can I ask someone to interview his replacement so that I can fire him?

by Alison Green on April 13, 2015

A reader writes:

I manage a team that supports IT for a very large corporation. On this team of 10 people, I have 2 people with skills to support a particular product, John and Jenny. I have asked John, with the stronger skills, to train the rest of the team, so that we have less risk that we will have no one to support the product at some given time (for example, if one person is on vacation and the other falls ill). John has refused to train the others, saying that it will hurt his job security. He is also a negative influence on the team, causing drama and strife. I have clearly told him that his lack of teamwork and attitude are not acceptable, but he is not changing and it’s hurting morale. His coworker, Jenny, is much more of a team player, but is generally loyal to John.

I want to replace John, but I don’t want to leave Jenny with the sole responsibility to support this product. I have a contractor in mind who has the right skills on paper, but I want to have someone with these technical skills interview him to make sure he has the skills. Can I have John interview him for skills? I could have Jenny do it, but she is loyal to John, so I’m thinking that result won’t be much different.

I’ve tried to be direct with John, and I did tell him that training was part of his job and if he wouldn’t do it, I would get someone else who would. So even if I were to come up with some excuse for why I’m bringing on a contractor with his same skill, I think he would be able to figure out that his days on the team are numbered–especially since he thinks being one of the very few with his skill gives him job security. (In my mind, his unwillingness to train his coworkers was the last straw in my decision to let him go–so the opposite of job security.)

I don’t there’s any way to have John interview the contractor without risking that he’ll figure out that you’re working to replace him. It’s sounds like it’ll be pretty obvious.

But really, would you trust John’s input on the contractor anyway? If he’s gone as far as to openly refuse to to train coworkers and has told you that it’s to make himself irreplaceable, isn’t he likely to tell you that the contractor isn’t right for the job, simply to continue to preserve his own job security?

How would you evaluate candidates if John and Jenny were both gone tomorrow? Whatever the answer to that is, that’s probably what you need to do now. (One possibility is to work with an outside firm or consultant who has the expertise to help you assess candidates.)

And really, I’d consider moving John out sooner rather than later. You’re taking a risk by continuing to keep someone willing to sabotage your team’s success around.

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{ 215 comments }

{ 215 comments… read them below }

  1. AMG*

    What documentation do you have that you could use to provide to a consultant for facilitating hiring? Also, what if Jenny flies solo for a short period of time while you hire and onboard someone?

      1. AMT*

        Makes sense. She’ll be more likely to hire someone competent if she knows she won’t be able to keep afloat without that person (versus knowing she’ll be hiring someone so the OP can fire her friend).

    2. Dutch Thunder*

      This was my first thought too – if you’re worried Jenny won’t train anyone out of loyalty to John, she might have a brand new perspective once the option of sharing the work load with John is no longer there.

      1. M-C*

        Not to mention once you’ve made it clear to Jenny that you take the issue of training seriously enough to fire John.. For all you know Jenny is only being compliant to John because he’s a bully and she thinks that keeps him in check. And once he’s gone she can grow into the main role, and handle training the rest of the staff well and gracefully. Not to mention hire a good counterpart for herself without drama.

        I have to say that this smacks of prejudice to me – you’re not supporting Jenny in the workplace against John, you assume she can’t do the job even though she has been already, you’re not even looking at allowing her to expand her role in ways that would suit you better than the jerk. If I were her, I’d see the writing on the wall and dump you soon as well. Good luck with your (presumably male) consultant.

        1. Daria*

          “You’re not supporting Jenny in the workplace against John, you assume she can’t do the job even though she has been already, you’re not even looking at allowing her to expand her role in ways that would suit you better than the jerk. If I were her, I’d see the writing on the wall and dump you soon as well. Good luck with your (presumably male) consultant.”

          Quoted for TRUTH. Why are you ignoring Jenny’s skills? Why wouldn’t Jenny be in on the interview?

        2. Letter Writer*

          I’m the original poster. Jenny has told me that her skills aren’t as strong and she relies on John to do some aspects of the job. I’m sure she is capable of learning them, but not if John is unwilling to teach. As a woman with a technical background, myself, I’m aware of the common bias against women in IT, which doesn’t, of course, mean I’m immune to being biased, but I don’t think that’s what’s going on here.

          1. Just Another Techie*

            Two words: imposter syndrome. Look it up.

            While you’re at it, also look up confirmation bias and stereotype threat. These are all almost certainly at play, both in how Jenny evaluates herself and how you evaluate her.

            1. The HR Witch*

              Thank you! I’d not heard these specific terms before, although I see them in action in the workplace.

            2. Marina*

              While imposter syndrome is certainly common and worth keeping an eye out for, please realize that you’re implying both that Jenny is unable to accurately evaluate her own job skills, and that the letter writer is unable to evaluate the team she’s managing… all without knowing what either of their jobs actually are. One of the ways we as a culture can do away with issues like imposter syndrome and prejudice in the workplace is to accept women’s assessments of themselves and their own jobs as accurate, especially when they do actually know more about something than you do.

              1. Not Australian*

                Stupidly late to this discussion, but that’s a heck of a good point; thank you for making it.

  2. SouthernBelle*

    If that person is a contractor, can you try him out in a temporary role first and then decide if he can actually do the job? Then you can see for yourself if he brings the same value that you feel John provides.

    1. AW*

      This! Even if this contractor isn’t as good, they’ll probably still be better than someone actively hurting the team.

  3. Kelly O*

    You really do need to have a way to interview technical candidates that’s not dependent upon current staff. Those things can change for reasons outside of your own control, putting you in an even more precarious situation.

    And I do agree with Alison, you really need to do something about John sooner rather than later. It’s good that Jenny is a team player, but sometimes loyalties can be misplaced and she might not even realize how destructive John is truly being to the team. (And honestly, loyalty is a difficult conversation anyway – do your loyalties to your coworkers trump any loyalty you might feel toward your employer? Are you as a manager cultivating a sense of loyalty for your team?)

    It just brings up some challenging questions. But the bottom line is that you’ll need to figure out how to replace John, and any other future openings that fall in your area, independent of current team members.

      1. Rita*

        We call it the “falling off the roof” scenario. Because that happened to one of our team members, one who was the only person who did several things on a regular basis. He ended up being out for over 3 months. There were some backups in place, but it was definitely tough going for a couple of weeks at first.

        1. Meg Murry*

          One place I worked referred to it as the “won the lottery and took a trip around the world” scenario in order to make it seem more positive (something good happened to the coworker to cause them to leave, not bad) and because there was a local small business that actually had an issue not long ago where a majority of the employees were together in a lottery pool that, while not enough to leave anyone set for life, certainly gave all the winners the ability to just say “forget you” and walk away from the working world for at least a few years.

          1. BritCred*

            I do remember one boss joking (partly) that he needed to put in place a “lottery win” contingency plan once he found out a lot of the staff were in a pool….

          2. Connie-Lynne*

            Oooh, I like that one. We use “abducted by aliens,” suggested by a team member when I shared that I actually once took over from a syseng who was hit by a car during my onboarding.

        2. Anna*

          Man, you wish that were a “worst case scenario ha ha” situation, but to have it be literally what happened? Wow. I feel like I’m going to have to stop asking what happens if a person is hit by a bus.

        1. Alston*

          How about fell off a pogo stick? Broke both arms that way last year. The output of my department dropped a lot but they were able to carry on for the 6 weeks I was out because of the cross training and the training manual I’d made.

      3. The_artist_formerly_known_as_Anon-2*

        Or the REALITY of the situation. What if John or Jenny are offered better jobs elsewhere – or, BOTH of them, at the same time?

        Welcome to the IS/IT world – where it happens often. This happens often in offshoring/outsourcing situations.

        And management’s plans to “internationalize and globalize” , (translation = hire people offshore for peanuts, while greatly inflating their own frequent flier miles) often are bamboozled when the employees needed for the transition refuse to participate in what might be considered a suicide mission.

    2. Dr. Johnny Fever*

      There’s a possibility that Jenny isn’t so much loyal to John, as she goes along with him to make her job better. If he’s willing to standup this strongly and offensively with his own boss, how is treating his coworkers when you aren’t as visible?

      Getting rid of John would be a good thing, to cite Bob Sutton’s No Asshole Rule. It’s possible that Jenny may be become a better asset once she can step out of John’s shadow.

      1. themmases*

        I was thinking the same thing. I don’t want to second-guess the OP about how close John and Jenny really are, but I can totally imagine myself being the way you’ve described.

        In a workplace with a lot of drama, where you don’t expect anyone to get pushed out or at least don’t have the authority to do it yourself, it can be a good strategy to just try to be Switzerland and appear to like everyone. The risk is that you’ll naturally end up appearing, and maybe even being, close with people who share a lot of your work. I can think of difficult coworkers from the past that I had some rapport with and that I’d be sorry to see lose their jobs even if it’s for the best. Though that obviously wouldn’t extend to sabotaging the process, I’d also be really happy to be kept out of it.

      2. Letter Writer*

        I’m the OP. I think that you are probably right that Jenny is making the best of a bad situation rather than being loyal to John per se. I just know it takes a long time to fire people at my company. She probably knows that too. I wouldn’t be doing her any favors if she selected John’s replacement.

        1. snuck*

          So bring in the contractor as a training consultant, get him ALONE TIME with Jenny regularly to teach her the gaps that John won’t.

          If the contractor works out then you can formalise his employment through your normal processes…

          And if John arcs up you can have more fodder to fire him. I assume you are building your case in a paper trail already… and having to hire someone in to do John’s job basically spells it out for him.

