>> Rich Stokely: All right. Let's get started. Hello. My name is Richard Stokely. Welcome to
the MSR Visiting Speakers Series. When Amy Draves asked me if I'd be willing to roast Scott
today I said I would be more than happy to. She then went out of her way to explain that this
was not a roast of Scott and that I needed to give a proper intro. I also know Scott has an hour
and a half to make fun of me after I speak, so on with the proper intro. Scott graduated from
Carnegie Mellon. He studied computer science and philosophy. He then came to Microsoft
where he was here almost ten years. He spent a lot of that time on Internet Explorer 1 through
5 so if you have any back button questions or problems, [laughter] he's the guy to send mail to.
After his time at Microsoft he did something very unusual, something I think a lot of us don't
really have the guts to do, which is he left a great job and a lot of great people behind and he
went out and pursued an untested passion; in his case writing. Ten years later he is a best
selling author. He has four works leading up to The Year Without Pants. He also regularly
contributes to national newspapers and has been an expert on a number of news programs
including NPR, CNN, MSNBC and the like. What I always loved about Scott's writing is his style
is quite casual but it's, he always focuses on things that are actionable, so not only is his writing
entertaining, but don't tell him this, it's also pretty useful, so I encourage you to go back and
look at his previous works. They're great. That brings us up to The Year Without Pants. I had
the opportunity to read the first draft and it was awful [laughter]. But it gives me an
opportunity to talk about one of Scott's superpowers. Scott, and you have just one
superpower, in a kind of relentless pursuit of the truth and understanding, Scott has a
miraculous capability to quash his preconceptions, his biases, and most importantly, his ego in
pursuit of really understanding a project. That's a very rare gift. With that, I consider Scott a
trusted source on the topics he chooses to write about and after the volumes of negative
criticism we gave him, I'm confident that The Year without Pants will be another best seller for
Scott, so please join me in welcoming Scott Berkun. [applause]
>> Scott Berkun: Hi. Hi. How are you doing? Welcome. It's good to be back here. I haven't
been back here in awhile as Stokely mentioned and this book is unusual. What I'm going to do
is tell a story about the book. The book is a large story. It's called The Year Without Pants for a
reason. The word year doesn't appear in many business books because a lot of authors write
about subjects that they haven't experienced firsthand in a very long time. As Mr. Stokely, my
friend, mentioned I've been on my own as a writer for about ten years so then I'm one of those
people that you guys see and invite to events and maybe your groups hire consultants to come
in and be experts and give expert opinions. I remember when I was a manager working on
Internet Explorer I would often see these people who were experts come in and the question in
the back of my mind was, wait a second. When was the last time this person had actually done
the things that they are giving advice about? Was that a month ago, a year ago, ten years ago?
Why is it that all of their stories are from other people's companies? Why aren't any of their
stories from the first person? And I had this feeling as I became an author, I've written four
books. Most of them have been popular. They're largely about ideas and working with ideas,
creative thinking, managing innovation, how to persuade and pitch people on ideas. These are
all things that in the larger sense are about work. As my career as a writer has gone on I
realized slowly I was becoming one of those people that gets invited to speak to large groups as
the expert and gets all this attention for opinions, but these are on things that I have not done
in a long time. My own sense of my integrity was waning and I knew at some point I needed to
go back to work on a real project in a real company with real commitments, so I couldn't just
give advice and take some money and walk away and to find out how much of my own advice
did I actually practice. So that's the story behind The Year Without Pants. I had the opportunity
because of books themselves, Matt Mullenweg, who is the founder of WordPress. How many
of you know WordPress? You've heard of WordPress, maybe use it? Microsoft’s blogging
platform got transitioned over to WordPress. WordPress inherited many Microsoft creative
blogs, so they thank you for that. They are very happy about that. I came to know Matt
Mullenweg the founder through one of my books and he had me come in and do some
consulting for them and then once his company got large enough they wanted to become a
little bit more normal. I'll explain why they are abnormal in a second. They wanted to become
a little bit more normal and actually form teams for the first time, he reached out to me and
said Scott, would you like to come and work at WordPress.com and manage a team? In that
moment that he asked me given this thing that was in the back of my mind, this notion I had
about going back to work, when he made that offer to me I had two completely polar opposite
responses. It was awesome and horrible; it was aw-horrible. It was a combination of those
things. It was fantastic. I use WordPress. It's a popular product; it's a popular thing in the
world. You don't get that many opportunities to work on things that are popular and that you
use. That maybe happens once or twice in a career, but at the same time it was terrifying to me
because I knew I had written all these books, had given all this advice in all these lectures. I
don't remember half of what I say anyway. I certainly change my mind enough times. How am
I going to go back to work and try to apply all of the stuff that I had learned? But I decided that
this was exactly the kind of book that I wish someone else would write and since I don't know
of anyone else who has done a book like this, as a writer I realized I was obligated to go and
give it a try. So that's the story behind The Year Without Pants. I'm going to spend about 20
minutes, 25 minutes telling you parts of that story and explaining to you why I think parts of the
story are related to the future of work that will affect everyone. I'll also explain why parts of
the story are ridiculously absurd and I don't recommend anybody even emulate or attempt at
home even if you are wearing a crash helmet and a bulletproof vest. And I will open up the
floor for questions. Since this is a unique opportunity, at least for me, I used to be employed in
the same place that you guys are now, the kind of conversation that we can have about the
contrast between this very different place and the place you are is a unique opportunity I want
to spend as much time doing Q&A as possible. Does that make sense? Does that sound like a
good plan for the next hour? You don't have a choice. [laughter]. So be enthusiastic and have
faith. One complaint I have about most books about the future of work, or the future of
anything really, is how completely oblivious they are to all of the other books that attempt to
predict the future and how horrible a job they do. We are horrible at prediction. We are awful.
