Great engineers rarely make great managers - the skills behind brilliant code have almost nothing to do with leading the people who write it. So how do you build a company developers actually want to work at, let them grow in their careers without forcing them into management, and lead in a way that clears obstacles rather than hands down orders?
Drawing on nearly two decades co-founding Fog Creek Software, Stack Overflow and Trello with Joel Spolsky, Michael Pryor traces the ideas that shaped those companies - dual career tracks for makers and managers, servant leadership, and fairness in pay - while staying candid about the failures along the way, from CityDesk to Copilot.
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Thank you. How how many people came to my talk yesterday? Just a show of hands real quick. Okay. I don't wanna cover all the same thing and bore you. So we're we're gonna be discussing a a different bent because this is the engineering track today.
And I think I've been really looking forward to this because I'm of the age, I guess, just by way of context, where I kinda grew up as a developer reading Joel on software. And Joel Spolsky, for those of you who don't know, is cofounder Michael and a couple of different companies.
And basically, there were two strands that I got from really following the development of Fog Bugs that have really influenced me. And that is how you guys set out to build an environment and a company that was dedicated to this idea that you wanted to build a place that engineers wanted to come and work at.
And the second was the discussion around how you hire, mentor, find the best engineers out there. And so I guess the question that I would have for you is, you know, kinda how did you guys come up with that? I know you're both kinda programmers or working in tech and you decided to to start on your own thing, but how did you come up with that idea and how did it lead to really Trello and what we more know about today?
Sure. You know, it's a roll back the clock to two thousand and it was quite a different era then. And I think most of the time when you were a programmer you were you were not really the focus of the company. Right? Like Google didn't exist back then, Facebook didn't exist.
Actually maybe Google did. I'm not sure. They did exist, but like there were there weren't there wasn't this idea of like a tech company, you know, where developers were in charge, that they were building the product. They were the interesting part. Like, worked at a a company called Juno, which kinda competed with AOL.
That's how I met Joel. And it was essentially their play was, we're gonna give people free email. You know, like AOL charge you twenty bucks a month. Their idea was, hey, we'll give away the email for free, but our client will show you ads.
So like disrupt AOL through showing ads. And the way that they thought about that company was, it's an ad company. And so even as a programmer there where it's like you're the the the only way that people connected with us was through the software.
Right? Like that was their entire, a hundred percent of the way that they they thought of Juno and the product. But the company itself thought of themselves as an ad company. And so, that sort of, you know, trickled down in the culture. Right?
And so programmers were kind of support function, know, like, oh, yeah. Okay. You know, they I I I see you have some concerns about privacy. That's nice. You know, like they didn't they weren't really paying attention to us. And Joel and I were just I don't know.
We were just frustrated. And I was really young and naive, and so I thought I could start my own company, and I was too too naive to realize how hard that was. So we were just like, sure, let's do it. And Joel and I set out to start a company and for a very long period of time, it was like playing house.
Right? Like it was totally fake. Like I remember spending a lot of time getting our like thinking about our logo and getting little pens made up. Like, totally the wrong thing. Like, we should not have been spending any time on that. But that was, like, easy to do.
It took a long time before it actually became a real thing. But along that way, you know, Joel was blogging about that adventure. And it turned out a lot of people were really interested in it, and also not many people were blogging then.
Right? So, you know, part of our success with Fog Creek, I think was building that audience. And Joel for Joel's a great writer. It was easy to read. It was it was at a time where there wasn't a lot of noise in the blog world.
Actually, don't even know that term existed when Joel started writing. So that sort of gave us a lot a big audience. Right? And so we built software and it was ideally, like it was nice to build software to that was appropriate for that audience.
And so this was essentially, we were content marketing at the time, you know, before that was a term. We didn't even know that's what we were doing. And and when we built the company and the culture that we built around it, was just very much from, you know, a programmer's mentality of fairness and openness and transparency.
I think like, I don't know why, but like, you know I mean, you see this open source. Right? Like that imagining that in the legal world, where like all lawyers get together and share. Like that would never happen. Right? Like it just doesn't it it doesn't exist in that world.
