Leadership Lessons from Supporting WordPress Global Events

My friend Andrea Middleton has an incredibly complex job leading a diverse organization of volunteer event organizers located around the globe in her role as Dot Organizer for the WordPress community.

A job she does with grace, thoughtfulness and caring since 2011.

The events are called WordCamps and there is typically 1-2 going on every weekend throughout the year around the world.

In fact there have been over 1,000 WordCamps, in 75 cities, 65 countries and 6 continents since they started in 2006.

I got to interview her this week and in this recording, we talk about a number of topics like:

  • Leading volunteers
  • Managing conflict
  • Keys of effective conference organizers (“hosts”)
  • and more

Originally my thought in interviewing her would be centered more on the practical tips on running in-person events … however it turned out to be a much more AMAZING discussion on leadership.

The WordPress community, one I’ve been a part of since 2006 is better for having Andrea’s leadership in it.


You can learn more about WordCamps here.

You can learn more about Andrea on Twitter, at WordPress.org and Make.WordPress community section.


Full Transcript (Lightly Edited)

Cory: 00:01 Hey, I’ve got my good friend, long time friend, Andrea Middleton to come on. She is so experienced in some of these areas we’re going to talk about in a second. I said, I just want to just ask some questions of you. And I’m gonna let her talk more about her specific role, what she does, but we’ve known each other for, we’re trying to go back, like scale back. She started her position in 2011 so I know at least in that time period we’ve known each other and worked together in various capacities with her role in my past as a participant in the industry and the conferences she puts on. But she has an incredibly complex job and I told her this last week, I said, you’re in like in the middle of gunfire, sometimes, and I think you’re in a hole and you pick your head up a little bit and that’s kind of a way a visit.

Cory: 00:55 But it’s not really that the way you lead a, the role you do with community leadership, with all of these, they’re called ward camps happening across the globe. There’s one or two happening every weekend to know, cause I used to have the calendar updates on my phone. Now’s as word camps plus a in WordCamp, a little conferences for WordPress geeks. WordPress is software that powers a third of the internet or so. And this awesome lady is the person that wrangles all these volunteers from, I mean 65 plus countries, 75 cities, six continents. I mean, WordCamps are all over the globe. So I thought who better to talk about community leadership than my friend Andrea? So thanks Andrea for taking some time to talk to me.

Andrea: 01:42 Well, thank you so much for the invitation and uI’m very uncomfortable with,uhow important you made my job. So, but it’s a, it’s a real honor and a pleasure to have work with this much complexity and uand constant new interesting dilemmas and uand, and kind of ideas,ubecause I really thrive on, on learning and variety and,uI will say the WordPress ecosystem and community has been kind enough to give me pretty much uninterrupted opportunities to grow over the past eight years or so. So that’s great.

Cory: 02:28 So you can characterize it so well, but I was thinking as you’re saying that, there’s never a dull day for you in what you do in the work.

Andrea: 02:39 I mean, we have a, a huge, and I should be clear, like I used to be just me back in the day, but these days as a, the WordPress open source projects, community programs continue to grow. I’m lucky enough to work with a huge number of people who contribute to our programs, both our monthly meetup program as well as our WordCamp program. And the word camps are the annual conferences organized by the community leaders that, that organize our meetups. And we have some people who are paid full time to work on the programs and we have a huge, a huge group of really dedicated volunteers who give us as much time as they have available, more time sometimes than I can believe. And so these days I I’m certainly not alone and I think our, our programs are stronger and more more impactful than ever.

Cory: 03:45 Absolutely. What do you remember those days when it was kind of you scrambling and and try to take over? I mean, there was so many things going on at that time and then over time you have helped with your team. You’re so gracious to give credit to your team organize and, and make them for the benefit of the organizers, the conferences and the participants. And I’ve seen it happen. I’ve been to at least, I think 45 of these conferences over 11 years, 12 year period of time. And they have gotten better. And and it’s, it’s such an interesting conversation around all of this because like we’ve kind of said volunteers from different cultures we’re talking about before we started the recording and how culture affects, you know, what kind of drink you serve, for instance. So I’m gonna Oh, before I dive right in with the questions. So what is your official title?

Andrea: 04:40 My title at the company that pays me, which is Automattic, which is a company behind wordpress.com and with WooCommerce and a bunch of other great products and they, they pay me full time to specifically work on the open source project. That is WordPress and wordpress.org. My title at that company is dot organizer because I organize at WordPress.org. We are whimsical in the technology sphere, but yeah, that’s my title.

Cory: 05:14 Okay. So I wanna I want to pull some to that for a second. You, you are a loaned executive more or less from a for profit company to, to run all this. And by the way, I wanted to say that was something of inspiration for our own nonprofit. So we had, we had, we paid our executive director is loaned executive to work in our nonprofit similar to how Automattic does that so graciously. Okay. So thank you for that. And I did see that you were the dot organizer and wonder where that came from, but now you’ve explained it and that makes sense. Within geekdom and autumn automatic. Matt came up with that title himself. I was quite pleased with it. So hold onto it for awhile. That’s awesome. Okay. So within

Andrea: 05:58 All this, as things get impact, but first and foremost, how’d you get started in this role? You know, this role came to me quite out of the blue. I was recruited by a a friend and a colleague that I had known for well, gosh, since we were both in our twenties and canvassing for Greenpeace together in Portland back in the 90s. And she at the time at the time she went by the name Jane Wells. She changed her name to Jen Milo. And that’s the name she uses now. And at the time, back in 2011, she was, I think, gosh, project managing Corps overseeing the, the design of WordPress core and then also creating the community programs that we have today, creating the seeds of them. And she needed somebody to do one of those three full time jobs. And she reached out to me.

