As good as slack is for communicating I don't think it should be used as a "knowledge" store. At a previous employer I found that commit messages were a great way to store information. Maybe commit messages aren't as great for question and answers, but searching slack doesn't seem very intuitive.
Idea: A slack bot that searches for questions and answers and creates a wiki out of the scraped information.
What's really great is when you go back in the Slack history from the day you interviewed and see what people said about you... I imagine that can sometimes be awkward.
>As good as slack is for communicating I don't think it should be used as a "knowledge" store.
It's not that it shouldn't be, but that it probably won't be when it should. My company uses HipChat and not Slack, but ever since we first adopted it about 4 years ago I have been preaching that our in-house technical support staff use its search function before asking the developers for help. Maybe 10% of them do, if I'm being generous. The rest think their issue is unique and requires immediate one-on-one developer attention.
We also have an in-house wiki that doesn't get consulted as often as it should. I spend at least half a day documenting, from a end-user perspective, every project I complete on our wiki and still find myself repeating what I've written in a one-on-one chat on a daily basis.
But if they choose to leave, do not offer them money to stay. Any employee who stays is not being very smart, the only interest the company has in paying you more is keeping you long enough to train your replacement.
If you were not worth X the day before you quit, how are you suddenly worth X the day you decide to quit?
I've seen people accept a counter-offer from a company, and very few of those lasted more than 6 months, or the amount of time it takes the company to make them no longer indispensable.
I wouldn't begrudge an employer for negotiating my salary and not paying me what they think I'm "worth," but I also wouldn't feel guilty about doing the least amount of work necessary to fly under the radar at the job and not get fired. (Not a direct response to your comment, I know -- it just made me think of how annoyed I get when the former is considered "just business" while its equivalent on the employee's end is usually regarded as "mooching" or a moral failing.)
>"If you were not worth X the day before you quit, how are you suddenly worth X the day you decide to quit?"
This can easily happen when you are actually worth X, but the company thinks you are worth X-Y because they have a history of underpaying and perhaps were able to get away with it when the economy was down. If the market is willing to pay X for someone like you, you are worth X regardless of what your current employer thinks you are worth (as long as you act on it).
There's a particular failure mode that bears pointing out with regards to compensation:
Suppose you have a person you've brought on, and they agree to do some amount of work at a salary and tiny equity split.
After some amount of time, they realize that they've produced a good deal more value than you have compensated them for. They're going to feel jilted.
It's not enough to say, "We'll take advantage of you less in the future"...you might have to say, "Wow, okay, we screwed you, how can we make this right?"
And sadly, the optimal capitalist strategy is to just lay them off and enjoy the surplus they unwittingly made for you.
"And sadly, the optimal capitalist strategy is to just lay them off and enjoy the surplus they unwittingly made for you."
Maybe for a dumb capitalist. The optimum strategy is to pick a level of compensation that works for them and you while realizing there is a transition cost to new people and talent is worth something.
No, the optimum strategy is to determine if compensating them to a mutually agreeable level is more or less expensive than losing their expertise and rolling someone new in.
Just because parent said optimal strategy is to lay them off doesn't mean you have to act like that's _never_ going to be the case.
For the given hypothetical, the 'ol "get them to unknowningly train their replacement by pretending like you're rewarding them with more compensation and a direct report" could be the "optimal" strategy.
> Just because parent said optimal strategy is to lay them off doesn't mean you have to act like that's _never_ going to be the case.
I thought it went without saying that you cannot force someone into an agreement. Agreements sometimes don't happen and then you pay the additional costs out of necessity.
> For the given hypothetical, the 'ol "get them to unknowningly train their replacement by pretending like you're rewarding them with more compensation and a direct report" could be the "optimal" strategy.
That might be someone's interesting play, but I think it is a poor strategy because it shows your employees and anyone else you are going to make agreements with that you are of the duplicitous sort and cannot be trusted. This will affect your long term prospects in a negative way. Never mind its a pretty poor way to go through life.