Like it it's it's a little bit too competitive. For some reason in programming, like programmers are just interested in that. They they totally will share with other people and not expect anything in return. Like that's Stack Overflow is built on that. Right? And so when we built the company, the way that we set it up and the sort of like, you know, even in the beginning Joel is is ten years older than me, had a lot more experience than I did.
And when we started the company, we just he said, let's just split it fifty fifty, which is like kind of dumb. Like he never had to do that, but that was it we avoided so many issues along the way because that was the way that we started, you know.
And that's always been his advice, like if you're gonna start a company, like just split it. Like don't worry. Like you you vest people so that if they leave, you're not they're not stuck with half the company. But it was just, know, sort of this equitable place and we we we did profit sharing from the beginning.
You know, we were like, if we make profit, we'll distribute that for with all the employees. We gave people equity, which at the time was really kind of hard to do. You know, it became easier as time went on with with options. Options became more of a standard thing.
Actually, lot of the stuff that we did became fairly standard. Not not because of us, but also because of Google and Facebook and and those companies having a lot of success. And so, kind of the the nouveau ideas that we had back then in two thousand are kind of run of the mill for a tech company nowadays.
Even like our compensation system, like the way that we we paid people was very much, you know, like against the idea that, hey, if you're a better negotiator you get paid more. Like we were like, nope. Like, and you see companies like Buffer, where they just publish transparently like the entire salary structure of the company.
We didn't go that far. Think In my personal opinion, that creates a lot of other problems. But we were basically said, if you have two people and they have the same experience, you're you know you're gonna get paid the same amount. Yeah. So And it's interesting because like nowadays, a lot of those ideas they're being trumpeted by other companies.
And some people that are that were reading the blog are like, was those were old ideas from JoLynn Software and Fog Creek and so on. But even then, it was kinda like you guys were putting into practice ideas that were really in a book called Peopleware.
Right. You know, there's even tactical ideas around office space and so on and eating lunch together. Maybe just talk a little bit about that because I think that's amazing when you're based in New York City and you put this stuff in a practice that is expensive, but but should make a difference and This is Joel used to work at Microsoft.
And I think a lot of the practices that they had were, you know, thoughtful and you know, like close the door. We have an office that with a door that closes for programmers. And, you know, so he had had that experience then had gone to work at a media company, Viacom in New York City, which you know, as a programmer you're kind of like support function.
And then same at Juno. And so he saw the you know, the different ways like a company that's focused on software versus a company where the software is just the support function. And so that was I think in that experience, you know, it was important for us to create a company that that did take into account all the things that people had learned and people were.
And you're right. And so that wasn't we borrowed from there and and and just sort of made it more and just practiced that. But when I when I think about though, like, this team of you and Joel, you you guys created Trello, Stack Overflow, Fog Bugs was a big deal, particularly at the time.
And it almost seems inevitable. Oh, yeah, of course, Trello is going be the blowout success or whatever. But they're also the thing I love about this story is that also a number of failures along the way as well. So wasn't City Desk the first product?
That was the first product. That was was a failure. Yeah. Yeah. Yeah. Mean, it's just like, if you think about it, like you said Stack Overflow and Trello, and those are things that came later. Like Trello was in twenty eleven, Stack Overflow was twenty ten.
That's a decade of failures that we learn from. And in fact, you know, we made Fog Bugs in two thousand. And it was it was like a thing that Joel had written at Viacom and, you know, carried over to Juno. We called it Juno Bugs at Juno.
And then we started Fog Creek, so we called it Fog Bugs. Worst name ever. Like, we're just awful at naming. We got better. But City was we thought Fog Bugs we were like bug tracking, like maybe somebody will buy it. But CitiDesk was where we thought we would make a lot of money.
And CitiDesk was, at the time, know, Joel's blogging. More and more people are blogging. We're like, hey, this content management space is really gonna heat up. And we saw that people were trying to install type pad or movable type it was like really complicated because you had to have shell access to a web server, you know, figure out what public underscore HTML was and get you know, set up Apache so CGI bin directories were executable and like, then you had to download these Perl scripts and it was a nightmare.
