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Ask HN: A colleague is leaving. How to investigate what went wrong?
80 points by theSage on Aug 24, 2019 | hide | past | favorite | 94 comments
A colleague at work is leaving the company soon saying "I don't feel like I'm a fit for <xyz> company". I'll be speaking to them in unofficial capacity soon. What all should we talk about? A few things that came to mind:

- what all do you need to get a new job?

- why do they feel they are not a "fit"

- is there a systemic problem?

- when did this feeling arise since they joined with lots of enthusiasm?

- what could I have done personally / in official capacity that might have stopped this

- how do you think we missed this?

To the HN community: What other things can I ask them to prevent/improve this situation in the future? Is there even something to improve here?

Your curiosity, professional or personal, probably has little bearing on what they tell you. The wording you use doesn't matter - exit interviews are always framed as "what we could have done better/could do better in the future?" but it is rarely so innocent in reality, and people know this. At best, companies use divulged complaints as a basis for negotiation retain the employee (what if we raised your salary to match your offer? What if we reassigned you to a different manager?) but often it is simply used get the employee to sign a waiver relieving to company of any legal blame. And a likely outcome is that their complaint about their boss gets passed along and it bites them in the ass when they need a referral down the road. So what advantage do they have for being honest? In what way could it possibly benefit THEM to tell you anything?

To be honest, a company should always know or be able to figure out the real answer to this question if it their own doing. Either the employee got a better job or the writing was on the wall. If you as a company have people leaving and no one knows why, you don't ask the leaving people you ask the people who are staying - Bob is leaving, is there anything we can do to improve YOUR experience? When they are out the door it is too late, so focus on the employees that are there.

Well stated. Once the employee is out the door, they're really just a MacGuffin to drive the real plot: management trying to figure out how it can improve the company and culture to avoid this situation again. Even if I was happy to see the team member depart, I still want to think about why they were hired in the first place, where did things go wrong, what are we not seeing.

At my org, I introduced post-mortems (call them Exit Retrospective so it's doesn't sound too morbid). When an employee leaves or is terminated, we (manager, hiring team, anyone else who makes sense) are invited to an Exit Retrospective. Manager prepares talking points on the following topics:

- Candidate

- Manager

- Team

- Organization

For each topic, manager lists areas where the individual or entity failed/struggled and succeeded/thrived.

Last section is Lessons Learned. That's the agenda. It's shared before the meeting.

During the meeting, we go through each section, discuss a bit, note any actions items we can take on to improve things going forward. Meeting is about an hour. Prep another hour or two.

The HR at my last job were so incompetent they tried reaching out to me (repeatedly) for a exit interview three weeks after I had already left.

I cannot argue their competence, but giving someone a 3 week cooling off time to reflect on why they left seems reasonable.

Although trying multiple times does not seem reasonable.

Many companies I have left, never cared about why.

Just let them know your day rate.

wow !!! which org ?

> but often it is simply used get the employee to sign a waiver relieving to company of any legal blame

Why would anyone sign anything when leaving a job?

Even though the companies are required to pay you out your last check and unused PTO, many HR departments will hold the envelope with the check in front of them and give you the paper to sign. They will not use words, because that will be illegal, but they will let you think that if you don't sign you don't get the money. It's up to you to know that you don't need to sign to get your money.

For money. Companies will withhold severance and/or extra healthcare pay.

In fact from a contract law perspective you have to exchange consideration for an agreement.

I never thought of this. Thank you.

Also, while asking people that sort of question, ask yourself whether improving the situation is within your reach, whatever is the cause? If you think you could -- do you think people you are interviewing, also believe you can?

I wouldn't tell anything to a person who has no power or no incentive to improve things, and sadly, this covers 100% of people one usually has exit interviews with. So I always declined them, politely.

You wouldn't believe how much respect and good contacts this attitude earned me over the years.

I don’t really know you or this situation... but there’s a chance that you’re part of the problem. And they won’t tell you that.

