Firstly, we recognize the situation we've put ourselves into. Allowing one employee to hold us hostage was a problem that sneaked up over several years. We've since been pushing for everyone to better document their processes, and share knowledge across the org where appropriate. However, as we're a very small company, hiring multiple employees dedicated to the same job isn't feasible even in ideal circumstances.

Now, the issue at hand.

There is an employee at my company whom we want to terminate.

Our biggest concern is knowledge transfer and off-boarding processes (e.g. revoking VPN credentials when they're the only one with access). We're also mildly concerned about malicious behavior if the employee learns we intend to imminently terminate them.

We've identified several courses of action, but all seem to have significant drawbacks:

  1. Hire a replacement now, let the employee bring them up to speed, then terminate the problematic employee.
    • Because there isn't a lot of work for admins here, even under the guise of reducing bus factor (which we recognize must be done long term regardless), they would find it highly suspicious and likely block training of the new hire.
  2. Terminate the employee immediately, then search for a replacement.
    • This leaves us exposed technically until we find a replacement, which historically hasn't been a quick process. On boarding the new hire would be difficult with the lack of system documentation. We have other technical staff with some knowledge of the network, but they're not admins.
  3. Set a task to explicitly document everything, then terminate them.
    • This ask is reasonable as it's something we've been pushing for a bit now. The company would still be at risk until a new hire arrives, but would at least give them and existing staff something to work off.
  4. Hire a contracting firm to work with the employee for knowledge transfer (under the guise to the employee of reducing bus factor), then terminate the employee.
    • This provides some first hand knowledge transfer, the firm would know how to deal with system issues that do arise, and would be able to transfer knowledge back to the new hire. However this is expensive, and it may involve some dishonesty to the firm to get them to participate.
  5. Terminate the employee, have other technical staff take over in the interim.
    • This isn't ideal given the other technical staff are a little distributed, and aren't admins themselves. Combined with a lack of documentation it's not ideal.
    • We could do this with proper knowledge transfer from the problematic employee to an existing technical employee. It still wouldn't make up for missing core admin skills, but would help get us through the hiring period, and on-boarding of a new hire.
  6. Hold out until our system is in its back in a stable state, then terminate the employee, and pray the product is much more hands off than it used to be while a replacement is found.
    • The big issue here is having everyone continue to work with the employee for another 6-12+ months. This is a liability not just in terms of company morale and productivity, but in continued incidents caused by them and completing their work with potentially bad practices. Documentation should be significantly better at this point as well.

Is there another angle or other points we haven't considered? Right now it feels like there's no clean path forward. All options are a mix of drawbacks between expensive, slow, and leaving us vulnerable (to normal problems and malicious behavior). We're leaning towards the last option and putting up with them for a while more for the sake of keeping the system alive until their part of the improvement project is complete, however the idea of having to work with them for another 6 months or more is not sitting well with many of the staff.

  • 1
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    – Kilisi
    Nov 10, 2023 at 0:21
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    All solutions involve termination, is there no way to make peace? Nov 10, 2023 at 22:08
  • 5
    Doesn't seem like it matters to get an acceptable answer, but I bet I'm not the only person reading this who doesn't know what a "bus factor of 1" is. Nov 11, 2023 at 6:17
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    @ToddWilcox Bus factor is the number of people absolutely required for a project to exist/work - as in "how many people can be hit by a bus tomorrow morning without affecting business?" Bus factor of 1 means that a project is very dependent on 1 single person - if that person is hit by a bus tomorrow (or anything else prevents them from working), the world stops, because they have most of the knowledge from this area. Nov 11, 2023 at 8:07
  • What happens if this person finds out what you want to do, and gets angry and want to hurt you? What happens if it takes a while for you to find out this has happened? Nov 23, 2023 at 9:20

11 Answers 11


One solution I've been involved with multiple times is hire an expert consultant to do the documentation and work out how everything needs to be handled that has this skillset and leave it to them.

Realistically all an expert needs is the admin rights, they can work out the rest if absolutely necessary and given the authority to do so.