Andrea: 07:01 And my background previous to this kind of phase of my life and working in technology included a number of different professional areas. I have been high school and junior high school teacher. I had been a salesperson for a beverage distributor ship. I had been a marketing and HR professional in the construction industry. So I kind of, I had a, a wide range of course, my activism back way back in the day. So I had a wide range of experience. And she recruited me and trained me quite intensely for about the first year. I was a WordPress user and I loved WordPress, but I, I didn’t know a lot of the stuff that made our makes our, our community so interesting and idiosyncratic. And so I have a lot of, like, I still think back to like all of the stuff that I learned over that first year in 2011 and have a lot of empathy for the people who are just coming into WordPress and like learning where people are sensitive and where people just kind of assume everyone knows the same stuff and all that stuff.

Andrea: 08:17 So, so that was, so I, I was hired to basically implement the program that she had created. And I did that on my own for about a year. And the program was a way to kind of give some more infrastructural and kind of ideological support for people who are organizing these conferences, word camps that are WordPress based conferences that are organized, staffed and managed exclusively by volunteers all over the world. And yeah, so it, it’s a lot of working with volunteers. It’s a, a lot of international considerations and it’s a lot of you know, if you’ve ever been involved in organizing a conference there are some mission critical things that you really have to pay attention to and get done at a certain time. And so supporting people in that and a volunteer role has been really fun.

Cory: 09:25 I know I keep saying this, but it’s such a unique, you know, it essentially, there’s people listening just to hurt that what you were saying. It’s volunteer, ran lead tickets are around 40, $30 in, in typically participants get lunch, an incredible lunch coffee or whenever caffeine beverage, you said other choice and access to a wealth of talent and, and experience as speakers and then the genius bar or happiness bar. Yeah. Some

Andrea: 10:00 Kind of technical support volunteers, volunteers there too. Yeah. And I mean, what’s, what’s really kind of mind blowing to me about WordCamps and to a lot of other people is that all of our speakers are volunteers. And of course all the staff has volunteers and all the organizer are volunteers. And it’s this really really inspiring, I think it kind of model for what people who come together with a common goal can accomplish. And it’s interesting you were asking me a little bit about earlier when we were chatting about my work with the community because when I took this job, what I really thought it was, is at, and the way it was kind of explained to me was like, Andrea, you’re here to keep the organizers organized, right? Like to like, and to make their jobs easier and to shield them from risk.

Andrea: 11:06 And to make sure that the attendees that they’re serving are well-served to help them prioritize what, you know, where money should be sent spent on all this stuff. And that’s what I really took on as my, my mission was like keep everyone organized. And my understanding of my role has evolved a lot. And then my understanding of what the, of what our volunteers role has has evolved a lot. And it’s been, I was thinking about it this morning. It’s, it’s kind of happened in parallel. And a really interesting way because a couple years into the job I realized I’m not actually here to organize people because we have, because it’s volunteers, people kind of move in and out of the program with a lot of regularity. And so if you’re strategic, you have to plan for attrition, right? You have to, it’s, it’s otherwise you’re left in the lurch and with WordCamps and, and any enterprise volunteer organized and run enterprise that has a financial component like you, it really is dangerous if you just, you know, throw $20,000 at something and just cross your fingers.

Andrea: 12:30 Right? So so that resilience and engagement has been a real something that we really have been working on for a long time. And I had this epiphany about like two or three years in. I ha I’m hardheaded. So if you told me to do a job, I will just keep doing that job until I figure it out. About, you know, I’m not actually here organizing organizers, I’m training organizers. I’m, because we have developers and designers and SIS admins and all sorts of people. Like you don’t have to have a lot of experienced to organize our events. You have to have a passion as, as GSFI likes to say, we don’t call the qualified, we qualified the called. And so we bring people in who have the passion and want to achieve the mission and the goal of bringing WordPress enthusiasts together to make connections and inspire them to do more with WordPress.

Andrea: 13:31 And then we train them how to do that. And so last slide. Oh, I get it. Now. I’m a trainer and the program shifted a little bit for me and like the, the mission I was setting with our kind of meta volunteers, people who are like helping do the admin work and supporting all of our volunteers that way. That shifted. And then Corey, then, and this totally ties into your work, I realized again, like again, about two years ago, I were not training event organizers. We’re training leaders because the, the work of creating a community and our events are not just a single unit. Like the events are an ends to a meet at, sorry, a means to an end. Where we use the, the, the kind of team building exercise of creating a meetup or a word camp as a way to bring the community together. So the mission of our organizers isn’t to create the best event possible. And I knew this from way back, but it hadn’t clicked for me until later that the mission of those organizers is to use the event to create a space and to create a shared mission, their local community. And so what these people come. So our volunteers come to us with, frequently with very little leadership experience or with leadership philosophies that vary widely and they come into our space and what we’re training them to do is lead in a very specific way that’s strongly influenced by open source. Yeah.