I think one thing to reflect on is why you didn’t know this about the pointlessness of exit interviews and the danger of “real talk.” Don’t worry though - I didn’t for a while either. Experience will get you there.

That’s why it’s so important to start that feedback loop early when that person onboards. It helps establish a communication culture.

I don't think it's that hard to get people to be honest. I've seen plenty of situations where two parties absolutely hate each other, but once the anger is out of the way, they get along just fine and become good friends.

The sincerity needs to come from both sides. When someone has left, they probably distrust or dislike the company. And the first thing to do is to fix that distrust. Otherwise it seems like an exit interview is just part of HR's job.

Most of the time people leave bosses, not the job or the company. Almost all interactions are relatively close by, colleagues and their direct boss and if that isn't a comfortable environment with trust then usually that is what leads to resignation.

If you don't know this individual it is unlikely they will honestly tell you why and the boss or coworkers may very well give no honest insight either regardless of the questions. They want out and they don't want your organisation ruining their future prospects with a bad reference. Most people do try to fix the problem before they just leave so at this point they consider it not worth voicing the problems further.

Every time I left a company it was because of the pay and promotion structure and not because of my coworkers or direct bosses.

Right now I am considering leaving because the deadlines get squeezed more and more. This also comes from way up management and not from anyone I interact with directly.

Yeah, 100% this. While quite a few people do indeed leave companies because the boss is terrible or they hate the working environment there, a lot of the time it's simply because opportunities for advancement or making more money are limited in said company. A tiny startup or lifestyle business can't exactly pay FAANG level salaries, and there's not much room for a promotion if the company has less than 30 or so employees.

And if their situation changes outside of work, then finding a better paying job can be a necessity regardless of how much they enjoy their current one.

Why doesn’t your management push back?

A lot of managers are either spineless (afraid of arguing with people higher up in the food chain) or two-faced (overpromising to management because if they deliver it will look good, while simultaneously telling reports that they tried their best at reducing the workload)

Most middle managers don’t have much power. If your CEO gets it into his head that a project needs to be delivered at a certain date you can push back but what can you do if nobody listens?

Dates are only one lever, there are three others:

Cut scope

Increase resources

Decrease quality

Shit runs downhill.

The reality is that if the people up top have abusive practices, no one below them can fix it. They cave to keep their paycheck or they leave.

Thanks for putting this into words.

During bad times it’s awful, during good times it’s “only a matter of time”.

I wish I knew how I could avoid feeling so helpless. So far I have tried “pretending to not care what happens to me and my career” and “fantasizing unrealistically about freelancing”

I wish I knew how I could avoid feeling so helpless.

Try to leave at a time of your choosing. Try to set some parameters or goals for how/when to do that, such as paying down debt, having a savings cushion or lining up another job.

Control some piece of it to some degree.

In tech, there’s also lots of outside of work professional opportunities, too. Obtaining certifications helped me feel more secure in a previous, awful work experience. I also did a number of home projects that I could add to the resume.

Also, I’d tell anyone in a tough work environment to ensure they're keeping their mental and physical health up. I needed PT from all the muscle strains the one place gave me, for instance.

I also drank roasted cacao daily for a good theobromine and caffeine kick! It really did help me feel like “it’ll all be ok” during the worst of it.

As long as you don't overdo it, caffeine can help provide some oomph for the adrenals during short-term stress. When paired with the right nutritional support, such as better quality salt, real licorice and coconut oil, it's sustainable for fairly long periods and makes a real difference in your ability to rise to the occasion.

And from a pure business/money point of view it may make sense to burn people out.

I concur with this. I am in the same boat with my current company.

I'm their coworker and this is what I'm afraid of. I am haunted by the question "what if it has been our work environment that caused the move?"

I don't suppose toxic people think/know that they are toxic, so how do I find out if we are?

Here's the thing. Your writing doesn't make it sound at all like this person trusts you, and you said you're doing this in a quasi-official capacity.

Those two things make me think your management either sucks, or fucked up and wants to know what your coworker will say.

