Recently we learned that Google spent $2.7 billion to re-hire a single AI researcher who had left to start his own company. As Charlie Brown would say: “Good grief.” 🙄
This is an (incredibly!) extreme example. But back in the halcyon days of the zero interest rate phenomenon (ZIRP), smaller versions of this tale played out daily. Many rank-and-file engineers have stories about submitting their resignation, or threatening to quit, and their managers plying them with stock or cash or promotions to stay. This happened so much that it started to seem like the normal thing to do when you wanted a raise or a promotion. Job hopping for better comp also happened, but people quickly figured out that by merely threatening to leave, you could often get the loot without the hassle of having to actually switch jobs.
Many of these stories have been embellished dramatically over time, as real anecdotes fade into legends of the “my friend knows a person who” or “I read it on Blind” varieties, but the lore is based in reality. It really did happen. The legacy of these episodes is…not great.
To be clear, I do not begrudge employees trying to maximize their wages and comp by changing jobs. It’s the gamification and brinksmanship I object to, and all the ways it ends up distorting company culture and values and outcomes. In the overheated ZIRP environment, lots of companies felt like this is what they were forced to do to compete for talent. Maybe so, maybe not. But money is not the only thing people value, which means that this is not the only way to compete for talent.
After all, the hot air of the inflationary ZIRP bidding wars is what led to the post-ZIRP job market collapse. The boom and bust cycle is stressful and counterproductive, which leads to uneven, disastrously unfair outcomes and an oppositional, extractive mindset on both sides. We can do better. We must do better. Let’s talk about how.
You should stay at your job as long as it fulfills your career priorities
How long should you stay at your job? As long as it’s the best thing you can do for your career, or at least a reasonable, smart career choice, in alignment with your own personal career goals and life priorities.
Maybe this sounds mind-numbingly obvious to you. But far too many people stay far too long at jobs where they aren’t happy, aren’t growing, and aren’t setting their future selves up for success. Hey, I’ve been there…these decisions can be brutal. 💔
Your career is an appreciating, multimillion dollar asset, probably the largest single asset you will ever own. How you define what is best or right for you will inevitably shift over the course of your 40-year career, and that’s fine. This is normal.
But you have to make these decisions based on what is right for you, your career, and your family. Not because, say, you feel responsible for protecting your team from upper management, or you’re afraid of what will happen to the product or the team if you leave, or you feel like you owe them something. Nor should you stay out of fear, whether that be fear of interviews, that this is the best you can do, etc.
Sometimes your top priority might be making the most money, so you can get out of debt. Sometimes it might be a simple, uncomplicated paycheck and low expectations so you can spend a lot of time with your family. Sometimes you may be on a hot streak and raring to go, working like crazy and making a name for yourself in the industry. When in doubt, my advice is to 1) preserve optionality, 2) follow good people and 3) lean into that which energizes you.
The company should employ you as long as it’s a good fit
There are certainly companies where people get fired too quickly or in bad faith. There are also companies where people who are not working out linger on and on and on in the role. It might be tempting to conceive of the latter situation as more worker-friendly, but in all honesty, neither situation is great.
If the wants and needs of the company and the employee are not aligned, you aren’t doing them any favors by dragging it out or keeping them around in a prolonged state of purgatory. If things are decidedly not working out, I promise, they are miserable.
If you are a manager, your number one job is to bring clarity. What are the expectations for the role, what does success look like, what support does the employee need in getting there? When things aren’t going well, your job is to work with them to figure out what is happening, and come up with a plan. Is there a shared understanding of what success looks like in this role? Is it a skills gap, are there relationships that need mending, do they need some time off to deal with personal issues? Are they still interested in the work? Is it still a good fit?
There is an extremely short list of jobs that can only be done by managers, and managing people out (which does sometimes mean firing them, but not always), is at the tippy top of that list. Making sure the right people are on the team is job number one. Figuring this shit out swiftly — we’re talking months, not years — is critical.
Also, none of this happens magically or automatically. This shit is hard. Which is why it is important to invest in these skills and set expectations for your managers.