          Even better… give John the ultimatum… “I have found someone with the skillset I require to close these gaps, I want you to have Jenny up to speed within X time on these and documentation completed by Y date or I will have to bring in this other person.” and leave the threat open. It might take forever to fire someone, but that conversation makes it clear to John you are planning it.

          And document, so he can’t later claim discrimination or whatever.

      3. TootsNYC*

        Also, she’s loyal to him because she works with him now, and it may not even be a negative. She knows him, she works with him, she likes him well enough. People are often loyal to their colleagues.

        That doesn’t mean she’ll be a -problem- if you fire him, beyond the obvious trauma that most firings result in. And that “trauma” is mitigated if the fired person is felt to have been treated fairly. So…..

        Unless someone has resigned, I don’t think it’s fair to ask them to help interview someone who will replace them. And -Jenny- may easily deduce what you did, and even if she’s OK w/ your firing John, she may not be OK w/ your “tricking” him into evaluating his replacement.

        So I agree: Figure out some way to get an expert to help you evaluate the technical skills that you aren’t good at evaluating.

    3. Lia*

      This. I used to work for a company and the Holder of All Information, who had been one of the original hires 20+ years earlier, died rather suddenly (he had been ill, but no one knew how ill he was). He did not leave much in the way of notes or documentation behind — not because he was a John in the example, but more because he maybe was in denial of his own mortality.

      It took them roughly two YEARS to get back to where they had been before the man passed away and even when I left there, five years after he died, we still had things pop up from time to time that only that guy had known how to handle. Sigh.

        1. JB (not in Houston)*

          I should have said “perfect example of why cross-training is important.” “exactly why” makes it sound like this kind of situation is extremely common. And maybe it is, but I think it’s more common that people simply leave.

  4. HigherEd Admin*

    I’ve tried to be direct with John, and I did tell him that training was part of his job and if he wouldn’t do it, I would get someone else who would.

    So it sounds like you’ve said that if he wouldn’t train someone else, you’d hire someone who would, but it’s not clear to me if you made it clear to John that this means you’d let him go (rather than just bringing in an additional person). It seems like he doesn’t understand his job is not as secure as he thinks it is.

    1. AMG*

      Maybe, maybe not. But a person with common sense ould know that’s a Big Deal. It also sounds like he has other issues and OP is still justified in firing him.

      1. maggie*

        I have to agree. Unless OP said it smiling and appeared non confrontational, there’s no way to see that incorrectly: you out, foo!

    1. AnonEMoose*

      Agreed. And if I were the OP, I’d be working with HR and whoever else to make sure John’s systems access is revoked the moment he’s called into the termination meeting.

      1. Dynamic Beige*

        At OldJob, there was a “John” who was the only person who had all the access codes for all the key systems. “John” refused to tell anyone what they were even when directly ordered to, and from what I had heard, higher ups were scared crapless to fire him, because he was an asshole and they knew he would do something to completely scupper everything if he had half a minute.

    2. Helka*

      Absolutely. I would consider him an active danger to the company, particularly as an IT person — if he is willing to sabotage the company by refusing to train others to support this product as a way to (in his mind) ensure his job security, how else is he willing to sabotage? You won’t get any documentation on procedures from him, that’s for sure. And changing passwords or similar is also very possible.

      1. Beancounter in Texas*

        I’ve seen this play out for the worst. Company hires super sharp guy to be The IT Guy (as no more than one was needed) and he offers to write custom programs for Company. Guy decides that he owns the software he writes is his property, not the Company’s, and sets up remote access controls and monitoring from home, including Company files being stored at his home server. Meanwhile, he also is a huge PITA with which to work, generally refuses to cooperate with others and flat out refuses to do tasks he dislikes.

        Finally, Company gets their ducks in a row and fires The IT Guy, with Other IT on standby to catch any fall out. The IT Guy goes home and disconnects his server with Company Files. Company never recovers files and never uses IT Guy’s custom software again, in spite of IT Guy’s attempts to negotiate a service agreement. Other IT removes IT Guy’s remote access and uncovers a host of problems, including the fact that the server was routinely being hacked from Russia.

        2. Ann without an e*

          Honestly though, I think if you were to hire an electrical engineer, straight out of college, s/he would have the skills necessary to fix most of that. The files are gone. That said, in a work for hire situation anything you develop while at work or with employer resources belongs to the employer and the burden is on the inventor to prove that the idea that fueled the patent worthiness of an idea was not born of the work being done for the employer. Also didn’t this guy sign a non-compete. Most of the stuff he has done is in direct violation of most standard non-competes I’ve seen. Guys like this are why those stupid contracts keep getting worse and worse for engineers……hire a lawyer and make him pay.

        4. Steve G*

          I worked with someone who was the first paragraph and it was one of the top 3 reasons I left the job. Not only did they do all of the IT work, but they also got involved in the business decisions pertaining to the IT they were working on. Their hand were in WAY too many pots. The owners seemed smart, so I don’t know why they allowed this – especially in a regulated industry where you need to have a risk management plan in place + need to sign affidavits every year that basically say you have enough operational limits + splitting up of authority within your company.

      2. baseballfan*

        Yes, this. I’d be scared to death of an IT person who had it in for the boss or the company. This guy is capable of wreaking havoc without even trying very hard. He needs to go NOW.

    3. James M.*

      Agreed. One of my favorite sayings from an old professor (computer architecture, iirc) is

      To be irreplaceable, become totally replaceable.

      Which means going the extra mile to make the path smoother for your peers/replacement. The exponential increase in your team’s productivity translates into rock solid job security.

      John is just another example of the contrapositive.

      2. The_artist_formerly_known_as_Anon-2*

        Unless they want to eliminate senior people making the most money. In IS/IT – offshoring and/or outsourcing of one’s job is a REAL threat.

        James – that’s a “happy happy joy joy” scenario. In real life. many people are protective of their livelihood.

      3. TootsNYC*

        I do that! I train everybody on anything that comes up; I document like a maniac; I back up; I place files in all sorts of logical places for access.

        And right now, I feel pretty secure in my job.

        For one thing, every time I teach someone something, I look *SO* smart! “Wow,” they say, “she really knows her stuff!”

  6. NickelandDime*

    I’d consider moving Jenny out too. She’s “loyal” to John? To the detriment of her manager, her team and her own paycheck? IT departments in general, much less large corporations, are usually very busy. The drama they bring doesn’t sound like it’s worth it. Maybe they can help each other with their resumes and job leads.

    2. Colette*

      It’s possible that Jenny is loyal to John, but that she is aware he’s being an ass (I’d be willing to bet someone who sees himself as untouchable isn’t being quiet about refusing to do what he’s been asked to do) and would. It out her loyalty to John above her loyalty to the company or team.

      2. Juli G.*

        Agreed. There are plenty of people who might personally like a coworker but also recognize they’re a cancer to the team/company.

      3. Cat*

        Or that she’s loyal to John because she has no idea he’s being an ass. I’m not so sure he would have broadcast that he refused to do this.

        1. Ann without an e*

          Jenny could go one of two ways.
          1. She sees him as a mentor and someone to emulate…….unfortunately, and her loyalty to him outweighs everything else and it will be a matter of time before she leaves learning all the wrong things.

          2. Once the toxic mentor is fired and the reasons for witch were explained to the mentee she could learn a very valuable lesson from it and grow both personally and professionally and become very valuable.

      4. Dutch Thunder*

        Or that she’s loyal because life with John is a lot easier when John is on your good side. If this guy is a jerk to his manager, he’s probably downright awful to a co-worker who disagrees with him too.

        1. KimmieSue*

          Agree with Dutch. Jenny may not agree with his behavior but if he’s more senior, “playing nice” might allow her to have a better work day. She might go home and say “what a jerk”.

        2. August*

          Exactly. May be she knows that he will make her life a living hell if she is not in good books with him.

    3. V2*

      I’m not sure that there’s enough from the letter to justify firing Jenny. “Loyal to John” could just mean that the OP has observed them being friendly. It doesn’t mean she wouldn’t understand why John had to go. And John has to go. If he senses his so-called job security is in jeopardy, what else might he do? Change passwords and not tell anyone to make it harder for him to be fired? Encrypt files? Delete documentation? I’d take my chances with being short-staffed and show this person the door immediately.

      1. AdAgencyChick*

        +1.

        And given John’s past behavior, if he’s allowed to interview the candidates, not only is he unlikely to provide unbiased assessments, he is also likely to try and discourage good candidates from taking the job in the likely event he figures out what’s going on.

    4. The Cosmic Avenger*

      Eh, I was wondering about Jenny myself, but I was actually thinking that, since the OP hasn’t taken any action against John yet, maybe Jenny thinks that they are capitulating to John, in which case training others when John refuses to do so could cause her a lot of trouble. It would still be the right thing to do, but it wouldn’t be easy. I think Jenny is still a big question mark, but the OP does need to proceed as if she would follow John’s lead, at least.

    5. Celeste*

      I think Jenny is only loyal to John because he’s there. He’s acting as queen bee, and Jenny sides with him probably because she doesn’t want to be bullied by him. I think once Jenny sees that the OP has had enough of John’s behavior and that in fact it cost him his job, she’ll straighten up. I agree with the advice to bring in a contractor for a time, and use that time to get everyone trained up on the other work. That will show that John’s reign is over more than anything else.

      1. Dr. Johnny Fever*

        I alluded to this above, but I agreed. I’m willing to bet she isn’t so much loyal, but conciliatory, in her actions with John.