If you had a good relationship w/ this person already, you could take them out to coffee and pretty much ask, "so, what happened?". Since you don't, and since your coworker is presumably not stupid, you're probably going to get the same answer that your management team would get.

Which brings me to my next point: your management team should know. If this person's boss isn't doing weekly 1-1s and closely monitoring this person's enthusiasm for the job and company, then they're an incompetent boss. That's table stakes for competent management.

Particularly when a coworker quits over an "I'm not a good fit", that means (1) there's a problem, and (2) I don't trust management. Acting as an agent of management isn't going to get the answer.

Totally agree with this, and I'll take it one step further - if they trusted you and were on friendly terms, they probably would have already told you or asked you for help on what is going wrong, long before they quit.

The leaving coworker can still be friendly and trust their colleagues but may not share details so as not to ruin their colleagues' perception of their employer.

First, what is toxicity? What one person considers toxic, another might consider normal interactions. I was playing competitive Overwatch the other day. We were getting stomped and I got on comms and said, "guys what are we doing? We're just standing around the choke, we need do make a play!" and some guy said, "don't be toxic." I didn't think I being toxic, I was trying to get the team to become aware of its lack of action. But this guy took it as toxic. Who's right?

You can sit and worry all day, every day about whether or not you're toxic in the eyes of someone else. I wouldn't be surprised if there are specific instances you can think of where you had an interaction with this person that didn't go the way you wanted it to and now you're worried you're the reason they're leaving. It's very unlikely.

Some people will always just interpret your actions / words in a way you didn't intend. This, in my opinion, is why it's so important to be true to yourself. Live your life by your principles and the way you think is right. If someone thinks you're toxic, and you're confident you're not, then it's fine. You're not going to get along with all 7 billion people on earth.

>I am haunted by the question "what if it has been our work environment that caused the move?"

What's haunting about it? They say "yes," you guys are toxic. Okay. You find out what it is they thought was toxic. You evaluate it within your framework of right and wrong. And you either say, "yep, I was toxic. I'm sorry. Whoops, better do better next time," or you say, "I don't think I was toxic, but I can see how you'd think that. I'm sorry about that, thank you for telling me," or you say, "this guy is a nutjob if he thinks that is toxicity. Good luck in your next role," and you move on and live your life.

It sounds to me like you're not confident in your interpersonal interactions, and you're worried that you're coming off as toxic. And that if someone thinks you were acting toxically, that it's some kind of life sentence that will stay on your Permanent Record. Don't sweat it. We're all trying to figure out how to act with people. Some people are much better at it than others. People make mistakes, and people move on.

It is rather stressful for the leaving coworker to answer these questions. Just put yourself in their shoes. He/she could be thinking "I don't wanna see these guys anymore", and you're asking at the same time about the reasons. To begin with, try to ask about their plans for the next several months, their future work etc. If they're super excited about it, maybe they just need another challenge. That's totally OK. Wish them the very best and be thankful for the work done together. If they say "oh I dunno, their MacBooks are slimmer", then probably the main reason lies within your company.

If the resignation caught you by surprise, it's unlikely he/she will tell you the real motivation. People often start the contemplation long before they decide to leave. IMO.

Asking about what's next is great for conversation in any case, whether OP's colleague is a friend or not. Maybe they don't have future plans but want to talk about it anyway to feel out the opportunities. It can be helpful and it stays forward-thinking.

If it was a surprise, there's also a non-zero chance they were fired. "Not a good fit" is vague enough to not really mean anything, but good enough to be able to move on with.

Besides that, OP is going to have a very short question if their idea of speaking to their colleague is to interrogate them, and what the OP is thinking about feels very official.

I think hoorayimhelping has the bulk of what you should keep in mind with regards to toxicity.

To add a little from my perspective, one good way to find out if you are toxic is to speak to some psychologists. Either industrial organizational psychologists for the business or a traditional therapist for the individual.

Alternatively, if there is enough data, some metric comparing rates of resignations over time to your industry norm may be instructive.

