Firing People

How can we fix the firing process
if we're not even talking about it first?
So here's my story, and everything I've learned from it.
March 16 2016

So it’s been a little over a year since GitHub fired me.

I initially made a vague tweet about leaving the company, and then a few weeks later I wrote Fired, which made it pretty clear that leaving the company was involuntary.

The reaction to that post was pretty interesting. It hit 100,000 page views within the first few days after publishing, spurred 389 comments on Hacker News, and indeed, is currently the 131st most-upvoted story on Hacker News of all time.

Let me just say one thing first: it’s pretty goddamn weird to have so many people interested in discussing one of your biggest professional failures. There were a few hard-hitting Real Professional Journalists out there launching some bombs from the 90 yard line, too:

If an employer has decided to fire you, then you’ve not only failed at your job, you’ve failed as a human being.


Why does everyone feel compelled to live their life in the public? Shut up and sit down! You ain’t special, dear..


Who is the dude?

You and me both, buddy. I ask myself that every day.

The vast majority of the comments were truly lovely, though, as well as the hundreds of emails I got over the subsequent days. Over and over again it became obvious at how commonplace getting fired and getting laid off is. Everyone seemingly has a story about something they fucked up, or about someone that fucked them up. This is not a rare occurrence, and yet no one ever talks about it publicly.

As I stumbled through the rest of 2015, though, something that bothered me at the onset crept forward more and more: the post, much like the initial vague tweet, didn’t say anything. That was purposeful, of course; I was still processing what the whole thing meant to me, and what it could mean.

I’ve spent the last year constantly thinking about it over and over and over. I’ve also talked to hundreds and hundreds of people about the experience and about their experiences, ranging from the relatively unknown developer getting axed to executives getting pushed out of Fortune 500 companies.

It bothers me no one really talks about this. We come up with euphemisms, like “funemployment!” and “finding my next journey!”, while all the while ignoring the real pains associated with getting forced out of a company. And christ, there’s a lot of real pain that can happen.

How can we start fixing these problems if we can’t even talk about them?

Me speaking at Bath Ruby

I spoke this past week at Bath Ruby 2016, in Bath, England. The talk was about my experiences leaving GitHub, as well as the experiences of so many of the people I’ve talked to and studied over the last year. You can follow along with the slide deck if you’d like, or wait for the full video of the talk to come out in the coming weeks.

I also wanted to write a companion piece as well. There’s just a lot that can’t get shoehorned into a time-limited talk. That’s what you’re reading right now. So curl up by the fire, print out this entire thing onto like a bajillion pages of dead tree pulp, and prepare to read a masterpiece about firing people. Once you realize that you’re stuck with this drivel, you can toss the pages onto the fire and start reading this on your iPad instead.

The advice people most readily give out on this topic today is:


“Fire fast”, they say! You have to fire fast because we’re moving really fuckin’ fast and we don’t have no time to deal with no shitty people draggin’ us down! Move fast and break people! Eat a big fat one, we’re going to the fuckin’ MOOOOOOOOON!

What the shit does that even mean, fire fast? Should I fire people four minutes after I hire them? That’ll show ‘em!

What about after a mistake? Should we fire people as retribution? Do people get second chances?

When we fire people, how do we handle things like continuity of insurance? Or details like taxes, stock, and follow-along communication? How do we handle security concerns when someone leaves an organization?

There’s a lot of advice that’s needed beyond fire fast. “Move fast and break people” doesn’t make any goddamn sense to me.

I’ve heard a lot of funny stories from people in the last year. From the cloud host employee who accidentally uploaded a pirated TV show to company servers and got immediately fired his second week on the job (“oops!” he remarked in hindsight) to the Apple employee who liked my initial post but “per company policy I’m not allowed to talk about why your post may or may not be relevant to me”.

I’ve also heard a lot of sad stories too. From someone whose board pushed them out of their own startup, but was forced to say they resigned for the sake of appearance:

There aren’t adjectives to explain the feeling when your baby tells you it doesn’t want/need you any more.

We might ask: why should we even care about this? They are ex-employees, after all. To quote from the seminal 1999 treatise on corporate technology management/worker relations, Office Space:

The answer, of course, is: we should care about all this because we’re human beings, dammit. How we treat employees, past and present, is a reflection on the company itself. Great companies care deeply about the relationship they maintain with everyone who has contributed to the success of the company.

This is kind of a dreary subject, but don’t worry too much: I’m going to aspire to make this piece as funny and as light-hearted as I can. It’s also going to be pretty long, but that’s okay, sometimes long things are worth it. (Haha dick joke, see? See what I’m doing here? God these jokes are going to doom us all.)


One last thing before we can finally ditch from these long-winded introductory sections: what you’re going to be reading is primarily my narrative, with support from many, many other stories hung off of the broader points.

Listen: I’m not super keen on doing this. I don’t particularly want to make this all about me, or about my experiences getting fired or quitting from any of my previous places of employment. This is a particularly depressing aspect in my life, and even a year later I’m still trying to cope with as much depression as anyone can really reasonably deal with.

