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Comment by rbetts | Hacker News Reader

As managers, we've had many individuals tell us "everything's fine; I like it here..." and then leave because "I'm ready for something new." So we often hear "I'm fine" and translate that to "I'm bored/unhappy/disengaged but I'm not telling you that because I don't think it's in my interest to reveal dissatisfaction to my manager."

The first step is creating enough trust and openness in the relationship to get past this communication impasse.

Promotion ladders are one (of many) tools for expressing what the company desires of its employees. For employees seeking advancement, they also work as a tool for discovering an employee's motivation. If promotion isn't the motivation - express what is the motivation. Figuring out that someone loves the puzzle of debugging, or takes pride in being the expert, or is a 9-5 journeyman who wants a stable, competitive salary for their contribution can be the key to having a fruitful conversation.

Once both sides are honest about motivation and satisfaction (the manager obviously also needs/wants something from the employee...) then there's space for adult-to-adult conversations about how and if those motivations line up.

In my experience, managers rarely turn away skilled, drama-free, reliable contributors. But we know our employees aren't totally truthful/open with us about these sensitive topics - so we don't take "I'm fine... leave me alone" at face value.

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In my experience companies don't have long-term plans or vision for their products, and it leads to work becoming tedious. You come in excited with no understanding of the product, you get knowledgeable and learn what's good and what's bad. Eventually you fix the bad you can fix and learn what bad you can't fix, and then the frustration outweighs the enjoyment.

I've tried to bring up these kind of big picture frustrations with managers before, but they're always focused on surviving the next 3-6 months.

A hundred times this. Bad management is so painful. I work at a design agency acquired by a fortune 500 company. People starting leaving because the culture they liked vanished as everything became enterprise-y. The response from the management team after >30% of employees resigned was: ....nothing.

Nothing to retain employees, nothing to acquire new ones, nothing to retain the DNA of the original company.

I'm sure it would make sense if you saw the balance sheet.

Acquiring companies normally don't really want to preserve the culture or DNA of the acquired company, in my experience (even when they say they do).

Ultimately, they want the whole company running by the same policies and procedures. They don't want to maintain carve-outs for subunits that used to be separate companies.

True. I am always amazed at the “we just got acquired by $HugeEnterpriseyCorporation, it’s been an amazing journey and nothing will change we remain the same, just as a part of $BigCompany”

As soon as the delayed bonus to the execs is due (usually 1–3 years), everyone quits in troves and it’s downhill from there.

I have been through this four times by now, usually everything is alright and there is the promise nothing will change, then uniformization of company culture starts and everyone skilled enough to find something else leaves.

On my case the average was around three years between acquisition and atriction leading to first wave of leaves.

I’m one of those “All is fine, leave me alone” who is planning to leave the company soon. My reasons:

- I take pride on what I do, I really care a lot about my career, but my main motivation for working 9-5 is my paycheck. I want more money but not more responsibilities (sounds crazy, I know, but the outcome I produce allows me to ask for this). No company out there is going to give me a free salary raise, hence I switch jobs.

Ditto

I dont claim to have significant experience with job market, but I wouldnt throw the possibility of "free salary rise" out of the window without even asking first.

Most people don't ask because the raise is lower than switching jobs.

Some people also believe that their work speak for themselves and they shouldn't have to explicit ask for a raise.

>Some people also believe that their work speak for themselves and they shouldn't have to explicit ask for a raise.

Sure. but closed mouths don't get fed. That's how we end up in the opposite situation that brought about this topic. Or worse, the oft-common "promotion" of a happy IC to management role who frankly isn't a good manager, despite being an amazing IC.

> closed mouths don't get fed

IMO, it's the manager's responsibility to advocate on behalf of the employee, especially if they want to retain them.

There's also the matter that a raise doesn't need a promotion. Don't promote people upwards unless they are willing and already working at this level. Give them a simple raise instead.

Agree, but then one is completely dependent on the manager being a thoughtful participant in the corporate meta game. The employee asking makes it _easier_ for the manager to advocate on their behalf.

> There's also the matter that a raise doesn't need a promotion.

This is a critical point. I've been a manager at companies where the primary, and sometimes only way, to get someone a raise is to promote them because of strict salary bands defined by level. This creates a perverse incentive to promote too early.

Salary bands are usually in place to -- ostensibly -- make sure salaries are fair. Fair salaries are a good thing. That being said, there HAS to be a mechanism to reward top performers with additional cash that doesn't require promotion otherwise it can feel like "teaching to the test."