Tech people (in general) do not make job decisions based solely on money. They want recognition, good work, good teams, good leadership, a meaningful product, etc. If your solution to morale problems is to increase salaries, you have already missed the mark in some of these other areas.
Sometimes it is about the money. Recognition, good work, good teams, good leadership, meaningful product, etc. don't feed my kids. I left all that once because I was at half market value (evidenced by finding a new job at double the pay).
> Tech people (in general) do not make job decisions based solely on money.
Actually, money is a huge factor for most tech people. I don't know many developers who wouldn't move jobs for a 30-40% increase in pay.
Not to mention salary is fairly closely tied to value within a company... unless you are getting ripped off. And once somebody realises they are getting ripped off they are likely to leave.
> Take the time, on a regular basis, to talk to your employees about their lives, goals and challenges. Ask them what they hope to accomplish, not just in the next week, but in the next year, five years and ten years in their careers. Listen intently to what they say, and think about how you can help them achieve that. And then act.
Anyone who asks me those questions will get double the loyalty out of me - they'll know before I even think of going elsewhere. I've been at way too many places that just don't give a damn, or assume that people will look out for themselves. They will, but probably to another place. But if you want them to be dedicated and loyal to working for you you need to get out in front. Solve the little problems before they become big ones, or lose your best employees (who can easily get a job elsewhere) and let your companies morale and productivity die.
OK, but that doesn't change the point of their post. It can easily be rephrased as something like...
"Would an employee feel honest telling their boss their 5-year goals? What if it isn't "leading a larger team at this company" or "designing and developing more and/or more-important portions of the company's projects"?
What does a typical 5-year goal sound like? I always struggle to come up with anything when this sort of question comes up (not necessarily in an employer-employee conversation, just in general).
I have no clue what you're supposed to say, but the closest thing I'd have to a 5-year goal is "increase my net worth by at least 20% per year". Which has almost nothing to do with my job except staying employed.
"Be managing a full project on my own", "Manage group of people", "Become an expert in X technology", "Build 2 products into production", "Get to 100,000 users" etc etc etc.
How do you want to grow? Do you want to stay in the same spot? Maybe for now, but do you want to be doing this exact same thing for the next 5 years? Not even minor improvements? Getting faster/better/stronger?
> Take the time, on a regular basis, to talk to your employees about their lives, goals and challenges. Ask them what they hope to accomplish, not just in the next week, but in the next year, five years and ten years in their careers. Listen intently to what they say, and think about how you can help them achieve that. And then act.
Ah, the dreaded one-on-ones. This would actually make me want to leave the company if I have to be open all the time. Why should I have to divulge my personal aspirations to my employers? That's private information.
You should divulge your personal aspirations because your company might actually help you achieve them.
It pays to start thinking about how your interests which you are a little bit afraid to share might help your career... because this is how you get your employer to pay for them.
It depends on the employer. I wouldn't say "I want to quit this dump and become a water colour artist and photographer". But I /would/ say "I think that studying some art subjects would really benefit my front end design work here".
I wouldn't say "I want to get away from you and write poetry" but I /would/ say "I would like to improve my written communication skills, which will really help the clarity in my correspondence with clients and in my detailed documentation and commit messages. Would work fund this course I have found"
If there is any cross-over at all between where you want to go and what benefits your employer, it's in both of your interests to put that spin on it and get them to pay for it.
The one-on-ones are only something to dread if you don't know how to ask for things in a way that is mutually beneficial. As you get older and more experienced in negotiation it becomes easier.
Remember, its "career aspirations", not "personal aspirations".
You shouldn't have to, but it makes a lot of sense to discuss your professional aspirations with the company who is currently a part your professional career. The only reason I wouldn't want my boss to know what my professional goals would be if I don't trust him/her to help me achieve them. If that trust isn't there then I'm already looking for a new job and this topic is one I make sure we discuss at some point if interviews get serious.