Honestly I think this is fairly poor advice. 'Toxicity' isn't a condition that a professional psychologist can diagnose.

Meanwhile some answers in this thread are inadvertently confirming that the theSage actually has a problem they need to deal with and might actually be toxic, with practically zero evidence to support it.

theSage sounds like he's worried about being the reason his colleague left; that it's his fault. We've all had that kind of worry sometimes when something unexpected has happened, and we think it's because of us for some reason.

And in that case, what theSage needs isn't someone to confirm or deny his so-called toxicity, it's a close friend they can confide in over a beer or whatever. They can talk about what work has been like and how someone quit and how they feel about it without involving their ex-colleague.

Thanks for your reply, it addresses a common thread that I’ve noticed in this overall post and it is worth elaborating on.

More directly to your reply, toxicity is certainly something worth discussing with a professional. Not everyone has close friends that they can rely on and using friends as an echo chamber can be detrimental to growth.

The worry that you noted can often indeed be normal but it is also absolutely within the scope of a counseling psychologist to consider for treatment if it is a pervasive, detrimental thing.

Similarly, worrying excessively about the departure of a colleague can be abnormal in some situations. I understand the normal reaction to generally be along the lines of wishing the best for the person, rather than to perform an inquiry (nigh investigation) into the full details of the matter. Granted, if this were a departure along the lines of a foundational employee, then some inquiry would be appropriate, and generally so for any random employee, of course. But the choice of language, at the least, does seem to imply a concern beyond the norm. Not having details, perhaps it is entirely justified. At the same time, if theSage (hi you), is concerned about worrying too much, dismissing that out of hand as something that can be solved over a beer may not be sufficient advice either.

To your point about diagnosing toxicity, there are indeed conditions, both organizationally speaking and individually speaking, that overlap with “toxicity” as a symptom. There are a number of personality issues that can give rise to behavior that would be considered to be toxic to healthy people. Similarly, industrial organizational psychology does include organizational dysfunction within its scope of inquiry. For example, what traits, beliefs, and attitudes, when held by management, are toxic to the health of an organization?

Perhaps an IO psychologist could be consulted by theSage to provide a checklist of organizational traits to be marked as observed or not observed, by the departing colleague. Such a thing is a practice performed during exit interviews for large enterprises.

The issue really is the word ‘toxic’. It’s an intense label that shouldn’t be used so lightly, because we all present a lot of potentially toxic behaviours throughout our lives that, with the help and support of those around us, and our own awareness and resilience, we successfully nagivate through without issue.

The conditions that can be identified and diagnosed might have deeper roots so, yes, it’s better to take that to a professional than to hash it out on a forum. But it should not have been framed as being toxic - that just adds another layer of complexity to the situation.

Yeah, the modern insult “toxic” is pretty interesting. It’s become a meta meme that supersedes the original meaning of the word. I’m pretty sure that the term toxic workplace predates, quite much, the more contemporary, gamer use of the word toxic.


This is straight bulllshit. This is the first source:

> a toxic worker is defined as a worker that engages in behavior that is harmful to an organization, including either its property or people.

By that definition, you become toxic when you introduce a bug. You become toxic when you make a mistake.

It’s not bad as far as operational definitions go. Operational definitions are intended to be refined over time and to be used as a starting point, not necessarily an ending point. Qualifying the types of behaviors might have been too restrictive of a definition for their study.

For example, if it read “engages in unethical behavior that is harmful”, you then need an operational definition of either ethical or unethical behaviors. It’d be an understatement to call that a difficult thing to define.

Maybe there’s some way they could have incorporated intentionality into the operational definition, but I suspect that it would introduce some gaps as a model of reality.

I’d argue that an intentional pattern of creating bugs would be the toxic thing whereas a pattern of accidentally creating bugs would be incompetence. Isolated or routine cases of bugs being introduced would be the normal course of software implementation.

Business processes and development techniques would be the organizational defense against the introduction of bugs and would probably be the source of the dividing line between when a worker toxically creates bugs and when not toxic.