Like, only way you could do it was your programmer. So we were like, oh, I know. We'll build a desktop app that, you know, is just like you add a new article, type your article, it's WYSIWYG, you know. And then you save it and then you push a button.
And then the sort of mashing up of the site and the generating of the HTML will be done on your desktop. And then the only thing you have to know is the FTP credentials for your web server. So we're just FTP up. Which is actually an interesting idea.
It solved the problem that we saw. But but Movable Type and and Typepad and those and Blogger, those companies also saw that problem with their own software and solved it themselves. And with probably the first SaaS based, you know, like kind of use the web page itself to configure the web application and bootstrap it.
And so they solved that problem and Citydesk just went it went nowhere. There was actually, I think, Macromedia had an app, a similar app. But, so Citydesk, total failure. Like it was like the right idea, but the wrong execution. So like the idea of making a client's like app was just totally wrong.
And Fogbugs actually started the sales, you know, were doing pretty well. And it was, you know, you'd make like like fifty dollars one day, and then you make like four hundred dollars the next, and then you make like two dollars. You know, like it was sort of bumpy and but you made a little bit of money, and over time we used the profits from Fog Bugs to fund a lot of other failures along the way.
You know, and so we learned a lot of lessons. Like, learned we had another product called Copilot, which was a screen sharing tool that we needed ourselves because when we're installing Firebugs on people's computers, it was like complicated, you know, patchy configurations or IAS configurations as you're trying to debug this stuff.
And you're like, if I could just see their computer, could solve this instantly. And they're telling you what they see on the screen. You're like, tell me what you see on the screen, you know. And you're like, so we were like, we could use VNC to to look at their computer, but that was complicated.
So we bundled that up into a screen sharing tool. And at that time, it was like two thousand six, two thousand seven, it wasn't there wasn't another tool that did it quite like that. There was like a box you could buy and install in your in your office, but you know, thousands of dollars.
So we thought, hey, we'll build something that does this. We we got a bunch of interns to do it. We made it. We actually filmed it. It would took a summer and we made a movie. I actually have that. Oh my gosh. It's the nerdiest movie ever.
Was the low point of the naming, I think, maybe. Yeah. It's called Aardvark. Yeah. Well, that was the because we started naming our intern classes and they weren't like a b c d's. You had to pick a a name for it. It started with a, so we did animals.
So they were the aardvarks. So Copilot was a great product, made a deep made a little bit of money, it was pretty good. But the lesson there, the fail the big failure there was, it was the right idea, the right time, and the right market.
Because you know, GoToMyPC and LogMeIn came out right around there, right after that became both became billion dollar ideas. And Copilot, know, we only made like thirty grand a month at its high point, which was pretty good for us. That was awesome. But that was a billion dollar idea.
And if we had invested in it and marketed it to the right people, probably could have done a lot better. So we we realized, you know, we we marketed to customer support agents because that was how we used it. Instead of thinking much more horizontally like, hey, lots of people wanna get to their computers, or IT people wanna get to the their employees computers, or and we just didn't understand how important that that piece was of how you're marketing it to it.
We also were a little bit, you know, Joel's blog was super great for us because it brought in people, but it also kind of narrowed the kind of people that we could talk to. And we didn't have a muscle to talk to anybody else. Right?
Because we didn't we never had to. We were like, oh, great. We have this audience of techy developer people. And so if we're gonna market a tool to, you know, outside that, it was like, well, how do you do that? I don't know.
We didn't have any Google AdWords experience, you know, we didn't have any we weren't doing any other kind of content marketing. And you actually think back to the true sort of directory of Fog Bugs and it was doing great, but you know, Jira came out two years after we had had started selling Fog Bugs and, you know, Atlassian's eight billion dollar company now. Right?
So and they they weren't doing they didn't have Joel's blog. Right? They had to just market themselves and figure that out and did an amazing job at at at doing that. So yeah. But we so we like took decades worth of failures and then, you know, had like when we built Stack Overflow, there was like a plan there for how to do it and not to make the same mistakes and it was the same with Trello.