By no means should anyone ever feel required to divulge them. If you are the private about yourself and your things, then thats completely fine. Maybe you want to quit in a year to go off the grid or something. Thats perfectly fine. But if someone is interested and you think the person wants to know and help out, maybe you tell them 2 months prior instead of 2 weeks. Thats still a big gain.
You can document institutional knowledge and try and make sure nobody is indispensable but ultimately you will still take a huge blow.
You should focus most of your attention on improving retention.
I left a full 200 page notebook full of product ideas/customer notes/requirements/designs when I left my last job. Hopefully it helps the team but it is only in note form and completely unordered. More likely they won't look at it and the knowledge will just be lost.
About to do an exit interview tomorrow, and this article resonates with me, in the general case.
There are also the cases of pathologically bad employees, or just underperforming.
However, in some cases, it is personal. It's not some growth stage for the employee--they could well be leaving an early employee role because you, the founder(s), have fucked up. You've found yourself with an employee putting out tremendous amounts of work, transferring their knowledge, coordinating their team even as they're leaving, and who generally would be great except for the fact that, for some reason, they're leaving.
Things you should be asking yourself and your employee:
Did you ignore, multiple times, their domain expertise because you {thought you knew better, couldn't afford to follow it, felt like it, didn't like them}?
Did you support them in front of their team? If not, did you support them at all? Did you respect the chain of command, or did you reallocate their resources under them?
Did you lie to them? Was it for a good reason, because of {team morale, need-to-know, legal liability}? Whether or not you ever lied to them, did they feel like they could trust what you said?
Did you give them information when they requested it? Did you give them resources when they requested it? If you didn't give them resources, why not, and was it worth it in the long run?
Did you spend enough time with them, communicating not just about work but bullshitting and building a friendship? If you didn't, was it because you {were busy, had other leads, didn't like them, are an "introvert"}? How did that lack of communication factor into their departure?
Did you display any competence at all by some objective metric in your facility as leader? Whether or not you did, did the employee feel like you were competent?
And yeah, I think you should feel bad. You've wasted their time and the company's resources because of your mismanagement. If you're really luckily, maybe you can learn from it and keep from losing anyone else--because if you don't, you don't deserve to be followed.
Note that the amount of these questions these leaders will ask themselves is inversely proportionate to their own ego. I watched half an engineering team leave a company over 2-3 months and each and every time the 3 managers up the chain found ways to explain it that didn't involve their competence or methods. Last I saw they were circling the drain.
And then, instead of recovering in a few minutes, imagine the shock and pain slowly turning into disappointment, anger and dread.
Don’t you realize how important you are to the team?
How could you do this to me?
It was what I felt right then and there. Betrayal. Sadness. Despair about the future.
Umm, companies pull the plug on employees all the time. In most cases with vastly less forethought and regret than employees engage in when leaving their jobs (even jobs they hate).
I guess it can sort of "hurt" on the management side, when employees leave. But given the pain that employees go through (hint: the immediate threat to their own physical safety, as well as that of their families) when they're let go, I'm not sure how one could begin to consider the two situations as remotely comparable. Let alone get so emotional, and feel such a sense of "despair" when an employee (even a particularly valued one) leaves.
That quote is really out of context. His point is that this is the wrong reaction, but a very natural one. Here's what directly follows this quote:
> It doesn’t matter that these questions weren’t the right ones to be asking.
It doesn’t matter that they weren’t even remotely accurate, and frankly, incredibly selfish.
It doesn’t matter that they run counter to everything I’ve learned about managing employee exits since then.
It was what I felt right then and there. Betrayal. Sadness. Despair about the future.
It's pretty easy to get overly emotional on anything that you've put significant amounts of time and effort into. The point of the article is that you shouldn't actually follow these feelings and that there are much better ways of handling it.
> I guess it can sort of "hurt" on the management side, when employees leave.
I agree on the "hurt" part, but it is a well known fact that employees do change jobs in this industry. If a manager is not aware of that, and has not already made contingency plans for when that difficult time comes, then he is not very good at his job.