Even the people who are professional predictors are awful. And you can't do a good job in a
talk about the future of something, I believe, unless you spend a little bit of time thinking about
the history of stuff, because that gives you a sense of well what did they predict then and what
happened and what did they predict the following decade and what happened? And it gives
you some basis of maybe getting better predictions. So the reason why there's a picture of a
cave painting up here is one of the questions I had about work and how most people are not
really that happy in the workplace. I'll talk a little bit more about why I believe that to be true
and some data to support it, but let's assume for a second most modern knowledge workers
are not that happy. They are not completely happy in their workplace. They don't find a lot of
meaning in their work. If you go back to the first work, the oldest kind of work there is, the
furthest back you can go in terms of the history of work, work meant working to survive. You
had to work to find food and shelter every day. That's the first work we had. You can't go
before that. And that work was incredibly meaningful. If you didn't do that work, if you didn't
do it well, you died. There's no greater higher meaning than work can possibly have. And then
if you follow the progression of work and what we call work moving from agricultural to
industrial and now to our knowledge age and you look at that transition, those transitions as
proud as we are, we believe it's a kind of progress, meaning has declined. The amount of
meaning people get from their work has declined. So there's an interesting question that's
underneath all of my experiences at WordPress that I poke at in the book periodically. I step
back and poke at and go what does this mean? Is this a way to make things better, to give us
more meaning out of our work experiences, or is it just another technology, another fad or
another trend that doesn't help us progress in some of these things that are actually most
important to us? So a quick note about WordPress. You all raised your hands that you are
familiar with it. Since WordPress itself is an open source project, they do no marketing. There's
no marketing team. There's no television advertisements. It's all completely customer led
evangelism about the product itself. WordPress powers about 70 million websites. That's one
out of every five, 20 percent of the web runs on WordPress, which is an astounding number.
It's a ridiculous number. It doesn't get enough attention because there's no marketing team
behind it pushing that number in your face all the time and that number has been growing.
WordPress.com which is where I worked, which is a place you can go to actually get a blog. It's
not only free, the software is not only free, but the hosting is free too, gets about 4 billion page
views a month. Last week WordPress.com passed Yahoo to be the number eighth most
trafficked website in the United States. It's number eight. This is serious stuff. This is not a
jokey startup that does funky weird things because no one cares what they make. This is a real
serious thing. It affects the future of not just the web, but the internet and the internet
industries themselves, just because of the scale and the popularity of how it works. Specific to
the culture there and the culture shock that I experienced, so I told you, I worked for about a
decade at Microsoft. You guys know what that is like. I then spent a decade working mostly on
my own as a writer. You can imagine what that is like, a lot of talking to my dog, [laughter] a lot
of abuse of alcohol and other stimulant substances [laughter]. You can imagine what that's like.
What you probably can't imagine, because I couldn't imagine, is working in an environment
with all these really unusual characteristics. Maybe these are things that are coming for all of
us and maybe not. The first is no one using e-mail. No one uses e-mail. Half of you in this
room are probably thinking about what's in your inbox right now, or you think of e-mail you
want to send. I'm certain the people that are watching at home, I'm sure I'm only getting their
ears and their eyes are glued to their inboxes and sending e-mail and distribution lists and
whatnot. They don't use e-mail. I'll talk more about how they get away with that in a second,
but there are core ways that people communicate and e-mail is not part of that. Second,
everyone works remotely. So this is the thing that many people know about WordPress.com
and Automattic is actually the corporation that runs WordPress.com, so forgive me if I switch
those two names periodically, Automattic and WordPress.com. One of the reasons the book is
called The Year Without Pants is a reference to the fact that everyone works remotely. The
team that I led and managed, one guy worked in Ireland, another guy was from Australia,
another guy lived in LA and as the course of the year went on, my team got bigger and I had
employees that were living in Europe that I never saw. The entire company, one hundred
percent is remote. There are very few rules. There's this very strong emphasis on autonomy,
so you once you're hired you are given a great deal of control about what you work on, how
you do it, what tools you use. These are all things that are common at most young startups, but
WordPress.com started in 2005. They’ve been doing all of this stuff for a long time. The list
goes on and I probably can't even cover all of the astounding things that they do there. The
book documents my year going through all of them and how I dealt with the culture shock of
trying to overcome them, open vacation policy. What I want to focus on instead are these
three things. There's big questions. I'll talk specifically about how daily work
worked@WordPress.com which is something I'm sure you are curious about and then I'll leave
you with some thoughts about why I think you should care. I alluded to in my opening
preamble or intro about statistics. A lot of studies are not worth their headlines. I think you
guys probably know this. You guys are all smart. The claims that journalists or bloggers make
based on the data in most studies is pretty sloppy. I'm a critic of most studies that I read. One
study that was published recently that I like I think is telling about the state of the workplace is
this poll from Gallup which was done this year, and the poll was about the American workplace
and engagement. The primary statistic and the value of method they used with people self
reporting about how engaged they were at work. Seventy percent of all the respondents
responded that they were not engaged at work. That's almost 75 percent, three out of four.
Not engaged, and of that number half of them were actively disengaged at work. Actively
disengaged should terrify you. Think about having an actively disengaged brain surgeon
[laughter] actively disengaged, I mean they're not even faking it. They are not even faking.
They're playing solitaire, angry birds and they're scalpeling at your head [laughter]. They're
actively disengaged. That's half of that number. The other half is just not interested, so not
engaged, but not actively disengaged, which is really not that good either. And what does this
mean? Well this is where people get into trouble with studies. What does it mean? It's hard to
know exactly what this means. I think part of what it means is the failure of management. I've
had in my career before I was fortunate enough to come to Microsoft, while I was in college
and high school, I had a lot of really crappy jobs. I worked as a waiter, I did telemarketing; I did
direct mail. Some of those jobs I was fully engaged in because of the people I worked with or
the people I worked for or there were certain elements that were created in the environment I
was doing those things. So I look at this number as an indictment of anyone in a leadership or
management role. This is something about how the work has been structured, the culture that
has been created that allows people to feel most comfortable not being engaged. That's the
only way that they can maintain their dignity or their self-respect. Something personal about
meaning is missing so they keep themselves out. The book doesn't spend a whole lot of time
talking about the history of work. It's something I studied because I don't feel like I can write
about stuff well unless I know the back story, and there's a lot of argument about how the
industrial revolution has transformed into the knowledge age, and whether we're still being
victimized now by Taylor and this notion that workers are changeable, interchangeable.