Cory: 15:16 Well, okay, so this is so interesting and I’m going to get off a little bit, but yes, the, the, the fact is it just hit in my head that I would suggest any young person that’s interested in leadership go volunteer for an event like this because you do have leadership is so interesting. You know, we can’t, as managers, CEOs, directors, whatever our title is, we can’t force anybody to do anything. We have to lead them. And what’s so interesting, the parallel to my background, the closest thing I had to something like this would be church work. I didn’t, I was about six years in church ministry work servers on staff and you worked with primarily volunteers. While I always knew there’s buckets of time and energy that people had. Absolutely. They had to be passionate too. They had to care about the work and I couldn’t go in and be a jerk. I couldn’t go in and tell them to do something. I had to inspire and move and try to share, you know, walk with them to do things. And I think, you know, just any young person looking to do leadership at some points you go and volunteer for something like this because it is a melting pot. Like it is the perfect laboratory to learn a proper I I would say proper leadership skills.

Andrea: 16:31 I would also say proper leadership skills because the thing about working with volunteers is positional authority is practically nonexistent. Like P and N, anyone on your team can walk at any time and, and may do so inadvertently, right? So they may end up walking because of a family tragedy or a life transition or something else like that. Or they may just not have interest anymore. Right. And so, I feel like anyone can rely on positional authority to try to accomplish goals from a leadership position. But as you, and, and probably a lot of the people that you work with know positional authority is the weakest tool in your toolbox. And so learning how to motivate and how to inspire volunteers to work on a project that isn’t for them. It’s for other people.

Cory: 17:35 You’re not getting paid to do their own time and probably even money, gas and stuff.

Andrea: 17:39 Oh, yeah. Yeah. There’s, there’s a, there’s that component too. And yeah, so I, that is the best leadership training that I can think of because it teaches you the most important parts. If you have that part, once you get the positional authority, it’ll, you won’t even need it. Like an important, and there’s so many different levels in there, right? Like you can lead a little group. And, and that’s the other thing that I think is particularly exciting about the leadership training that we’re, that we’re providing through community programs is an open source. Open source has this kind of philosophy of leadership that doesn’t rely on a title that it, that strongly benefits the great idea and also the level of commitment you have to the group. And training people to focus more on what benefits the group than what benefits themselves is another really important component to fantastic leadership.

Cory: 18:49 Yeah. What a, what an amazing, I did not even know where we’re going to kind of get here, but this is the magic. This is the special stuff and why I wanted to talk to you. You’re absolutely right. I think too often we get promoted into a position where it’s like, okay, here’s the title. And then, you know, the way I’ve seen it, and I’ll admit to, to be in here too, is when you get the title, you feel like it’s a bat, right. That you can, you know, bully people. Honestly, I mean the, it is that, but when you’re coming up from something like this, this is why I said my, my experiences in the church work before I started the company of other themes. So invaluable because I had to learn that everybody is a volunteer.

Andrea: 19:33 Yeah, yes, yes. Anyone can leave your organization that anytime and, and again inadvertently. Right. So like that, that resilience training of like sometimes the most pivotal person on your team for this launch might get sick or something like that. But yeah. Yeah. That the, that I, some of the stupidest mistakes I made in my first year or two in this world, we’re, we’re relying on some kind of a positional authority, which is such a culture. No, no, in the culture of open source. So, yeah.

Cory: 20:07 Yeah. Well, and I think that’s the transition within business and in leadership in general is, you know, it’s not command and control. It’s, we’re all volunteers and we better work together. And by the way, you’ve got me segwayed on this. I love it. But I want to ask you some other questions. The other thing that, that is, well, I forgot my thought, but anyway, that’s so we could spend the rest of the time talking about this and now we’re going to have to come back.

Andrea: 20:35 I have one more thing before we move on. Yeah. So then, cause Cory, I have had another in the last year, like probably I could do a talk on like the three jobs so far. My next my most recent kind of, I won’t say epiphany, but like when it really settles, like when you know about something and then all of a sudden it’s settles into your brain. That thing is, the other thing we’re training our leaders to do, our community leaders to do is to train new leaders. And that is like, I’ve, I’ve really struggled with learning that. And, and how, how to see my success and my as, as a reflection of the work that the people that I’m, that I’m working at with can accomplish. Right. and then also, I mean, that’s just such a, I haven’t quite figured out a way to, to package that for our community of like not only do you need to work on, on growing yourself as a leader, but at the very beginning of that process, you should also be training the next generation of leaders throughout your tenure.

Andrea: 22:03 Yep. And in our role here. And and that is tough because frequently we still have the problem with our volunteers that they don’t realize that their position as a leadership position, we have so many people in open source and, and in but even in the community programs specifically who don’t realize that their position is a leadership position. And so and, and, and the problem with that for one thing is your vision is too short, right. Your focus just on the task and not on the mission. But then also the problem is, is your touch is too heavy. If you don’t realize how powerful your words are if you just think that no one’s listening to you and I, if anyone’s going to listen to you, you gotta like make a fuss. Or that even if someone does listen to you, they won’t do anything about it.

Andrea: 23:06 That the quality of your dialogue with the world and with your community really is different, right? But if you’re aware of your power, if you accept the idea that like, Hey, I’m going to say something and it’s going to make people think so I’m going to really think about how I say it. Like that’s, that’s a [inaudible]. That’s one of those kinds of second year of, of leaders kind of lessons that I’m really trying to figure out how to get into the first year. And that’s, that’s gotta be so tough.

Cory: 23:46 But again, another great takeaway for leadership in the business world or any other facet of life or we’re leading other human beings is that we need to be training that next generation that if we’re not, I’m multiplying our own leadership and a good and healthy way. We’re doing a disservice to the people that follow behind us. And I think that’s a core. And so, you know, particularly with WordCamps, I know I think it’s like two years, you could be the lead organizer for two. You rotate off. When I first heard that, I’ll be honest with you, I was like, but all the institutional knowledge that person goes away. But there is such a bit when the benefit that you’re saying is you’re also training new leaders as they are pulling in and step up. And I’ve seen that throughout the United States in particular as for the word camps, I’ve been to where one year was this person, three years later I come back and it’s a whole new regime and the, the feel of the camp is so different because that new leader or leaders have infused their own kind of DNA. And values.

