set up a few minutes away. She competed (in one case sucessfully) for our contracts, claiming she got all of our developers and that we're going out of business (neither of which is true -- I'm the only qualified developer on the project she managed to steal).

    She left a huge trail of slime on the way out...

    No idea what you should do. I'll see how our management handles it. But I think they learned at least one big lesson: Offsite backups of contracts with employees.

  41. Software development cycles (Re:Too late!) by Zey · · Score: 0
    A lot of the people commenting here seem to be assuming that this CTO will be likely to take the "secrets" of the current system and use them in the next. But, even if their new company was starting from scratch and had no pre-existing legacy software, who's to say that in between the finish of initial development and bedding it down into a stable state he hasn't figured out much better ways of doing things.

    That in itself may be one of the reasons for his move. Some people simply prefer active new development, with a free reign, to supporting and hardening existing apps and existing interfaces, with clients and managers who scream loudly if tweaks and new features break things in minor ways. The start and end of the software development cycle naturally appeal to very different types of software developers.

    In the end, your developer should have been expected to document his procedures and the software along the way. At the least, his code needs to be commented and located such that it can be found and used by the next guy whose job is to keep the monster in check.

    1. Re:Software development cycles (Re:Too late!) by Glonoinha · · Score: 1

      >Some people simply prefer active new development, with a free reign,

      Ummm I am guessing No. Nobody bails on a CTO slot in today's economy unless he is really really frustrated, really really mad, or going to make GOBS more cash at his next position. Line coders -maybe- but not at the Chief Technology Officer level.

      People often -say- they are leaving because they don't like to maintain code, or want to work in the exciting initial phases of development, or whatever ... but that is generally a front, fluff to hide their true motivations (frustrated with impossible work environment or another worker, pissed off about something, or want more money.) Everybody says they leave for a more stimulating work environment, but how many people do you see bailing on developer job to join the Marines (gunfights with Iraqi front line forces are VERY exciting, but the pay sucks.)

      Sort of like when you are interviewing with a new company and they ask why you are leaving your last job ... you have to say something, and instinct says that 'this position pays more than I currently make' will make a bad impression so you have to make something up like 'blah blah personal improvement, more responsibility, blah blah.' Responsibility sucks, and being held responsible for the actions of a bunch of underlings sucks big time (a newbie coder spills ice coffee on his laptop and you get screamed at - sucks) but people are always saying they want more responsibility. They don't want more responsibility, they want more money. Give someone the option between twice the responsibility for the same money, or twice the money with the same responsibility and they will be all over the money like a puppy on a pork chop.

      --
      Glonoinha the MebiByte Slayer
    2. Re:Software development cycles (Re:Too late!) by Harik · · Score: 1
      Ummm I am guessing No. Nobody bails on a CTO slot in today's economy unless he is really really frustrated, really really mad, or going to make GOBS more cash at his next position. Line coders -maybe- but not at the Chief Technology Officer level.
      Sorry, the job shortage is for us peons. Executive level staff are being headhunted like mad. Since medium-small companies can't get a big name C-type, they're pulling from small-small companies. He's just advancing his career.

      Best way to keep them is to have them own the company, especially at the micro-company level. Calling someone a 'CTO' when they're just a sysadmin/programmer is great for their resume, and bad for you keeping them.

      --Dan

  42. Bullshit. You are the one in a prallel universe. by jotaeleemeese · · Score: 1

    If you think that crackers are going to have pity of you because you are an small company you are more deluded than the people that think the Matrix has a religious undertone.

    Lets see:

    -Hire a security team to secure your systems.

    What is so intractable about that? It is a one of cost that could save the very existence of your company. These companies (or a consultant with a good trackable record) will charge you a few hundred bucks for an assesment and then will charge you the normal hourly rate of any IT person. If you r company is small the work needed is proportionaly smaller.

    -Make sure they remove all existing accounts on all systems, and start with new ones, with very secure passwords. This is a good time to require a password rotation policy, and password length & strenght requirements as well.

    The point here is that you should take steps towards securing your use accounts. That costs you nothing, specially if you make a policy and stick to it. Most modern OSs provide enough tools to have sane policies out of the box.