Despite all the rhetoric we have about being creative and innovative and trying new things and
experimental attitudes and cultures and agile teams in all of that rhetoric, many managers and
executives manage their organizations in Tayloristic ways. They see individuals and developers
and designers and even program managers as cogs and wedges, widgets that can just be
replaced and swapped around. So there's still this model built into our culture, our
management cultures, that's very old, very old. There's this anecdote that I think is interesting
that most people don't think about, that the birth of management as a discipline, as a
profession came from the industrial age. It came from the need to manage large banks and
railroad train schedules. These were the huge growth industries in the 1850s, ‘60s and ‘70s and
those were the people, the robber barons of that age, those were the people who started the
first business schools. You can go and look it up. There's a direct correlation between the
philosophies behind those business schools and the notion of what management even is and
the Vanderbilts and the Rockefellers et cetera. There are certainly exceptions to that. I haven't
looked up the founding members of every business school in America, but this is true for many
of the prominent ones. That's reflected in the culture that is inherently built into how
management as a discipline is thought about. It's centered on command-and-control with
workers and individuals in the culture just being cogs in the wheeel, things that are replaceable
and that the most important person in a corporation, a creative force, the genius force is the
executive, is the manager and everything else just satellites around what they do. Another fact
to offer and this is probably the last statistic I will offer for you, is just about remote work,
because I get asked about this all the time regarding the book. People go, a whole remote,
completely remote company, like that's kind of ridiculous. That's kind of extreme. What's
actually going on? Is everyone going to work remotely? The data on this is pretty clear, that
the numbers are going up. Currently across the planet in terms of the professional workforce
about 20 percent of the people work remotely. That's one in five across the planet. In
companies or companies that are open to technologies, it's much higher than this, certainly
companies that are permissive about allowing workers to telecommute or work remotely at
least part of the time. There's a narrow definition that we use for remote work and I think
that's part of the problem. If ever you or any of your parents or grandparents ever had a
conversation with a coworker on a telephone, guess what you were doing? You were doing
remote work. When you are on Facebook with a family member who is miles away and you
haven't seen them in a year but you still consider that a relationship, that is a remote
friendship. We do lots of things remotely and the basis of a company working that way,
although I was never an advocate or a zealot about that being a preferred way. The potentials
or possibilities of that we know remote activities have been part of our lives for a long time and
are a growing part of how we do all kinds of interactions in our lives. So the book itself before I
even worked there I came up with a list of questions I wanted to answer. The goal of the book
is to go and use my own story, my own guinea pig experience going back to work at a real job to
answer. The first one I mentioned already, which is kind of personal about how much of my
own advice do I practice. Stuff that I preach, do I actually do any of these things? If you are
familiar with any of my other books, then maybe that is of interest to you. If you've never
heard of me before, you probably don't care at all, which is fine. The other questions though
are much more interesting. What are the work conventions that we accept as status quo as
almost required in any job that serve no purpose. What are they? Which ones can be stripped
away because they are just artifice, things that we've just collected over time and forget to
question anymore? 9-to-5 working hours, try to find a study that supports the claim that 9-to-5
working hours make people more productive, or that wearing a tie makes you smarter, or a
dress. You won't find any. These are artifacts of culture. We inherited these things long ago
for reasons we don't even know anymore and once we get hired into these cultures we adopt
the same assumptions about those things and then we defend them and protect them.
Questions about hierarchy, meetings, status reports, all of these things that we assume to be
true, I wanted to go into an environment that doesn't have any of these things and report firsthand, hey, do we need that? Can I function as a manager without being able to see my team
mates every day, without having the decision making authority focused on me as a manager all
of the time? And of course this larger question about remote work and location. So the picture
you see here is a month after I was hired; this is my team. And it looks like an ordinary, I don't
know, it could be anything. It could be three college students on vacation who just don't like
each other very much so they are spending their time on Facebook or something. Who knows?
You can't really tell from this what's really going on. You can't even really tell where they are.
It turns out that this photo was taken in Athens Greece in our hotel lobby while we were doing
project work. The laptop in front is actually mine. I took a step away to take the photo. This is
what our work life looked like, the limited number of times that we actually worked in the same
room together. On the left is Mike Adams and he actually is a main character in the book,
because he was one of my primary developers. In the middle is Adam Peteling who is from
England and Ireland, and that's Bo Lebbons on the right who is from Australia. In the course of
managing the team for a year and a half, I met face-to-face with these people maybe six or
seven times. The reason why we're in Athens Greece is an interesting story on its own. When
it came time for us to decide who wanted to meet together for the first time, face-to-face,
which was something the company supported. When teams were new I was hired to be one of
the first team managers. We were told if we wanted to, if we thought it was important, meet
together in the same physical space a few times a year. There was no policy written down. It
was just, I don't know, let's see if it matters. So we were one of the first teams to do this. We
asked Matt Mullenweg, my boss and company founder where we should go and he said Athens
is good this time of year. So I said great [laughter] and I doled out the right expense reports to
make it happen before he changed his mind. There is actually a logical reason behind it. It
wasn't that self-indulgent, because Peteling was from Ireland and Bo was from Australia. We
had flexibility to where the most logical place to go that would be for us all to meet. The
question that I had personally in all of this as a manager in a company that never had a
management before, this is one of the essential questions of the book. Being brought into a
company with the experience I had as a program manager at Microsoft in a place that doesn't
know what a manager really is, doesn't have schedules for things, doesn't have any organized
systems for doing many of the things that you guys probably believe are impossible to succeed
without. The question that I had is how do you introduce the notion of teams and structure
into a young noncorporate culture that thrives on chaos? This is a terrifying question. I mean
this is a question you can ask yourself about whatever your role is. How could you function if
you had to go into an environment that knew nothing of the assumptions and the foundations
that you base your work on? In the first two weeks that I was at the company I was trying to
figure out an answer to this question. I needed an answer. I thought about methodologies. I
thought about processes. I couldn't find another book where someone was crazy enough to do
something like this, so I came up with the only answer that made sense to me, which was these
two things, clarity and trust. I know it's not much. Clarity and trust. The conclusion that I
reached was and this is a hypothesis; it was not a conclusion. One hypothesis that I had is that
I'd last a month and everyone would figure this was a bad idea I would get fired. In fact, in a
conversation that I had with Mullenweg, the founder of the company, about the whole
prospect of this, I told him that. You know, this could be a real big disaster because I could
totally get in the way and screw everything up. I mean I did that a few times while I was at
Microsoft where it was built to have program managers. I told him that and he's like, yeah, I
know. He liked the prospect of trying something different just to see what would happen.