The expert has multiple options which they can pick from after analysis of the situation.

Best practice is to get the consultant in before removing the employee and involved with onboarding the new hire as well.

  • 128
    I've been that expert a few times, and have had to tell people that their indispensable genius was not in fact that wonderful. Often that toxicity that makes firms want to get rid of this person is covering up a technical lack. The advantage of an outsider writing up all the stuff the genius knows and does is that they can also evaluate it. That's missing from all the other options. Nov 9, 2023 at 13:09
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    BTW, I would do it when the employee is still there and I'd be pretty open about it other than "we want to fire you." Something like "Name, we've had documenting procedures on your task list for ages and it's not happening. We get it, you're busy with stuff that needs to be done now (or makes us money, or keeps our customers happy or whatever) and the documentation has to wait. So we're bringing someone in to do it. We'll expect you to find a few free hours every few days to answer their questions but the rest will be taken care of. We really want to capture your expertise on this!" It's true! Nov 9, 2023 at 13:30
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    @KateGregory You should make this a full answer. I've been the consultant myself a few times in such a situation too. Important point is that the consultant must be aware that the person that "needs help with documentation" is on the "to be fired list". And first priority is to get control of admin-accounts and remote access to the systems. I was kept in the dark about it the 1st time and when he discovered why I was really hired (his manager let something slip) I got the full brunt of his anger, without knowing myself what set him off. It nearly got physical. Continued...
    – Tonny
    Nov 9, 2023 at 15:32
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    @KateGregory Continued... He was fired on the spot then and luckily I had already establsihed enough control of the systems to lock him out. He tried to get in via the regular user-VPN and via an out-of-band management interface that was "accidentally" exposed to the internet, but I had revoked his access and closed the firewall just in time. Point is... That was sheer luck. I had not been looking to get control of those things first, but I happened to already have it by the time the situation escalated.
    – Tonny
    Nov 9, 2023 at 15:39
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    Wow! I do not understand people who bring in experts but tie their hands. Always tell your consultant your goals for the engagement. "We need to be free to fire [person]" is a perfectly legit goal and one a consultant can be trusted with. I don't lie. I can keep secrets and I do it well. Nov 9, 2023 at 16:22

I would ask what the reason for termination is - as that has the potential to change the advice given.

As an example - if the reason was say illegal activity at work or activity that could result in a lawsuit (Sexual Harassment as an example) then I'd say kick them out the door, bite the bullet and accept this as the learning experience that it is.

If the reason for termination is less... Imminent... e.g. it's been a long slow process, maybe a PIP was involved and there's been X number of written warnings etc. then perhaps here is what I would try (depends on the Employee though and what motivates them):

  • Sit down with them.
  • Let them know that you want to discuss their 'voluntary' exit from the company.
  • Tell them that you are giving them this advance notice, so that they have ample time to find alternate employment
  • You'd be happy to provide a good reference
  • As a condition of this advance notice, you would like them to help document their roles/responsibilities as part of the exit.
  • Also as a condition of this, here is the lump sum exit bonus that you are willing to pay (suggest 1-3 months salary) on the condition that they leave amicably so that they are financially motivated to leave on good terms.

Now - it's still a big risk - but consider this: What is the cost of 3 months' worth of Salary vs:

  • a Lawsuit
  • a Data loss/security incident
  • hiring contractors/consultants to reverse engineer your environment

This is very 'Carrot' rather than 'Stick' - and does have a number of risks associated with it - that is they take the money but fail to honor their end of the bargain - I would suggest a contract be drawn up for that.