Your manager should try to make this a great career opportunity for you, for as long as possible
It’s the job of your manager to ensure that this role is a great opportunity for you, for as long as possible. For mid-level engineers this means making sure you are learning and expanding your skill sets, that you have access to mentorship and support systems, that you get to follow your curiosity to some extent and work on things that interest you. For more senior folks, this might mean looking out for opportunities to lead projects or wear new hats.
But that won’t be forever, for anyone — not even your CEO or founders! And that’s okay. This is not a family, it’s a company, and hopefully something of a community.
Sometimes you get an opportunity you can’t refuse. Or life takes you in a different direction. It happens! It is not a tragedy when people leave for a better opportunity or something that excites them.
Real-life example: Paul Osman left Honeycomb because he and his family were moving to NYC and needed a Big Tech salary. He was a wonderful staff engineer (at a time when those were scarce), a high performer, effective across the org, beloved by all; he was even on our board of directors, our first elected employee board member! But when he let us know he was going to leave, we … wished him well. We couldn’t match the salary he needed to pull down; he knew that, we knew that. Nor would it have been fair to all the other staff engineers if we had tried.
Managers need to be actively engaging in career development and planning with their reports. The more you know about someone’s personal values and priorities, the better you can do to try and set them up with opportunities that appeal to them and the trajectory they are on.
Your manager should also be honest if you could find better opportunities elsewhere
I also believe that good managers will be honest with their employees when they feel like this may no longer be the best place for them. Not every opportunity exists at every company, at every time.
It can be hard to admit to your star employee that if you were them, you’d be looking elsewhere for opportunities. Maybe you have an incredible, ambitious senior engineering director who is hungry and chafing to move up, but you don’t expect to see any openings at the VP level over the next year or two. They deserve to know that, I think.
To be clear, you are NOT firing them. Usually, you are holding your breath and praying they will choose to stay. Often they do! Maybe they love their job enough that they’re happy to stick around for another couple years just to see if any openings do arise, or they switch into passive job search mode, taking interesting calls but not actively looking. Maybe you have a conversation about ways they could build their career in other ways, by doing more writing and speaking. Maybe they decide this is a good window of time to have another kid.
But if you can’t honestly look them in the eye and tell them this is the best place for them, given what you know of their ambitions and priorities, you have to say so. It’s on them to decide what to do with that information. But if you want them to trust you when you say this is a great opportunity for their career, you have to be truthful when the opportunity is just not there.
Some amount of employee turnover is natural and healthy
When I worked at Linden Lab in my early twenties, I remember vividly how much pride we took in the fact that people never left. I was there for 4.5 years, and I think we had a single-digit number of departures that entire time. I remember thinking to myself how incredibly special this company must be, because nobody ever wants to leave.
It was a special company. ❤️ But when I look back now, this part makes me cringe. Yep, nobody ever left. No one was ever managed out, even the people who never seemed to do anything but hang out in Second Life or work on whatever the fuck they personally felt like doing. It was a little bit … culty? There were some incredible engineers there, but also a systematic inability to row in the same direction or make a plan and execute on it. In some ways Linden felt more like a social club than a business.
I loved working there, don’t get me wrong, and I learned a lot. But in retrospect, some amount of turnover is good. It’s healthy. It means you have standards for yourselves, and someone is paying attention to whether or not we’re actually making progress and getting shit done, or whether or not the people we need are in the right seats.
Tenure functions somewhat differently at very large companies; it may take years for someone just to come up to speed and learn how to operate within the system, so they do their best to retain people for decades. When you’re a startup in growth mode, though, you become a completely different organism every few years. People who are happy as clams and supremely productive from $0-$1m or 1-50 people may or may not adjust well to the $50m or $200m environment. People who are superstars on one side of the Dunbar number are sometimes bitterly unhappy on the other side.
There’s “regrettable” and “non-regrettable” attritions, but the company should be able to go on operating even in the face of “regrettable” departures.
There are, of course, exceptions. So let’s talk about these.
Sometimes people sit in critical roles at critical moments
At any given time, there exists a subset of people who are disproportionately critical to the success of the business at the moment, people whose departure could seriously jeopardize the company’s ability to meet its goals this quarter or even this year. It sucks, but it’s a reality. This happens.