      2. Ama*

        Yeah, I think if the OP has in place a plan for making sure Jenny doesn’t get saddled with all of John’s work in the transition when she explains to Jenny what’s happening, her “loyalty” will shift right back to the OP. Part of her allegiance to John may in fact be because she fears what will happen if he leaves.

      3. DarcyPennell*

        I totally agree, it may well be that “loyal to John” means Jenny is smart enough to realize how unpleasant he could make her daily life if she didn’t get along with him. I can’t imagine that someone who is that aggressive with his boss is easy-going with a peer.

      4. Mephyle*

        Jenny could be ‘loyal’ to John, along with the above suggestions, because she is attempting to be a team player. In non-pathological conditions, you don’t want an employee who decides (on their own) that their co-worker is disloyal, and does end runs around them and over their head.

      5. Daria*

        Exactly. Especially since management is allowing it to continue. Why stand up to the bully that you have to work with every single day if you are not confident that anything will come of it?

        1. AnonyManager*

          This! Sounds like Jenny has no indication that she will be protected from John’s behavior if he gets away with defying his supervisor. What the OP is reading as “loyalty” may very well be “self preservation.”

    6. Sunflower*

      I’d need to know more about what ‘loyalty to John’ means. It doesn’t sound like OP wants to fire Jenny at all so obviously whatever this loyalty entails can’t be that bad. Is Jenny aware of the issues between the manager and John? If not, it’s possible she thinks since John is more technically skilled and the only one being asked to train people(aka she is getting passed over), she might be viewing him as the gold standard to achieve.

      1. themmases*

        I agree, there is a huge range of what loyalty means. Loyalty could be anything from really egregious like following John’s lead on not training her coworkers (probably not since OP doesn’t want to fire her) to something pretty innocuous such as not wanting to badmouth John. Sure, it would be misplaced in this case because John’s behavior is objectively horrible. But misguidedly trying to be nice or not get in the middle doesn’t imply loyalty so deep that someone can’t be trusted to do their job.

        1. TootsNYC*

          exactly.

          Or it could mean “giving John his due when talking about work, etc.”
          So, John is the one who knows the stuff and does the stuff, and so she acknowledges that.

          Or “not bad-mouthing John,” or “keeping her counsel about mistakes John makes” or “not telling everybody all the crabby stuff that John obviously says.”

          I think most people I work with would think I’m loyal to them. And I am. Right up to a point.

    7. Laurel Gray*

      Jenny’s loyalty to John is only understandable if John pays her rent/mortgage, remembers to put the seat down, and drops the kids off at school in the morning. See where I am going with this? Anyway, I like AMG’s suggestion above.

      1. NickelandDime*

        That is my line of thinking. That’s why I suggested she may need to go to – I’d talk to her and see where her head is at. It’s easy to lay all the blame on John, but if he has people supporting him in his nonsense they are a problem too.

    8. Graciosa*

      I don’t think Jenny is much of a team player if she isn’t listening to the leader of the team.

      The OP – and Jenny – both need to be very clear that this is the OP and not John.

      OP, I don’t think you need to move Jenny out yet – her behavior is correctable. You do need to follow up after firing John (the timing should provide some emphasis) and have a very direct conversation with Jenny.

      The theme of the conversation is not “See what I did to John and watch yourself” as that really needs to remain in the subtext (and you don’t want to be a manager who shares private disciplinary matters with other employees).

      The theme of the conversation is “These are my expectations, and I need you to meet them if you’d like to remain on the team.” Those expectations include not only working collaboratively with co-workers, but also ensuring that work will continue to be performed regardless of the make up or availability of the current team members.

      Most importantly, these expectations include following your direction and respecting the priorities you set for the department. Anything else is insubordination, and you can’t allow that on your team.

      OP, it’s very good that you’re getting rid of John (it can’t be too soon) and not allowing him to assert control over the team, but you need to make it clear to Jenny and the new employee that you are the one in charge.

    9. Just Another Techie*

      I’ve been in Jenny’s position in the past. I think it’s just as likely that her “loyalty” is really “going along with John’s whims to protect herself” and that she’ll immediately forget all about him once he’s gone. Especially if the OP has kept the two employees’ genders in giving them pseudonyms. It’s tough being a woman in tech, and having a domineering asshole as a senior engineer in your group.

      1. quietone*

        Agreed. I was lucky cause when I started my boss explained that dramafilled-coworker was on the way out – but still to do my job I had to “make friends” enough to get stuff done. I’m sure an outsider would have thought we were friendly if not friends.

    10. Lola*

      I agree that Jenny’s loyalty should be to her organization vs. specific players, especially those actively hurting the organization. However, I’d first give her an honest conversation to help her realize how her misplaced loyalty is hindering her own career prospects. That would be her one chance to shape up and be a team player or follow John on his way out.

    11. Adam*

      My first impression on Jenny as OP described her is that she’s may be a bit of a peacemaker or maybe allots more respect to John than is merited in hopes of not stepping on his toes. It sounds like everyone knows John is the more skilled one, and since he has such a poor attitude it may have established a pecking order that Jenny abides by but may not necessarily enjoy. Only OP is equipped to judge that whether or not that’s the case of course.

    12. Sammy J*

      Jenny might just be in an uncomfortable situation. She has to work with John and she may just be trying to ease the drama. Don’t throw the baby out with the bathwater without figuring out what’s really going on with her.

    13. Mike B.*

      The immediate reason we’re talking about firing John is his overt insubordination. The bad attitude and the other issues would perhaps be worth initiating the firing process (written warnings, creating a PIP, etc), but refusal to follow a reasonable order is serious enough to merit sending him right out the door. Jenny isn’t there yet, and her “loyalty” may well evaporate as soon as somebody else is sitting in John’s old spot.

      1. Journalist Wife*

        Frankly, regarding someone else sitting in John’s old spot, wouldn’t Jenny instantly become the senior techie if John were to leave? I am wondering if framing it that way might not be enough to make clear expectations. I don’t know if there is a promotion available, per se, upon John’s departure, but it sounds like he’s above Jenny in the pecking order as it stands now, even if the titles are the same, so then Jenny would naturally be involved in the training/initiation of anyone new brought on to help pick up this workload as a mentor. Maybe it would be an organic way to get her on board, like, “Well, John’s gone now, so congrats on being the senior team member! We hope you understand why we let John go, and what will be expected of our IT team going forward.” I suspect her loyalty to John will evaporate very quickly for all the above-mentioned reasons.

        I will echo the other commenter that pointed out that it is HARD to work as a woman in tech, particularly under a polarizing male leader, and have to juggle being civil/loyal to your senior mate while hearing the grumblings of his toxicity from others dealing with him. You have to do damage control, and sometimes, you are grateful to senior IT guy for taking you under his wing and teaching you, but at the same time realize that others don’t like him. You want to be loyal, but you also want to avoid being lumped in with the toxic environment by attempting to make excuses for him to others complaining, but in a vague way. It is a difficult dance to master, and one it sounds like Jenny might be in right now.

    14. Meg*

      She may be loyal to John because it mollifies him and makes her life easier. It can be extremely tricky to be the person caught between a colleague (specially one you work closely with) and management. Maybe the OP could have a private chat with Jenny to dig a little deeper and see how she really feels.

    15. Anonypoo*

      This needs to be between you, OP, and John. Leave Jenny out of it. Completely out of it.

      If you as a leader choose to manage en masse rather than work with individuals, you are creating a culture of Us and Them and you will reap what you sow.

      Scenario:
      OP: ” Jenny, you seem to like John. I also get the impression you’re discussing your employment here amongst yourselves. For these reason you’re fired.”
      Jenny *can’t answer as she’s imagining the piles of cash she’ll sue for.*

  7. The IT Manager*

    can I ask someone to interview his replacement so that I can fire him?

    No. Basically he’s untrustworthy so if he says potential employee doesn’t have skill set, you cannot trust him. Jenny would be a better person to ask to do the interview depending on her level of loyalty; although, I presume that John is Jenny’s manager so having her doing the interviews would be an obvious sign of what it to come.

    1. TheLazyB*

      And if he does realise his job is under threat, surely you can’t trust him if he says they do, either? Could be one last opportunity to wreak havoc.

  8. Laurel Gray*

    Whoa, John! Didn’t a similar issue come up in the last few weeks – employees withholding job knowledge and refusing to train as some sort of delusional idea that it creates their job security? I’ve never pushed back EVER when asked to do any kind of training. I refuse to believe the less others around me know the more my job is safe.

    1. Elizabeth West*

      I seem to remember us talking about that but I can’t recall what the thread was. Bottom line, nobody is replaceable, and it’s good for the company to have people cross-trained in case someone has to be out for any length of time.

    2. Lola*

      Completely agree. Moreover, to boil down my worth to the organization to a set of SOPs that are teachable to any warm body in a short period of time is steeply discounting my decades-long experience and considerable soft skills. If John is that insecure about his worth, there’s probably a good reason for it. I’d doubt his hard skills as a consequence of this secrecy.

    3. Graciosa*

      This is not the first employee I have known who was fired for pulling this kind of a stupid power play with the mistaken belief that it would ensure job security.

      Businesses need to continue to function even if a key employee is struck by lightning. Every responsible business has contingency plans to cover this kind of thing – even (especially) if the employee at issue is in the C-suite.

      If a company won’t allow a C-suite employee to make himself indispensable, why on earth would someone imagine this would be allowed for an individual contributor?

      I think this could have been added to Alison’s thread a little while ago about the most surprising thing about AAM letters.

    4. Liane*

      I do not like–& it annoys me, to put it gently–when I have to train a new supervisor to do my job*, especially when they think they know everything &/or that I am “just a minion” or don’t bother to pay attention because “I won’t have to do this.” I don’t like it any better when it’s a trainee for my position who hold those attitudes or is otherwise a bad fit.
      So guess what I do? I do my best to train the person! I may grumble about it a lot–off the clock & well away from work.