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    Harassment is one of the reasons. They also regularly make unprofessional and inflammatory comments. More technically, if they're not interested in a certain aspect of their job they simply won't do it. Maintaining our flaky system for one - they're more than happy to work on the improvements, but if something needs to be done on the current iteration they try to ignore it and/or pass the work off to anyone they can (doing that work is very much in their job description from when they were hired). Thank you for the carrot idea, this might be suitable just to get us out of this situation.
    – benjamin
    Nov 9, 2023 at 14:38
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    "You'd be happy to provide a good reference" Wow. That is certainly unethical. You're firing them because they're toxic and do shit work, and then tell their future employers that they're fantastic to work with? Why would anyone want to do this? Makes references totally useless. Nov 9, 2023 at 18:12
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    @CrisLuengo - Reading between the lines of what the OP has said - it sounds like the worker is only interested in working on the things that they are interest in. I've seen this before in technical roles - If it's System A that's Worker A's baby - they'll burn whatever Midnight oil they need to, to make it run smoothly, but System B that is a different Tech stack can rot for all they care. So you talk about their work ethic and skills for System A. It's not lying, or unethical IMO. Nov 9, 2023 at 18:42
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    @CrisLuengo: From a legal standpoint, most companies cannot do more than provide a good reference (well, sometimes they can do little more than state that the employee worked there), so it's not really lying. They can state what did go well with the employee, and employers can read the lacunae. Nov 9, 2023 at 20:36
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    @CrisLuengo: References are totally useless anyway. I mean, they prove that the person didn't completely fabricate an entire job on their resume, but that's about all they're good for. Many companies have a standard policy of providing flat "worked here from date X to date Y" references, with no additional information.
    – Kevin
    Nov 9, 2023 at 21:01

Pay them off, handsomely

You made the bed, now you have to sleep in it. Tell them they can leave with 2 years severance paid upfront as soon as they have trained a replacement successfully. Or something like it. An offer they cannot refuse is your only reasonable option - the person in question will likely detect and sabotage your other options.

  • 32
    Are you the person @benjamin wants to fire? :D
    – Greg Woods
    Nov 10, 2023 at 10:38
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    Wow, talk about negative incentives! As soon as they do what you want, they have to leave??
    – TonyK
    Nov 10, 2023 at 13:36
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    @GregWoods No, haven't quite reached the same bus factor yet. Working on it :P
    – Stian
    Nov 10, 2023 at 18:47
  • @TonyK, isn't that more like, "as soon as they do what you want, they get to cash in and say good riddance to a place that doesn't really want them". I don't know, but it sounds like a win to me.
    – ilkkachu
    Nov 10, 2023 at 19:17
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    So you are proposing not to pay them while they train up their successor?
    – TonyK
    Nov 10, 2023 at 23:40

How hostile is this soon-to-be-ex-employee?

If you have actual reason to believe he is hostile (eg: he has pulled the bus factor on you to get his own way), or is doing something illegal, boot him NOW. You can make up for lack of documentation and technical debt another way, you might not be able to survive a rogue admin.

If they aren't hostile but otherwise uncooperative, consider getting someone else in under the guise of "extra hands". This will allow them to learn the systems and act as an extra pair of eyes, making malicious acts a little harder to do. If that looks too suspicious, just tell them that you're trying to prepare for potential future workloads when you start expanding.

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    Potential problem with booting him now: It sounds like the problem employee might be the only one with the access and knowledge needed to remove his own access. If you have any suspicion that he might become actively malicious, you need to have the ability to lock out his access without his cooperation before you can safely boot him.
    – Douglas
    Nov 9, 2023 at 17:43
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    The question mentions that one possible problem is "revoking VPN credentials when they're the only one with access". It appears that this person is so ingrained in the IT infrastructure of the company that "booting him now" would cripple the IT of the whole company, and thus the company itself. So that doesn't seem to be a viable option.
    – Philipp
    Nov 10, 2023 at 9:57
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    @Douglas True, but he will also actively sabotage any attempts to wrest that control from him. A typical Windows Admin should have the skills necessary to at least boot him from the AD, and if it is integrated well, the VPN will follow suit. Failing that, if it's a commercial VPN solution, their tech support will have all you need to clear him out. If it is open source/'community edition', then the solution is in the docs. Nov 10, 2023 at 13:53

More technically, if they're not interested in a certain aspect of their job they simply won't do it. Maintaining our flaky system for one - they're more than happy to work on the improvements, but if something needs to be done on the current iteration they try to ignore it and/or pass the work off to anyone they can (doing that work is very much in their job description from when they were hired).