If that’s a very long list of people, however, or if it’s the same people over and over, or if the actual survival of the company would be in jeopardy and not just a subset of your goals, then your leaders are not doing their fucking job.
Part of the job of running a company is developing talent to be successors to key people. Part of their job is to replicate and distribute critical company knowledge and skills. None of us should be irreplaceable — not even the CEO, or CTO, or founders. If the company’s future depends irrevocably on the continued employment of any individual person, the company’s leaders are fucking up, full stop.
There are two types of disproportionally critical employees: superstars and SPOFs
The right time to determine who is on that critical subset is NOT when one of them resigns. You should be asking yourselves somewhat regularly — which people are our superstars, the ones we really, really want to make sure are happy and fulfilled here, and which people are single points of failure, the ones we cannot easily replace, or function in their absence?
Note that these are not necessarily the same two lists!
This doesn’t have to be a heavyweight process, but if you are large enough to have a People team or HR team, they should be ensuring that talent reviews and succession planning conversations are happening like clockwork, once per quarter or so.
Your superstars are the people who are standout performers, carrying a ton of load for the company or generating uniquely creative ideas, etc. You should identify these people proactively and make sure they are feeling challenged, supported and valued. What are their values — what lights their fire? Where are they trying to go in their career, in their life? How do they like to receive recognition? How does it manifest when they feel overwhelmed or demotivated?
Managers tend to devote most of their attention to their lowest performers. Be wary of this. Yes, give people the support they need. But the biggest bang for your buck is typically the time you spend on your highest performers. Don’t neglect your superstars just because they are doing well.
Get to know your superstars, and compensate them
And compensate your superstars. Whatever pool of money is set aside for high performers at your company, make sure they get a slice of it — a raise, a bonus, direct equity, etc.
But money isn’t the full story, it’s just the first chapter. This is where you need to dig a little deeper and get to know them better — their values, their love languages, how they like to receive recognition. Make sure other company leaders know who is kicking ass and what kind of opportunities they’d be into.
Being a superstar should earn you more than money — it earns the right to experiment, try a moonshot, be first in line for a lateral role change into another area of interest. Maybe you can line them up with a work coach or continuing education, support them writing or presenting their work at conferences…the list is endless What do they value? Find out.
It is normal and desirable for your shortlist of superstars to shift over time. If it’s always the same few names on the list, that may reflect a different problem: that you are handing out all of the opportunities to take risks and shine brightly to the same few people, over and over again. It’s your job to cultivate a deep bench of talent, not one or two lead singers with everyone else in the chorus.
Work on a plan to de-risk your SPOFs
And then there are your single points of failure, people who are the only person who knows how to do something, or the only person in a function. In the early days of any startup, you have a ton of these. As you grow, you should steadily pay down this list.
If superstars are the people you want to keep out of joy, SPOFs can be the people you need to keep out of fear. You can’t function without them, even if they’re mediocre contributors. This is bad on several levels.
This is just a risk analysis you need to work through as a leadership team. Have a plan, have a backup options, and steer a path out of this state as soon as you can afford to.
I’m not naive. The realities of business are real, and sometimes something takes you by surprise, or you need to try and do a diving save for someone who has just announced they are leaving. But that should not be common. The normal, expected reaction when someone tells you they are leaving should be, “ah, that’s too bad, we’ll miss you! I’m so happy for you and this new opportunity you’re excited about!”
Most jobs will be saved or lost by boring organizational labor, not heroic diving saves.
Here is one important reality that many employees don’t seem to grasp:
The harder your employer is affirmatively working to do right by you, the fewer heroics they will be willing or able to do to retain you. And the harder the company is working to be fair and equitable, the less they will be willing or able to make exceptions to their existing compensation framework.
Here is one good end-to-end test of the system: you should not be able to get a higher salary or a larger stock grant by quitting and getting immediately re-hired. If you can, your company is not doing the work to value the labor of its existing employees by the same yardstick as it values new hires.
A lot of companies fail this test! Because in order for this to be true, your company needs to consistently adhere to pay bands, pegged to market rates, adjusted and reconciled each year. They need to do something like boxcar stock grants. They need to periodically audit their own levels and comp and look for evidence of systematic bias. They REALLY need to not make exceptions to their own god damn rules.