      *they have to be able to *do* my job–not just know what it involves–because they provide coverage for me, per the bosses, when no one else is scheduled

    5. TootsNYC*

      I think the OP should immediately approach Jenny to ask her to start some **low-level** training and documentation. Get her started. Ask her to observe John closely and make notes of the problems he solves. Then she should write her own documentation and notes about how she would fix it.

      And she should also be assigned a few people or types of issues to actively teach people in short little 15-minute sessions.

      She may find herself learning -faster- without waiting for John, especially since she’s got the beginnings of those skills. Teaching almost always makes people learn more and faster.

      She may also find that she knows more than she thinks she does.

      And our OP will also have some evidence of what training skills Jenny has. She could be your trainer, even if you do end up hiring someone who has stronger skills than she does to replace John.

      But start with that now. Don’t make it be “since John won’t”; make it be, “I think this is a great area for you, as the junior, to get us started in. We’ll bring everybody up to -your- standard!” And then you’ll see, I bet, that her standard rises quite a bit.

  9. Anonymouse*

    I think being as upfront and clear as possible is the way to go. Someone said, “It should be clear to John that this is a Big Deal.” I beg to differ. This would be assuming that John knows it’s a Big Deal, but maybe he doesn’t know. So be as clear as possible with John that it is a Big Deal.

    Also, it sounds like you’ve already made up your mind about firing him. If you’ve seen John improve after your conversation with John about his attitude and neglect of responsibilities (if it is his responsibility to train the team per his job description and duties) , then please re-consider firing him and please be open and honest with yourself about this and with John. If he’s made serious improvements and you’re satisfied, please let the past be past. Maybe John needs more open communication.

    I was just fired from my job on Friday. For six months I was under the impression that I was doing a good job. After my 90 days I was met with “your work is fantastic!” In December I made a mistake on an email that went out to 5,000 contacts. (The mistake was saying year end is in X days whereas it should have said today). I apologized. I tried to pay more attention to detail and my job. But my entire job unraveled from there. Every small mistake was pointed out. I was told I wasn’t communicating enough when I thought I was. I followed directions to a T from my supervisor. If the email didn’t say to copy anyone then I wouldn’t. But I still heard about it. If I submitted a draft of a document for review, I wouldn’t hear back for weeks, even though I followed up on it, and then I would hear that it was incoherent and not at all what was expected (even though I passed it by coworkers who said that it looked good).

    I believe that her decision to fire me was made long ago and I don’t believe that’s fair. I believe that I made improvements, but the relationship was beyond repair. It wouldn’t have mattered if I did everything absolutely perfect.

    So, when you’re dealing with John, please be open and honest and if you see improvements, try to work ahead with John, instead of firing him anyway.

    1. AMG*

      I am really sorry this happened to you. I said the ‘Big Dea’l thing and you have a fair point about it.

      1. Beancounter in Texas*

        Agreed. I’m sorry you got the short end of the stick there. I hope you find an awesome employer with a job in which you kick butt and take names.

    3. Helka*

      Yikes, I am very sorry that happened to you.

      Regardless, though, I think your situation and John’s here are very different — you made a mistake, John was openly and deliberately insubordinate, in a way that essentially amounts to sabotage of the company.

      1. JB (not in Houston)*

        Yeah, the situations are totally different. John has expressly refused to follow an order from his manager because he doesn’t think it benefits him to do it. Your situation (which sucks) is nothing like what the OP is dealing with in John.

    4. Ann Furthermore*

      Ugh, that is terrible, and I’m sorry that happened to you. When I first read your reply I thought your error was on 5000 contracts, and I thought, yikes!! Then I re-read what you wrote and saw that it was contacts. Yes, unfortunate, but likely nothing legally binding, or anything that cost your employer additional money, right?

      I’ve had jobs where no matter what you do or how hard you try, you just can’t win. In my situation I also thought my manager was trying to figure out how to get rid of me, and it wouldn’t have mattered how perfect and flawless my performance was.

      I hope you find a much better job very soon!

    5. The Strand*

      I’m so sorry this happened to you. At the beginning of my career I went through something similar in a front-facing service position.

      As much as it hurt to have that happen, I moved onto different positions. Over time I was able to work with better human beings. Speaking of humanity, you weren’t allowed to have any – to be human, which includes the occasional mistake. I have faith that you will probably find yourself working for better people next time – or at least since this experience, better able to spot bad people earlier in the job, or the job-hunting season. But for now, know you’ve got a bunch of pals here at AAM who believe you and your experience.

  10. Artemesia*

    I was a consultant to a business with someone like ‘John’ here and the Jennies who were ‘loyal’ because he was a bit of a bully. Not being willing to share expertise is a fireable offense. What I did was get the director of that office trained and cross trained a couple of other key players and fired ‘John.’ In our case ‘John’ had needlessly complicated processes so he controlled everything and convinced the rest of the staff that it was VERY VERY complicated work and we were all unreasonable to think they could do it. It wasn’t and the office’s productivity immediately improved when ‘John’ was gone and attitudes improved as well.

    You can’t have him interviewing; you should also move quickly and decisively as you don’t want John around undercutting everyone during a transition. You need to find another way to make sure a candidate has the needed skills. And when you do hire the new guy, have John gone quickly thereafter.

    1. Graciosa*

      I’m tempted to assume IT would know this, but just in case, I’ll mention it anyway.

      Have a VERY good plan in place to ensure that John can’t access or damage your systems after he finds out that he’s being fired. Jamie has several good posts on this (probably searchable) and I’m going to hope that the OP has a good handle on what to do, but still –

      Anyone who would behave like this as an employee cannot be trusted to behave professionally as an ex-employee.

    2. Anony-moose*

      We have a John in the office. The processes for “privacy and security” are…unwieldy. Having done many of the tasks myself I see exactly what you describe… complicated processes and lots of “this is very complex. Let me do it.”

      So my question – do you think people do this in purpose or is it some subconscious power play that left unchecked grows and grows?

      1. JB (not in Houston)*

        It really could be either or both. I work with someone who is very controlling, and she’s never trained me to do some parts of our shared job (this is not IT for what it’s worth). I know a part of that is a subconscious desire to keep control. But a whole lot of that is also because the training would take longer than it would take her to keep just doing it herself.

        1. Anony-moose*

          Right – we’re also not in IT and many of the areas of control are administrative/project management. I want to think the best of the John’s of the world and assume they’re just trying to do the best job available, but when there are these clear power struggles I can’t wonder if it’s a bit deliberate.

          At any rate, working with a John is REALLY difficult. I was remarking to my partner this morning that they’re the only part of my job that I dread.

          1. JB (not in Houston)*

            Isn’t that the truth. People who need to be in control can turn nasty when they don’t get as much as they need. Their self-defense mechanisms just go into overdrive.

        2. Ann Furthermore*

          That’s still no excuse for not cross-training though. I’ve been in situations where there are huge deadlines looming, and although I really appreciate people asking if they can help, sometimes the deadline has to be the top priority. But at some point, if it’s relevant to their job, I’ll make time to sit down and cross-train them.

          1. JB (not in Houston)*

            Oh, no, I agree that’s not an excuse. Cross-training should always happen.

      2. Ann without an e*

        Well when it comes to IT stuff I don’t know. But when it comes to code, and writing applications the mark of a good programmer is one who’s logic is concise and straight forward who’s code does as much as possible with as few lines as possible while still being easy to follow with out the comments but comments well throughout anyway.

        Lots of people that do hand waving and go on about how complicated it is just aren’t capable programmers. I know this because I am not a capable programmer.

        1. Ife*

          Haha, yes. I was reading through some old code I wrote as an undergrad and I… very much did not understand some basic concepts! I was definitely in hand-waving mode at that point. I have come a long way since then!

      3. A Non*

        Could be deliberate, on a conscious or unconscious level. I’ve also seen it happen for a couple other reasons, the biggest one being that “it’s difficult and complex” guy usually doesn’t actually know what he’s doing very well. It’s difficult and complex for him. He probably doesn’t know the easy/correct way of doing it. He builds nightmares, and kind of knows he’s doing it, but it’s easier to convince himself that the work is hard than to admit that he’s not an expert at this particular task. This breeds insecurity, which breeds more talking up of how difficult and complex it is…

        The other one I’ve seen is the guy who’s trying to impress the organization by putting things together out of open source software. Why pay $$$$ for a mail server when he can do it for free? It’s often done with the best of intentions, but the net result is, well, you get what you pay for. There’s no support available, so you have to have in-house experts. Experts are expensive. Don’t choose open source software because it’s cheap – it’s not, I promise you.

        I actually spent this morning dealing with a disaster caused by a dude with both of these mindsets. He no longer works here.

      4. Artemesia*

        I think it is often a power play. My guy got all the support staff riled up after he declared to them that we expected them to do stuff way too complicated for them at their level. When I interviewed him he said ‘it is unreasonable to expect support staff to work with advanced mathematics like boolean algebra. . .’ at which point I said ‘you mean ‘or’ and ‘and’? — it really was that simple. When someone has a chip on their shoulder and is actively insubordinate and undermines the operation, they need to be gone. We gave him a chance to work with us on cross training and he got ‘testy’ (the word of the day apparently for insecure twits); so we moved him out.

    3. Steve G*

      I commented above about how I left a job mostly because of a coworker like this.