But I don’t know how to talk about this in the abstract. The specifics are really where all the important details are. You need the specifics to understand the pain.

As such, this primarily comes at the problem from a specific perspective: an American living in San Francisco for a California-based tech startup.

When I initially wrote my first public “I’m fired!” post, some of you in more-civilized places with strong employee-friendly laws like Germany or France were aghast: who did I murder to get fired from my job? How many babies did I microwave to get to that point? Am I on a watchlist for even asking you that question?

California, though, is an at-will state. Employees can be fired for pretty much any reason. If your boss doesn’t like the color of shoes you’re wearing that day, BOOM! Fired. If they don’t like how you break down oxygen using your lungs in order to power your feeble human body, BOOM! Fired. Totally cool. As long as they’re not discriminating against federally-protected classes — religion, race, gender, disability, etc. — they’re in the clear.

Not all of you are working for companies like this. That’s okay — really, that’s great! — because I still think this touches on a lot of really broad points relevant to everyone. As I was building this talk out, I ended up noticing a ton of crossover with generally leaving a company, be it intentionally, unintentionally, on friendly terms, and on hostile terms. Chances are you’re not going to be at your company forever, so a lot of this is going to be helpful for you to start thinking about now, even if you ultimately don’t leave until years in the future.

Beyond that, I tried to target three different perspectives throughout all this, and I’ll call them out in separately-colored sections as well:


You: your perspective. If you ever end up in the hot seat and realize you’re about to get fired, this talk is primarily for you. There’s a lot of helpful hints for you to take into consideration in the moment, but also for the immediate future as well.


Company: from the perspective of the employer. Again, the major thing I’m trying to get across is to normalize the idea of termination of employment. I’m not trying to demonize the employer at all, because there are a lot of things the employer can do to really help the new former employee out and to help the company out as well. I’ll make a note of them in these blocks.


Coworker: the perspective that’s really not considered very much is the coworker’s perspective. Since they’re not usually involved in the termination itself, a lot of times it’s out of sight, out of mind. That’s a bit unfortunate, because there’s also some interesting aspects that can be helpful to keep in mind in the event that someone you work with gets fired.

Got it? Okay, let’s get into the thick of things.


I’m Zach Holman. I was number nine at GitHub, and was there between 2010 and 2015. I saw it grow to 250 employees (they’ve since doubled in size and have grown to 500 in the last year).

I’m kind of at the extreme end of the spectrum when it comes to leaving a company, which can be helpful for others for the purposes of taking lessons away from an experience. It had been a company I had truly grown to love, and in many ways I had been the face of GitHub, as I did a lot of talks and blog posts that mentioned my experiences there. More than once I had been confusingly introduced as a founder or CEO of the company. That, in part, was how I ultimately was able to sneak into the Andreessen Horowitz corporate apartments and stayed there rent-free for sixteen months. I currently have twelve monogrammed a16z robes in my collection, and possibly was involved in mistakenly giving the greenlight to a Zenefits employee who came by asking if they could get an additional key to the stairwell for a… meeting.

Fast forward to summer of 2014: I had been the top committer to the main github/github repository for the last two years, I had just led the team that shipped one of the last major changes to the site, and around that time I had had a mid-year performance review with my manager that was pretty glowing and had resulted in me receiving one of the largest refresh grants they had given during that review period.

This feels a little self-congratulatory to write now, of course, but I’ll lend you a quick reminder: I did get fired nonetheless, ha. The point I’m trying to put across with all this babble is that on the surface, I was objectively one of the last employees one might think to get fired in the subsequent six months. But everyone’s really at risk: unless you own the company, the company owns you.

Around the start of the fall, though, I had started feeling pretty burnt out. I had started to realize that I hadn’t taken a vacation in five years. Sure, I’d been out of town, and I’d even ostensibly taken time off to have some “vacations”, but in hindsight they were really anything but: I’d still be checking email, I’d still be checking every single @github mention on Twitter, and I’d still dip into chat from time to time. Mentally, I would still be in the game. That’s a mistake I’ll never make again, because though I had handled it well for years — and even truly enjoyed it — it really does grind you down over time. Reading virtually every mention of your company’s name on Twitter for five straight years is exhausting.

By the time November came around, I was looking for a new long-term project to take on. I took a week offsite with three other long-tenured GitHubbers and we started to tackle a very large new product, but I think we were all pretty well burnt out by then. By the end of the week it was clear to me how fried I was; brainstorming should not have been that difficult.

I chatted with the CEO at this point about things. He’s always been pretty cognizant of the need for a good work/life balance, and encouraged taking an open-ended sabbatical away from work for awhile.

My preference would be for you to stay at GitHub […] When you came back would be totally up to you

By February, my manager had sent me an email with the following:

Before agreeing to your return […] we need to chat through some things


First thing here from your perspective is to be wary if the goalposts are getting moved on you. I’m not sure if there was miscommunication higher up with my particular situation, but in general things start getting dicey if there’s a set direction you need to head towards and that direction suddenly gets shifted.