I would go as far as to say that he could do worse than to look at what other parts of his job he might been ignoring (hopefully) without noticing. Maybe that would explain why the employees leave in the first place.
If a leaving employee is so important, you should ask yourself "Am I really 100x-1000x (whatever ratio your equity is to their equity) more important than this employee?"
Founder equity is typically on a completely different scale than that of employees (even first hires). So we shouldn't be surprised that their loyalty is on a completely different scale, as well.
Exactly. My main problem is that the CEO's stance is entirely hypocritical, because he would demand real equity or quit (probably even faster) if he was in the employee's position.
Once you have access to millions in funding its tough to see people who have to work for a living as human just like you. You expect them to lovingly accept terms that you would be insulted at.
Now if your talent is so great that you dwarf all your employees it might be justified. But when you are pained at losing productive workers chances are your favorable terms exist mostly because of your connections.
This is exactly as I see it. A company and it's investment in me is how I determine my investment in it. Pay market average expect an average 8 hour work day.
You have a considerable chip on your shoulder, and are projecting things onto the article that aren't there. The article spends a lot of time discussing how things are from the departing employee's point of view, and not (as you suggest) looking down from an ivory tower.
I know for some people that article may feel like this article talks about them one way or another. It may also seem a little self involved to think that it does if you are an employee.
But a word of advice for such talented employee as some of the recommendations go both ways. I'm 5 weeks away from being done with a 6 months-ahead notice to my employer that I would be leaving because I knew nobody could enter "the kingdom" that I ended up holding the key to. I felt too bad leaving them in that situation especially since I was given opportunities may developers would never expect their current employer to go for. I also know that despite that long transfer of knowledge they'll have a heck of a hard time dealing with.
You don't want to be irreplaceable just as much as they don't want you to be, especially in an era where software developers are in such ridiculous demand. And in no way does this mean you can't be as good as you work to be.
It sounds like you were given opportunities you wouldn't get elsewhere and in exchange you showed them loyalty and didn't leave them in the lurch by giving them 6 months notice. To me that's a great success story for both sides.
Do you feel like the advantages given to you weren't worth the 6 months extra you felt like you had to stay? Why?
The first company I worked for full time made me the solution architect for a 20 person project even though I only had 2 years of work experience at the time. Successfully completing that project put me an easy 5 years ahead of my peers in terms of career growth and very few of them have caught up in the 10 years since.
If an employee is so valuable that it hurts when they leave, maybe they should have been given more incentives to stay.
You can't say that an employee is selfish when they're the ones doing all the hard, laborious technical work and getting almost nothing out of it aside from a below-average startup salary.
This might come as a shock to some, but engineers have feelings and ambitions too. In this highly competitive market, it makes sense to give your employees more equity if you want to hold on to them. When you consider supply and demand, the ratio of founders to engineers is now much higher than it ever was. Great engineers are rare.
I've left quite a few companies, even a promising startup - Would I have left if I held even 5% equity in that company? Probably not.
If you don't give your 'valued' employee decent equity then you are the selfish one and I hope that they do leave (if only out of respect for the profession).
I've seen too many self-important founders who think that they deserve twenty times more equity than their best employee (just because they're friends with a rich investor). Taking risks is easy (and kind of fun), doing mind-numbing programming every day for 10 years is not (and working for a single company, in a single problem domain for that long IS mind numbing).
Also, let's not pretend that engineers aren't taking risks. 5 years of a young engineer's life is a huge risk especially when you consider that a lot of engineers start to slow down as they get older.
The way you treat exiting employees is just as important as how you treat them when they are still there from a recruiting perspective. If you treat someone well when they decide to leave, they are more likely to recommend your company to others looking for a job.
There have been places I left for various reasons that were great employers that I still recommend to this day for others looking for a job.....and might even thing about joining if the right opportunity came along.
I made this point at a previous firm I worked at. That the number of potential employees in any town is a finite number, and so you want to treat people leaving as brand ambassadors of your firm so you won't have trouble hiring in the future.
As someone who left, and is now hearing of the rest of the team leaving....
