Gretchen Anderson on Writing

My guest today is Gretchen Anderson. Gretchen spent the first part of her career consulting with world-renowned design firms. More recently, she’s led design and product teams at various companies, including PG&E, California’s largest energy company. Currently, Gretchen consults with clients to inform their product strategies and improve their team collaboration skills. She’s now written a book about collaboration, and in this episode,​ we focus on how she managed her information during the writing process.

Listen to the full conversation

Show notes

Read the full transcript

Jorge: So Gretchen, tell us about yourself.

Gretchen: Well, I’m a product designer by a background. I worked for a bunch of consultancies like frogdesign and Cooper, and most recently have been on the client side. I was recently at PG&E, which is the energy utility here in Northern California. And while I was there, I really became interested in the topic of collaboration because as designers we get. Training in how to collaborate. I mean our work doesn’t really come to fruition, if we don’t collaborate with engineers and product managers and the like but I noticed that others sort of speak in praise of collaborating and but their practice of it seems to be like get some people together shove them in a room and cross your fingers. So I wanted to write a book to capture for a general business audience how collaboration works and give them some real practical tips and techniques and really kind of the realpolitik of collaboration. Because at the end of the day, it’s really about people.

Jorge: That sounds fantastic. How does information play into this, into both writing a book and collaboration?

Gretchen: Well, I think to start with how it works in collaboration, as I was doing research and talking to people — which I can share more about — things that stood out to me beyond sort of the obvious, things that we as designers know about. Oh, I don’t know divergent thinking and getting people to open up and generate ideas. It was really that collaboration is about people and that people need to understand one another and really have trust. Which requires opening up and can kind of sharing personal information with each other or not. Not like a PIN code, but being vulnerable with one another came up a lot. And then the other big thing related to information was the idea of having really clear objectives and really taking the time and everyone sort of says that but I noticed that we often skip over the step of sitting down together and saying very clearly what do we know? Know what where are we starting from? And what are we making guesses about and what are we trying to achieve in some kind of structured way? Because otherwise people kind of go off and running and if you aren’t clear about where you’re headed those interpersonal dynamics that become really challenging and make collaboration difficult will just tear you apart. Now when I think about collaborations that fail it’s not that like, oh you release something that ends humanity. It’s more that the collaboration sort of disintegrates and everyone’s left with a bad taste in their mouth for working together and they kind of retreat back to their silos where they can control things. And so now the information around what do we all know? And what assumptions do we all have — and acknowledging that if you’ve done a good job of getting a diverse team those are likely to be different and potentially not in alignment at least at the beginning. And then the last thing I really discovered is this, you know, for people who are kind of in the room collaboration is one thing but often collaboration also involves stakeholders who are interested in and accountable for a collaboration, but they’re dropping in and out and you’ve got to be able to keep them apprised of what’s happening and using storytelling techniques is really what I discovered to bring them along. I can’t talk much more about this but we’re kind of hardwired to understand the stories and I think when I’ve seen collaborations struggle and had this experience myself and sort of the Groundhog Day: “I already told you this stuff. Why don’t you remember? We had a meeting last month.” And realizing it’s not enough to just say information; you’ve got to make it stick for people.

Jorge: It sounds almost like the the book is like a manual or how to guide for people who behave as curators of these collaborations; that act to kind of bring together these disparate threads. Is that a fair assessment?

Gretchen: Yeah, I definitely focused on those who would be shepherding the collaboration because someone’s got to do that and I feel like if I could reach those people that would go a long way. I mean one of the things that inspired me was watching executive who I really admire and respect try to pull off a big reorg and how about this lead up about wanting it to be a collaborative thing and wanting people’s input and then with 10 minutes left to go in a meeting putting up a solution and saying, “any questions?” And it’s like oh no, I think I could have helped you.

Jorge: Yeah, there are do’s and don’ts to the to getting that rolling right?

Gretchen: Hmmm. There’s some low-hanging fruit. The title of the book is mastering collaboration and for those who really do want to master it there’s a lot there and I think there’s also just some quick things you could do to make it go better in the meantime.