They other factor is matching the pay bands to the market correctly. If the HR team outsources this to national averages rather than assessing peer companies, especially in software, the bands are going to be too low. Which means if want to retain anyone (not just your high performers, but your average employees) you are forced to inflate to just match market rates.

Usually I see this in the form of bonuses, especially ones that will basically always trigger unless you piss someone off (e.g. based on boss’s performance review, where you both know it’s just going be approved unless you really fuck up). Though this still maintains the risk/burden on you; e.g. boss changes; but it keeps HR happy, lawsuits away, and employees with a proper paybump

Usually I see this in the form of bonuses, especially ones that will basically always trigger

Every place I worked bonuses are decided according to a strict formula based on the performance of an entire departments and even the company as a whole. There is no way to reward an individual or even a project group with a bonus unless the whole larger office also hit their targets.

>Don't promote people upwards unless they are willing and already working at this level. Give them a simple raise instead.

I don't disagree, but I don't think there's anything simple about the process at all.

1. this obviously works against the company's interests, if they assume the employee is satisfied. short term business sense says they want to get away with paying as little as possible for labor, whereas employees want to be paid as much as possible. It's an eternal tug of war. And to be honest, one the tech sector has relative advantage over compared to other industries.

2. Even if we get over this short term block, figuring out how to give "merit based" raises can get very tricky, very fast. Especially if you leave the onus to not the developer, but to the manager's perception of the developer to determine.

This not only has bias on how much they/the company values a project (e.g. would working on a "simple" adtech feature be worth more than the labor overhauling a failing product to fail less? The ad product makes the company more money after all). But on their bias as a person. Would Manager give Bob a bigger raise because he goes to Karaoke on Thursday with the company, over John who has to get back to his family after work? Worse yet, would Manager implictly give Janet not a different raise than Bob due to subconcious sexism and not actually doing more work (be it preferential towards or against Janet)?

It's a whole mess, which is why companies try to objectify the whole thing. At least there, there is no room bias outside of who can pitch themselves better (if we assume equal work done).

3. Even if we arrange all of the above, raises aren't typically something a direct manager has easy access oo. It involves several lines of commands to appeal to and approval, beholden to a bunch of budget issues beyond a typical manager's control. Even if they truly want to compensate properly, the company itself may simply decide that they'd rather take chances hiring someone new when/if they need to maintain a potential void, over potentially compensating someone who was

I think the 3rd point is an interesting quandry since it goes against the usual mantra of "People leave managers, not companies".

That is a reflection of the incentive structure of most companies. It's not overtly in the interest of the business to pay their employees more money without extracting more labor from them. If a business either cared about or was at least cognizant of employee satisfaction, then rewarding good work would be a part of the management team's culture. The initiative management usually takes is in giving out new titles to employees and raises that aren't that far off from inflation, which is essentially just milking more out of employees they think will handle more work for roughly the same cost.

What you are essentially saying is that employees should beg not to be devalued, which might make sense in a contractor-client relationship, but W2 employment comes with such a tilted balance of power (especially with non-competes and clauses that bar doing work for other companies on the side) that there just isn't that much to gain from trying to negotiate. Employees are better off changing jobs every few years so they can completely shed any baggage from their last position and get a much fatter paycheck. (industry variations notwithstanding)

This isn't to say that I think that people are being sinister. It's just behavior that the system incentivizes.

>Some people also believe that their work speak for themselves and they shouldn't have to explicit ask for a raise.

I used to think that too but at the end of the day if you don't ask you don't get. Doesn't matter how you wish things were.

For what it’s worth, I have literally never asked for a raise in 30 years and have had my pay double in the span of two years at multiple companies. I am an individual contributor making an embarrassingly good total comp. Maybe the key is that deep down, I keep trying to provide value commensurate with what they pay me, and I never feel like I get there.

Perhaps if you negotiated, you could have gotten substantially more?

Substantially more guilt- based productivity maybe. I think I’ll be fine.

First step: ask for a raise, even a substantial one. You mightn't get it, but you might, and it's a lot less hassle than changing jobs

Don't you generally need to get an offer to have leverage/know your market worth?

The hassle is mostly prepping for the interviews. If I can't cut out that step, I am basically being saved the effort of cleaning up my desk and going to a new one.