Just do this. Take whoever the problem employee usually tries to pass this stuff off to and task them with doing the boring maintenance work which your problem employee is happy to give them anyway. If they have any questions, they can ask the problem employee for help. When they've learned enough about it, fire the problem employee. You can hire someone new for them to train at that point, or not, however you like.

  • My immediate thought that I wasn't sure if it necessarily was the best answer to here myself, but based on this, I'd figured I'd mention - if there are multiple people who are being handed the maintenance work, having them divide and conquer the information might not be a bad idea - that way, you start immediately turning the Bus Factor to 2, rather than 1, after the problem employee is terminated; when they have the information, you can ask them to pass on the information they know to the other person/people who divide and conquered other components of the task. Nov 10, 2023 at 10:55

Firstly, we recognize the situation we've put ourselves into. Allowing one employee to hold us hostage was a problem that sneaked up over several years. We've since been pushing for everyone to better document their processes, and share knowledge across the org where appropriate. However, as we're a very small company, hiring multiple employees dedicated to the same job isn't feasible even in ideal circumstances.

The reality as a small company is that you have to accept certain people as key. You can't afford to double-man every job.

It's not really a problem that has sneaked up. It's a choice you've made and enjoyed profits from, the alternative being that your business may not have been able to run at all.

There is an employee at my company whom we want to terminate.

You may want to, but be unable to without risking major disruption. This is the same as in any small company where key people fall out, and even large companies can't be cavalier about sacking the most senior staff out of pique.

From all the information provided, it sounds as though you're already somewhat short-staffed in IT, that you have quite some resources to throw at a solution, and that the fundamental problem is around the perceived attitude of the existing staffer and the balance of attention they give to different responsibilities.

Why not consider hiring a complementary staff member, who can cover the things you think are being neglected, who can provide some backup for the existing staff member, and who will probably reduce the strain of the environment (potentially improving relations)?

In a year or two, you'll then be in a much stronger position to consider termination if still necessary (and actually execute it without leaving a key business function completely derelict), but there's also the potential that the problems will have been solved anyway by allocating the right amount of resources.

Also, as a small business, I'd forget about documentation - especially when the only purpose is to wage war against the person who would write it. You can't replace a carpenter with a handbook on carpentry and an inexperienced worker. You certainly can't tell the average carpenter to write a book on the whole job of carpentry - you'd just get incoherent nonsense.

What you need is another person in place, capable of covering broadly the same responsibilities.


If it's reasonable to do so? Maybe a modified 1?:

  1. Hire a replacement now, let the employee bring them up to speed. Arrange so they have different duties that only overlap in the area you want redundancy. Then terminate the problematic employee.

If you want to transfer knowledge you need to create only a reasonable amount of redundancy. The problem being this probably takes twice as long as first you need to change their duties. You might even find they improve with changed duties.


One thing you can do right now is offload certain small tasks to other staff, with the excuse that Mx. Bus appears to be overworked, and each task being offloaded gets a full doc writeup. Pick a bland neutral set of small tasks that technically competent people who are not specifically admins can be trained to do, and make sure that one of those tasks is the process for onboarding and offboarding employees.

Thus, the day that Mx. Bus gets called into HR to be terminated, you have someone trained and knowledgeable who can revoke all of their access while they are in the meeting with HR.

(Source: The long detailed instructions I had to leave to my team on how to revoke all of my access after my last day at a particular job when all contractors were let go in a reorg.)


Discuss and work things out with the employee instead of firing them. Odds are good that the employee has a different story to tell. In situations like these, it is the employer that is at fault about 50% of the time.