After I got fired, I talked to one of my mentors about the whole experience. This is a benefit of finding mentors who have been through everything in the industry way before you even got there: they have that experience that flows pretty easily from them.

After relaying this story, my friend immediately laughed and said, “yeah, that’s exactly the moment when they started the process to fire you”. I kinda shrugged it off and suggested it was a right-hand-meet-left kinda thing, or maybe he was reading it wrong. He replied no, that is exactly the kind of email he had sent in the past when he was firing someone at one of his companies, and it was also the kind of email he had received right before he was fired in the past, too.

Be wary of any sudden goalposts, really. I’ll mention later on about PIPs — performance improvement plans — and how they can be really helpful to employees as well as to employers, but in general if someone’s setting you up with specific new guidelines for you to follow, you should take it with a critical eye.

At this point things were turning a tad surprising. By February, the first time I received an email from my manager about all this, I hadn’t been involved with the company at all for two months through my sabbatical, and I hadn’t even talked to my manager in four months, ever since she had decided that 1:1s weren’t really valuable between her and me. This was well and fine with me, since I had been assigned to a bit of a catch-all team where none of its members worked together on anything, and I was pretty comfortable moving around the organization and working with others in any case.

I was in Colorado at the time, but agreed to meet up and have a video chat about things. When I jumped on the call, I noticed that — surprise! — someone from HR was on the call as well.

Turns out, HR doesn’t normally join calls for fun. Really, I’m not sure anyone joins video chats for fun. So this should have the first thing that tickled my spidey-sense, but I kinda just tucked it in the back of my mind since I didn’t really have time to consider things much while the call was going on.

At this point, I was feeling pretty good about life again; the time off had left me feeling pretty stoked about building things again, and I had a long list of a dozen things I was planning on shipping in my first month back on the job. The call turned fairly confrontational off the bat, though; my manager kept asking how I felt, I said I felt pretty great and wanted to get to work, but that didn’t seem to really to be the correct answer. Things took a turn south and we went back-and-forth about things. This led to her calling me an asshole twice (in front of HR, again, who didn’t seem to mind).

In hindsight, yeah, I was probably a bit of an asshole; I tend to clam up during bits of confrontation that I hadn’t thought through ahead of time, and most of my responses were pretty terse in the affirmative rather than offering a ton of detail about my thoughts.

After the conversation had ended on a fairly poor note, I thought things through some more and found it pretty weird to be in a position with a superior who was outwardly fairly hostile to me, and I made my first major mistake: I talked to HR.

I was on really good terms with the head of HR, so the next day I sent an email to her making my third written formal request in the prior six months or so to be moved off of my team and onto another team. I had some thoughts on where I’d rather see myself, but really, any other team at that point I would have been happy with; I had pretty close working relationships with all of the rest of the managers at the company. On top of that, the team I was currently on didn’t have any association with each other, so I figured it wouldn’t be a big deal to switch to another arbitrary team.

The head of HR was really great, and found the whole situation to be a bit baffling. We started talking about which teams might make sense, and I asked around to a couple people as to whether they would be happy with a new refugee (they were all thumbs-up on the idea). She agreed to talk to some of the higher-ups about things, and we’d probably arrange a sit-down in person when I came back in a few days to SF to sort out the details.


Don’t talk to HR.

This pains me to say. I’ve liked pretty much every person in HR at all the companies I’ve worked for; certainly we don’t want to view them as the enemy.

But you have to look to their motivations, and HR exists only to protect the company’s interests. Naturally you should aim to be cordial if HR comes knocking and wants to talk to you, but going out of your way to bring something to the attention of HR is a risk.

Unfortunately, this is especially important to consider if you’re in a marginalized community. Many women in our industry, for example, have gone to HR to report sexual harassment and promptly found that they were the one who got fired. Similar stories exist in the trans community and with people who have had to deal with racial issues.

Ultimately it’s up to you whether you think HR at your company can be trusted to be responsible with your complaint, but it also might be worthwhile to consider alternative options as well (i.e., speaking with a manager if you think they’d be a strength in the dispute, exploring legal or criminal recourse, and so on).

HR is definitely a friend. But not to you.


Avoid surprises. I’ve talked with a lot of former employees over the last year, and the ones with the most painful stories usually stem from being unceremoniously dropped into their predicament.

From a corporate perspective, it’s always painful to lose employees — regardless of the manner in which the employee leaves the company. But it’s almost always going to be more painful for the former employee, too.

I was out at a conference overseas a few years back with a few coworkers. One of my coworkers received a notice that he was to sit down on a video chat with the person he was reporting to at the time. He was fretting about it given the situation was a bit sudden and out of the ordinary, but I tried to soothe his fears, joking that they wouldn’t fire him right before an international conference that he was representing the company at. Sure enough, they fired him. Shows what I really knew about this stuff.

Losing your job is already tough. Dealing with it without a lot of lead-up to consider your options is even harder.