Talk to your friends and coworkers about salaries. No one needs to reveal where they're at, but just talk about what the market's paying for relevant employees.

Also ask them if their company is hiring and has reasonable interviewing practices. Not everyone makes candidates jump through hoops.

Everyone revealing where they're at exactly (cash + bonus + stock + extra perks/PTO/whatever), while potentially a little uncomfortable in the beginning, is better for everyone long-term. I used to be against it, if only because I was typically at the top of the pay band for my role so had little to "gain" from the practice, but I've come around the last couple years. There's really very little downside, even if you're a top performer.

1. People who are legitimately being taken advantage of can more quickly realize it and either work to correct it or leave.

2. Top earners should be able to justify their outsized compensation to others, including peers.

3. Some people just legitimately don't know you can negotiate things like non-discretionary bonuses, extra PTO, etc.

4. Maybe your company pays everyone below-market, not just you, and at least knowing this will make it easier to decide if it's worth the lower pay (for QOL/WLB or whatever) or if you want to leave.

Also if there's a quick change in market rates (happening now in the US?) the more people you share information with the sooner you'll find out.

I used to be against this as well, until I worked at a company that abused this and leveraged it against it's vulnerable employees. Basically, more Jr. or bootcamp people were making _way_ less than market even though they have been working for a while at the company and delivered as much if not more value than coworkers.

Also, if this results in underpaid workers getting better salary, this results in the average salary going up and then the max salary going up.

This is what happened with CEO salaries after "transparency" laws were passed making them public.

Now, it's tough to say whether that can be extrapolated out to knowledge workers, but it is a useful datapoint non-the-less.

Leverage helps of course but I don't think it's unreasonable to expect someone asking for a raise to know whether or not they're asking for a reasonable number. If market rate for a given position is $150-200k TC and you ask for $300k not only are you going to get told no (quickly) but it's going to make you look really bad.

I've gotten 10-15% raises before without a competing offer or any other leverage simply because I could show that I was a certain "percentage of market rate" when I was hired, but the market rate had increased ~teen% since then. So it wasn't as much me asking for raise, it was me asking to have my compensation keep pace with the market/inflation.

There is literally no barrier to just asking. If you believe you're undervalued but like working at your company/with your manager, just ask. If they're a decent manager they'll be straight with you about money and market. If the answer is "No, that's outside of our payment band for this market", you could go get an offer and then have them counter, or you could just leave, but there's generally no harm in just asking.

I surprised myself and asked for a ridiculous raise last week. It came through yesterday without any push back. Companies may be be starting to see the light.

I have done this a few times. Usually along the lines of "Hey i like it here and I've done good work, but this is out of whack." 35%+ initial bump and usually accelerates further raises. This pattern suggests I'm terrible at negotiating initial offers but decent at navigating once in the door.

I can get a free salary raise of 3% when staying, or 20% when leaving.

To be fair, I took their matching counteroffer, but that would not have happened without me leaving in the first place.

I make it clear that things aren't working as soon as I can without giving ultimatums. If that isn't enough to trigger a response, then a desperate counter-offer is doing it for the wrong reasons.

Beyond a threshold salary, where your lifestyle is already comfortable, salary is unlikely to be the primary reason you look for a new job. Even if your current employer match, it's probably better long term for you to move on with your career and garner broader experience

You only know this if you ask for it and are denied. I can think of multiple times in my career (at least 3 or 4 over 11-12 years) where I asked for a raise without any corresponding promotion or increase in responsibility, and got it with little to no haggling.

It doesn't (necessarily) mean you're underpaid currently, it's totally possible your boss recognizes your contributions, wants you to be happy, and has the budget to give you what you want or close to it.

Or you ask, and get flagged as a troublemaker. No thanks. I'd rather not risk dismissal from a stable job while planning my jump to the next thing.

Asking for a raise doesn't get you "flagged as a troublemaker" unless you're really an ass about it.

You are assuming that the management is rational at your company. That's quite a big 'if'.

If they flag you and management is not rational that's one big red flag to leave that place ASAP

This is the thing that many people in this discussion are missing. There are many many many bad managers out there. Maybe this thread has all the good tech managers in the industry who would never do anything against their employees interest - but that isn't the reality facing most tech workers.

In my experience - good managers tend to get promoted quickly, while average/below average line managers tend to stagnate. In this environment, it's likely most line managers aren't the greatest managers and the ones interacting directly with ICs have a lot of skills to develop in the manager role.