    -No non-secure connections to non-public systems from outside the company, period. Or at all, if you can get away with it. No connections from dynamic-IP connections to internal systems, either. (make sure all allowable connections to internal systems are from a list of known IPs).

    This is only policy for goodness sake. Use ssh. Enforce policies regarding who can connect. One of cost implementing the policy (albeit small since it should have been done in the first place).

    -Make sure PHYSICAL access is secured! Lots of ex-employees keep security cards, keys, etc, and can often get back in after the fact.

    How much does a good lock costs? How long does it take to write down a list of people authorized to acces your small computer room? Or your small company's installations? This should have been done anyway in the first place.

    -Make sure your people know about 'social engineering'!

    Cost: neglegible. Just direct people to many of the fine articles in the net about the topic.

    -Don't use inherently-insecure technology from companies who don't give a rat's ass about your security. No bonus points for correctly guessing which company I'm talking about. This becomes stupendously more important if you're the sort of silly-ass company that only has one techie on staff at a time. Lots of updates are to be applied, no matter what platform you go with.

    Moan as you wish, but this is true. You have to invest the time and money to get this right or go out of business. If your comapny relies in any way on IT to do business you need to carefuly select what you use. Knee-jerk "buy X or buy Y because is what everybody else is using" is irresponsible and unprofessional.

    -Now's the time to separate systems if you host stuff. Hosting stuff should go in a co-lo facility (since you obviously don't have the staffing resources to handle your own data center), and you should have separate systems for business needs, like e-mail, etc., in case your website gets DOS'd, it won't impact your e-mail, etc.

    Let assume your company is so pitifully small that can't do this. Still you can get a 2nd hand computer to handle your email or to handle your vital operational data. The principle is the same. 200 bucks for a second hand machines is nothing, even for an small firm.

    I am tired. I think you are just writing out of ignorance. Even 1 person shops have to be mindful about sefety and security of their data, the size of a company is no excuse to avoid investing the time and money necessary to maintain data and systems as secure as possible.

    --
    IANAL but write like a drunk one.
  43. keep him on the books by Anonymous Coward · · Score: 0

    Give him a nice severance package and keep him on the books as a technology/security consultant until the next guy figures everything out. Make his pay contingent on there being no major break-downs or break-ins.

  44. MultiMan! by Glonoinha · · Score: 1

    Too bad you are AC - you sound exactly like who I was five years ago. Want some tips from someone that has been there, done that?

    You are IT. Also known as IS, MIS, and 'the computer guy'. The entire weight of the company rests on your shoulders, from the systems that run AP/AR, maybe Payroll, the custom apps, printing, networking, backup, and developing / maintaining a hundred little internal use apps. Maybe you get farmed out a few weeks a year at $160 an hour ... and yet you feel you are horribly underpaid and overworked. And the company would falter and crash if you got hit by a bus.

    Tip : even though you get farmed out from time to time, even billing enough to completely cover the cost of the IT department, you and all your associated pricey toys (servers, printers, software licenses, desktops, training, etc...) are tallied by the bean counters in the 'expenses' column. IT (MIS) is an expense on the company and the only way to positively affect the bottom line is to reduce expenses. Increasing your resources (pay, more hardware, better toys) can only negatively affect the bottom line and that is why they begrudgingly do it, if ever.

    Want more respect, power, and money? Work with whoever is in charge and get moved into a 100% billable position. They will have to hire another guy to do the IT work (which you will train in your spare time) and you will be off-site doing billable work as much as the sales staff can keep you busy. All of a sudden you have moved from money pit (IT) to a profit center (billable resource) and are in the 'profit' column of accounting - and they are more willing to do whatever it takes to make you happy.

    Your situation is not going to change unless you change it. I know, I was there.

    --
    Glonoinha the MebiByte Slayer
  45. She? by Anonymous Coward · · Score: 0

    >A contract manager stole her NDA/NC and some key employees ...

    Your company let a woman into a position of responsibility / authority? What were they thinking? They deserve all the pain they got.