Obviously, I did too because I was willing to take the job and write the book about it. But clarity
and trust were the things that I came down to. I felt like if I could earn the trust of these guys,
these people independent of how little they knew about me, if I could find ways to earn their
trust, and then I could provide clarity around how to be smarter, how to make a better
decision, or how to come up with a better plan, or how to make their work as programmers and
designers more valuable. If I could be the source of clarity then I would naturally emerge, even
in the chaos as a leader in the group. That was my theory. The book follows the story of me
trying different things and failing and experimenting with different ways to try to achieve that.
The question most people want to know and I have just a few minutes left before I open for
Q&A is just daily work. How do you function when everyone’s remote, everyone's in different
time zones, there's no e-mail, how do you get anything done? And the answers are these three
things. This is how 90 percent of the communication inside Automattic is done. IRC, Skype, and
something called P2. P2 is just a word press blog. It's a theme. It's a freely available theme. If
you get bored you can do a Google or a Bing search, almost got in trouble there, for -- a few
laughs in the front -- you could do a search for a WordPress P2 theme and you could read all
about it. IRC is just internet relay chat. It's an old ancient creaky chat program from like 1988.
It's really, really old, but the open source community has embraced it and used it. So most
open source projects in the world probably have a bunch of people who communicate through
IRC. So at Automattic, at a private IRC chat system, so you can have chat rooms and that's the
hallway. That is the equivalent of your hallway. The only requirement wasn't even a
requirement. It's sort of a cultural imperative. Whenever you are working from wherever in
the world you are, and again, you could be anywhere. You could be on a Jeep in Africa chasing
tigers or whatever, as long as it had good Wi-Fi and you're still answering questions and stuff,
no one cares. They may not even know where you are. Anyway, as long as you are working,
wherever you are in a Jeep, on an airplane, whatever, you have to be in IRC because it's the
hallway. So that's where you go when you have a question you can't figure out, when you are
looking for advice on something, when you want someone to review your spec, though they
didn't really have specs, review your code or your design, that's where you go. And it was
informal just like your hallway is. You run into people you know better, some you don't know
as well, and that's where any of that serendipity or that random communication would take
place. That's the hallway. Skype, which you should all be familiar with, Skype is the lifeblood of
most other communication. If ever I want to have a one-on-one chat with someone who is on
my team or someone else in the company. They were working on something. I need to give
them feedback on it or have a decision to make. We needed to do a meeting, that's what Skype
was for. Skype had a weird interesting political challenge in the organization because one of
the benefits of IRC is that it's logged. This will sound really scary and terrifying, but all
communication there is logged and public to the company. So if I had an argument or a debate
with a coworker in the hallway in IRC and a week goes by and people go Scott, why did you
make that decision? And I go, I don't know. And so we go and search and see what exactly I
said was my argument for that thing. That is seen as an asset. You don't have to archive it in email. You don't have to dig through your e-mail archive to figure out where was that message
instead it's just there and there's a search engine on it and you can search it. So anyway, Skype
has become increasingly popular with the company. It's used for one-on-one communication.
It is private and secure, so all of my dealings with my team that were more of a personal nature
about their performance or giving feedback, it's probably not appropriate to be broadcast to all
of their coworkers; that's what Skype is for. On the day that I convinced my team to have a
team meeting, a weekly team meeting -- let me say that sentence again. I had to convince my
team to have a weekly meeting. This was like a breakthrough for me. When that happened we
did it in Skype. And six months after doing that I managed to convince the team, or we agreed
together. It wasn't so focused on me. After six months we agreed to do it with voice [laughter].
This was the breakthrough moment, actually hear each other's voices. P2 on the right is
technologically the least interesting of these three. It's just a blog. The theme is set up so it's a
little bit more like Twitter. You don't have to login. There's no posting, editing box. You just go
to the screen and whatever thing you have, whatever document or decision or thing you want
to feedback on, you post it. Like all blogs are good for, someone posts something and there's a
comment discussion thread underneath of it. All of our work, all of the documents that you
send around perhaps in e-mail if you are asking for feedback or whatever, that's all managed
through the blogs. And it's not a surprise that WordPress.com is heavily dependent on blogs to
do communication. It's the lifeblood of the company. So something like 95 percent of all
communication I had inside the company was through these three things. Most of the e-mail I
sent or received was to people outside of the company. Occasionally, there would be uses for
it, that it was just the most effective tool and we would use it. There was never a decree.