Andrea: 24:44 And there are some misconceptions in there. Like some people think like you can be the one lead organizer cause we do, I mean we do have one position authority position because a, the central organization needs one point of contact, right? So there’s a lead organizer and you can do that role for two years in a row without, until you switch out. But that leader organizer can still stay on the team and and then can come back again in next in and subsequent years. But then also we have a mentorship program that once you’ve done your two consecutive years as lead organizer, you can grow into a different kind of leadership position within the central organization where you are mentoring other new organizers coming in. And, and helping grow them through basically coaching and mentorship as you know, and that, and, and then your influence and your, and your leadership can really spread around your region or even around the world depending on when you have time to talk to people. So, so yeah, we, we were really worried about that, like losing the institutional knowledge. And also just, you know, you grow leaders and you’re like, bye, see you later. Now that keeping them in to kind of help multiply that, that that guidance and that support has been,

Cory: 26:06 Okay. We kind of backed into some of the answers to this question, but I want to ask it specifically is, so I think about all this and I go, it’s hurting cats. Like, you know, if you gave me, you had said one foot foothold group and when you talk about volunteers with, by the way everybody has an opinion, but in WordPress specifically, people would have a just take that up a couple of notches. And I’m, I’ll say that for myself too, but it presents this interesting leadership dilemma. So what are, what are some keys you’ve seen is from your job specifically to others in the organization? In the different camps and things about leading, leading people. And then we have this nuance too. It’s not just America. Yeah. Even the North Northern hemispheres. It’s the entire world now. It reaches across crazy just looking at all the last continents. Yeah. So, so what are some thoughts, what comes to mind when you think about hurting cats? A K leading volunteers and participants all over the world?

Andrea: 27:08 Well, we’ve, we did touch on the fact that in my opinion it’s the same as any. Well, I, the way I do it is the way I would do any leadership, let’s put it that way. Because in my ethical framework that it is simply the most ethical way to lead people. But you know, it is, so primarily the first thing I want to do is, is give people an idea of what they could accomplish as part of the whatever organization that they’re joining. Right. and try to be as clear as possible about what we’re going to ask and then what they’re going to get in response. And, and there is a huge misconception, not necessarily in the nonprofit sector, I think, but where like technology and nonprofits intersect, sometimes that volunteer work is unpaid on acknowledged. But the, you know, there are ways that volunteers get something back from their experience.

Andrea: 28:15 I recently wrote an article for our team blog about this on make.wordpress.org/community about the forgets of community organizing. And and, and laying those out as the context of like, here’s what we’re going to ask for you and here’s what you have the potential of, of benefiting from personally. Is is a great way to get started. And those gets, I sometimes forget one of them. One is impact, right? So like you’re doing this work and it has a benefit, the benefit that affects people that you care about. Right? the second is training is growth. You get the chance to gain skills in an environment that will not affect necessarily your M your, your [inaudible] your day to day job, right? So you can like, if you’ve always wanted to be a project manager and there’s no way to do that in your, in your job come on over to us cause we’ve got projects in the role and you can start, start, you know, learning those, those Ana in a sphere.

Andrea: 29:28 That doesn’t mean that your boss is going to get mad at you or something like that. Right? So that’s happening over here. And, and, and it’s progressive, right? So you can join you know, you can get small bites and then bigger bites and then bigger bites as it goes. Then certainly support. So being able to, you know, not, not being out in the desert by yourself, but having a network of people with experience that can help you identify ways to get past challenging situations or share other solutions. You know, your part, it’s that connection component. Right? and then finally in our program at least there is a safety aspect. Like we like no volunteer in our organization has to spend their own money on the on buying the badges. Or if they do, they’re reimbursed and they don’t.

Andrea: 30:29 We, we shield our volunteers from like tax liability and insurance liability and stuff like that through our kind of infrastructure. So like laying those things out of like, here’s, here’s how this transaction is going to go of you benefiting us with your opinions and your work and us benefiting you with this growth and impact. And then, you know, certainly creating a lot of psychological safety for people never hurts. But most of all showing people how they can both benefit others and themselves at the same time generally makes the program pretty sticky for people. Right. there are very few people who are successful in our programs that are not interested in the benefit for other people. We’re not, we’re not great. For people who are mostly motivated by personal benefit, we’re highly altruistic. So but yeah, that, that’s my in a nutshell.

Cory: 31:38 Yeah. You kind of get to understand that when you give without the get you do actually get a lot. Yeah. Yeah. But you can’t have the get as your first primary and [inaudible]. Some of my dearest friends are WordCamp organizers all years. I’ve met some [inaudible] friends at word camps. I have never been an organizer. I’ve told you this years and years every probably every year that we’ve known each other. I’ve never wanted to be an organizer. I want to go support organizers, [inaudible] help, whatever that is. But I, Oh, it’s such a, a tough role to be an organizer because you’re given so much of your own self. But the best ones I’ve seen feel like they’re hosts, that they, they, you know, are behind the scenes and love. I see their smiles when they just see things happening and no good things are gonna happen in the space that we call WordCamps.