Right. So walk me through the evolution then. It's basically two programmers start a software company that's building tools for programmers. And how long till the first hire were you coding ninety percent of your one hundred percent of your time in the first couple years?
How did that evolve out? And what did you learn along the way? Yeah. So the idea we didn't build Fog Creek software to be a it the company didn't exist because we had a product idea. It just existed because we wanted to make a a place that developers wanted to work at.
Right? That was our mission. So the products, we were sort of ambivalent about what we sold. We just we were gonna in the beginning, we just did some consulting and we thought we would get ideas for cool products to build. That's where City Desk came from.
You know, we sort of had Fog Bugs. We were like, okay, we'll package that up and sell that for a little bit. But in the early days, Joel and I were doing all the programming and we sort of took turns doing the administrative stuff like Quickbooks and, you know, filing the fees and all that kind of stuff.
Who was the better programmer? Joel was. He was way more experienced than I did. And so, you know, did that for a long period of time. In fact, Joel Joel did Joel was like the, he did the admin function for like four years, and and then I switched and took over for four years.
And, you know, we sort of co led the company. He's he was the CEO. I was the president. And, you know, we we had specific ideas about career progression and how programmers should progress in their career. Ideas around like, you know, we we created like, I don't think I don't think developers necessarily make good managers.
Like the skills that you have as a developer. I know this for me, like the nothing I learned as a developer has anything to do with what I do today. Right? And would not have prepared me for what I do today. It's just they're they're completely not related.
And so you might find somebody that's a good developer that could be a good manager, but they're but it's not a good idea to sort of make that the career progression for developers. So we created two tracks, which is similar I think to Microsoft's setup, you know, borrowed a lot from them.
And so we had like a management track and a, you know, just an individual contributor programmer track. And we had we basically all the programmers, they were just members of technical staff, which we I think we also stole from Microsoft. And, you know, we had one distinction.
It was like, we didn't wanna create a lot of levels and things like that. So we had we had member technical staff or senior member technical staff. That was it. But, you know, there was this this idea of career progression on as just a developer.
Like, you didn't have to become a manager in order to progress in your career. So then what did you guys have a litmus test or some kind of thing that you would look out for or talk about with the team? Because I think a lot of times, you know, if you're a programmer, you want to try out management just to see and if your management, you know, maybe rarely goes the other way, but there had to have been that tension at times.
How did you guys manage that or was there in your experience? Because now you've managed hundreds of people Yeah. All the way through that. What what is I think it's a question a lot of people in the audience will have. What is the thing that sets you up to be a good manager or even just to enjoy management?
I think actually, before I came here, talked to our the the engineering manager for Trello because he's actually from Edinburgh. It's Barry Clark. And I was like, can you give me some tips for this talk? Because I think you're a fantastic manager. So he gave me some great insights into how he thinks about it.
Stealing other people's ideas is also a good piece of man's deserves the credit. I mean, know, say it's actually talking about manager, we're talking about CEO versus manager and and we can come back to this because I think like as a CEO it's a whole another set of problems.
Like, or or or skills that you have to sort of have in order to be a CEO, which you know, being a manager doesn't even prepare you for that. But he he he sort of talked about this this three month period where I think a lot of people figure out really quickly whether they are gonna miss being a developer.
Because when you're a manager, you're not a developer anymore. And some people that's actually a really hard transition because I think like, I know this even for myself. I feel some, you know, I don't know. I feel bad that I don't write code anymore.
I feel a bit like, I liked writing code. Was fun. It was also like concrete, like you made a thing. Yeah. Right? And as a manager, you're just like talking to people all the time. It's like, what am I doing? You know, like, where is the output?
But there is output, it's just like you can't see it and measure it. And in fact, what your output is is the output of the people that you're managing. Right? And that's a hard thing to understand. It's like the more effective they are, and it's also like, I think early on, it's also hard for you to step back and let like if you're used to making and building to step back and like help other people make and build.