Only special kind of person will tell you that you are toxic if you are. It takes even more special person to be able to explain it to you in terms you will understand.

Friends are people who are cool with you, by definition. Even if you are toxic.

You are toxic is also meaningless. Professional can tell you more exactly what is problem and help you solve it.

Also a good friend isn’t going to use the word toxic. They might say you’re being a dick or an asshole about something, and give a gentle nudge within the boundaries of that friendship, but ‘toxic’ is the kind of thing you put out there when you’re breaking the friendship off. At that point the toxic person ignored every opportunity to change, even make a small effort, and either refused to or doubled down on their act.

"Most of the time people leave bosses" I feel like is a linkedin clickbait link with almost no data to support.

> what could I have done personally / in official capacity that might have stopped this

Were you their supervisor/manager/lead? If so, the standard answer is to have regular 1:1s with your staff, so things like this do not come as a surprise.

And you cannot always keep everyone. Sometimes things really are not a fit. The last job I left was for reasons that had nothing to do with the team or product, or anything easily changeable. I simply wasn't OK with the commute to a new office. There are a myriad of personal reasons that someone might not want to work somewhere. That doesn't mean the company is flawed - it just means people are different, and have different preferences and needs.

I'd recommend spending less focus on why one person left, and more on ongoing discussions with the people who remain, as well as being sure new staff has every opportunity to learn about the company, so they can self-select out before they are hired if they see anything that would not work well for them.

Amen. I'll throw in a pitch for "High Output Management," which does a good job of describing how and why to do 1-on-1s. Everyone hates meetings, but they're the primary way for people to propagate information and vent feelings. If you don't have 1-on-1s, people will bottle up feelings that don't have an outlet in other standard meetings. And if you don't have an environment of trust, no one will talk to begin with. So focus on creating an atmosphere where people can talk and then formalize and consistently create occasions for them to share their feelings-about themselves, about their careers, about their projects. Anything that you want visibility into needs to have a channel. And then just accept that your organization will evolve and you can't keep everyone, or make every project successful, or always beat your competition. Life isn't perfect. Being a leader is about driving a strategy and culture while bound by the constraints of your particular situation and the world in general.

I left my corporate job for personal reasons largely unrelated to the job per se. I certainly had my criticisms of the company, but probably needed to leave regardless.

So while you try to gather information, keep in mind that "not a good fit" could be a polite way of saying "It's none of your business and kindly butt the hell out of my private life, thank you."

Not everything that happens around you is about "you"/the company. That's not how life works.

I understand. Maybe if the conversation takes that tone we'll just have a nice tea and go back to life.

I think it depends on your trust level with the colleague. Or rather, their trust in you.

When you leave sometimes you don't want to help improve things for people staying, you just want/need to get the heck out. It can feel petty to present a laundry list of things you wish your former employer would change.

I'd approach that head on and assure them that:

1. You will keep anything they say confidential (unless there's anything illegal that surfaces)

2. You are acting in an unofficial capacity, not as a company person

3. You are having the conversation to help the other team members, not the company (because they will likely care more about them)

4. You want to hear whatever they have to say, no matter how big or small

The time to listen for "what's wrong" would be before they are leaving.

But I generally find that people who are leaving are quite open about the reasons, when asked. Especially if they are more about the job rather than themselves.

If you search workplace.SE for this you will know that the consensus is to say nothing in an exit interview


If you google "exit interview" you will find tons of opinions and ideas (example [1]).

Timing is important -- if you want to get useful information, you need to time the exit interview 1-3 months after departure so there's (typically) no fear of repercussion so folks' views tend to be more candid.

[1] https://hbr.org/2016/04/making-exit-interviews-count

Why would you submit to an interview with a company you’ve already left months ago? Are they paying for your time to do that? What on earth is in it for you at that point? All you can do is piss people off with your criticism.

No one has to, but like all things in life, some people do for whatever reason... I guess enough do for "exit interviews" to even be a thing.