It was noted in a comment:

they're more than happy to work on the improvements, but if something needs to be done on the current iteration they try to ignore it and/or pass the work off to anyone they can

This makes no sense to me. If the employee has a particular working style, maybe try to work with him in this style. What is the meaning of something needing to be done on the current iteration? Are you as the employer routinely disrupting his work? The role of the employer is to prioritize the backlog, subject to dependency constraints. If the employee is refusing specific work, offer clarity about the work and try to understand the basis for the refusal. Remind him of his obligation as per the job's original description, and optionally offer a small raise for compliance.

It was also noted:

Harassment is one of the reasons. They also regularly make unprofessional and inflammatory comments.

Again, this can be highly subjective unless it is a serious open-and-shut case. If it were serious, the employee would have been terminated already, which leads to think that it isn't. Sometimes, employees can need coaching. It should help to sit down with them, bring up exact examples, and encourage the employee to adjust. Multiple coaching sessions over time can be necessary. Offer a bonus for behavioral adjustments. Love is the way.


Seems to me that every option you consider is a way for the employee to "dig his own grave" by following your orders. You are out to screw this guy over, and you know it. Sounds like the relationship is sour already, as well. The post is basically asking "how can I fix this issue, and make sure that the employee comes out as a sucker in the process".

Is this within your personal set of values? Is this within the companies set of values? Do you want to be seen doing it? Are you a good enough liar to convince the employee in question that the trap is not a trap?

I am not here to tell you "don't be evil", just don't underestimate the skillset you need to go out and be ruthless, either. Neither am I saying that it is possible to work something out with the employee.


This is somewhat similar but more detailed than an existing answer. It's actually a combo of two ideas that were already stated:

  1. Hire a consultant and
  2. Use a carrot to incentivize the outgoing employee to cooperate.

Specifically, make the outgoing employee a consultant, post-termination, under very specific carrot-like conditions:

  • Stop employees access 100% immediately.
  • Terminate them for cause immediately after stopping access
  • Hire a short term security contractor to prevent risk such as back-doors
  • Then, during the exit interview with terminated employee, propose to them the following contract:
    • They will be employed as a contractor by your company for X time, tasked with documenting everything that they know
    • The contract pay will have both ongoing and performance bonuses. Ongoing pay will be low. Performance bonuses will be literally tied to specific measurable deliverables - preferrably, measured by "ability of an existing employee to perform specific tasks based on your training/documentation".
    • There will be an end bonus for "zero issues" at the end of contract - either issues caused by his malicious actions, or even just harassing employees or whatever else led to the termination.
    • If the contract terminates successfully (using same metric as performance bonuses), his termination will be changed to "layoff" instead of "for cause" (so he can collect unemployment insurance), dated post-contract (so he can have a "clean" resume), and he will be guaranteed good references instead of bad.
    • IMPORTANT - during the contract execution, the employee would NOT have unsupervised access to ANY computers in the company. Any commands they need to execute will be done by a current employee assigned to liaise with them. Any exceptions where they need access will be monitored by the liaison employee (who knows that he will be terminated if he fucks up) and a higher level manager.
    • To sweeten the carrot, if you legally can, offer to continue their non-salary benefits such as health insurance if they agree to the contract, but only subject to hitting performance targets
  • I don't think you understand the consequence of "for cause". It is an easy way to open the door to an unnecessary and avoidable lawsuit for no benefit at all.
    – Asclepius
    Nov 11, 2023 at 2:48
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    Reporting anything but the truth of why the employee was terminated would constitute fraud. Don't suggest illegal action. Also, an employee who just got terminated would have zero reason to trust the employer. Offering a contract that pays (almost) nothing unless conditions completely in the company's control have been completed, would make most people hesitate to take the contract. I don't think any sane person would take a contract in these circumstances unless desperate without any other option. Nov 11, 2023 at 4:40
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    Absolutely ludicrous answer. I don't believe this will come across as a "carrot" to any reasonable person - in fact it comes across as threatening and risks a vindictive response. And even at the best of times, measuring the quality of documentation is difficult, and few have the skills to produce it to a useful degree. At gunpoint, with someone who has never written documentation, and with someone busy looking for their next job, you're just going to get a load of written tosh.
    – Steve
    Nov 11, 2023 at 9:15

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