Cory: 32:36 So I think that’s so special. Okay. So you know, one nuance too is that we’re talking about a community with WordPress community, which is pretty much virtual. You don’t see each other every day face to face perhaps. But this venue is something that I think I even read in your bio before this was that it is providing what you just said this earlier, a space to meet face to face, which is really, really special. It’s a lot of people that are spread out that probably don’t even know who each other are coming to the space to meet face to face and the value of that. Yeah. What, so what have you seen with that? What, what is that special value of being able to,

Andrea: 33:19 Well, not, not to toot my program’s horn and in an annoying way, but I really feel strongly that the amount of focus that we have in WordPress on in-person gatherings sets our project apart in a, in an amazingly integral way from other open source projects out there in the world. The emphasis and the amount of kind of infrastructural support we’ve given community events is unheard of throughout the open source world. We provide so much more support in WordPress than, than any other group does. And I think it really shows, like we, we are a group of passionate people who care a lot about sharing our opinions and like all of us like being right. So like throughout open source, right. You don’t come to open source. If you are cool with just complying with somebody else’s ideas you come to it because you have a thing that you want to get done and then you maybe stay for more things.

Andrea: 34:36 But, and, and so open source communities tend to be fairly high conflict but, and, and WordPress’s is no different there. But the level of grace and dignity that we have in our conflicts compared to other communities is unusually, I think, unusually high. And I lay that completely at the feet of our in person events program because you get people together in the same space and, and the quality of their interaction changes and that carries over into the online sphere. And are events welcome people are our funnels into WordPress con contribution. And so, and so the behavioral expectations that we set at our in person events, that’s how humans work, right? You come into a group, you check it out, you’re like, okay, how do people here, how do people interact? What’s okay, what’s not okay? And the, and human brains change based on what the expectations of the group are. And so when we set that expectation for highly inclusive events for, I mean swearing is very unusual in our space. For for respectful communication, for focus on collaboration and transparency. When we set those expectations in our in person events that follows people onto the internet and provides an ameliorating effect for that kind of troll behavior that we so frequently see when people disagree online.

Cory: 36:21 Oh yeah, that’s, I can see that. Totally. you know, I’ve seen comments that people are made because you’re anonymous or so you think on the lab and that you would never make in person. And I totally see that effect in you know, I know cam specifically have been have benefited the software WordPress as a whole because of the in person events. Okay. So you brought up, you brought up something that I wanted to ask you because I think again it’s this word WordPress is the community is not immune to conflict and perhaps there is a lot more conflict. And then I shared this online that it’s just like most families were dysfunctional in, in, in ways, and we have our fights and conflicts. But you know, I’d love to hear some thoughts that you have about dealing with conflict as humans just in the world together. We’re going to have conflict. But I’d love to share that cause I think that’s such a mint. It’s part of leadership too, is I’d love to hear some thoughts that you have on, you know, dealing and managing conflict.

Andrea: 37:29 Oh yeah. So this has been a really rich space for me, this role. I I don’t like fighting with people. And I don’t like my family history isn’t high conflict. And so like there was a big learning curve for me with like interacting with people online with grace and dignity. And, but something recently kind of shifted the way I’m thinking about this. I heard a talk by [inaudible], someone who works on the 10,000 year clock project. And this is a project creating a clock that will last for 10,000 years. And, and, and it really shifted some of the, gave me some interesting stuff to chew on as far as like, what’s the scale timescale that a lot of are working in when we’re doing this work. You know? And he mentioned something about how to antiquarians or historians, everything is on fire all the time because everything degrades, right? Like metal rusts thing like entropy is happening all the time. And so the way he described it was everything is always on fire. And so you can’t keep things from being on fire. You can just optimize for the rate of the burn. Right. and and I, I frequently think about the, the discourse in, in our professional community as, as sometimes we have like fires come up. So that really got my attention when he was like, everything is on fire. I was like, no, I thought I put some stuff out.

Andrea: 39:38 But, but, you know, and, and, and a lot of people that I really value in this organization, like we talk about how we run into the fire, you know, like the, our, our mediators and our, and our a lot of our leaders in WordPress seek to deescalate and, and find it, identify what the problem is that’s causing conflict and go into it rather than run away from it. But that idea that just like, what if we don’t, what if we don’t expect there never to be conflict? What if we just optimize the rate of burn? Hmm. Yes. Fascinating space for me to explore right now. I’m just really thinking because I mean, I’ve been doing this work for almost nine years. Yeah. There’s, there’s never been a time that someone wasn’t upset about something. And not because everyone’s a jerk, everyone is not a jerk.

Andrea: 40:40 Like is, is we, we have big fights and, and it’s not because we want to hurt each other. It’s because people deeply, deeply believe that they’re right or that they’re protecting someone that needs protection or that they’re, that, that the thing that they want to have happen will benefit a large number of people in a way that’s important to them. So like the motivations are almost never malicious, right? A lot of it comes down to like, are, did it get personal? Did we identify the person as the problem instead of the behavior or the, or the issue? Right. And that will escalate a conflict into a place that can make it difficult to come to that optimal rate of burn. Right. or there are a few other kind of escalating factors that can get up there. But like, and so I’ve, I’ve been doing some reading about conflict resolution and mediation lately, and I think the, that kind of, that rate of burn that opensource wants to land in is like, we disagree on the issue, but we agree in each other’s value in, in the organization.