About a year and half ago there was a CEO of a company. I forget the name of the company,
that the creed no one would use e-mail for like three months, and he did it. I don't remember
what the outcome was, but he decreed it. This is not a culture where there were decrees for
anything. Instead it was for us as a team and individuals on the team to decide for ourselves
what we thought the tools that were best to get our work done. There was never any
philosophical debate about which tools we would use or how much we would use one tool or
another. This is actually the P2 I mentioned. It is a publicly available theme. You can go and
play with it and use it on any WordPress blog. It's a lot like base camp if anybody has ever seen
or used base camp or something like it, where it's built for workflow without a lot of the
overhead and all the advantages of blogs where you can search it and archive it et cetera. So
the last thing I want to leave you with about why you should care, I think that you can look at
the book and the Q&A would come out too as a journey of taking this large inventory of
management and leadership methods, many of which I accumulated here at Microsoft, that I
wore out in that tool belt. I used them well to be an effective program manager and manager
of program managers, taking this toolkit and then going to an environment that is completely a
generation or two ahead at least in attitude and toolkit. And finding out how much of this stuff
works and what of someone like me who is supposed to be an expert about all this stuff, what
in that toolkit ended up being useful. Which things should I throw away? I look at these
numbers and I think that all corporations, certainly all knowledge-based workplaces are facing
these two trends, that employee engagement generally is down. The 70 percent number from
the Gallup poll should be terrifying to anyone who organizes or leads a group of people. That's
a terrifying number. One out of four of your people are actually engaged and you guys can
think for yourself how engaged you are. I mean you can't be that engaged if you came to a
lecture at one o'clock [laughter] so there's something else that you're looking for and you're
hoping to get. The bottom number, of course, is about this remote thing. In some companies,
Yahoo has come up in this about having this really strong opinion that oh, it's bad. That's a
complete failing of this distinction between process and traditions and results. And one of the
questions that comes up in the book again and again in all of these experiences that I faced
including the things I thought were stupid or bad or broken, but this forcing of evaluating, am I
rejecting this because of tradition, because of my own philosophy, or am I rejecting this
because of results? In the face of remote work this is just one simple example where e-mail is
another. Why wouldn't you let an employee try these things? Why wouldn't you provided you
tell them your performance has to be just as good or better? If you can tell an employee that,
hey, go work remotely, but your number of check code, check ins or the number of specs you
write or whatever, you're being evaluated on, it has to be just as good. You're inspiring them to
find a way to make it work, and if they come back and make it work and they achieved the
same performance, you lose nothing. You probably gain their trust. That's a keyword as I
mentioned I think to being successful, you gain their trust because you are willing let them go
and prove something to you. If they come back and fail and don't meet the results, you still win
because you showed you were open to try. In so many of the workplaces I visited as one of
these author or expert guys seem so locked down and so unwilling to even experiment or try
anything on these traditions. And that's really the larger question that I hope the book and the
stories from the book raise. I'm not a zealot advocating everyone should copy what they do,
but the questions that they ask and the way that they go about trying to find answers I think is
inspiring and informative to most of the working world. With that, I will thank you for listening
and I'll open the floor for questions. Yes sir? I'm supposed to repeat the question, I assume,
right? Yes. Okay.
>>: I'm curious about the story, about the back story as to why they wanted to bring in teams
and some sort of management, what was the driving force behind that?
>> Scott Berkun: The question was what is the back story as to why they wanted teams at all,
and I am culpable in the story. They had two things going on. The company was growing. As
WordPress.com grew the company itself was growing. They reached about 40 or 50 people and
Matt Mullenweg and Tony Schneider the CEO of the company, realized that they were starting
to have some problems, staying coordinated. Even as much as they love chaos, even they were
admitting that there were problems. So they asked me to come in as a consultant and I spent
some time with them and I gave them what seemed like an elementary consultanty kind of
suggestion, how about teams? [laughter]. And they thought it over and they thought yeah. I'm
sure they had thought about it too, but to hear it from an expert gives it a certain -- you guys
know this part about what experts get paid for and so people can go hey, it's not just me saying
this. Expert Guy who I happen to pay a lot of money, what a surprise, he's saying the same
thing I'm saying. That's a lot on how marketing, how consultants and experts make a living. It
shouldn't be a surprise. Anyway, I was that guy. I offered that to them, and then about four or
five months later that's when Matt Mullenweg said hey. We're doing this. Why don't you be
one of the team leaders? And just like I mentioned before, I had one of these excited, terrified
moments. I had it again because it's terrifying as an advisor to go and be the tool by which your
advice is carried out [laughter]. If it goes wrong you're doubly to blame [laughter]. Anyway.
That's the story. Yes?
>>: When did you start having the feeling that you needed meetings and how often did you
have them?
>> Scott Berkun: When did I start feeling like we needed meetings and how often did we have
them? I thought going in that it would be an inevitable consequence of calling something a
team, because by nature calling something a team it means that you are doing stuff together. If
you are doing stuff together it probably means that you should talk about what you are doing.
Having a set time when you make that happen just seemed logical. We met once a week. That
was the basic unit. I'm a fan of calendars. Many of you I'm sure are familiar with all of the
different software development methodologies. I'm familiar with many of them too. I just like
the calendar methodology. How do we know that what we do today is good? How are we
going to be sure this week’s work is good? How are we going to be sure at the end of the
month that we have something to show? Some Agile methods are more calendar based.
Anyway, I don't like to use any of that vocabulary. I thought it would be a bad idea to use that
vocabulary there. This is just a week and eventually we got more sophisticated and we would
talk about the most important assignment that people had for the week, most important thing
by Friday. And since WordPress.com is a service, it was rare that we had large schedules to
manage or delivery dates. One chapter in the book follows a story of Jet Pack which is one of
the major projects we worked on. It's a very important plug in. It's a lot of cloud, sophisticated
cloud stuff. It's actually very important strategically to WordPress, but it required a specific
launch date, so that was a real challenge, and it's maybe the most interesting chapter in the
book for you guys because I had this toolkit of all the big projects I worked on at Microsoft,
Windows and whatnot, two-year schedules and all of the dependency trees and tried to figure
out how much of that to use and how to fit it into this culture that had no experience with that
before. It's probably a month into being on the team that we started having meetings once a
week and then whenever we needed to we would have more frequent meetings. Yes?