One of the best ways to tackle this is with a performance improvement plan, or PIP. Instituting a PIP is relatively straightforward: you tell the employee that they’re not really where you’d like to see them and that they’re in danger of losing their job, but you set clear goals so that the employee gets the chance at turning things around.

This is typically viewed as the company covering their ass so when they fire you it’s justified, but really I view it as a mutual benefit: it’s crystal-clear to the employee as to what they need to do to change their status in the organization. Sometimes they just didn’t know they were a low performer. Sometimes there are other problems in their life that impacted their performance, and it’s great to get that communication out there. Sometimes someone’s really not up to snuff, but they can at least spend some time preparing themselves prior to being shown the door.

The point is: surprise firings are the worst types of firings. It’s better for the company and for the employee to both be clear as to what their mutual expectations are. Then they can happily move forward from there.

At this point, I finished up my trip and flew back to San Francisco. It was time to chat in person.


I was fired before I entered the room.

You’re not going to be happy here. We need to move you out of the company.

That was the first thing that was said to me in the meeting between me, the CEO, and the head of HR. Not even sure I had finished sitting down, but I only needed a glance at the faces to know what was in the pipeline for this meeting.

You’re not going to be happy here is a bullshit phrase, of course, but not one that I have a lot of problems with in hindsight. My happiness has no impact on the company — my output does — but I think it was a helpful euphemism, at least.


Chill. The first thing I’d advise if you find yourself in the hot seat is to just chill out. I did that reasonably well, I think, by nodding, laughing, and giving each person in the room a hug before splitting. It was a pretty reasonable break, and I got to have a long chat with the head of HR immediately afterwards where we shot the shit about everything for awhile.

You ever watch soccer (or football, for you hipster international folk that still refuse to call it by its original name)? Dude gets a yellow card, and more often than not what does he do? Yells at the ref. Same for any sport, really. How many times does the ref say ah shit, sorry buddy, totally got it wrong, let me grab that card back? It just doesn’t happen.

That’s where you are in this circumstance. You can’t argue yourself back into a job, so don’t try to. At this point, just consider yourself coasting. If it’s helpful to imagine you’re a tiny alien controlling your humanoid form from inside your head a la the tiny outworlder in Men in Black, go for it.

My friend’s going through a particularly gnarly three- or four-weeks of getting fired from a company right now (don’t ask; it’s a disaster). This is the same type of advice I gave them: don’t feel like you need to make any statements or sign any legal agreements or make any decisions whatsoever while you’re in the room or immediately outside of it. If there’s something that needs your immediate attention, so be it, but most reasonable companies are going to give you some time to collect your thoughts, come up with a plan, and enact it instead of forcing you to sign something at gunpoint.

Remember: even if you’re really shit professionally, you’ll probably only get fired what, every couple of years? If you’re an average person what, maybe once a lifetime? Depending on the experience of management, the person firing you may deal with this situation multiple times a year. They’re better at it than you are, and they’re far less stressed out about it. I was in pretty good spirits at the time, but looking back I certainly wasn’t necessarily in my normal mindset.

Emotionally compromised

You’re basically like new-badass-Spock in the Star Trek reboot: you have been emotionally compromised; please note that shit in the ship’s log.

I’m still not fully certain why I got the axe; it was never made explicit to me. I asked other managers and those on the highest level of leadership, and everyone seemed be as confused as I was.

My best guess is that it’s Tall Poppy Syndrome, a phrase I was unfamiliar with until an Aussie told me about it. (Everything worthwhile in life I’ve learned from an Australian, basically.) The tallest poppy gets cut first.

With that, I don’t mean that I’m particularly talented or anything like that; I mean that I was the most obvious advocate internally for certain viewpoints, given how I’ve talked externally about how the old GitHub worked. In Japanese the phrase apparently translates to The tallest nail gets the hammer, which I think works better for this particular situation, heh. I had on occasion mentioned internally my misgivings about the lack of movement happening on any product development, and additionally the increasing unhappiness of many employees due to some internal policy changes and company growth.

Improving the product and keeping people happy are pretty important in my eyes, but I had declined earlier requests to move towards the management side of things, though, so primarily I was fairly heads-down on building stuff at that point rather than leading the charge for a lot of change internally. So maybe it was something else entirely; I’m not sure. I’m left with a lot of guesses.


Lockdown. The first thing to do after — or even while — someone is fired is to start locking down their access to everything. This is pretty standard to remove liability from any bad actors. Certainly the vast majority of people will never be a problem, but it’s also not insulting or anything from a former employee standpoint, either. (It’s preferred, really: if I’ve very recently been kicked out of a company, I’d really like to be removed from production access as soon as possible so I don’t even have to worry about accidentally breaking something after my tenure is finished, for example. It’s best for everyone.)

From a technical standpoint, you should automate the process of credential rolling as much as possible. All the API keys, passwords, user accounts, and other credentials should be regenerated and replaced in one fell swoop.

Automate this because, well, as you grow, more people are inherently going to leave your company, and streamlining this process is going to make it easier on everyone. No one gets up in the morning, jumps out of bed, throws open the curtains and yells out: OH GOODIE! I GET TO FIRE MORE PEOPLE TODAY AND CHANGE CONFIG VALUES FOR THE NEXT EIGHT HOURS! THANK THE MAKER!