      I used to lean towards being a “it’s very complicated” type person until I realized that the stuff that truly was “very complicated” came back to me after a coworker tried it out for a few months, and/or no one every wanted to help with it. Most of the work though didn’t come back to me, though I had to help the people who took it over sometimes….

    4. Windchime*

      We had a “John” working in our office for years and years. Everyone (end users and some people in IT) thought he was a guru, that he did magical and complicated things. “Oh, that’s something that John did! It’s so wonderful and complicated!”.

      John wasn’t a team player. He wouldn’t share knowledge and he wouldn’t even attempt to learn new things. He wouldn’t put anything on servers; he had stuff running on a workstation under his desk. He got laid off a few months ago, and guess what–it turns out that the rest of us are quite capable of figuring out his ancient VB6 spaghetti code. Nobody is indispensable.

    5. TootsNYC*

      ‘John’ had needlessly complicated processes so he controlled everything and convinced the rest of the staff that it was VERY VERY complicated work and we were all unreasonable to think they could do it.

      I worked with someone like that–he complained all the time, and things *did* seem to take forever. He left on his own, we all said, “oh, HOW will we replace him?!?!” and the new guy did stuff in probably 1/8th the time and was fun while he was at it.

  11. illini02*

    I don’t get the secrecy. If you are going to replace John, why not just tell him and see if you can work out some exit strategy that works for everyone. This just seems extra sneaky and unnecessarily so. You seem to have a valid reason to get rid of him. But this going around it just seems like a way to foster resentment not only with him, but with Jenny as well. If you will need her there too, then just be an adult about it and explain to John the situation and let him leave with some dignity or respect, as opposed to you trying to con him into hiring his replacement (which essentially is validating his fears).

    1. Serin*

      Because a person who would openly say to his manager, “I’m going to refuse a direct instruction from you because it’s not good for my job security,” sounds like a person who wouldn’t be above other methods of ensuring his job security, such as deliberate sabotage.

      1. The Cosmic Avenger*

        Exactly.

        He’s already shown that he can’t be trusted; he’s outright refusing to do things within the scope of his job when he’s been told to do them by his employer, and he’s explicitly said that he’s doing this harm to his employer for completely selfish reasons. The OP has no obligation to give him any more chances or warn him, especially when this could cause further harm to the company.

      2. illini02*

        I guess I’m just not the type of person who assumes that just because someone doesn’t want to do a direct order that the person would then try to maliciously harm the company. I’ve had jobs where I HATED my managers, and probably sometimes didn’t do things they asked of me, but if they wanted to come up with a transition for me to leave because it wouldn’t work out, it doesn’t mean my first thought would have been to sabotage the company. I understand certain things can be done, but without more info, I’m not going to make the leap to guess that he is going to change passwords or something like that. Again, you don’t HAVE to do those things ever, but I definitely think that its a good thing to try to end these things on the best possible terms when possible. Maybe he wouldn’t react well, maybe he would.

        1. JB (not in Houston)*

          But if you’re in management, and this person has to capacity to do serious harm, and from what you know about him, you can’t rule it out that he would do something, why take a chance? You don’t know he would, but importantly, you don’t know he *wouldn’t.* It’s like leaving your child for an evening with someone who has ignored in your presence your instructions about not doing something to or around your child. You don’t know they do anything while you’re out, but why would you take a chance knowing what you know about them?

          It’s certainly possible that the OP knows him well enough to know that he’d never do anything. But just from what she’s described, a lot of us immediate thought of the Johns in our lives who would or did. If there’s any possibility, I wouldn’t take a chance.

        2. JustMe*

          Illini02, I agree to some degree. People do tend to get more vengeful when they feel sabotaged. If you do talk to those people respectfully and let them leave with some dignity things can, and often times do end well.

          It sounds like John may have been mismanaged in the past, and it has now led to this. I’ve experienced it before. At old job, management allowed one person to have sole ownership of a system. That person became extremely territorial. I asked her questions about the system; she did provide the answers, however, the problem was my colleagues and I discovered ALL her answers required research and fact-checking. Mgmt thought she knew, when in essence we knew she was just bs-ing her way through. Our John became our manager. We all left (at least, the few of us that weren’t her buddies).

        3. TootsNYC*

          If you decide John is the type of person to sabotage (so you safeguard the system), and you’re wrong: It won’t hurt in the least. He’ll never know, and you’ll be pleasantly surprised.

          If you decide John is NOT the type of person to sabotage (so you do NOT safeguard the system), and you’re wrong: You’re screwed.

          It’s like what I tell visitors to NYC: When you’re unlocking the front door of the apartment building, say “please use your own key, or ring the bell,” and shut the door in the face of whoever it is that’s coming up the steps behind you.
          If they’re a “good guy,” they’ll understand (and they’ll have a key, or the person they’re visiting WANTS them to ring the bell). If they’re a mugger, you don’t want them entering the building with you.

      3. College Career Counselor*

        And because the OP doesn’t want to be short-handed with someone who is not as technically proficient as John while hiring someone else. What the OP needs to figure out is whether the cost of John’s continuing insubordination is balanced by whatever else he brings to the table while the OP looks for a replacement. Like others here, I am leaning toward “move him out immediately” and do damage control while you bring someone else in. I would hope HR would be helpful here in helping you terminate quickly, without allowing the opportunity for sabotage.

    2. Lily in NYC*

      A disgruntled IT person can do a lot of damage if s/he feels like their job is in danger (if they have a vindictive streak).

    3. Florida*

      This is not someone who needs an exit strategy. This is someone who needs to have their passwords change by someone else while the termination meeting is happening.

      If he said to his manager that he won’t train someone because it hurts his job security, this guy is bad news. I’ve worked with people who thought like this, but never with anyone who was so arrogant to actually say it out loud.

      1. Windchime*

        Yes, this is how IT terminations are done where I work. Your passwords and access (including badge access to the building) are being revoked as you are in the meeting getting the news. Anything else is just plain unsafe, especially with a disgruntled worker who has already made it clear that he does not have the company’s best interest in mind. The last thing we need on top of a firing is some jerk trying to get into the server room or log into a server remotely from his desktop to cause damage.

          1. TootsNYC*

            It hasn’t been the case in the non-IT layoffs I’ve seen lately. And I haven’t heard of any sabotaging. Of course, these are not people w/ access or the power to do that much damage; these are not firings for cause or with any animosity; these layoffs have been handled with great respect and compliments and apologies on the part of management.
            In one case, an entire operation was folded; in another, long-term/highly paid employees were laid off in a clearly necessary belt-tightening.

            I must say that I prefer this more recent approach when it’s a layoff. It’s so much less traumatic for everyone.

            Now, layoffs in IT might not be the same–I can see changing passwords and access immediately while still allowing the laid off people time afterward to clear off the desks, empty their email, and say goodbye.

        2. Katieinthemountains*

          Yes, this is standard in IT. It’s done even for good people, and they understand, because they know how much damage they could cause if they wanted to. You just can’t risk it, OP, especially if you think Jenny isn’t quite as competent as John and wouldn’t be able to fix it.
          And I hope that she really shines once he’s out of the picture and your whole department is healthier. Please update us!

    4. Artemesia*

      People who do IT and are hostile and secretive are in a position to blow up your operation. The first step in firing such a person is to secure the data and make sure he can’t access it or mess it up. His password should be retracted before the conversation takes place.

  12. Mike C.*

    Does John have any reasonable reason to believe that he would have been replaced soon after training everyone else? Is this something that has happened before?

    If not, then yes can him. If so, you reap what you sow.

    1. TT*

      This – John’s behavior may be stemming from an outside source, like previous/current management that actively looks for a way to get John to hire his replacement without him realizing that he’s hiring his replacement.

      Maybe it’s just that I’ve been a subordinate longer than I’ve been a manager, but OP’s original plan doesn’t sit well with me.

  13. Anonymous Educator*

    As someone who works in IT, I’m a bit confused as to what product at a large corporation John could be supporting where he would be the only person on the planet who could support the product.

    Yes, maybe Jenny isn’t fully up to speed on it, but unless this is an in-house product that John himself developed with no help from anyone else, you can just get rid of John, and someone else can get up to speed on it.

    I’d worry less about the technical skills and more about the aptitude. Some tech knowledge is a prerequisite, of course, but I’ve walked into situations with 8-year-old documentation or no documentation and eventually figured out and improved existing systems I knew nothing about before starting the job.

    Find someone with basic tech skills and a good attitude, and let that new person get up to speed right after you fire John.

    1. Anonymous Educator*

      P.S. If you are in this kind of situation (unless this is an in-house product that John himself developed with no help from anyone else), then that’s your real problem, not John. No one person should ever hold the keys to the kingdom. I’ve done development work, and I’ve always shared the heavily-commented source code with my employer every step along the way.

    2. Meg Murry*

      Yes – unless it is an in-house developed product, very worst case scenario is you calling up the company that sells it and hiring someone from there to do tech support on a short term basis. It would be expensive, but it wouldn’t shut down your systems. Even if its an old, obsolete system, chances are you aren’t the only people in the world using it, so there is probably some consultant out there that could support it for a price.

      1. Anonymous Educator*

        But, additionally, if it is an in-house developed product, there should still not be only one person who can work it.

      2. TootsNYC*

        That’s a possible source of your expert to help you evaluate candidates: the company who wrote the software.

    3. JB (not in Houston)*

      I got the impression it was that it was too much for Jenny to do alone, not that Jenny isn’t up to speed on how to do it. In my non-IT related job, that happens a lot. We do replace people when we need to, but we try to minimize the amount of time that one person is doing the work of two.