Not sure how many people would actually go to an exit interview after they have left and presumably started somewhere else.

I imagine you could offer an economic incentive to give the feedback

You’d probably be getting some real feedback though.

These conversations don't work in the same way that conversations about why you declined to hire someone don't work. They always push into negotiations between the decider and the person who didn't like the decision. They have decided to leave, that is that.

If you want to avoid these things in the future, a reasonable strategy is to be really clear in setting expectations of the people who work there and the metrics by which they are evaluated. Then check in with them regularly and talk about both of those things. That will keep the employee and the manager on the same page and it will be a surprise to neither of them when things change.

"what went wrong"? I don't like the phrasing. People leaving and wanting to do something else is perfectly normal. There is nothing wrong about it. It's just a fact of life. The best way to deal with it (apart from offering a better compensation) is to wish them all the best and say they are always welcome back.

Hmm, perhaps I should have said "How to investigate if something went wrong?".

You're right that people leaving is normal. What I'd like to be sure of is that they are leaving because of the right reasons.

Just ask them about what they're doing next and what they're excited about. If they want to get into details it might give insight into what they've been missing, at least you'll get to know them better.

This will all depend on what your role in the company is today and what your relationship with this person is.

If you are in a leadership role at the company he/she may not want to open up to you for fear of reprisal even if you two have been friendly. If you two are teammates and you do not have a leadership role they may still not feel comfortable opening up to you because likely they have made comments and if no one picked up on it to discuss with them then they will feel you are complicit or accepting of the situation and don't want to create tension.

There is no harm trying to learn why for sure, but also know sometimes (especially with more senior people) people recognize when their thought processes, methodologies just don't align well with a team or company so they will remove themselves. This doesn't actually mean there is anything wrong with the company/team or with that person, just they recognized the differences and know those would create conflict, tension or struggles for themselves on the team. This is a healthy thing to have happen. That said, it is a very small number of the people that leave usually, more common reasons of leaving are for a lack of recognition, money and/or progress.

If you and the person leaving are both IC's then ask them from a place of curiosity to better understand what they might have seen that you haven't. This is probably the best way to get data points and be non-threatening to the person. When I say non-threatening, I don't mean you literally threatening them, but if you come at them with 20 questions it can start to feel like an interrogation and the persons self defense mechanisms will go up and conversation will go no where.

If you are in any kind of leadership role at the company, come at them from the place of not wanting to lose a good person, but respecting that sometimes people move on for a whole host of reasons. From your perspective you are trying to confidentially understand what the company could do better or change that might make the difference for the next person. Approach it this way, once they tell you if the asks are reasonable say if we made these adjustments would you stay, but don't approach the entire conversation from a place of would you stay. Approach it from the point of view to make sure issues are resolved for the rest of the team and the next people coming in. This is the best way to get data points usually and do so in a way people feel more open to chat. If at the end you ask them if these changes were made would you stay and they say no, then ask why not? That sometimes will open up a more true reason.

*edit: changed a word for readability

I don't understand what IC's means. Is it a standard term?

Individual contributor - people not on the managerial path, who can continue to grow and be rewarded in their career as do-ers (as developers or whatever else)

It's what we used to refer to as "the talent".

Sorry, I should have spelled out the IC (individual contributor), but discordance gave a good description on this.

Are you their friend? "Hey, why are you leaving?"

Not their friend? Why on earth would you think they owe you an answer to any of the questions you listed?

The zeroth order term in persons leaving is usually some sort of systemic insult to them. As a manager, identify the insult. Later, your organization will have to judge whether these conditions are "worth it" or localized to the individual.

> I'll be speaking to them in unofficial capacity soon. What all should we talk about?

The weather.

You are talking in an unofficial capacity I don't think any of your proposed questions should be discussed; except maybe showing interest in their future, did they already get another job? If not let them know you can be used as a reference.

> What other things can I ask them to prevent/improve this situation in the future?