>>: [indiscernible] everybody choose what they would be working on?
>> Scott Berkun: Yes.
>>: So how did it work [indiscernible] managing [indiscernible] how did you review their
performance?
>> Scott Berkun: Okay. The question was how did people pick what they worked on and what
was my role as a manager or as a leader. At the time I was hired the answers to these
questions changed. All three of those people who I showed, they were all interested in this
team idea. They wanted to work on things that were bigger than what they could do on their
own. Even though all three of them were very good programmers, they all realized inherently
that they wanted to work on stuff that was bigger than what they could do themselves. So they
were more open to having a little bit less choice about what they worked on. Had you done a
book about the company six months before I got there, the answer to that question probably
would have been very different. Built in to, it's hard to imagine. I remember my experiences
working here. Because they're so little structure, there's not a five level, eight level structure
where there's all this reporting about personal goals and six-month goals and midyear reviews.
There's none of that. It's completely informal. There's no -- it's hard to explain just in Q&A how
different the culture was around a lot of these things. And the best answer I give you is an
anecdote and it's in the book. The first time I met them -- the company has a meeting once a
year where everyone is there. Once a year everyone's there. They do believe that it's
important for people to spend, to get all the intangibles together. It happens once a year. And
at that meeting which was the first time I met them we had our first little, at a dinner table,
talked about how we wanted to work together, and the meeting went fine. They were open to
me being the leader, at least giving it a shot, this experiment. Before it ended I asked them a
question. And it was a question that had been on my mind since the day I was hired. The
question I asked them was how do you know if you are doing a good job? I said it to all three of
them. How do you know if you are doing a good job? Because I'm thinking, not only just
Microsoft, but most companies have a performance system. It's all about promotions and da,
da da. And I knew that as far as I knew WordPress.com did none of that. So I asked them that
question and all three of them looked at each other and said I don't know. [laughter]. I don't
know. And it was kind of don't know of like, not only why are you asking me this question, how
does that factor into what we're doing here? The explanation for the answer is that the culture
of WordPress comes from the open source project which is volunteer-based. When you have
any sort of roots in your, whatever thing you're doing, that's volunteer-based, it's sort of builtin to the way people treat each other that anyone can walk away, which is sort of an attitude
about how people treat each other. There's a lot of positives to that. There's some negatives
and the book talks about those too, but there's a lot of positives to that where people are doing
the work because it's meaningful to them. The work itself, not that carrot in front of it, they are
excited to be working on the features that we worked on. They were excited to be able to
make WordPress better for whatever reason. Some of the motivations were purely selfish.
They just like the technology. They liked the intellectual challenge of it. For some of them the
motivation was more empowerment, of which I'm sure for some of you is true. Because when
you work at Microsoft you work on projects, you get the rare opportunity to make things that
millions of people will use. Those are intrinsic meanings. It's not about the structure or how I
was going to evaluate them or what the scorecard was going to say at the end of the year. They
had no familiarity with those things, but they didn't understand why you would even need
them, which I think is fascinating. Will that still be true ten years from now at WordPress.com?
I don't know. But for right now, I think there's some element of that wouldn't you rather
manage a team of people who had an intrinsic motivation to do the work itself and value the
contributions that other workers were making? Wow. That's a powerful thing. I think any
manager at any company would want to create an environment that was like that. The
challenge for me was how do I find a way into that without ruining it, without spoiling it with all
of these very logical structured ideas for how teams should work. Yes?
>>: Sort of a question, we do a lot of that stuff using Yammer and Link, you know, we record
every team call, you know, [indiscernible] working there. We are all remote basically, but I've
got a couple of questions. Time zones just kill us. 11 PM Seattle time is the only time our
whole team can be awake and that is in between 12 and 5 AM. So that's one thing. And the
other one that as you bring in external organizations, so within Microsoft Travel we deal with
American Express. We deal with companies, call centers and MSIT and dealing with all these
different [indiscernible] a little disconnect and go on for months sometimes, something you
thought would be obvious, but it's like oh, that wasn't in the stack. How do you get over those
sort of things when you are not actually the ones who built it?
>> Scott Berkun: Okay. So there are two questions, one was just about basic remote work
challenge of time zones and the second was about the little details that get lost when you are
working with people who are -- so the time zone question comes up in the book. There's a
chapter called Follow the Sun. There's a moment in time where my team was at maximum evil
distribution on the planet. There was no good time. We were all eight hours apart and that
means someone has to be up at 2:30 in the morning. It was Bo who is crazy enough. He's right
yeah, I want to try that. It was a complete disaster for him [laughter]. The time zone thing
becomes a burden for the team if everyone wants to keep everyone engaged, you come up
with ways to work around it. Ideally, you divide up tasks in a way that have logical sequences,
so it can become an advantage where if you have two people who are good at working as a
pair, they are taking turns. One guy is going to sleep and then wakes up the next morning and
his partner, she gets up and the stuff shows up. The next piece has been done. So if you have
good collaboration between -- it never works for everybody, but you can find people that pair
up, that just naturally do a better job at this leapfrogging each other. Certainly in terms of
design work or programming. There are no marketers at the company. There is no real
product planning so I couldn't say the same thing for those things, but as leader, that's one of
the things I'm thinking about. How do I make it so that I put the burden of that challenge on
the part of the team that has the best relationship to manage it? There's no universal answer
for it, absolutely not. Another advantage that they have is that everyone's remote and so by
virtue of the fact that you applied to work at the company, you had to go past -- I didn't have a
chance to talk about this, but the hiring process is just amazingly simple and smart. There's no
interview loops. You're hired by trial. This sounds radical, I know, but to get the job you have
to show that you can do the work you'll do in the job [laughter]. Whoa! Who thought of that?