        1. JB (not in Houston)*

          I agree that’s what needs to happen, and I wasn’t trying to suggest otherwise. I made my comment because I read yours as based on the impression that Jenny didn’t have the knowledge–maybe I was reading your “why is he the only person with knowledge/Jenny isn’t up to speed” part wrong. I commented only to clarify; it’s not that Jenny didn’t have the knowledge, it’s that she was just one person. If I was reading your comment wrong, then my comment is moot.

          I think maybe I don’t phrase things well when I jump in to disagree with a commenter on what I think the OP said. It seems like half the time I do, I give the impression that I’m taking a stand opposite the commenter on what needs to happen, when really I’m just an over-stickler on being correct on the facts. It is probably my lawyerness coming through–we can’t come up with the right answer if we don’t all agree on the facts! Maybe I write things in a way that sounds more antagonistic than I meant, when really it’s just that my literal brain can’t get past the literal meaning of the words I’m reading. I have this conversation with my boss all the time. “I am just telling you that’s not actually in the evidence. I am not arguing with you on what the law is, I’m just saying you keep saying X happened but it didn’t. I 100% don’t care what you do with the information you have, but please use the correct information in deciding.”

          1. Anonymous Educator*

            I don’t know if Jenny has the knowledge. I’m basing that on this part of the original letter:
            I have asked John, with the stronger skills, to train the rest of the team

            If John has “the stronger skills,” I’m assuming part of it is person power / workload coverage, and part of it is Jenny not having the skills (or thinking she doesn’t have the skills).

  15. Observer*

    I have to agree with the people who are expressing concern about that John might do. I think that in this situation I would do the following.

    1. Make sure I have a current list of supervisor passwords to EVERY system, especially the one that John administers, and make sure that there is at least one admin level user for that system that John has no access to, so he can’t change it on you. Also, make sure I have impeccable generational backups that are secure (eg off site backups that John does not have admin rights to.)
    1b. Start working on finding a replacement for John, without making use of him OR Jenny. Keep it discreet.

    2. Work with HR and IT to create a termination plan, that includes shutting down John’s access to your systems WHILE he is being informed of his termination. Make sure that includes remote access. I’d have someone walk him to his desk to pack his stuff, but his computer should be off (and possibly carted away) by the time he gets to his desk, and he doesn’t get to turn it back on. Make your plan and then terminate – whether or not you have a replacement in place. I know this stinks, but can you really afford someone like this on your team?

    3. Hire a replacement as soon as you can.

    One thing you should try to do is to create a communications plan with HR – this kind of sudden termination can be fertile ground for all sorts of rumors, and if you allow a deep shroud of secrecy to surround the firing, it can get ugly very quickly. Agree on a brief version of what you will proactively tell people with a legitimate reason to know (eg the IT staff in your department) and what you will say in response to questions. It doesn’t have to be detailed or convey so much information that it violates norms of privacy. It should just be enough so that it’s clear that this was not just someone’s whim or temper tantrum at work.

    I would also consider not fighting unemployment. I’m not suggesting that you whitewash the reason for his termination – you absolutely want to be clear and honest (although not piling on) when asked by the unemployment folks why he was let go. But, you do not have to go beyond that. Once you tell your story you can bow out. If he chooses to deny it and claim that he was fired for any other reason, you don’t have to respond. That can’t be used against you should he decide to sue. (On the other hand, if you tell unemployment that he was let go because of “restructuring” or any other such reason, that could create problems for you down the road. So, DO tell the truth.)

  16. Apollo Warbucks*

    OP if you’re reading this perhaps you could share what sort of tech it is that you are needing to find out about? there maybe some of us in the comments here that can help.

    Otherwise you could maybe look at a specialist IT recruiter who has some knowledge of what you are looking for, or even a trade or professional body might be able to offer some assistance.

    My niche area has a very active community.

  17. BethRA*

    “I was a consultant to a business with someone like ‘John’ here and the Jennies who were ‘loyal’ because he was a bit of a bully. ”

    This. I’ve seen this in a number of instances and contexts, where people have played along with a Troublesome Character to make their own lives easier. This is especially true where staff believe that bringing up their concerns, or not cooperating with Troublesome Character will result in nothing be being seen as a problem themselves (not saying that’s the case here)

    1. Meg Murry*

      I’ve seen this too, and in the case of IT, ways that “John” can make it difficult or impossible for “Jenny” to do her job – changing passwords and locking her out, or even logging in to systems as her and causing destruction.

      It also may be that Jenny has a lot of work on her plate and therefore isn’t prioritizing training others, as she has seen that John has flat out refused to train others and had no consequences.

      OP, have you tried directly saying “Jenny, I need you to cross train Wakeen on the ABC system” and then providing both Jenny and Wakeen with enough time in their schedules to make it happen? Because if you told me you wanted me to cross train someone, but you didn’t specifically tell me who to cross train, and you didn’t lessen my other priority projects, it wouldn’t be high on my priority list.

      Also, how much of this needs to be cross-training vs creating written documentation that anyone fairly technical could follow? Cross-train me on something once and then I don’t need to use it again for 6 months until the 2 people that regularly use it are both out of the office? Recipe for disaster. Hand me written documentation for a system I’ve never used – I could probably work my way through it

      1. JB (not in Houston)*

        I’ve also seen situations where until John was gone, Jenny didn’t realize how much John was not doing his job properly.

        1. nona*

          I haven’t seen it in person, but I’ve read a really surprising number of these stories here. Turns out that the person making a big production of their job wasn’t doing it well (or wasn’t doing it, period).

  18. Juni*

    “John, training your coworkers is part of your job. The VP and I would consider declining to do part of your job as asked to be insubordination, and if that were the case, I’d have to let you go. The training needs to start on Monday, so I’ll need your decision by Friday as to whether you’re going to perform this part of your job, or whether we need to plan for your transition.”

    Have that contractor on speed-dial. In fact, call her now, and let her know that it’s possible that you’ll be needing her services, so get the rates and stuff figured out in advance. If John decides on Friday that he’d like to take the job and shove it, you’ll have a contractor lined up and ready to go while you look to hire a replacement. If John wants to be a trainer on Monday, he is likely to have a bad attitude. Bring the contractor in on Monday so that John can dedicate all of his time to training, while the contractor does the product/user support part of his job. John will have no rock to hide under.

    1. NJ Anon*

      I wouldn’t even give him the warning. He will then have a chance to sabotage the IT systems. He has already said he won’t do it. I would use Observer’s plan and go with that. Why take any chances.

    2. Anonymous Educator*

      No, I agree with the commenters above. John’s already shown he has no issues sabotaging the company. If you give him any kind of heads-up that he may be let go before you revoke his access, there’s no telling what kind of damage he could do before he leaves.

  19. Joey*

    So you want to fire someone who relies on hoarding knowledge to hire the best person? Even if he doesn’t figure it out its his replacement don’t you think he’s likely to hire someone who would allow him to remain the knowledge hoarder? He’s going to hire someone who can’t do it just so he can come to the rescue.

  20. TT*

    Maybe it’s just me, but OP’s original plan is not sitting right with me. OP is basically looking for a way to trick his subordinate into selecting his own replacement so that he can be unceremoniously dumped. Which is difficult because John is already suspicious. Gee, I wonder why John would be like that, he has no reason to think that his boss would take advantage of his skills/knowledge base right?

    1. HAnon*

      I agree (with the part about the plan being a little unethical). A really good friend of mine and I worked at the same company, and the boss decided she wanted to get rid of friend (not for performance issues, for personal reasons). Boss brought me into the loop and told me that she was hiring a replacement and I was under strict orders not to give anything away. My friend had to meet and greet the people that were interviewing for her position (without knowing that was the case), seat them in the interview room, and bring them water, etc. I felt so terrible and uncomfortable throughout the whole process. I wasn’t able to “tip” my friend off that she was being replaced because my boss swore me to secrecy, and it was incredibly agonizing to deal with. She and I actually both got “laid off” — on the same day, back to back…she ended up expecting hers, I had no idea mine was coming. Bottom line — it’s a really sucky way to replace someone.

      1. TT*

        Dang, I’m sorry to hear that HAnon that must have been horrible. I understand that terminations have to be kept under wraps for one good reason or another, but something about the OP and what you’ve described add insult to injury.

        I’m actually surprised that there aren’t more comments about the dubious ethics of the OP’s original idea.

      2. Mephyle*

        Sorry to hear about that sucky experience. I wonder whether it was symmetrical – that your friend was similarly warned and sworn to secrecy about your lay-off but not hers – did you compare notes afterwards?

    2. JB (not in Houston)*

      I think your sarcasm is a little out of place here. I don’t see anything in the OP’s letter to indicate that the company’s management practices have caused John to become the way he is. It’s because he’s insubordinate that he’s wanting to be replaced, not that the company’s tendency to replace people in a hamhanded or deceitful way that makes him insubordinate. I don’t think the OP’s plan is smart and is borderline sketchy (it’s questionable if it’s applied to someone who had no idea they weren’t performing, so you can make an argument that you shouldn’t do it here, either). But this person has been told clearly what his job requires and he has clearly said he flat out refused to do it, so we shouldn’t react to this the way we would if it were someone who had no reason to believe they were doing everything fine.

      1. TT*

        1. John is afraid of being replaced, and is acting irrationally due to that fear.
        2. His boss is trying to trick him into hiring his own replacement.
        3. See #1.

        That’s what I picked up from the letter. I’m not defending John here, I’m just saying that based on the original post I can understand why the man might be a tad paranoid.

        Also, my sarcasm is never out of place. It’s perfectly positioned between my collection of Snark, my basket of Withering Glances and my extra large jar of No Cares Given.