The reality of most people is that they go to the job for a paycheck and put up with the (bad) management as a cost of that. In this environment, the most effective path towards higher pay is switching jobs, instead of risking navigating the inclinations of typically bad management.

Job market isn't equally friendly for all of IT around the world.

Why do you want to stay at a company in this situation, then?

You may not have other option. IT workers aren't drowning in jobs in many places around the globe.

Asking for 30% or else, is kind of assholish. But quite reasonable for new job.

Not if you're making 40% below market (and can prove it).

Have you ever seen that happen, or heard of it? I can't think of a time I've heard of an employee being fired for asking for a raise

If it gets discussed among management it's because the person already has a reputation as a troublemaker. The salary demand (in that case) is just icing on the proverbial cake.

I worked at a very small company where HR was directly reporting to the CFO (who was gunning for CEO and trying to also spawn his own grandiose IT projects). Our DBA made his negative opinions known in the midst of a data warehouse project sponsored by the CFO. This triggered Mr. Pointy Hair CFO and put the DBA on his shit list.

One day the DBA casually submits a query to HR asking "what is my package if I quit?" The HR director immediately runs to the CFO and tells him about the question posed by the DBA. The CFO flips his shit and is quoted as screaming something about wanting him fired immediately. We just had a change in management and the new CIO wasn't having it. He just ignored the CFO. It didn't end there. Over the next six months the CFO plodded on and eventually got the DBA fired...though the DBA was not trying to smooth anything over. He went to HR a second time to ask about his package. LOL.

Yep, this is how reality works. Have to be careful about what you ask.

That's why I never bothered asking my company if I could permanently WFH, just went along with everything until I found a new job.

Right on. If they think you're about to leave, they'll also be less likely to promote you.

Focusing on switching jobs when you already have a stable job puts you in a win-win situation.

Yeah, if I want more money I won't look for a promotion in my company because the salary increase will be something like 5%, maybe, due to the way internal promotions work in most corporations. I'll go somewhere else where I can get the same job I'm doing but negotiate a much better pay bump. Every significant pay increase I've had in my career has been by moving companies. I've never had anywhere near the same % increase with internal promotions.

> I'll go somewhere else where I can get the same job I'm doing but negotiate a much better pay bump

Can confirm this works in our current employment market in the US for Software Engineers. In fact, I have less responsibilities because I don't know anything about the tech or product yet and got a 30% pay increase (granted I was close to underpaid).

Obviously YMMV.

I've had the same experience - going to do the same job for another company is how you end up with 20% or more increases in pay. I've never gotten more than 10%(and that was just once) from a current employer. What's worse, if you do get the 10% bump, their attitude shifts to thinking you owe them for it - or at least my employer's attitude did.

This gets brought up here lots, but the whole "leave for 20% more pay" thing only is true earlier in your career. You will eventually plateau. Your next job switch will maybe be 15-20%, your next one 10-15%, etc. until you reach the inevitable compensation plateau. I'm over 20 years into my career and my last job change was for +1% or so, and I looked! No company would offer more.

So then your strategy shifts, right? You start looking for more interesting, novel, less stressful or more stimulating work for the same pay.

As a counterpoint , at most big tech companies that value their engineers, promotions are usually > 20% compensation increases.

There’s many reasons why FAANGS dominate, but one reason is their ability to attract and retain talent.

Not always though. A lot of companies have pay bands that nearly overlap. You can be performing well and be near the top of your band, get promoted, and then the raise to near the bottom of the next band is pretty minimal.

Is this across titles or even for promotions within the same title?

Promotions within the same title ... aren't really promotions.

I've worked at companies where titles beyond junior & senior (and "senior" means 3 years experience) don't exist

AFAICT, these companies don't really promote within a title - they use a leveling system. The definition of a promotion is to move from one level to another.

Vague job titles like "senior" or "junior" can be useful in limited circumstances, but if a company can promote you within the same title, it's a bit of a smell.

// I want more money but not more responsibilities (sounds crazy, I know,

Not really. wanting less money and more responsibilities is what would be crazy.

Here is some autistic-level honesty that would be impossible to say out loud. It is probably the basic perspective of all disgruntled workers:

"I want to be recognized and compensated proportionally to the value I create on your behalf. Furthermore, I suspect that the tasks/goals you choose for me are wasting opportunities for me to learn and for you to grow. Hence, I am bearing the long-term risks of your investment-decisions in my time, and you are reaping the short-term benefits.