Ideally this should be as close to a single console command or chat command as possible. If you’re following twelve-factor app standards, your config values should already be stored in the environment rather than tucked deep into code constants. Swap them out, and feel better about yourself while you have to perform a pretty dreary task.

Understand the implications of what you’re doing, though. I remember hearing a story from years back of someone getting let go from a company. Sure, that sucks, but what happened next was even worse: the firee had just received their photos back from their recent wedding, so they tossed them into their Dropbox. At the time, Dropbox didn’t really distinguish between personal and corporate accounts, and all the data was kind of mixed together. When the person was let go, the company removed access to the corporate Dropbox account, which makes complete sense, of course. Unfortunately that also deleted all their wedding photos. Basically like salt in an open wound. Dropbox has long since fixed this problem by better splitting up personal and business accounts, but it’s still a somewhat amusing story of what can go wrong if there’s not a deeper understanding of the implications of cutting off someone’s access.

Understand the real-world implications as well. Let’s take a purely hypothetical, can’t-possibly-have-happened-in-real-life example of this.

Does your company:

Totally hypothetical situation.

Yeah, totally was me. It was hilarious. I was laughing for a good three minutes while someone got up to grab the door.

Anyway, think about all of these implications. Particularly if the employee loses access to their corporate email account; many times services like healthcare, stock information, and payroll information may be tied to that email address, and that poses even more problems for the former employee.

This also underscores the benefit of keeping a cordial relationship between the company and the former employee. When I was fired, I found I still had access to a small handful of internal apps whose OAuth tokens weren’t getting rolled properly. I shot an email to the security team, so hopefully they were invalidated and taken care for future former employees.

Although now that I think about it, I still have access to the analytics for many of GitHub’s side properties; I’ve been unable to get a number of different people to pull the plug for me. I think instead I’ll just say it’s a clear indicator of the trust my former employer has in my relationship with them. :heart:

One last thing to add in this section. My friend Reg tweeted this recently:

I really like this sentiment a lot, and will keep it in mind when I’m in that position next. Occasionally you’ll see the odd person mention something about this over Twitter or something, and it’s clear that firing someone is a stressful process. But be careful who you vent that stress to — vent up the chain of command, not down — because do keep in mind that you’re still not the one suffering the most from all this.


Determine the rationale. Once someone’s actually been fired, this is really your first opportunity as a coworker to have some involvement in the process. Certainly you’re not aiming to butt in and try to be the center of everything, here, but there’s some things you can keep in mind to help your former coworker, your company, and ultimately, yourself.

Determining the rationale I think is the natural first step. You’re no help to anyone if you get fired as well. And sometimes — but obviously not always — if someone you work with gets fired, it could pose problems for you too, particularly if you work on the same team.

Ask around. Your direct manager is a great place to start if you have a good relationship with them. You don’t necessarily need to invade the firee’s privacy and pry into every single detail, but I think it’s reasonable to ask if the project you’re working on is possibly going to undertake a restructuring, or if it might get killed, or any number of other things. Don’t look desperate, of course — OH MY GOD ARE WE ALL GOING TO GET SHITCANNED???? — but a respectful curiosity shouldn’t hurt in most healthy organizations.

Gossip is a potential next step. Everyone hates on gossip, true, but I think it can have its place for people who aren’t in management positions. Again, knowing every single detail isn’t really relevant to you, but getting the benchmark of people around you on your level can be helpful for you to judge your own position. It also might be helpful as a sort of mea culpa when you talk to your manager, as giving them a perspective from the boots on the ground, so to speak, might be beneficial for them when judging the overall health of the team.


Be truthful internally. Jumping back to the employer’s side of things, just be sure to be truthful. Again, the privacy of your former employee’s experience is very important to keep, but how to talk about it to other employees can be pretty telling.

Be especially cautious when using phrases like mutually agreed. Very few departures are mutually-agreed upon. If they were thinking of leaving, there’s a good chance they’d have already left.

In my case, my former manager emailed her team and included this sentence:

We had a very honest and productive conversation with Zach this morning and decided it was best to part ways.

There certainly wasn’t any conversation, and the sentence implies that it was a mutual decision. She wasn’t even in the room, either, so the we is a bit suspect as well, ha.

In either case, I was already out the door, so it doesn’t bother me very much. But everyone in the rank-and-file are better-networked than you are as a manager, and communication flows pretty freely once an event happens. So be truthful now, otherwise you poison the well for future email announcements. Be a bit misleading today and everyone will look at you as being misleading in the future.

The last bit to consider is group firing: firing more than one person on the same day. This is a very strong signal, and it’s up to you as to what you’re trying to signal here. If you take a bunch of scattered clear under-performers and fire them all on the same day, then the signal might be that the company is cleaning up and is focused squarely on improving problems. If the decision appears rather arbitrary, you run the risk of signaling that firing people is also arbitrary, and your existing employees might be put in a pretty stressful situation when reflecting on their own jobs.