        1. JB (not in Houston)*

          But your “gee I wonder why” sarcasm only has any merit to it if behaviors like #2 came before #1. If my boyfriend starts acting in weird ways because he’s paranoid I’m going to break up with him, and that strange behavior is what makes me break up with him, he doesn’t get to say “See! Gee, I wonder why I was being paranoid about you breaking up with me.”

          2. TT*

            This is truly funny – the first thing that popped into my mind was a dating analogy. What the OP is asking for IMO is equivalent to me saying, “I really want to break up with my boyfriend, how can I get him to move all of my furniture to the new guy’s place without him knowing?” It just feels incredibly callous and – to me at least – it says a lot about how the OP handles dealing with people. Fire John if needed (again, I’m not excusing his behavior), but the tone of the OP indicates that perhaps John’s paranoia has a cause. I can only imagine how the other team members would feel after seeing that happen.

    3. nona*

      The plan doesn’t sit right with me, either, but OP isn’t “unceremoniously dumping” John. He’s refusing to do part of his job and OP has already tried to work this out with him.

    4. some1*

      I comepletely agree. So John needs to be let go — fine. It’s crappy to wait on that because you need something from him first.

  21. Brett*

    Bring in an outside technical interviewer.

    I have done this a handful of times for other organizations. They need to interview someone who is supposed to have specific technical skills, but have no one on staff who can evaluate those skills. So, I was brought in just to do the technical side of the interview.

    Generally, the organization contacting me knows who I am already and trusts me to assist them (often because of existing relationships between their organization and mine). But I am public sector, this is easier to do in the public sector.
    Another route though is to contact your software vendor. I have had that happen before too. Someone contacted a software vendor, who then referred me as an outside technical interviewer. In some cases, the vendor themselves will be able to provide people who can act as outside technical interviewers. In other cases, they can refer people to you from other private or even public organizations (though likely the public person has to do this off the clock and without compensation if you are a private organization).
    You will probably have to restructure your interview process. Separate the technical aspects from the non-technical so that you can have the technical interviewer only sit in on the technical aspects. You are already going to have a touchy interview process anyway since you are trying to keep John and Jenny out of the loop.

    2. Brett*

      Just thought I would add that I do these outside interviewers to be a responsible professional. I am not paid (getting paid would actually be extremely complicated for me). But I recognize that assisting other companies in my industry in hiring competent candidates only improves the profession, especially locally, and improves my job prospects and access to professional development. So, I see it as a professional responsibility to provide this assistance to the best of my abilities when asked.

    3. Letter Writer*

      I’m the OP. This is a great idea. I will reach out to the software vendor to see if they can help with the interview. Thanks!

    4. TootsNYC*

      Also–have your outside technical interviewer create tests or something, and have them do the initial screening, and have them send you only the people who are worthwhile.

      Then interview the people they send to you.

      Though…maybe that’s more expensive. Maybe it’s better for you to screen for numberical experience level, and for suitability, and then have the advisor interview only those people that pass -your- screen.

      The advisor might also be able to help you come up with some brief screening test or question that you could use to help winnow the field.

  22. Rebecca*

    Wow – this gives me a flashback to my first job. Got called into the office with another person in my department, manager said “oh, we’re going to start cross training so we make sure all bases are covered due to vacation, illness, etc.”. This was the other person’s primary job, he had no backup, and fast forward about 2 months…I came back from vacation to find that he had been let go, and I now had his job responsibilities (that I wasn’t trained completely for, as person who was let go gave me some of the basics, but that was all).

    Fast forward 2 years. I got called into the office, with another person in my department, and the exact same words came out of my manager’s mouth, directed to me this time, about cross training, etc.

    I found a new job post haste. But this was in 2002, not now, so jobs were more widely available and I could make a lateral move.

    To this day, when someone mentions “cross training”, I get that sick feeling that I’m going to be laid off or fired.

    1. illini02*

      Exactly. John’s paranoia isn’t exactly out of nowhere. These things happen. Everyone saying he is sabotaging the company is kind of only looking at one side of things. While I do agree that its insubordination, it seems that his concerns are somewhat valid based on OPs plan on tricking him into hiring his replacement.

      1. JB (not in Houston)*

        Someone who is refusing to train others so that he can keep imaginary job security is sabotaging. What if he decided he had a better offer somewhere else and left with little to no notice? What if he gets hit by a bus? He’s refusing to do a part of his job for his own benefit.

    2. JB (not in Houston)*

      I see where you’re coming from, but your experience is because your management sucked. It’s actually a great idea to have cross-training, and managers who don’t do this regularly are not looking out for the organization. It’s not just for when people are going to get fired. People take vacations, people get sick for long periods of time or go on maternity, people get promoted into other areas, people leave for other jobs, and people die. You should always have as many people as reasonably possible trained for different jobs if it’s at all possible so that there’s as little disruption as possible when someone can’t be there to do a job.

    3. Observer*

      JB is correct. In addition, you can be sure of one thing – your job would not have stayed safe had you refused to cross-train.

      The other thing is that you don’t know for sure what really happened. It’s possible that the plan all along was for the other guy to train you and then fire him, just to save some money or the like. But it’s possible that the person was being pushed out for good an sufficient reasons, or that the decision to fire him was for reasons unrelated to the decision to cross train.

  23. ali*

    I work in a 2 person department, and we are very very specialized in what we do (in fact, at one point long ago when we were a 5 person department and they needed more help, they contracted out to a consulting company…who failed miserably in every task they were assigned). If something were to happen to both of us, while it wouldn’t be impossible to fill our shoes, the knowledge that we have that no one else does would take a long time to replace. The amount of work that would be lost while someone else tries to get up to speed would be devastating to the product we work on. There are a few people I’ve tried to train over the years, my own boss being one of them. He and one other person in the company have enough knowledge that they could do the small tasks. We don’t have enough work to even keep an intern on, but we have way too much for just one person (they did actually try that for a brief period of 4 months). It is SO hard when one of us is out for more than a couple of days. My coworker is going to be out with a new baby very soon, and I’m incredibly stressed out. But that will end and he will come back and it will be fine. I have tons of support from my manager, which goes a really long way.

    So OP, you are definitely correct in that at least one other person needs to be cross-trained here, and John is in the wrong. Can you have Jenny train someone or will you get the same attitude from her? Or can YOU quickly pick up enough of the job yourself to conduct the technical part of the interview? I’m guessing Jenny really isn’t part of the problem and is just going along with John, as everyone else says. I think you need to just let John go – he is disobeying a direct order, as it were – and Jenny will just have to deal (with lots of support from you) until you can hire someone new. It sucks for her, but those are in fact the realities of a two person team.

  24. KTM*

    I can’t get past the failure in logic by John. He says he doesn’t want to train other employees to ensure his job security, which I presume means keeping his current job. The OP says he needs to train others as part of his job and has given clear feedback that not providing training is not ok. Unless John thinks there’s no way he’s ever going to get fired even if he’s insubordinate (which would be pretty oblivious in the face of OP’s feedback) – he’s risking his job security.

    I think we need some clarification in the last section by the OP – he says he directly told John that if he (John) wouldn’t do the training that he (OP) would find someone else who would. Did the OP mean that he would replace John? Or that he would find someone else in addition to keeping John. Maybe he needs to be more explicitly told that he will be let go if he doesn’t do the training even if the OP thinks that’s been communicated clearly.

    1. Letter Writer*

      I’m the OP. I was worried that John could have come away with that same impression, so I met with him again and spelled it out. If he didn’t train his coworkers as I asked, it would be considered insubordination and I would let him go. He said he would get back to me, which was exasperating, but ultimately fine because HR didn’t want me to fire him on the spot.

      2. Chriama*

        HR needs to let you fire him. Have you stressed the sabotage potential here? He knows that his days are numbered. If they’re worried about suing or whatever, have them give him a decent severance package.

    2. Mike B.*

      Some people are really that oblivious to the dynamics of their relationship with their employer. I’d wager John thinks this is an unbeatable trump card when it’s nothing of the sort…and doesn’t realize that no company can afford to keep around an employee who’s adversarial enough to try to play trump cards.

      Alternately, John knows that his days are numbered and is grasping at straws in panic.

    1. Florida*

      Click on the ad and watch the video. Alison deserves the money for the work that goes into this website. AAM has been a great resource for me, so I’m willing to deal with ads and click on one occasionally (even if it’s not something I’m interested in.)

    3. Ask a Manager* Post author

      I’m sorry that ad problems are still popping up occasionally; it’s proved really hard to eliminate them 100%.

      I’m going to ask people to try to live with the occasional issue (the ads, while occasionally misbehaving, are paying for the constantly increasing costs of running the site), and if it becomes a real problem (meaning more than occasional) to email me about it rather posting here — it’s a lot easier for me to troubleshoot* that way. Thank you!

      * To troubleshoot an auto-play ad with sound, I need the URL it links to. I can’t track it down otherwise.

      1. Evan Þ*

        How would I get that URL? I came across one of those ads last week, and I really wanted to send you a message, but I didn’t know what to do since no link was given and I didn’t want to actually watch it through to the end.

        1. Ask a Manager* Post author

          Usually clicking on it should take you to another web page — the URL of that one is the one I need. (Occasionally an ad won’t have that, in which case they’re very hard to track down.)

  26. J-nonymous*

    Fire him immediately. This employee has already made it clear he is willing to sabotage the operations of his platform / the company to ensure the company needs to keep him employed. He will likely go further to sabotage things. I’ve seen it happen before in large and small companies.