"Because you seem to be unable to recognize the value I produce, and because you are squandering the opportunity of my time, I do not believe you are suitable for your job. It is possible there exists a job definition for which you are 'killing it', but it is not apparent from my perspective.

"So it is impossible for us to have an open honest conversation."

>I want to be recognized and compensated proportionally to the value I create on your behalf.

but who calculates this "value"? And what is it relative to? That's partially why stocks exist, to try and answer that question.

The fact that a lot of workers are able to find an employer willing to give them a raise to come work for them indicates that there was perceived unrealized value. If you cannot find a better deal, then that probably means you are operating close to your "true perceived value".

As long as there is disagreement, it's difficult to move forward. Managers could help show where/how value is created by collecting and sharing information.

To understand, explain and illuminate how value is created should be one of the first basic tasks for managers. Part of the purpose is to eliminate as much disagreement with and among "reports".

Stocks determine a value by constantly trading on the market. The value is whatever price the asset last sold for.

That is how we end up with our high turnover culture today.

The value is whatever price the asset will sell for today. This is informed by but not determined by the price it was last sold for. This difference is important.

You're right, this approach is going to fall flat.

Imagine someone coming to you and saying it.

Assume (as manager) instead that it is the 'default' rational attitude in a high entropy state, and work on ways of changing the circumstances to move out of that state.

> It is possible there exists a job definition for which you are 'killing it', but it is not apparent from my perspective.

Tangent: That comment showed me, after 40+ years of adult working, that any individual person is filling multiple roles, each defined by other peoples' perspectives and needs. Indeed, that individual may not even be aware that they are in those roles, much less that those roles may be crucial to those other people.

Note that I almost edited "multiple roles" to "multiple work roles," but this probably applies to most social relationships.

Huh.

An honest 1-on-1 between two adults who trust each other would go along these lines:

- Hey, how's life? What do you think about this project?

- Well, it's shitty, to be honest. Didn't expect it to be this boring. And this on-call... I'm looking for a job that would pay 50% more for 50% less work.

- Yeah, that's the way it is in this company. The owner is a greedy crook, and the fish rots from the head, you know. We're told to lie to employees that there's no budget for pay rises, while the profits have doubled. It's all bs. But I can refer you to a few places that pay what you want. I'm thinking to leave too, btw.

This. An honest 1-on-1 between two adults is called an exit interview.

Sincere question: why be forthright in the exit interview? I’ve always politely left doors open.

I have no idea why someone downvoted you. Keeping cards close to your chest in an exit interview seems like a strategic move. Sure, you can sugar coat and hint at things that can be improved, but why spell that out? It might clear things up, but it might just make you look picky and high maintenance, closing the door on a future working relationship.

And it’s very unlikely to change things for those still stuck there anyway. I can’t think of an upside to being honest in an exit interview.

I feel you can be more honest -- while still being polite -- in an exit interview, since your alternatives are no longer hypothetical. If you have a competing offer on the table that pays 50% more, then you are no longer demanding, you are informative.

I haven’t ever had feedback about a company which I could both politely give and hadn’t already given directly to my manager (and other coworkers) before leaving the role. What does HR need to hear that’s both appropriate to say and not best told directly to the team?

The concept of exit interview feels strange to me, as European.

Most to the time one just needs to give HR the resignation letter and that's it.

If one has enough vacation days to fill up the notice period, they don't even need to show in the office again, if they feel like it.

Naturally everyone will want to know why one is leaving, including the boss, but one isn't required to hold such conversations.

Did you consider the possibility that both of those statements could be sincere at the time they are made?

"This work is good enough for me for now, but in the future it might not be anymore, in which case I'll want to take it into my own hands to find something new. But since for the moment I like the work, I'm not necessarily thinking about that possibility in the future."

>"everything's fine; I like it here..." and then leave because "I'm ready for something new."

If we aren't taking people at face value I don't know why we should assume the second comment is the truth. "I'm ready for something new" sounds like the "It's not you, it's me" of reasons for leaving a company. It often doesn't benefit an employee to give a real reason they are leaving and many times those reasons have nothing to do with how their employer handled career progression.

For example, if a engineer works at a large company (i.e. one in which a single engineer or manager has no real power to push for organizational change) there is little reason to voice their opposition to the overall direction of the company during performance reviews. It also doesn't make sense for that person to burn bridges by unnecessarily criticizing that direction on the way out the door.