1st, if someone is so darn important, it is your job to have a backup plan for when they quit, or for that matter get hit by the proverbial bus. Anything less is managerial incompetence, spend a day or two reading about business continuity.
2nd, there are these things called golden handcuffs, if you don't understand the concept I refer you to the above.
3rd, if you don't have the money for 2, then you better not be seen driving around in your brand new lamborghini, or spending all your time at over the top expensive restaurants while your employees have a tiny fraction of the company, and slave away for 70+ hours a week eating crap ass food from the fast food joint they are paying for themselves. (This really happened!)
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[ 3.6 ms ] story [ 131 ms ] threadIdea: A slack bot that searches for questions and answers and creates a wiki out of the scraped information.
It's not that it shouldn't be, but that it probably won't be when it should. My company uses HipChat and not Slack, but ever since we first adopted it about 4 years ago I have been preaching that our in-house technical support staff use its search function before asking the developers for help. Maybe 10% of them do, if I'm being generous. The rest think their issue is unique and requires immediate one-on-one developer attention.
We also have an in-house wiki that doesn't get consulted as often as it should. I spend at least half a day documenting, from a end-user perspective, every project I complete on our wiki and still find myself repeating what I've written in a one-on-one chat on a daily basis.
But if they choose to leave, do not offer them money to stay. Any employee who stays is not being very smart, the only interest the company has in paying you more is keeping you long enough to train your replacement.
If you were not worth X the day before you quit, how are you suddenly worth X the day you decide to quit?
I've seen people accept a counter-offer from a company, and very few of those lasted more than 6 months, or the amount of time it takes the company to make them no longer indispensable.
On the other hand, why would they have paid you X even if you were worth it, if they could get away with less?
This can easily happen when you are actually worth X, but the company thinks you are worth X-Y because they have a history of underpaying and perhaps were able to get away with it when the economy was down. If the market is willing to pay X for someone like you, you are worth X regardless of what your current employer thinks you are worth (as long as you act on it).
Suppose you have a person you've brought on, and they agree to do some amount of work at a salary and tiny equity split.
After some amount of time, they realize that they've produced a good deal more value than you have compensated them for. They're going to feel jilted.
It's not enough to say, "We'll take advantage of you less in the future"...you might have to say, "Wow, okay, we screwed you, how can we make this right?"
And sadly, the optimal capitalist strategy is to just lay them off and enjoy the surplus they unwittingly made for you.
Maybe for a dumb capitalist. The optimum strategy is to pick a level of compensation that works for them and you while realizing there is a transition cost to new people and talent is worth something.
Just because parent said optimal strategy is to lay them off doesn't mean you have to act like that's _never_ going to be the case.
For the given hypothetical, the 'ol "get them to unknowningly train their replacement by pretending like you're rewarding them with more compensation and a direct report" could be the "optimal" strategy.
I thought it went without saying that you cannot force someone into an agreement. Agreements sometimes don't happen and then you pay the additional costs out of necessity.
> For the given hypothetical, the 'ol "get them to unknowningly train their replacement by pretending like you're rewarding them with more compensation and a direct report" could be the "optimal" strategy.
That might be someone's interesting play, but I think it is a poor strategy because it shows your employees and anyone else you are going to make agreements with that you are of the duplicitous sort and cannot be trusted. This will affect your long term prospects in a negative way. Never mind its a pretty poor way to go through life.
Strategy should be thought of as long term.
Actually, money is a huge factor for most tech people. I don't know many developers who wouldn't move jobs for a 30-40% increase in pay.
Not to mention salary is fairly closely tied to value within a company... unless you are getting ripped off. And once somebody realises they are getting ripped off they are likely to leave.
> Take the time, on a regular basis, to talk to your employees about their lives, goals and challenges. Ask them what they hope to accomplish, not just in the next week, but in the next year, five years and ten years in their careers. Listen intently to what they say, and think about how you can help them achieve that. And then act.