Firing is tough. If you’ve ever done it before you know it’s not necessarily just about the manager and the employee: it can impact a lot more people than that.

So, I was fired. I walked out of the room, got briefly locked inside the office stairwell, and then walked to grab my stuff.


What next?

It’s a tough question. At this point I was kind of on auto-pilot, with the notion of being fired not really settling out in my mind yet.

I went to where my stuff was and started chatting with my closer friends. (I wasn’t escorted out of the building or any of that silliness.)

I started seeing friendly faces walk by and say hi, since in many cases I hadn’t seen or talked to most of my coworkers in months, having never come back in an official capacity from my sabbatical. I immediately took to walking up to them, giving them a long, deeply uncomfortable and lingering hug, and then whispering in their ear: it was very nice working with you. also I just got fired. It was a pretty good troll given such short notice, all things considered. We all had a good laugh, and then people stuck around so they could watch me do it to someone else. By the end I had a good dozen or so people around chatting and avoiding work. A+++ time, would do again.

lol jesus just realized what I typed, god no, I’d probably avoid getting fired the next time, I mean. I’m just pretty dope at trolling is all I’m sayin’.

Egregious selfie of the author

Eventually I walked out of the office and starting heading towards tacos, where I was planning on drinking way too many margaritas with a dear friend who was still at the company (for the time being). Please note: tacos tend to solve all problems. By this point, the remote workers had all heard the news, so my phone started blowing up with text messages. I was still feeling pretty good about life, so I took this selfie and started sending it to people in lieu of going into a ton of detail with each person about my mental state.

In prepping this talk, I took a look at this selfie for the first time in quite a number of months and noticed I was wearing earbuds. Clearly I was listening to something as I strutted out of the office. Luckily I scrobble my music to, so I can go back and look. So that’s how I found out what I was listening to:


On My Own, as sung by Eponine in the award-winning musical Les Misérables. Shit you not. It’s like I’m some emo fourteen-year-old just discovering their first breakup or something. Nice work, Holman.

Shortly thereafter, I tweeted the aforementioned tweet:

Again, it’s pretty vague and didn’t address whether I had quit or I’d been fired. I was pretty far away from processing things. I think being evasive made some sense at the time.

I’ve been journaling every few days pretty regularly for a few years now, and it’s one of the best things I’ve ever done for myself. I definitely wrote a really long entry for myself that day. I went back and took a look while I was preparing this talk, and this section jumped out at me:

The weird part is how much this is about me. This is happening to me right now. I didn’t really expect it to feel so intimate, a kind of whoa, this is my experience right now and nobody else’s.

In hindsight, yeah, that’s absolutely one of the stronger feelings I still feel from everything. When you think about it, most of the experiences you have in life are shared with others: join a new job, share it with your new coworkers. Get married, share it with your new partner and your friends and family. Best I can tell, getting fired and dying are one of the few burdens that are yours and yours alone. I didn’t really anticipate what that would feel like ahead of time.

By later in the night, I was feeling pretty down. It was definitely a roller coaster of a day: text messages, tweets, margaritas, financial advisors, lawyers, introspective walks in the park. I didn’t necessarily think I’d be flying high for the rest of my life, but it didn’t really make the crash all that easier, either. And that experience has really matched my last year, really: some decent highs, some pretty dangerous lows. Five years being that deeply intertwined in a company is toeing a line, and I’ve been paying for it ever since.

Loose Ends

Good god, it really takes an awful amount of work in order to leave work.

There’s a number of immediate concerns you need to deal with:

The next thing to consider is severance pay. Each company tends to handle things differently here, and at least in the US, there’s not necessarily a good standard of what to expect in terms of post-termination terms and compensation.

There’s a lot of potential minefields involved in dealing with the separation agreement needed to agree upon severance, though.

Unfortunately I can’t go into much detail here other than say that we reached an equitable agreement, but it did take a considerable amount of time to get to that point.

One of the major general concerns when a worker leaves an American-based startup is the treatment of their stock options. A large part of equity compensation takes place in the form of ISOs, which offer favorable tax treatments in the long term.

Unfortunately, vested unexercised ISOs are capped at 90 days post-employment by law, meaning that they disappear in a puff of smoke once you reach that limit. This poses a problem in today’s anti-IPO startups who simultaneously reject secondary sales, which limit all of the options available for an employee to exercise their stock (the implications of which for an early employee might cost hundreds of thousands of dollars that they don’t have, excluding the corresponding tax hit as well).

Another possibility that’s quickly gaining steam lately is to convert those ISOs to NSOs at the 90 day mark and extend the option window to something longer like seven or ten years instead of a blistering 90 days. In my mind, companies who haven’t switched to a longer 90 day window are actively stealing from their employees; the employees have worked hard to vest their options over a period of years, but because of their participation in the company’s success they’re now unable to exercise their options.