Oh my God, so many games. Why can't I just do good work, get paid, and everyone get on with their lives?

Because you're in capitalist competition with everyone, laterally, vertically, and chronologically.

If you keep prying after "I'm fine... leave me alone" then you'll quickly become the reason for them going from "fine" to "not fine".

> The first step is creating enough trust and openness in the relationship to get past this communication impasse.

How do you propose doing that given that a manager -- by their very job description -- does not have your best interests at heart and will happily use those interests against you if doing so answers "yes" to the central question: "But Is It Good For The COMPANY?"

> "everything's fine; I like it here..." and then leave because "I'm ready for something new."

However, often that something new is just the same type of work.

E.g. imagine that the tech organization is an orchestra. All you play is the same small set of Bach concertos. Your lead violinist likes it just fine, until she leaves because she is ready for something "new". Turns out to be some place where they play the same dozen Vivaldi concertos. Or not even that, but just a different selection of Bach.

E.g. an embedded developer leaves "for something new", where something new is working on a bluetooth driver, exactly like now, but on a different SoC, with a different BT chip, and two kernel versions higher.

I personally can't have any respect for managers that clearly understand what "everything is fine" means and say they they want drama-free employees.

"Drama" is a way to express personal emotions, and probably wishes to change things to better, which I really hope my manager cares about.

As en employee, to be honest to my manager requires

1. that I trust her/him

2. that I believe he can actually push the change that would help me through the company

2 has been a problem far far more often.

Exactly. I've found that it's important to probe any hint of discontent. Sometimes it's just a badly-phrased comment, but other times, the employee is (consciously or subconsciously) trying to tell you something.

A phrase I used a lot is "what would you like to differently, or what would you like to learn?" That's often an opening to getting someone the kind of work they'd prefer to do, but are reluctant to bring up.

> what would you like to differently, or what would you like to learn?" That's often an opening to getting someone the kind of work they'd prefer to do, but are reluctant to bring up.

Just to give insight into why some ICs don't respond to this question. I asked my manager for promotion, he kept stringing me along. One of the reasons for said string-along was that the kind of stuff I want to work on is not big enough. Why couldn't he tell me this 6 months ago? I have no clue.

But I have learned to never trust managers with this experience. Managers will have to work hard to earn my trust.

There’s an art to discovering mutually beneficial arrangements. If an employee loves working at their current role, is good at, wants to keep doing basically exactly that, is at the right level for the work they’re doing, but wants a promotion, there’s a conflict. Maybe some of that six months was the manager trying to figure out if there was flex anywhere to find a solution that worked for both sides.

There sure is an art to finding mutually beneficial arrangements, but there is sometimes also a point where you need to recognize no such arrangement exists. It seems equally likely to me that the manager may have realized right away that there was no (or not enough) flex in the situation and decided that instead of the team member leaving immediately they could perhaps be strung along and provide value to the company for a few more months.

Some of the situations where no real flex exists are:

- promotion wish where there is no place. For example, someone 1 level below the CTO wishing to be promoted to CTO will not be able to get their wish unless the current CTO leaves. If they don't, promotion to the desired rank will not be possible without changing companies.

- salary demands that can't be met from the budget. Most middle managers do not have significant say over how much budget for raises they are allotted for the year. If one persons raise demand is bigger than the total then not all of it can be met.

- As in the GP post, the things the employee wishes to work on do not fit in the wider strategy of the company and/or will not provide value commensurate with the salary received. In this case, depending on how insistent both sides are, sometimes no compromise is possible.

100% agree. I look back to several situations in my own career as a manager where I did have this case arise and went looking around the org for other opportunities that might give my employee what they wanted. Some of those worked out, but many did not. The ones that did not would be indistinguishable to the employee from a manager just "stringing along" the employee to get a few more months out of them. (There are other cases where I was able to be more upfront as there was an obvious mismatch analogous to your CTO's direct report case.)

That wouldn't work if their primary discontent is with their salary.

If they're honest (including with themselves), it's as easy as saying something along the lines of "I'm happy with my role, my responsibilities, and what I'm learning every day, but I'm not content with my salary."

Sometimes the answer is just to give them a raise. Sometimes it's "you're already at the top of your pay band, sorry."

Not even at the top of your pay band, but "we simply don't have the budget for it". Very much the case for startups trying to compete with well-established companies, let alone FAANG-tier

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