Anyone who asks me those questions will get double the loyalty out of me - they'll know before I even think of going elsewhere. I've been at way too many places that just don't give a damn, or assume that people will look out for themselves. They will, but probably to another place. But if you want them to be dedicated and loyal to working for you you need to get out in front. Solve the little problems before they become big ones, or lose your best employees (who can easily get a job elsewhere) and let your companies morale and productivity die.
"Would an employee feel honest telling their boss their 5-year goals? What if it isn't "leading a larger team at this company" or "designing and developing more and/or more-important portions of the company's projects"?
How do you want to grow? Do you want to stay in the same spot? Maybe for now, but do you want to be doing this exact same thing for the next 5 years? Not even minor improvements? Getting faster/better/stronger?
Ah, the dreaded one-on-ones. This would actually make me want to leave the company if I have to be open all the time. Why should I have to divulge my personal aspirations to my employers? That's private information.
It pays to start thinking about how your interests which you are a little bit afraid to share might help your career... because this is how you get your employer to pay for them.
It depends on the employer. I wouldn't say "I want to quit this dump and become a water colour artist and photographer". But I /would/ say "I think that studying some art subjects would really benefit my front end design work here".
I wouldn't say "I want to get away from you and write poetry" but I /would/ say "I would like to improve my written communication skills, which will really help the clarity in my correspondence with clients and in my detailed documentation and commit messages. Would work fund this course I have found"
If there is any cross-over at all between where you want to go and what benefits your employer, it's in both of your interests to put that spin on it and get them to pay for it.
The one-on-ones are only something to dread if you don't know how to ask for things in a way that is mutually beneficial. As you get older and more experienced in negotiation it becomes easier.
Remember, its "career aspirations", not "personal aspirations".
You should focus most of your attention on improving retention.
I left a full 200 page notebook full of product ideas/customer notes/requirements/designs when I left my last job. Hopefully it helps the team but it is only in note form and completely unordered. More likely they won't look at it and the knowledge will just be lost.
There are also the cases of pathologically bad employees, or just underperforming.
However, in some cases, it is personal. It's not some growth stage for the employee--they could well be leaving an early employee role because you, the founder(s), have fucked up. You've found yourself with an employee putting out tremendous amounts of work, transferring their knowledge, coordinating their team even as they're leaving, and who generally would be great except for the fact that, for some reason, they're leaving.
Things you should be asking yourself and your employee:
Did you ignore, multiple times, their domain expertise because you {thought you knew better, couldn't afford to follow it, felt like it, didn't like them}?
Did you support them in front of their team? If not, did you support them at all? Did you respect the chain of command, or did you reallocate their resources under them?
Did you lie to them? Was it for a good reason, because of {team morale, need-to-know, legal liability}? Whether or not you ever lied to them, did they feel like they could trust what you said?
Did you give them information when they requested it? Did you give them resources when they requested it? If you didn't give them resources, why not, and was it worth it in the long run?
Did you spend enough time with them, communicating not just about work but bullshitting and building a friendship? If you didn't, was it because you {were busy, had other leads, didn't like them, are an "introvert"}? How did that lack of communication factor into their departure?
Did you display any competence at all by some objective metric in your facility as leader? Whether or not you did, did the employee feel like you were competent?
And yeah, I think you should feel bad. You've wasted their time and the company's resources because of your mismanagement. If you're really luckily, maybe you can learn from it and keep from losing anyone else--because if you don't, you don't deserve to be followed.
And then, instead of recovering in a few minutes, imagine the shock and pain slowly turning into disappointment, anger and dread.
Don’t you realize how important you are to the team?
How could you do this to me?
It was what I felt right then and there. Betrayal. Sadness. Despair about the future.
Umm, companies pull the plug on employees all the time. In most cases with vastly less forethought and regret than employees engage in when leaving their jobs (even jobs they hate).
I guess it can sort of "hurt" on the management side, when employees leave. But given the pain that employees go through (hint: the immediate threat to their own physical safety, as well as that of their families) when they're let go, I'm not sure how one could begin to consider the two situations as remotely comparable. Let alone get so emotional, and feel such a sense of "despair" when an employee (even a particularly valued one) leaves.