That's madness. There's no interview loops. There's no phone conversations. No one asked
you what your strengths are or tells about a mistake. And there's none of that. So by virtue of
the fact that you got hired, it means you probably communicate well and you're okay with the
remote thing and you are probably good at managing your time. These trial projects, a lot of
talented people apply for them and they can't manage their time to do it on Saturday or
interleave it with their other job, so the trial fades and they peter out. So why was I mentioning
the -- ah. That helps answer your second question which is by virtue of the hiring process, but
mutually, it filters out people who are probably not going to fit the challenges the way the
culture set up is going to work. Yeah, in the back.
>>: [indiscernible] because I'm wondering how you take somebody who's never had a job
before, a new college graduate, bring them into this culture and get them started. In a lot of
cases they don't have the ability or the background or the experience to work in a team, to
work remotely, to communicate, whatever, what proportion of the company was
[indiscernible]?
>> Scott Berkun: Sure. So the question was how do you take someone who's never worked in a
crazy environment like this, which is most of the planet, or worked at all? There's a chapter in
the book that talks about, it's like every seventh or eighth chapter in the book steps back and
tries to answer some of these bigger questions about all the crazy stuff I experienced. There's a
chapter in the book that talks about this and if you had to write an NBA style cultural evaluation
about who they hire and what the profiles are and what would they be like. They do hire a lot
of people that are that young. They do hire a lot of people that never had a job before. The
way they manage that, or why that isn't a complete disaster, is these are people who are
craftsmen, designers, programmers, web developers, so they are people that have a tangible
craft and they're good at it and they probably have done work where they are working
independently as a web designer or a web developer for clients. They never had a real job, but
they've worked with clients before and work with clients means they've had to juggle different
skill sets. That had to manage communication with people they don't work with all the time.
It's a high, at least while I was there, there, a high percentage of the employee base had never
worked at a corporation, had never worked at a big company, but had worked at a web
development shop, had done web development or web design work in college for their
department. So they had experience with the craft and the job is to craft. No one's hired to be
a middle manager of 700 people in six disciplines. That's not a function. Everyone there is
expected to be a craftsman of something. I had a sort of -- my background is in design, user
interface design, so the closest thing I had to that was that. I'm a designer. So until our team
had a full-time designer, I did the UI design work. That was my craft. But almost everyone at
the company has a craft and that explains a lot of the autonomy, a lot of the trust. Everyone
sees the tangible contributions that everyone else is making. There's no one who's job it is just
to make a schedule or just to send e-mails or just to manage distribution lists. Yeah?
>>: What was the largest team size that this scaled up to?
>> Scott Berkun: Now it's the company is almost 200 people, the company. And there are
teams that are, while I was there the largest team was what's called a happiness team. That's
some of these sort of, I thought they were sort of corporatey, you know, using rhetoric to cover
up, like whitewashing. The happiness team was a support team. Happiness team was one of
the largest teams. There were probably 12 people, 15 people and as it got bigger they divided
into sub teams, which is normally what you would expect. What will happen when that team is
50 people, or a hundred people? Who knows. How much of this culture will survive when
there is a little bit more hierarchy? I don't know. I think that they'll fare better than most
cultures will because of how much they diminished that from where they started from. It's also
built into the culture that leadership, my role that I have as team lead, is a role not a job. So it's
expected that those roles would change. That happened to me; right before I left I stepped
down as lead and I just became a designer, which I thought was fascinating. In the history of
teams I don't know of that that ever happening, the lead guy stepping down and becoming,
now reporting to one of the people he used to manage. That's just built into the culture of, it's
more of a role than a profession. Yeah?
>>: How did compensation work? Was it transparent, was there any sort of weirdness
around…
>> Scott Berkun: Compensation was weird, not a lot of discussion about it. The upside is that
there was not a lot of interest in it. Like I mentioned before, when I asked my team how well
are you doing, the main reason people have an answer for that is because they want to know if
they are getting a raise or not. They want to know if they can buy the new car or the new
house or whatever. The quality of life trade is part of why people apply there in the first place.
They don't have to relocate. I can't say how many, but certainly 20 percent, 30 percent of the
employees at the company can't relocate either for family reasons or for health reasons, so the
fact that they can have a job like this at a premier company is just a godsend on its own. Then
the fact that they can control their hours, how often they work, those freedoms is part of the
trade. They're taking the job for those freedoms and it tends to -- at least my experience there
was it made them less interested in these concerns about -- they're paid well. They're paid
industry averages, above industry averages, but it's not the focus. The focus is on the work and
on the freedom that they have to live their lives outside of work. Not everyone wants that.
Some people want to get a raise every month; they want to buy a bigger house and they will
find the culture probably doesn't fit that because it's just not the way that people are
motivated there. Yeah?
>>: You talk about clarity and trust and how you built trust in the team. How do you build
clarity and keep both the crispness and the transparency?
>> Scott Berkun: Good question. I don't know. The question is how do you keep clarity. You
do your best. I don't know. That was a challenge for me. Great. I came up with these two
objectives, clarity and trust. That's, you know, it's free to use those words. [laughter] It's free
to walk around. I am Mr. Clarity and Trust. Here's my clarity ray, beshuu. [laughter] You know,
like every decision you make has to, you hope, in the eyes of the people who you’re working
with help them do their job better. I don't know that I can give you a magic answer. I think that
once you earn the respect from people that they think you're good at making decisions, which
is a kind of clarity, and that you're trustworthy that you accumulate that over time. You can
then ask for more trust and then if you fail, they are more willing to forgive you because you
built up this reputation in basis. The question of clarity is a question about how do you think
well; it's a much bigger question than I can answer. Yeah?