I’ve talked a lot about this in greater length in my aptly-titled post, Fuck Your 90 Day Exercise Window, as well as started a listing of employee-friendly companies with extended exercise windows. Suffice to say, this is a pretty important aspect to me and was a big topic in the discussions surrounding my separation agreement.

I had been talking to various officials in leadership for a few months hammering out the details and had been under the impression that we had reached an agreement, but I was surprised to find out that wasn’t the case. I was informed 28 hours before my 90 day window closed that the agreement I had thought I had didn’t exist; it was then that I realized I had 28 hours to either come up with hundreds of thousands of dollars that I didn’t have to save half of my stock, or I could sign the agreement as-is and avoid losing half of my already-diminished stake. I opted to sign.


Get everything in writing. This also supports my earlier point of aiming to not do anything in the room while you’re getting fired; it allows you to take some time out and think things through once you have the legalese in front of you (and preferably in front of a lawyer).

I think it’s fully acceptable to stay on-the-record. So no phone calls, no meetings in person. Again, you’re up against people who have done this frequently in the past, and it’s a good chance these thoughts haven’t crossed your mind before.

A lot of it certainly might not even be malicious; I’d imagine a lot of people you chat with could be good friends who want to see you leave in good shape, but at the end of the day it’s really dicey to assume the company as a whole is deeply looking out for your interests. The only person looking out for your interests is you.

This also underlines the generally great advice of always knowing a good lawyer, a good accountant, and a good financial advisor. You don’t necessarily have to be currently engaged with a firm; just knowing who to ask for recommendations is a great start. If you can take some time and have some introductory calls with different firms ahead of time, that’s even better. The vast majority of legal and financial firms will be happy to take a quick introductory phone call with you free-of-charge to explain their value proposition. This is highly advantageous for you to do ahead of time so you don’t need to do this when you’re deep in the thick of a potential crisis.

All things considered, though, we did reach an agreement and I was officially free and clear of the company.

Life after

That brings us to the last few months and up to the present. I’ve spent the last year or so trying to sort out my life and my resulting depression. Shit sucks. Professionally I’ve done some consulting and private talks here and there, which have been tepidly interesting. I’ve also served in a formal advisory role to three startups, which I’ve really come to enjoy; after being so heads-down on a single problem for the last five years, it’s nice to get a fair amount of depth in multiple new problem spaces, some of which are new to me.

But I still haven’t found the next thing I’m really interested in, which just feeds into the whole cycle some more. For better or worse, that’ll be changing pretty quickly, since I’m pretty broke after working part-time and living in San Francisco for so long. Even though I helped move a company’s valuation almost two billion dollars, I haven’t made a dime from the company outside of making a pretty below-to-average salary. That’s after six years.

Think on that, kids, when you’re busting your ass day and night to strike it rich with your startup dreams.


It’s cool to stay in touch. Something that’s kind of cracked me up lately is the sheer logistics behind keeping in touch with my former coworkers. On one hand, you lose out on your normal chat conversations, lunches, and in-person meetings with these colleagues. It’s just a human trait that it’s harder to keep these relationships up when they’re out of sight, out of mind.

Beyond that, though, when you’re out of the company you’re also out of the rolodex. You might not know someone’s phone number or personal email address anymore, for example. A large part of the time you, as a coworker, might be in a bit better position to reach out to a former colleague than they are to you, since you still have access to these infrastructures. It’s possible someone would be up for a chat, but the difficulty in doing so provides a bit of a barrier, so it’s fine to reach out and say hi sometimes! Even the worst corporate breakups that I’ve heard about are usually able to insulate between bad experiences with the company versus bad experiences with you, so you shouldn’t be too worried about that if you weren’t directly involved.

The one aspect about all of this that you might want to keep in mind that I’ve heard crop up again and again from a number of former employees is around the idea of conversational topics.

In some sense I think it’s natural for existing employees to vent to former employees that may have left on bad terms about the gossip that’s happening at the company. To take an example from my own experiences, I don’t think there’s anyone else on the planet that knows more dirt on GitHub than I do at this point, even including current employees. I’m certain I gave two to three times as many 1:1s than anyone else at the company in the subsequent months following my departure; I think I was a natural point of contact to many who were frustrated at some internal aspects of the company they were dealing with.

And that’s fine, to an extent; schadenfreude is a thing, and it can be helpful for awhile, for both parties. But man, it gets tiring, particularly when you’re not paid for it. Especially when you’re still suffering from feelings from it. It’s hard to move on when every day there’s something new to trigger it all over again.

So don’t be afraid to be cautious with what you say. If they’re up to hearing new dirt, so be it; if they’re a bit fried about it, chat about your new puppy instead. Everyone loves puppies.

One of the very bright points from all of this is the self-organized GitHub alumni network. Xubbers, we call ourselves. We have a private Facebook group and a private Slack room to talk about things. It’s really about 60% therapy, 20% shooting the shit just like the old days, and 20% networking and supporting each other as we move forward in our new careers apart.

I can’t underline how much I’ve appreciated this group. In the past I’ve kept in contact with coworkers from previous points of employment, but I hadn’t worked somewhere with enough former employees to necessarily warrant a full alumni group.