> It doesn’t matter that these questions weren’t the right ones to be asking.
It doesn’t matter that they weren’t even remotely accurate, and frankly, incredibly selfish.
It doesn’t matter that they run counter to everything I’ve learned about managing employee exits since then.
It was what I felt right then and there. Betrayal. Sadness. Despair about the future.
It's pretty easy to get overly emotional on anything that you've put significant amounts of time and effort into. The point of the article is that you shouldn't actually follow these feelings and that there are much better ways of handling it.
So: apologies to the original author.
I agree on the "hurt" part, but it is a well known fact that employees do change jobs in this industry. If a manager is not aware of that, and has not already made contingency plans for when that difficult time comes, then he is not very good at his job.
I would go as far as to say that he could do worse than to look at what other parts of his job he might been ignoring (hopefully) without noticing. Maybe that would explain why the employees leave in the first place.
Once you have access to millions in funding its tough to see people who have to work for a living as human just like you. You expect them to lovingly accept terms that you would be insulted at.
Now if your talent is so great that you dwarf all your employees it might be justified. But when you are pained at losing productive workers chances are your favorable terms exist mostly because of your connections.
Creating a company is not hard; building it is, but employees contribute to that as well.
But a word of advice for such talented employee as some of the recommendations go both ways. I'm 5 weeks away from being done with a 6 months-ahead notice to my employer that I would be leaving because I knew nobody could enter "the kingdom" that I ended up holding the key to. I felt too bad leaving them in that situation especially since I was given opportunities may developers would never expect their current employer to go for. I also know that despite that long transfer of knowledge they'll have a heck of a hard time dealing with.
You don't want to be irreplaceable just as much as they don't want you to be, especially in an era where software developers are in such ridiculous demand. And in no way does this mean you can't be as good as you work to be.
Do you feel like the advantages given to you weren't worth the 6 months extra you felt like you had to stay? Why?
The first company I worked for full time made me the solution architect for a 20 person project even though I only had 2 years of work experience at the time. Successfully completing that project put me an easy 5 years ahead of my peers in terms of career growth and very few of them have caught up in the 10 years since.
You can't say that an employee is selfish when they're the ones doing all the hard, laborious technical work and getting almost nothing out of it aside from a below-average startup salary.
This might come as a shock to some, but engineers have feelings and ambitions too. In this highly competitive market, it makes sense to give your employees more equity if you want to hold on to them. When you consider supply and demand, the ratio of founders to engineers is now much higher than it ever was. Great engineers are rare.
I've left quite a few companies, even a promising startup - Would I have left if I held even 5% equity in that company? Probably not.
If you don't give your 'valued' employee decent equity then you are the selfish one and I hope that they do leave (if only out of respect for the profession).
I've seen too many self-important founders who think that they deserve twenty times more equity than their best employee (just because they're friends with a rich investor). Taking risks is easy (and kind of fun), doing mind-numbing programming every day for 10 years is not (and working for a single company, in a single problem domain for that long IS mind numbing).
Also, let's not pretend that engineers aren't taking risks. 5 years of a young engineer's life is a huge risk especially when you consider that a lot of engineers start to slow down as they get older.
There have been places I left for various reasons that were great employers that I still recommend to this day for others looking for a job.....and might even thing about joining if the right opportunity came along.
1st, if someone is so darn important, it is your job to have a backup plan for when they quit, or for that matter get hit by the proverbial bus. Anything less is managerial incompetence, spend a day or two reading about business continuity.
2nd, there are these things called golden handcuffs, if you don't understand the concept I refer you to the above.
3rd, if you don't have the money for 2, then you better not be seen driving around in your brand new lamborghini, or spending all your time at over the top expensive restaurants while your employees have a tiny fraction of the company, and slave away for 70+ hours a week eating crap ass food from the fast food joint they are paying for themselves. (This really happened!)