You're like, oh, come on. I'll just do it. You know, and Have you found a way to scratch that itch within the company or even external? Because I know that's something I I've really struggled with is how I wanna make something each day.
Yeah. I don't I I you know, sometimes it's just like trying to build something. We do at at Fog Creek, we had these things called Creek Weeks, I talked about yesterday, where we just like take a week and build things. At Atlassian, they have a similar thing called Ship It's, which are like twenty four hour hackathons.
And I try to get into that. It's you know, it's like once you start writing code though, it's hard. Because now you're not even I don't even know how to write node JS code. I'm like, let me get out the VB script editor.
Know, like if I have to do something, but I can write an Excel macro. I'm just so behind the times. But yeah, for us, I think letting people get a chance to manage and and just understanding that. You might be you might like it and you totally might not.
And that's totally okay because there's another career progression for you and you don't have to think of this as that's how I'm gonna be a better or have a better career. It's like to be a manager. So I think actually being a manager, the skills that I see, Barry has, is mostly just tons of empathy and caring about your people and being an advocate for them and trying to get things out of your way.
Like Joel wrote a big blog post a long time ago about servant leadership. And this idea that you know, that that being a manager is not it's it's not telling people what to do. Because of all, you're gonna be so far away from the actual problem that they have to solve.
So like really, you know, you're trying to get things out of their way and empower them so that they can solve their problem. That's hard. I I still struggle with that today because I it's like even with Trello, you know, I'm like, why aren't we building this feature?
Like this feature is the thing to build and we should build it this way. Right? You know, where it's like, we have PMs that are solving problems and they have to figure out what features are gonna solve those problems, and they have to figure out how they're gonna be built, and the engineers are gonna contribute to that.
And, you know, so it's a it's a struggle, but essentially, man being a manager is just a support function and trying to to help people and and make sure that they are happy so that they can be productive. Yeah. Another idea. So if we rewind back to the kinda late nineties, early two thousands, I think you guys were really instrumental in this idea of a developer first company.
But there's something else that I took away. I was I was reading Joel's blogs. He posted, what, about once a week? It seemed like. That's about right. And I was in Indiana. I was going to school out there, and it was one of the first times where I was reading something from a technical person, obviously very accomplished.
The company was going places, but he was very vocal about the fact that he was gay. And I, you know, I just think that that was an important thing. And has that did you guys ever did that ever manifest itself or did you ever see blowback or, you know, particularly now when we struggle with diversity in tech start up land, we usually talk about maybe racial diversity or whatever types of diversity.
But to me that was one of the first things that I can remember in the tech industry where there was diversity, it was celebrated and it was out there. Yeah. I mean, don't know about his personal experience and like I'm a straight, cis, white male, you know, like I've had so much luck and privilege in life that it's hard for me to to to sort of relay what what he dealt with as as he went through that.
But I think that that philosophy of, you know, equality and fairness and and was obviously, if you think about the way that we structured the company, whether it was because of his experience or whether it was just because that's like the way humanity should work and treat each other.
You know, it's like even with Trello, we The idea of building a product that's super horizontal for the entire world, it's like you can't build a product like that unless you build it with people from all over the world, from all kinds of different people.
And so, you know, that's really important and core to the culture that we built at Trello. And and I think it's not only is it like the right thing to do, but it's actually like an advantage for us, because like it's actually it makes a better product.
Like, if we're gonna build that product for the for the world, like, we have to understand the kinds of problems. And so, it might be language issues. Right? Like, it might be understanding, you know, just like how we come across in different cultures and the way that our copy is on our website or something like that.
It could be like a feature that we have in Trello, color blind friendly mode. Like if you have labels on cards and you can't see colors, like, what you know, how does that work? And so one of the guys at work, the designer just made it on his own.
It wasn't even you know, it's not it's not like like, think all these great things that make Trello so special, it's not because somebody told people to do this. Right? We just found people that were creative and amazing, and just sort of made space for them, and that's how these features came out.