Andrea: 42:02 Right. And when I say the organization, that’s pretty loose when it comes to open source, right? Because just people could just weird, we are, there are no walls in this community. Anyone can come in and drop their opinion on you with, with no context or history or a shared value establishment or anything. Right? So you’re, you’re literally working in the open, Oh yeah. Out in the open. Right. but that’s still an organization, even if it’s not very organized. And so like if we, if we can just identify like, Hey, we all have value in this organism, the WordPress organism and, and we’re always going to disagree but not about everything. Then that can kind of bring that level of, of burn down to a place that we can still work together. Right. and then the other thing that can of kind of kick us up into an unacceptable rate of burn is like misunderstanding or a place where, again, it gets personal, like we identify like you as a person or a bad person and something like that. Right. Or, or somebody thinking that, right. That misunderstanding either of facts or what the other person is trying to accomplish or what the other person thinks of you can lead to some pretty painful conversations and emotions in our [inaudible]

Cory: 43:39 I’ve seen by and large too is when he really pushed down to it. No matter if I agreed with the point or the perspective or not, is by and large, what I’ve seen in this particular community is it comes down to people that just care. Like you said, they happen to care about something. We were just kind of discussing how we got reconnected again was you know, I paint, I paint you on the something just, just to say you’re doing an awesome work and everything in it. It was this issue in, in, you know when you push down to it, it’s people that just care like, yeah, I think you hit it on the head, which is care about something going on. But it’s a unique perspective too because pretty known that empathy, you know, how insane this person is mad. As long as we don’t take it personal, we’ll be inflammatory about things and talk about issues and not character and things like that that if can look through each other’s eyes and sees perspectives that we probably all somewhere in there. What similar things.

Andrea: 44:37 Yeah, and that’s my process. Like before I respond to a criticism on the internet, I find my love for that person. I hold onto it when I’m even, no matter what they’re saying about my program or a decision I’ve made or a decision somebody else has made that I agree with or whatever, like I can’t let myself respond until I find our common ground. Even if it’s just on my part of saying, okay, this person is very angry or very disappointed because of a thing that I empathize with like this because we have a misunderstanding and they think that something bad is happening. I also don’t want that bad thing to happen, but I find my love for them and then I work out of my love for them.

Cory: 45:29 That’s so good. Finding that common ground, finding that care, humanity, whatever that is before you respond. That’s a good word for like any relationship, which is, I know some of the people that might be throwing barbs. I go, Ooh, you’re a special person, Andrea. Find that.

Andrea: 45:52 But it’s true. Like I, I, I really like, I used to think like back in the early days I was like, well this person wants to hurt people and I continue to meet people and none of them have ever wanted to hurt someone. Yeah. Never. I have never met anyone in this organization who I won’t say I will, I will take that back. I deal with a, a fair number of code of conduct reports. And so very occasionally I will meet someone who isn’t intending to hurt someone. And in those cases we do have to settle limit because to create our inclusive, safe space, we have to make it very clear. Like you can’t hurt people here. So that’s it.

Cory: 46:38 This is back to your, you know, the fostering psychological safety and physical safety, by the way, within these events that you have to have boundaries. And I think that is something that I have seen the code of conduct in particular for, for these that has been more and more visible and vocal, which is good thing of saying no, this will be a safe space for people so that people can come and you know, be inspired and get help and support and things like that for what they’re working on. Absolutely. OK, so practically speaking, the last couple of minutes we have,

Cory: 47:15 I’m curious, you’ve seen and helped run some of the biggest and then events that I’ve ever been a part of and then across all these wide space of helping organizers run events and all types of locations, cultures and setups. I’m curious some practical takeaways you might have for running a good

Andrea: 47:38 Oh yes. Absolutely. yeah,

Cory: 47:41 And I told you, I heard from one of the organizers, the best practice was make sure you have coffee and good wifi. That is so awesome. But our community that, those two things are super …

Andrea: 47:53 I tend to quibble about the wifi. I think that you can have a great event with no wifi, as long as you tell everyone that there’s not going to be wifi. People can’t be surprised by that. But yeah, I mean, so our organizers are tasked with the job to to create an event that will connect WordPress enthusiasts, inspire people to do more with WordPress and then contribute to the open source project. And there are myriad ways to accomplish that goal. But in general, what I like to see in an organizer or an organizing team is starting with empathy. Hmm. And starting with empathy for a person that you are not. So taking a look at like as many use cases as you can imagine for your attendees and planning for that experience and really kind of taking yourself back to your beginner’s mind or your stranger’s mind and thinking through.

Andrea: 49:03 Like, if I am going to an event where I know nobody and I don’t know much about this tool, what will make me put me into the frame of mind, where I can take advantage of connecting with people and where I can get inspired. Because what we know about brain chemistry is people don’t get inspired or aren’t willing to make connections unless they feel safe and welcome. And so that like, providing people the experience where they can feel safe and welcome is that’s just like, it’s table stakes, but it’s really hard to do. So like I encourage people to think about lots of different kind of backgrounds think about what they would like if they’re going into a different space. I would, I really encourage organizers and leaders in our community to go to events that are not in our ecosystem to get us both, to have that kind of empathetic experience of like, I’m a stranger help. What do I need to do here? And have that experience, but also does steal ideas cause we’re open source and yeah, like we look around and we’re like, Oh, I’m working that. But and then also know your own power. Like realize that like you are as an in of of an event, you are the host. And you are creating a space that you are inviting other people into. So act like a host responsibility for people’s experience plan out how you want them to feel and interact. I mean, part of the coffee thing or caffeinated beverage that is appropriate in your, in your culture is like there’s a huge amount of cognitive load when you are sitting in, in a place surrounded by strangers and getting new information. And so having something that people can add or some kind of frequently warm beverage that has a little bit of wake up power.