Don't ask, if they trust you they will let you know. May have nothing to do with your company at all.

Honestly, I think you need to ask yourself the questions you are proposing, if you are paying attention then you already know the answers.

To answer the last question, management needs to regularly have one-on-ones with engineers.

A lot of one-on-ones are done wrong. 80% of the talking should come from the employee not the manager. Ask them what they want, where they want their career to go, what anxieties/insecurities/discomfort they have with the company and what they're working on, what needs to be moved out of the way.

To answer the first question, this is what needs to happen. Just listen to them. Don't come in with a list of questions.

>"I don't feel like I'm a fit for <xyz> company"

This is a really good general cop-out answer because it avoids creating hard-feelings or burning bridges if there was actually a more specific complaint (I hate working with that guy, my manager sucks, the work is super boring, product is stupid, pay sucks etc.)

First thing to check is, where the person is next going, are they going to be making more money? If so that is likely a reason. Another reason could be that they thought their potential for advancement at your company was low, at least in comparison to somewhere else. If the employee is an engineer, it could also be that they thought their learning had slowed or they were not working on the right kind of tech they wanted to for their career. For me, these career related reasons are the most likely reasons I would jump ship.

It's important to note that you shouldn't take a career-motivated jump personally. The only thing you can do is try to reorganize your company to make this less likely, by paying more, giving more opportunity for advancement, or working on/with sexier tech.

If it's not about career, it's probably either interpersonal or cultural. Maybe they feel socially excluded? Maybe their manager is too distant, an asshole, or a creep? Maybe they don't want to work as long / the same hours as everyone else?

Regardless, there is a very good chance you will never get a straight answer, or will get some fake, nice excuses. This type of thing requires introspection, not an exit interview.

I would never tell the truth about why I leave a job. There’s nothing in it for me.

More often than not it's because their boss doesn't care about the answer to those questions, even if you their peer do.

Personally I would not say anything of substance at an exit interview. And I know many people wouldn't either.

Maybe wait until 2 weeks after the person has left and invite him or her out for a beer or a coffee and then have an informal chat.

Provided you've some relationship with this person / they feel free to speak I would try to get them to speak in a more open ended manner about the job and their experience.

Personally I find when folks ask me specific questions about my job ... we don't have a common language and I have no idea what they really mean by what they're asking.

Also be open to the idea that this was just bound to happen and it is nobody's fault. Some jobs just aren't for some people depending on any number of factors.

I don't think I fully understand what you've said. I'm sorry for butchering this but, do you mean to say that when specific questions are asked the underlying assumptions are so out of sync that you cannot formulate an answer they would understand?

I think an example would help?

I don’t think such a conversation would do any good. If you had had a good relationship you would probably already know what’s going on. I don’t like exit interviews where you get asked why you are leaving. These questions should have been asked much earlier.

Personally I don’t think seeking such a conversation when somebody is leaving won’t do good for anybody.

Look into underlying reasons

1) employees leave mostly because of manager

2) Not being challenged enough at work

3) Got a job at another company with better pay

4) personal reason, burn out etc.

Just to break out 1/2 a bit more:

1a) Employee not being given clear guidance of what they're meant to achieve

1b) Employee being micromanaged intolerably

1c) Employee being told to take responsibility for something while not being given the power to fix it

1d) Employee not being allowed any autonomy or scope for creativity

1e/2a) Employee being forced to spend their entire working life cleaning up others' messes with no chance to work on anything new and interesting ("because you're good at fixing problems!") while those same others go on to trainwreck each new project

2b) Corporate goals limiting employee's ability to build the best product they can build (through some attempt to avoid competing with another product line, for instance)

Talking about the quality of a "fit" can be misleading. It presupposes that the factors which make people leave are actually beneficial to other people or the company.

That's certainly not the case with toxic coworkers. Probably there are more examples...

I think in many ways it's too late at this point. Keep the conversation casual and if it happens to veer into productive territory in terms of figuring out motivations then fine, but I wouldn't be asking probing questions unprompted.