So like this color blind friendly mode, which gets remarked on all the time online. It just, you know, changes the colors into like patterns. Right? So like if you can't see colors, you can see the patterns, you can tell the difference. So there's like small things like that, that I think like you have to have a share, like an understanding of people's experience inside your company.
Otherwise, it's hard to build a product for I don't you eat your own dog food and then you usually build a product that is just for you. Right? So the more you can make your your company sort of see things from different viewpoints and use it from different ways, the the more well rounded your product's gonna be?
So at so at administrative, we got about sixty people, and I would say almost every team apart from the engineers use Trello in some way. So we probably have at least thirty, forty daily active users and we don't pay a single cent for it.
But you should. How? How do you actually buy and pay for Trello? There's button in there Is there like, I mean is this a common thing where, you know, that companies are running basically their whole business on it. It wasn't a choice, it just affects the company effectively and I mean, so our marketing budget was making Trello free, right?
Like we didn't actually do any marketing. All the sign ups for Trello are organic. Never spent money. You know, we for for went, for go, for I don't know what the past of that is. We went without the money in the early days, the freemium sense.
We gave a lot of value away, and what we got was a very big audience of people that are huge fans of the product. And I'm confident that as time goes on and we build things on top of Trello, that we can align the kinds of features that convert somebody from free to paid with somebody that gets a ton of value out of the product.
So like people that use it a lot will end up becoming likelier to become paid users. And that's like the kind of relationship you want. Right? Because they already understand the value and they could see even more value ahead and then they're happy to pay for it.
So in in in a sense, the strategy is you got freemium is the the iceberg. Right? It is where most of your effort has gone to date and you're trying to build on top of that Yeah. In the future? I mean, I don't I don't know if I would cut it up like that, like, all of our future work will be paid.
I I think of it more like, like, if you think about the power ups, like, the strategy for Trello is to be a horizontal product. There are ways that people are gonna wanna take it in different in different directions that are more vertical.
And so we came up with this idea that we would have power ups where you could take a board and you could sort of turn certain things on, and then it became more of, you know, more of a sales tool, or more of a onboarding tool, or more of a developer tool.
But it didn't have to change the core of what Trello was. And we said early on, we actually had it set up so that, you know, if you if you you got this power up for free, but if you paid, you got these.
And we realized, you know what, that's a bad platform because then people can't actually sample all those other power ups because they have to pay first. So we changed it. So it was like, you can turn on any power up you want on any board.
So you use this power up on that board, and a different power up on a different board, so you can figure out how they all work. But if you want more than one, you have to pay us. And that's how it is now.
I don't know if it will stay that way forever, maybe we raise the limit or whatever. But it's like a better way of saying, you know, people that want a lot they want a more specialized experience or they The next thing is, I think if you think about people that use Trello a ton, there's a Trello sort of missing some functionality in solving that problem, which is like, I've got a lot of boards, like what's going on?
Yeah. You know, and I we have great ideas about how to solve that and tie that into both free and paid, so that you can get the free free version will get some of those features and we also have to figure out what the trigger is that you can get even more when you pay us.
But so it's intentional, but, you know, if you wanna pay, go for it. We're happy to have you as a We've got very little time left, but maybe you could just tell us very quickly what was the worst bug you ever had to fix that just drove you the craziest?
Oh, so I'll tell you the worst thing I ever did. I checked in code that pointed our billing software at the credit card processor sandbox, so that it looked like all the charges were going through, and we were recording all the charges, and everything was happy and wonderful, and like the sales, the charts that were showing sales were still going up and up and up, and then our bank account, no money was showing up.
And so, then the worst part was to fix it, then you had to go back to people and be like, I know we said we charged you, but we didn't. We're gonna charge you again. And like no one, everyone was like, what? That's ridiculous.
There's that. That was the worst. Or the time I checked in code they forgot to charge sales tax and the state came in and said hey you owe all this sales tax and we had to write them a huge check. I mean like there's, I've done a lot of I've written a lot of bad code.
So Alright. Well well, thanks so much for coming and talking to us today. Alright. Thanks for having me. Cheers.