Andrea: 51:14 But also like not just coffee for people who can’t drink caffeine. Right? So like something that might be warming for a cold conference room or a cold conference venue. Something that you can use to, you know, to, to so you know what to do with your hands. If you feel awkward and you don’t know where to be. A place where you can go. Like the coffee thing is, is a functional and multiple levels. You run into people at the coffee station and you have a common experience cause you’re both trying to doctor your beverage. So now you have a thing that can start a conversation and make that connection. Like there’s there are lots of benefits to that, a warm beverage station, certainly. And then you can just extrapolate that out to the entire conference experience. Realizing the importance of food and, and that eating together creates a family and creates a community. And what it does to someone if they come to the table, if you will. And there isn’t anything they can eat. You know, like how, how, how welcome do you feel now, friend? Not very so like identify, making sure that the food situation is is inviting and welcoming and inclusive. Realizing the importance of having food, you know, like all of those things are, are really valuable to achieve that goal. I’m, I’m, I rambled. Did I answer?

Cory: 52:49 Oh, that’s awesome. I love the heart of it. I, I’ve long thought, and this is why I think we’re kindred spirits, is you’re driven by values and we’ve had these discussions over and over over the years, but I know at the heart is that you have these strong values and centered on people and it comes through when you talk about empathy and the host is creating this space, like you said, inviting people into it and connection and stuff. And I think that’s one of the reasons why camps have been very successful and girls much that they have. Okay. One, one last thing and we’ll let you get on with your day and I appreciate your time. Proudest moment part of the, the job that you do.

Andrea: 53:34 I’m terrible at this question because I am relentless about always pushing myself to the next thing. And one of my biggest weaknesses in my career is that I don’t stop to celebrate. My, my wins. But I gotta say one of my proudest moments recently was creating and delivering a workshop that I I gave to the people in my company who focus on the open source project that I’m really excited about bringing out to the broader community about conflict resolution online and in text and, and just realizing that all of these painful, sometimes painful learning experiences that I’ve had helping our community members find ways that they are more alike than they are different has resulted in some content and some training material that I’m, I’m really excited to kind of bring out into the world. I mean, my, my proudest moment, it’s kind of like asking someone about their favorite book or a wine person about their favorite wine. I have so many, but yes, certainly the, I, I take pride every single day and the way that

Andrea: 54:55 The leadership training and the empowerment that the WordPress project and the WordPress community a team engages in every day makes me really, really excited and proud. Especially when I think about how that will then spread out through the world. That’s what makes me excited to get to work in the morning and choose. Okay. Well, thanks so much. Where can people find you online? I am on Twitter sometimes I’m at A N D, D, M, I, D, D,L , E, T, O. N. and certainly in wordpress.org Slack, and also on our team blog, make.wordpress.org/community. And happy to let anyone know how they can become more involved in our programs.

Cory: 55:53 Awesome. Thanks so much, Andrea. I appreciate your time.

Need Quality WordPress Hosting? Check Out Liquid Web

The First-Things-First Disclosures: I fully believe in everything I’m saying here, or else I wouldn’t share it. My company, iThemes, is a partner of theirs (through our iThemes Sync Pro product). My wife, Lindsey Miller, is Liquid Web’s new partner manager, and I’m very good friends with Chris Lema, VP of Product, and A.J. Morris, Product Manager. Also, there is an affiliate link here. 

Simply put: The state of WordPress hosting mostly sucks. Since 2008, when I started iThemes, WordPress hosting has gotten worse and worse, and only recently have I seen many of the companies I once recommended start to get better.

If you’re looking for quality WordPress hosting … meaning you care about your site, and use it to build your business or organization … I believe Liquid Web has one of the most compelling offers around for a number of reasons … here are mine:

  • They’ve defined what hosting support should be — They don’t just offer 24/7/365 support … if you need help and ping their 800-number or live chat, you’ll actually be talking with someone who knows what they are doing, and aren’t trying to sell you something. The last time I check, 200 of their 250+ support team are Red Hat-certified. So Heroic Support isn’t just a tagline, it’s core to who they are. As I walked through one of their offices in Lansing, Michigan last year, you could just see and feel the commitment to a client-first, support-first culture. It’s part of their identity. I think few can actually claim they do “managed” support like Liquid Web can. Their NPS score, which puts them in a VERY rare category is a result I think of their focus on customer support.
  • They own their hardware — This is significant and rare and means they can control the whole environment as they aren’t relying on someone else. I’ve seen it (well, through a window!). If they have an issue, they go fix it … themselves.
  • A WordPress hosting platform that’s only getting better and faster — led by my friend Chris Lema, their WordPress hosting platform is killing it every week with new features that benefit you and your site. So whatever you buy now will only get better.
  • iThemes Sync Pro comes with it — We’ve partnered with Liquid Web to offer every WordPress hosting customer of theirs our awesome site management tools.
  • Just plain ole good people — Beyond my wife, Chris, A.J. and others, I’ve also met most of their Executive Team, in fact, some of them have been in our home in Oklahoma City.
  • Don’t just take my word for it — You should also read what Shawn Hesketh of WP101 and WordPress developer and Lynda.com instructor Carrie Dills have said about Liquid Web’s offering. (They give much more compelling technical reasons that I didn’t share here!) See also: SEO Bootcamp’s Giveaway, Kim’s review, Tara’s review, and Joe’s review too.  And I’m confident you’ll see more and more people recommending Liquid Web soon.

Go Check out Liquid Web’s Managed WordPress Hosting here. 

The Key Missing Ingredient to Effective WordPress Websites

So many times in my own freelancing web design experience, I’ve found that I’d get a website done for a client, only to wait for content. And wait. And wait. And wait.