  46. What's that strange probing sensation?!?! by Clover_Kicker · · Score: 1

    >If he wanted to leave some hard-to-find malicious timed-release
    >back-door-opening code running, it's certainly within his means.

    <PESSIMIST>
    How long has he been working there?

    If he wants to fuck you, YOU ARE ALREADY FUCKED!
    </PESSIMIST>

    <OPTIMIST>
    Since this guy is really smart, he'll realize that he'll be blamed for anything that goes wrong over the next 10 years. He has worked hard to build your infrastructure, and does not want to harm it.
    </OPTIMIST>

    <CYNIC>
    You seem very intimidated, you write as if this guy is a lot smarter then the rest of you. If he really is the one-man show you've described, then you *will* have technical problems, no matter how good his intentions were - the people you have left simply aren't smart enough to fill his role.
    </CYNIC>

  47. You are Scrod. by Zarf · · Score: 1

    That is the past-perfect-tense of Screwed. You are so completely screwed that it crosses into a whole new dimension of being screwed. You are now SCROD.

    It's like wanting to put on your seat belts after you've had the accident.

    Unless your ex-coworker has morals that forbade him from doing you harm your best defense is to warm up the lawyers and get them all nice an toasty just in case. There is precedent for ex-employees who leave "easter-eggs" for their employers getting sued for damages. That's all you got in the final analysis to keep the Scrod at bay... assuming your ex-coworker really is as golden as you say.

    --
    [signature]
  48. Other code? by Glonoinha · · Score: 1

    A little OT: but I have to ask ...

    What if the developer is on salary, develops a neat little software gizmo on his home computer when he isn't at work?

    To muddle things a little more, what if this guy telecommutes from home on that same computer two days a week?

    A little more - what if the code he developed dealt with / was similar to or an extension of things he generally worked with at work?

    What if he takes out a patent on stuff related to what he does at work?

    What if he takes out a patent on stuff absolutely unrelated to his regular day job?

    They are just questions, but I was hoping you might have some insight (as opposed to general speculation that I might come up with.)

    --
    Glonoinha the MebiByte Slayer
  49. take better care of your next cto, bucko. by Anonymous Coward · · Score: 0

    how could you let somebody that important go?

    are you planning on switching to toner sales?

    you must be a real passel of idiots over there...

  50. No no no! by Anonymous Coward · · Score: 0

    Nuke the site from orbit. That's the only way to be sure.

  51. A bad position to be in by Anonymous Coward · · Score: 1, Insightful

    You should have paid him more money, not overworked him, and kept him happy.

    Supprisingly, the several small companies I've worked for treated me like family but drove me off with a combination of mainly extremely long hours and low pay.

    I guess I forgot to tell the small business owner that he owned the company and I did not and therefore he had a huge interest in it making millions of dollars while I would at best get my salary increased 7% a year if things went good.

  52. All you pompous geeks listen up..... by cuteface · · Score: 1

    nobody is irreplaceable. Yeah, things may get rough for a couple of months but eventually it'll settle down. Trust me, seen it happening many times.

    --
    Reality is what we taste, smell, see, hear and touch yet we cannot comprehend it...only approximate it.
  53. Deal with it 6-12 months ago. by Jellybob · · Score: 1

    That's about all the advice I have... anything else is damage control if you think he'll do something.

    I've just been employed by a charity for the same reasons... ostensibly it's because they have too much work for one person (they do, but anyway). Practically it's also so that one person doesn't have all the keys, and knowledge of how things work.

  54. Double-Entry Computing by Anonymous Coward · · Score: 0
    When he designed the security procedures, he should have designed them so security activities were confirmed. The same principles as in accounting: cash gets counted at each step of processing and checked against known quantities (starting with the amount in the cash register being balanced with the record of activity), and activities by people are monitored or confirmed by others. The idea is to detect, correct, and protect from errors and other problems.

    For example, try to store the backups remotely and preferably with a business records service. Have the people who are authorized to request backups be different from those who create backups, other than the regularly scheduled backup rotation. Have random backup tapes be checked regularly. So nobody can quickly and silently damage all backups. The security staff can design this, document all scripts so they can be checked by others, and write themselves to do as few of the procedures as is possible.