As Emily Nakashima says, “Many companies hemorrhage great employees in underrepresented groups because they do all those things but they fail to bring a DEI lens to them — ‘we have salary bands! we have a fair comp system! we think about ladders and promo paths!’ and then they do zero work to make sure those things are applied equitably to all their employees, including across axes of diversity like race and gender.”
All of these things take organizational willpower, and they are hard. It means a lot of hard conversations. It means saying “no” to people. It’s much easier to give out goodies to the people who complain the loudest or threaten to quit, at least in the short term.
It’s easy to talk about fairness and equity, but it takes a lot of structural labor to walk the walk
A lot of work goes into building and maintaining a system that can pass the sniff test in terms of compensating people fairly and equitably, instead of based on their negotiating skills or how much they made at their previous job.
You need to have a job ladder and levels you believe in, ones that accurately reflect the skills, behaviors and values of your org and have broad buy-in from the team. You need a process for leveling people as new hires and at review time, and for appealing those levels when you get it wrong. You should have salary bands for each level, with compa ratios based on market rates. You should be able to show your work and explain your decisions. (For example, we target the 65th% for companies of our size and funding levels, and we pay everyone SF market rates, no matter where they are located in the world.)
This is why review-time calibrations are so important. Calibrations are not about calibrating ICs, they are about calibrating managers. Calibrations are to diminish the inequity that results when one manager has a different understanding of the level an engineer is operating at, so the engineer would receive a different level, band, or rating under a different manager.
Obviously, all of these sociotechnical systems are made and operated by human beings, so there will always be some intrinsic messiness and imprecision. This is why it matters that managers show up with humility and work to get aligned with their peers on what truly matters to the company and the org. This is why it is so important that we show our work and engage with ladders and levels as living documents.
A lot of this labor is invisible to employees, and not especially well understood. I think a critical part of making these systems work is helping employees understand the tradeoffs being made, and how having a consistent leveling system ultimately benefits them, even if they are personally frustrated about not getting promoted this half. Which means every manager needs to be equipped to have these hard conversations with their team.
It should be okay to tell your manager you’re thinking about leaving, and talk about your options
HR teams will typically bucket departures into voluntary and involuntary, aka “regrettable” and “nonregrettable”. In reality, almost any time someone leaves their job, it’s some muddled combination of the two.
In the optimal case, voluntary departures are rarely a complete surprise. Surprises suck. They’re hard to plan around, they often leave gaps in coverage or contributions, and they’re a bummer for morale. You should be able to be honest with your manager and tell them if you’re starting to look around, or if you’re finding yourself less happy and motivated these days. However, this requires a lot of trust in the relationship — that the manager won’t retaliate, won’t fire you, etc — and from what I gather, it seems to be fairly uncommon in the wild. 🙁
Employees do not owe their manager a heads up or a conversation in advance, but this is unequivocally the level of relationship trust we should aim for.
Steph Hippo says, “I love being the manager people want to work for, and it took me a while to figure out how to also be the kind of manager people wanted to have ‘fire’ them by helping them move on. I’m really proud of how many people I’ve been able to help move off my team because we found a better fit. Doing this contributes to your reputation as a leader and as an employer. I found it meaningful if someone that moved on from my team did so on good terms, came back to visit, or sent other people to check out our job listings. That’s a sign that you’re parting with folks on good terms.” 💯
Managers can prove themselves worthy of this trust by not reacting, not retaliating, not treating people any differently, not leaping to conclusions, not running ahead and making decisions or commitments ahead of what the employee has stated.
Should you ever try to change someone’s mind about leaving?
Not never…but rarely. You should always try to understand why someone is leaving. Exit interviews are a great tool here, especially in situations where there has been relationship friction. Departures are a trailing indicator, but often a very powerful signal of things managers should be paying attention to, to make things better for those who remain.
If someone has decided to leave, you’re not going to “save” them via bribery alone. I’ve never seen the tactic of throwing money and titles at someone actually get them to stick around in the long run.
However, I have seen departure announcements get turned around when they include some form of development — when you can identify real underlying sources of discontent, and meet them with action.