It’s a sad fact about most websites. They simply don’t have good content (or content at all) to properly market and sell their products and services. Their content does not get their site indexed and then ranked for that content in the search engines, which is essential to drive leads and sales for their businesses.

For many web designers, content is the biggest frustration. Their projects are completed, but left waiting on the client to provide the content.

From the client’s side, the website owner’s perspective, writing is tough.

Admit it: We all might think we can write the content about our business or organization, but when it comes down to it, we don’t have the time and energy, or perhaps even expertise to do it well. After all, if you’re a dentist, or a real estate agent, the expertise you might be paid well for isn’t writing web copy.

Getting a good WordPress website is the first step to growing your business online … but content is what drives the action, making that vehicle come alive and drive and grow business.

Content marketing is all the words, images, videos, etc that inform, educate and sell. And it’s absolutely essential for a good effective website.

That’s why I’m excited to share that my wife, Lindsey, an experienced entrepreneur, has started a content marketing business called Click Start Creative.

If you’re a web designer who wants a partner to help their clients with content, or a website owner stuck in neutral with content marketing, go check out Lindsey’s new business today. She can schedule a phone call to talk about your business and your goals and then translate that into an action plan to get your business growing online today.

As you might expect, I highly recommend her.


Why BackupBuddy Gold?

In the past I’ve been openly against “unlimited” and “lifetime” options, particularly in WordPress. (Don’t get me started on hosting.) You can check out my previous post on Sustainable Business Models in WordPress here for background.

This week though, we launched BackupBuddy Gold … which grants customers lifetime updates to all current and future features of BackupBuddy, our extremely popular WordPress backup, restore and migration plugin that is now 4 years old.

So you might be thinking, “Did you change your mind?”

Not really.

And I’ll unpack that below.

I’m sure there will be plenty of discussion, debate, and [gasp] criticism, so I thought I’d do a post sharing some thoughts about why we’re rolling this out. (I’m sure there will be comments that I don’t address here, so I’ll try to answer in the comments or by updating the post.)

First things first — we did NOT roll this offer this new package for BackupBuddy because sales were slow, declining or even plateaued. iThemes is financially healthy and strong, BackupBuddy is doing great, and our team of 20+ people is looking toward our next 6 years in business!

OK, so here are some answers to the question you probably are wondering about, “Why open the box?”

1. The real issue with unlimited is ….


Support is extremely expensive.

Particularly with what we’ve seen supporting commercial WordPress themes and plugins. That’s what I said about “compounding debt” in my previous post. (I use the word “support” about 15 times in that post.)

For instance, if someone buys the first BackupBuddy tier (2 site updates and support) and has to post in our forum, we’ve likely lost money. Compound that loss if Dustin, our lead dev, has to weigh in on the issue, which he does regularly.

That’s why we capped support at one year for BackupBuddy Gold.

For this conversation (one particularly debated within WordPress), it’s all about support.

Thus, BackupBuddy Gold does not give unlimited, forever, or lifetime support. We capped it at one year.

2. Renewal rates

We have some very loyal customers (who renewed every year and who we also offered generous discounts to for this offer — THANK YOU!). But the majority of people did not renew over the last four years of BackupBuddy.

Now we’re getting paid upfront for the equivalent of what we would have gotten paid over several years of renewals.

As the veteran and leader in the backup and restore space for WordPress, now those loyal customers will get a great deal to keep using BackupBuddy to back up their sites.

3. It’s a much higher price point.

We didn’t roll this out at $80 … we rolled it out at an introductory price of $297. That can and will probably change.

At $80, we wouldn’t offer one year of support plus lifetime updates. We think we’re giving it away now … so I couldn’t imagine doing it at a lower price point.

BackupBuddy has grown so much over the years and become such a more awesome product. Offering Gold at this higher price is more than justified because BackupBuddy is going to get even better and even more valuable over the years our customers will have access to it in the future.

4. We can always shut Gold offer down.

(… and of course grandfather in customers who bought it.)

We could be wrong. This could be a flop and a failure. And I’m ok with that.

That’s the thing with learning. But if we don’t try, how will we know if it’s good or bad? Without action, it’s purely an academic pursuit.

And I’m about action.

I’m tired of getting hung up in what ifs. We did plenty of that before launching this. We evaluated and debated this for several weeks and decided it was worth the potential risk to offer.

But I’m not afraid to fail. To step into the light and see if our thoughts and ideas have merit.

That’s why I reserve the right to be wrong about all the above and change my mind about any and all of this. 🙂


[Hat tip to Syed Balkhi for helping me think through offering what we now call BackupBuddy Gold.]

What Does the Future Hold for WordPress?

Reflecting on 10 years of having WordPress in the world (anniversary was yesterday), I just published a post titled The Future of WordPress and gave 6 keys and challenges for how this awesome software can stay relevant.

Six keys to the future of WordPress:

  1. Blogging
  2. Mobile
  3. Identity
  4. Security
  5. Freedom
  6. You

And here are 10 ideas for how you can give back:

  1. Help get someone started on WordPress.
  2. Write a blog post about why you love WordPress.
  3. Teach someone WordPress web design.
  4. Join or start a WordPress Meetup group in your city.
  5. Attend and volunteer at a WordCamp.
  6. Proudly wear your WordPress swag everywhere.
  7. Start a business around WordPress.
  8. Contribute to the WordPress documentation.
  9. Report a bug or submit a patch.
  10. Let your voice be heard.

And be sure to check out my full post here.