>>: One of the things I [indiscernible] people to make friends, socialize with people day by day,
do things. One, do you think this culture attracts people that perhaps don't [indiscernible] as
much or are more introverted, and perhaps the second point do you think that these are
people that do work for WordPress either miss that aspect or find that it's an advantage they
can dispense with that energy [indiscernible] activities?
>> Scott Berkun: So the question is how do you, this gentleman is saying that for him part of
the advantage, one of the things he likes about work is that there's a social network that you
get from that. You get coworkers to go to lunch with, to go to happy hour with. It's built into
your job, and not built-in here. How did that work? It's another trade-off that, well, there are
two things here. I think most people can guess that there is going to be less of that unless you
want to drive 700 miles every morning to go have coffee with someone, so people know that
and people like you who have strong feelings about that would probably never apply. Even
among the people who accept the job, and I felt this when I joined oto, that you don't get that
for free. You don't get the social network for free. Also, being online I showed you IRC, Skype
and the P2s, the blogs, no one is going to notice that you are depressed. No one's going to walk
by your office and go hey, Sally. Are you okay? You're acting a little different today. No one's
going to do that. They don't know. So there's this layer of just basic social interaction that you
don't get for free, totally true. And there's no compensation for that. I think that I learned that
I could get some of that just by, I had to be outgoing though. You have to go on IRC and say
hey. I just showed up to work today. There's a little bit you have to do to invite people then to
give you some of that back, so I got some of it. I did feel like I was on a real team, real project.
The book talks about this a lot, how we build camaraderie even though we were a thousand
miles away. It can be done, but it's definitely different. And most people who I talk to who had
been there -- it takes about two or three months to adjust to having a job where you don't get
those things for free. You have a job, you do, but you still got to find some other people to go
to coffee with. Co-working space is one answer and a lot of people@WordPress.com use them.
Do you guys know about co-working spaces? That's the, there are other people who are weird
like you and took a crazy job at a crazy company, but you're in the same place so you can talk
about how crazy your companies are.
>>: [indiscernible] a little structure or…
>> Scott Berkun: It's subsidized. At least it was…
>>: I mean is there like, you know, [indiscernible] official workspaces are for like people who
have strange jobs just like we are all at Starbucks.
>> Scott Berkun: No. Co-working spaces. It's very popular and trendy even in Seattle that
there are these places that you rent out a desk and so that's what I'm saying, at
WordPress.com, a lot of people, I don't know how many. Maybe one out of three, that's where
they'd work. Where they had a desk they could, where they could go and get that if they
wanted to. It's very common. The number of freelancers we have today, part of that remote
working number I showed earlier, the number of people we have who through their laptops,
that's how they work as freelancers, writers, designers, marketers, consultants. The co-working
thing is still on the rise. There's tons of spaces in Seattle that are just offices for coworkers. It's
crazy. Yes?
>>: How do they deal with a situation where a certain role isn't needed anymore or somebody
for whatever reason isn't able to get their job done anymore?
>> Scott Berkun: So the question is how do they deal when a role isn't needed anymore or
someone isn't doing their job. The role isn't needed anymore, given how they've been able to
hire, they hire people who have a craftsman but are versatile. These are not people who have
master’s degrees in anything. These are people who are independent consultants and so they
tend to be a jack of all trades or T-shaped is the fancy management term. It should really be an
inverted T, where there's one skill that they are really deep in, but there's a bunch of skills they
have basic proficiency in. So it's sort of like hiring a basic contractor for your house who's like
super good at roofing, but he can probably fix just about anything. He won't be the best guy,
but he can do almost anything, so most of the employees are like that, so when a project dies
or goes away, there's usually some other project that needs some of their skills. The
performance thing comes up in the book and there's definitely people who are not good
performers. Any environment once it's more than like three people you are going to have
people that are going to think that other people are not performing well. That's just the way
that it goes. It's just human nature. I've found that because of how organic even these team
structures were, that the people who were not performing well were much easier to navigate
around than most places I have seen. Because there's not this entrenched power structure and
it's all a service that anyone can update the code to or design things for and it's based on an
open source project where people are moving stuff around all the time. If we had a situation
where there's some developer who is supposed to be doing something and didn't do it,
eventually we would nag and nag and nag and eventually one of my developers would just go
and do it. The culture doesn't have a lot of turf lines, or they are certainly much softer than a
traditional company would be. Yes?
>>: You mentioned early on that people on your team didn't have a metric of gauging how well
they were doing their jobs. How did that evolve over time and was there a metric created while
you were there?
>> Scott Berkun: Yes. What a great question. The question was I mentioned when we first
started I asked my team how good a job they were doing and they said I don't know. And he
asked how that evolved over time. So I thought that was a primary way, a primary function I
could provide once I earned their trust. If they didn't trust me who cares what my evaluation of
their performance is. So I had to earn their trust first. So by the time the team was about six
months old it grew by a few people I started having one on ones, magical idea. One on ones
with them where I would talk about, give them feedback about what they were doing well,
about what they could do better. It was informal. It was done in Skype. Sometimes we would
use e-mail for that because we found that they would give more dedicated time to actually
having that discussion, but it evolved organically and it was something that was, there was
mutual interest in. They wanted that feedback. As a team they wanted to understand how am
I contributing and what else can I do to improve? Yes. So I am out of time, so I can say this. I
think I'm supposed to stay and sign books. I would be thrilled if you bought a book, so I could
sign it for you. But if you had a question for me that we didn't have time for and you think
about it later. My website has my contact info. You go to scottberkun.com. Go to contact.
Send me an e-mail. Just mention that you saw me speak today, so I won't ignore you
[laughter]. Yeah, say I was in the audience. What about blah. I promise I will answer your
question. I might not answer it today, but I promise I will answer your question if you get in
touch with me. So thank you for listening and I hope you check out the book. [applause]