Highly recommend pulling a group like this together for your own company. On a long enough timescale, you’re all going to join our ranks anyway. Unless you die first. Then we’ll mount your head on the wall like in a private hunter’s club or something. “The one that almost got away”, we’ll call it.

Xubber meetup

In some sense, I think alumni really continue the culture of the company, independent of what changes may or may not befall the company itself.

One of my favorite stories about all this lately is from Parse. Unfortunately, the circumstances around it aren’t super happy: after being acquired by Facebook, Parse ultimately was killed off last month.

The Parse alumni, though, got together last month to give their beloved company a proper send-off:

No funeral would be complete, though, without a cake. (I’m stretching the metaphor here, but that’s okay, just roll with it.) Parse’s take on the cake involved an upside-down Facebook “like” button, complete with blood:

The most important part of a company is the lasting mark they leave on the world. That mark is almost always the people. Chances are, your people aren’t going to be at your company forever. You want them to move on and do great things. You want them to carry with them the best parts of your culture on to new challenges, new companies, and new approaches.

Once you see that happening, then you can be satisfied with the job you’ve done.


Cultivate the relationship with your alumni. Immediately after parting ways with an employee, there will be a number of important aspects that will require a lot of communication: healthcare, taxes, stock, and so on. So that type of follow-on communication is important to keep in mind.

There are plenty of longer-term relationships to keep in mind as well, though. Things like help with recruiting referrals, potential professional relationships with the former employee’s new company, and other bidirectional ways to help each other in general. It’s good to support those lines of communication.

One way to help this along is to simply provide an obvious point of contact. Having something like an alumni@ email address available is a huge benefit. Otherwise it becomes a smorgasbord of playing guess-the-email-account, which causes problems for your current employees as well. Just set up an alumni@ email alias to forward emails from and keep it up-to-date through any changes in your organizational side of things.

The last thing to consider is that your alumni are a truly fantastic source of recruiting talent. Most employment terminations are either voluntary (i.e., quitting) or at least on fairly good terms. There are plenty of reasons to leave a job for purposes unrelated to your overall opinion of the company: maybe you’re moving to a different city, or you’re taking a break from work to focus on your kids, or you simply want to try something new. You can be an advocate for your former employer without having to continue your tenure there yourself.

And that’s a good thing. Everyone wants to be the one who helps their friend find a new job. That’s one of the best things you can do for someone. If the company treated them well, they can treat the company well by helping to staff it with good people.

If the company has a poor relationship with former employees, however, one can expect that relationship to go both ways. And nothing is a stronger signal for prospective new hires than to talk to former employees and get their thoughts on the situation.


It’s not your company. If you don’t own the company, the company owns you.

That’s really been a hard lesson for me. I was pretty wrapped up in working there. It’s a broader concept, really, shoved down our throats in the tech industry. Work long hours and move fast. Here, try on this company hoodie. Have this catered lunch so you don’t have to go out into the real world. This is your new home. The industry is replete with this stuff.

One of my friends took an interesting perspective:

I always try to leave on a high note. Because once you’re there, you’re never going to hit that peak again.

What she was getting at is that I think you’ll know. You’ll know the difference between doing far and away your best work, and doing work that is still good, but just nominally better than what you’ve been doing. Once you catch yourself adjusting to that incremental progression… maybe it’s time to leave, to change things up. Just thought that was interesting.

One of my favorite conversations I’ve had recently was with Ron Johnson. Ron was in charge of rolling out the Apple Store: everything from the Genius Bar to the physical setup to how the staff operated. He eventually left Apple and became the CEO at JC Penny, one of the large stalwart department stores in the United States. Depending on who you ask, he either revolutionized what department stores could be but ran out of time to see the changes bear fruit, or seriously jeopardized JC Penny’s relationship with its customers by putting them through some new changes.

In either case, there had been some discussions internally and he had agreed to resign. A few days later, the board went ahead and very publicly fired him instead.

We chatted about this, and he said something that I really think helped clarify my opinion on everything:

There’s nothing wrong with moving along… regardless of whether it is self-driven or company-driven. Maybe we need new language… right now it’s either we resign or get fired.

Maybe there’s a third concept which is “next”.

Maybe we should simply recognize it’s time for next.

I like that sentiment.

Firing people is a normal function in a healthy, growing company. The company you start at might end up very distinctly different by the time you leave it. Or you might be the one who does the changing. Life’s too nuanced to make these blanket assumptions when we hear about someone getting fired.

Talk about it. If not publicly, then talk openly with your friends and family about things. I don’t know much, but I do know we can’t start fixing and improving this process if we continue to push the discussions to dark alleyways of our minds.

When I finished this talk in the UK last week, I was kind of nervous about how many in the audience could really identify with aspects that I was describing. Shortly after the conference finished up we went to the conference after-party and I was showered with story after story of bad experiences, good experiences, and just overall experiences, from people who hadn’t really been able to talk frankly about these topics before. It was pretty humbling. So many people have stories.

Thanks for reading my story.

What’s next?