Another real life example: A couple years ago, Phillip Carter told us he had decided to leave and take another role in the industry. We had some intense conversations about why that was and what was missing, and realized he had been struggling to connect with the reasons behind what we were building, largely because he had never written or supported code in production during his time as a software engineer. He decided not to leave after that, and he is here to this day.
There will be times when someone has decided to leave, and you want to fight for them to stay. In those situations, you need to get really crystal clear with yourself before taking action. What are the underlying risks to the business, and how far are you prepared to go?
On extremely rare occasions, heroic measures may be the lesser of two evils
Sometimes you may have to try for a diving save. That’s just the reality of doing business, esp at startup stages where you have less redundancy, a shorter planning horizon, more overall chaos and a smaller overall operating budget.
Sometimes your goals are at risk, and you feel like you don’t have a choice. But any time you find yourself bargaining or trying to bribe people to stay after they’ve decided to leave, you should take a hard fucking look at yourself and how you got there, and whether or not you can justify your actions.
Exceptions are often the path of least resistance for the manager making the exception in the moment, but they impose a heavy, compounding cost to the business over time. Any time you make an exception to keep someone, you risk breaking your commitments to everyone else. And rumors about exceptions being made will fly fast and furious (sometimes it seems like there is a 10-20x multiplier of rumors to reality). 😣
I will not sit here and tell you no exceptions can be ever made. Systems made of people are systems that are never perfect. Once in a while, making an exception might actually the way to restore justice to a situation. Other times your ass is well and truly backed into a corner. But exceptions are SO costly to your credibility, you must at least build peer review and consequences for exceptions into the system.
A few checks and balances to consider:
- Individual managers should not be able to make an exception without the buy-in of their director, VP, and people team
- It should generally trigger some kind of review of the system policy in question, to see if it still serves its purpose
- You should be able to look in each other’s eyes and explain your reasoning, and not feel ashamed of it if word gets out
Shit does happen. But if this kind of shit happens on the regular, you can’t blame people for becoming extremely cynical about the way you do business, and you can expect to get way more people trying to game the system to get the same results for themselves.
People should not use threats of leaving to try and effect change or get raises. This should not be an effective tactic — and in order for it not to be an effective tactic, we cannot reward it with results. When you make exceptions, you all but guarantee more people will try this.
People work at jobs for money, but not only money
While writing this piece, a friend told me a story about when he became an engineering manager a decade ago, and soon noticed that his two women engineers were the lowest paid and the lowest leveled people on the team, which didn’t seem to correlate with their actual skills or experience. He asked his own manager what was up with this, and the response he received was: “Well yeah, neither of them has ever been a flight risk.”
This kind of attitude is, to put it politely, a fucking cancer on our industry.
There are two radically different philosophies when it comes to corporate compensation. In the first scenario, you pay people as little as possible, and consider it your job as a manager to extract the most work out of people for the least pay. Information is power, so information asymmetry is endemic in these environments, and people are paid according to their skill at negotiation or brinksmanship. You typically blow your wad trying to compete for the “best” talent in the world.
In the second scenario, you do your best to compensate employees fairly and competitively, balancing their needs and wants against other stakeholders and the overarching mandate for the company as a whole to succeed. You practice transparency and show your work, and actively work to counter systemic biases. You understand you can’t compete for every great hire out there, but you try to equip people with the information they need to evaluate whether or not you are mutually a good fit.
Companies that operate according to the first scenario are so alienating and toxic (and almost certainly illegal, in many cases) that few will openly claim to be this kind of company. Most companies at least pay lip service to equity and fairness. But because everyone is typically mouthing the same kind of things, employees will scrutinize your actions far more than your words, especially when it comes to comp.
At the end of the day, these are jobs. People work at jobs for money, but not only money. I think we would all be better off if we could get better at articulating the tangible and intangible rewards of our labor, treating each other with dignity and honesty, and being straightforward about our needs and wants and goals on both sides, instead of treating comp like some kind of high stakes casino game.
Huge thanks to Steph Hippo, Paul Osman, Phillip Carter, Lesley Cordero, Emily Nakashima for their feedback, critique, and stories.