What's your interest in this? Are you their peer or their superior?

Small plug for anyone interested here:

My company “Thanks For Sharing” is a straightforward app to help organizations avoid situations like these.

It’s designed to encourage employees to share feedback before issues reach an unsolvable state. Organizations can collect that feedback easily and built-in analytics will show trends to identify top issues.

We’re soft-launching next month... if you’re interested, shoot an email to the link in my profile and I’ll hook you up.

How is this any better than Google Forms, or Glassdoor?

Are employees answers anonymous?

If yes: How do you deal with employees not trusting your word on this? Especially given that, since it's an app, people would presumably need to install it on their own devices?

If no: How do you incentivize employees to give honest (both truthful and complete) answers?

Do you have any answer to the scenario where management ignores any feedback?

Do you give provide any analytics to employees that anyone is actually reading and acting on the feedback, or is this another one-way street?

I'm skeptical - I don't think this is a problem that can be solved by an app -, but I wish you luck. In the unlikely case that you succeed it'll be great.

Good questions. Hopefully you’ll be satisfied to know we’ve thought all them through.

It’ll be more sophisticated than other survey options that aren’t built for this purpose. It’s solely for internal use and NOT a public reviews website (so that bad eggs can’t use rage to infect others).

It will default on anonymous with the option to share your identity. Based off feedback, this seems to be the best route.

As for incentivizing honest answers, we believe, again based off research, that most people will be inclined to provide that on their own, especially if they have the shelter of anonymity. There are a lot of details I don’t quite want to give away yet, but you’ll see it soon.

We’re excited and learned a lot with the feedback we’ve gotten so far and are excited for the soft launch to get more data and iterate quickly.

If you want an honest answer, perhaps he or she does not like the singular they.

If I read your question, I'd not be a fit for this company either. It creeps me out when people use they for someone with a known gender.

Their gender is not "known"...by you.

Not to be rude, but rather to provide some perspective, and totally guessing here, but perhaps the person is leaving because you are always getting up in his business and acting like a tight ass.

Prefacing your statement with "Not to be rude" does absolutely nothing here. This is an entirely rude and unnecessary comment.

"Not to be rude" is one of those statements that does the opposite of what people who use it seem to think it does. It basically announces that that's exactly their intention and they think it gives them a get-out-of-jail-free card for saying it. It's always followed by something totally unnecessary, it's never followed by something useful or insightful that the other person might inadvertently take the wrong way.

These types of phrases are common and obvious enough that I'm surprised there's not a word for them. See also:

"I hate to tell you, but" (they don't hate to tell you, in fact the delight they get from telling you is why they're telling you)

"NOW, this may NOT be a poe-lit-tic-cull-lee core-rect thing to say, BUT" (in practice, for some reason it's very important to linger on every single syllable of "politically correct" when playing this card, maybe even roll it out so slowly that there are extra syllables, because apparently this is still 1995 and political correctness is some hot button issue that exists in their world that they're always inadvertently stumbling into) (also they're about to say something totally shitty and stupid, guaranteed, and political correctness has nothing to do with it)

"I'm not a racist, but" (they're about to say something so totally racist, and if they weren't racists themselves they'd know not to prefix anything with this phrase- it's up there with "but I have black friends" as being an obvious and transparent tell)

"I'm just keeping it real" (they really want to say the quiet part out loud and think this gives them license to do so)

"I'm a straight shooter and don't pull punches, and I hope everyone treats me the same way" (only ever said by the thinnest skinned people you'll ever meet)

"I'm going to be brutally honest" (in practice, the people who preemptively declare themselves to be brutally honest are always in it for 100% of the brutality and 0% of the honesty.)

I feel like it is, or is adjacent to praeteritio, apophasis, and such things.

See: https://en.wikipedia.org/wiki/Apophasis

Sounds like this person is your employee or direct report. Are you underpaying them? Do you use toxic “agile” practices at work? It’s very likely you can figure out why they left without asking.

you’re overthinking it

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