    Depending on where you’re finding your pool of contract resources, you may be able to lean on that company to do a thorough screening of the technical ‘chops’ of contractors. You may also, if budget and availability permit, want to look into using a vendor partner who specializes in this system to shore up your team. It could cost more in the short term, but in the long term could pay off.

  27. Snoskred*

    “He is also a negative influence on the team, causing drama and strife.”

    I was in a retail store with one of those about 10 years ago. The manager was one who prefers to manage by people deciding they want to leave instead of disciplining etc. I left because of the John, and I know two other people did as well.

    I went back there recently to visit. Even though the John was gone, his negative behaviours had been picked up by the people he worked with, and then they gave it to people who had never even met the guy.

    It felt to me a little bit like they all have a negative behaviour virus which is almost impossible to get rid of. The only way to make sure it truly leaves would be to sack them all and start over.

    I’d fire John ASAP, and like everyone says, make sure he cannot access the system again. Jenny might be rescuable but sometimes the damage is done and the negative virus has been passed on.

    1. Windchime*

      I love the analogy of a negative virus. It’s kind of like how the effects of the traffic jam are still in evidence long after the original accident has cleared; it takes a long, long time for the normal balance of things to become re-established.

  28. JustMe*

    I’m wondering about OPs other employees. If they see John ‘acting up’ to OP, and in their eyes nothing is happening to John I can’t imagine what they must be thinking. For starters I’m sure they’re thinking John is untouchable and they must put up with him. Jenny is probably thinking the same way too, so she’s being ‘loyal’ to John since no one has dared done anything to him. Who knows how long John has been able to bully others into thinking he’s untouchable.

  29. RO*

    I think that some organizational cultures cultivate this kind of behavior. If you are an at-will employee, why are you hoarding information that would make all of you better and framing it as job security?

    Each time I learn how to do something at work, I am usually excited to share it with others mainly because I would like you to know how to do it and also because I do not want you asking me the same questions all the time. I recently started a new job that is driving me insane because across the system there is only one person (usually a life) who can do xzy. I asked the senior team leads how this is acceptable and they have all referred to job security as being an issue for everyone. Needless to say I am looking to move one as soon as I hit one year.

  30. MH*

    I would first regain control of your IT system because John sounds like he still has power over it. It’s a chance he could hold that against you – if he’s the only one knowledgeable of the system/service. Have independent screening/hiring. Don’t have Jenny get involved.

  31. Stranger than fiction*

    Just wanted to say I’ve never understood this practice and think it’s in poor taste (making an employee on the chopping block unknowingly hire/train their own replacement)

    Now where I can understand it is in circumstances where a company is going through a merger or acquisition and can’t keep all the employees, but even when this happens , saw it once, wow what a blow to morale and in often wondered just how great or thorough that training was.

    1. Ruffingit*

      Totally agreed. In my mind, I’d be thinking “So I suck enough to fire, but I’m good enough to train the person taking my job? ALL THE NOPES, F**K YOU.” Seriously, this is just so incredibly disrespectful to do to a person. Want to fire someone? Do it. Don’t keep them around to interview/train their replacement. That’s like asking someone to choose their executioner.

  32. Kateyjl*

    This is more of a management issue than an employee problem. Schedule him to train others. Facilitate the training.

  33. Letter Writer*

    I’m the OP. For the record, I’m having all the employees in this department of ten cross train one another to increase the skills redundancy and reduce the likelihood of everyone with a skill supporting a software package being out. Everyone else is working with me to come up with dates and topics for training and has worked on the documentation to help their coworkers to learn the new skills. I’m not planning on letting anyone else go once the training is done.

    I’ve been straight with John that his attitude in general is unacceptable and told him what I expect and how he can improve. The lack of improvement and the refusal to train is the final straw.

    1. Editor*

      I don’t think you have any choice but to let him go, and the sooner the better. It’s pretty clear he just doesn’t want to share. It reminds me of the John McCutcheon song “Kindergarten Wall”:

      …But lately I’ve been worried as I look around and see
      An awful lot of grown-ups acting foolish as can be
      Now I know there’s lots of things to know I haven’t mastered yet
      But it seems there’s real important stuff that grown-ups soon forget
      So I’m sure we’d all be better off if we would just recall
      That little poem hanging on the kindergarten wall.
      (chorus)
      Of all you learn here remember this the best:
      Don’t hurt each other and clean up your mess
      Take a nap everyday, wash before you eat
      Hold hands, stick together, look before you cross the street
      And remember the seed in the little paper cup:
      First the root goes down and then the plant grows up!

      (And now I’m going to be singing that in my head for days.)

      In a way, I can understand John — I tend to think of my job as “MY” job. But really, it’s my employer’s job, and the employer gets to say what the job is. John’s inner toddler has forgotten that essential fact.

    2. Susan*

      This makes his response 100% worse. He sees everyone else cross-training, and believes he should be exempt? No.

      1. Chriama*

        Yeah. What’s his reasoning here? Does he think you’re planning to fire half the department? I honestly don’t think someone who acts like this is a good employee in other ways, and I would honestly question his so-called technical expertise. If you’re good at what you do, you don’t worry about sharing that knowledge with others because even if you teach them as much as you can there will be stuff that you know so intuitively that you’ll still be the best at your job.

    3. Observer*

      In that case, I would reiterate my advice, only more strongly.

      Secure your systems then lock him out. Do NOT depend on him for any help in transition. In fact, I would say the reverse – do not ALLOW him to have any input into the process.

  34. Anonypoo*

    Also, the oldest trick in the book is to rely on human nature. Bait the trap. People who won’t lift a finger or give a direct answer are usually *more than happy* to tell you why you got it wrong.

    Start a training guide yourself and let John correct and criticize the hell out of it. You’ll get some of what you need from him. A word of caution – you MUST do this yourself, knowing the criticism is desired to achieve an outcome. Don’t put a junior in the place a being bait for him and let them feel stepped on.

    1. snuck*

      Good idea! If he’s acting like a child, treat him sort of like one ;)

      I do the same thing with my kid about putting his shoes on :P

  35. Ruffingit*

    This is just wrong. I don’t care how much John sucks as an employee. You don’t do this to someone. You want to fire him, then do so and hire someone new. Asking him to surreptitiously interview his replacement is just…so crappy that there isn’t a word for it. And really, OP this situation points not to a problem with John, but a problem with YOU. You hired someone who is not a team player and you’ve allowed this situation to reach a point where you have a small number of people with a skill set that is apparently very important to you. The answer here isn’t to have John interview his replacement, it’s to make sure you get a team player next time and that you cross-train the heck out of people.

    1. Letter Writer*

      OP here.

      I didn’t hire this team. I was brought over from another team I was managing because this team was running amok with people not getting along. I’ve already let one person go who was stirring up even more discord than John (different skill set though).

      I will definitely be hiring a team player as a replacement.

      Obviously I wouldn’t have written the letter if I felt great about having John interview his replacement. I just need a way to make sure the applicant’s skills are real and applicable to how this team uses this software package.

      1. Observer*

        I just need a way to make sure the applicant’s skills are real and applicable to how this team uses this software package.

        Except it won’t work anyway. I don’t have any good answers for this dilemma, but I do know that this won’t work. Best case, you’ll get nothing. Worst case, it will cause a lot of mess for you to clean up.

  36. snuck*

    There seems to be several issues here.

    How can you find a person with the right skillset to replace John? Ideas could include talking to your industry peers, other users of the software, major clients, recruitment agencies etc… you can do this all on the quiet if you tap the right person on the shoulder in the right way and ask nicely, without a need to mention the exit of John.

    Can you trust John? Can you trust him to be involved in replacing himself? His track record suggests you wouldn’t be able to. Will you trust his choice – if he says the new hire doesn’t have the skills then is he protecting his job, or being honest? If he says they are ok you are faced with the same question.

    Can you trust John to leave quietly and peacefully? What does your gut instinct say? The fact that you are writing and worrying on this suggests you aren’t comfortable that he will leave easily… so plan for that assumption he’s going to go out in a big ball of fire and be alert, but hopefully not have to enact any of those things.

    Will John (or Jenny) straighten up and fly right? Well… John has made the power play already – he’s told you he won’t train anyone else to protect his job. You’ve allowed that to happen. He’s called your bluff… now if you want him gone follow through and make him gone, or call his bluff back, tell him he’s on his way out, and see if he gets down to doing that training.

    Jenny is a separate person and should be managed according to her own behaviour and attributes. If you feel she’s too close to John then proceed with caution, if you feel she’s just protecting her own work balance then leave her to the side until John the bigger problem is dealt with and see how it works out. She might also surprise you and be able to well step up.

    And in a replacement for John you might be looking for a skillset but it sounds like you are looking for a different personality and a team work approach more. A person with a few less skills but the drive and determination to be part of the team and build their career can easily learn the skills and fill their gaps. Harder to teach the soft and personable skills than the technical ones.

    Finally… what are you going to do differently to stop this from happening again? With John or John2?

    1. snuck*

      Oh… and a final thought?

      Why would you wait? Get everything lined up to see him gone if that’s your decision and act on it as quickly as you can… if the loss of John is going to cause such catastrophic failures then plan for them as best you can and alert your stakeholders quietly that you will go through a transition time and that if there’s any issues you want to know about them, ask if some tasks can be delayed or altered…

      And then resolve the issue.

      And if you feel guilty about firing John then realise that his skill set if so deeply sought after is going to see him in good stead and he can move on. You can even have a discussion with him about what you would or wouldn’t say about him in a reference and find ways to frame it so that it’s not negative necessarily. He mightn’t be the big Barracuda in the little fishbowl anymore, but that mightn’t be a bad thing for him.

Comments are closed.