Jorge: I’m very curious about this term used “shepherding the collaboration” and I just want to suss out this parallel that I’m seeing between the person who shepherds these collaborations in organizations and you as an author who are shepherding this subject because I and I’m kind of just in this period of disclosure. I’m one of the people that you interviewed for the book. And the sense that I that I got in our conversations is that you have a structure you have a set of themes and topics that you want to explore and then you are kind of curating these conversations with people who can help flesh them out and I’m curious if a if there is a parallel there and b, if you can tell us a little bit about your process for doing that and keeping track of those threads.

Gretchen: Hmm. Yeah, I mean I did. So on the topic of shepherding, I do think that you can all you can do is lead the horses to water. There’s no forcing a collaboration because again at the end of the day, the point of a collaboration is you’re trying to solve a complicated problem that you need diverse perspectives on and so it’s, you know, not enough to even just get the diverse perspectives, you’ve got to make the room for them to come out and be heard so you don’t have an embarrassing situation or you know terrible outcome where you just didn’t see something coming. We see tech headlines like this all the time, you know, the recent “Facebook is letting Netflix spy on you” situation is sort of, did somebody think about how that was going to play out? If someone found out about that. But you know, in terms of how I dealt with information in the book, I started with what I thought was a super clear all-encompassing outline. And I thought oh, I’ll go talk to some people who I know both do this and do this well, as well as people who do it in unusual non-product contexts. So I spoke with filmmakers and ER doctors. And as I did that, I noticed, you know, I was learning new things which was great and sort of the point of pulling them in I realized and you know many people have joked with me and I wrote a book about collaboration on my own. But I really did do it with many people like yourself who I interviewed and people who reviewed copies of the book and all along the way, I was learning new things and having to fold them in so, you know, I think in terms of how I did that. I was sort of naive at first. I think I even spoke to you early on. Uh, so the who has written books. And you said oh no, you got to get your notes under control and I was like no yet another control. But what I found is, you know, I needed a single place to put them I tend to be a notebook person, like I like to take notes by hand and I have lots of cute little fancy notebooks, but that was not exactly scalable and so I ended up kind of having this massive Google doc where I was adding everyone’s notes in and and things I was learning and then I could even while I was interviewing people kind of flip to someone I had interviewed previously and get people to tie things together. Because I tend to rely on my memory for that and my kind of intuition for that even as a product designer, but I think the thing that’s different about a book is scale. You know, I’ve designed really complicated systems and I try to be able to keep them — the system mostly — in my head because that’s the goal I want for my users. But a book at 200 pages… I just found the scale to be kind of overwhelming. When I got some feedback back out I’d have people say, “you’ve already said this.” I think, “oh did I say that?” I found myself needing more structure.

Jorge: How did you do that? How did you because I can relate to what you’re talking about. There’s this kind of like going off into the weeds and and putting down all the ideas on paper and then there’s this kind of top level view of what the overall structure should be. Did you come up with good mechanisms to keep zooming back and forth between the two or how did you deal with this problem?

Gretchen: Well, I’m I had a digital sort of outline that I would log, like any outline, my top-line thoughts in but I think the scale broke down at the details — like here’s the story level that I want to tell — “is this story illustrative of this point or that point?” — is where I started to lose track of it. At some point I eventually had to kind of… And I was doing this at home or I don’t have a whiteboard! It was really crippling. But I do have lots of windows and so at one point I did bust out the sticky notes and you know had the kind of medium-sized ones and one color for chapters and smaller different colored ones for main points and the stories that would buttress them, so that I could create that kind of map that I could see all at one time. And that interestingly happened kind of late in the process, maybe like three-quarters of the way through. You know, I will start kicking myself like “Gretchen, you know that you could have done this earlier!” And I find myself taking notes for next time. Although I’m not sure there will be a next time! Writing a book is hard. But I think that I probably couldn’t have done it any other way. I started out with an outline, I changed that outline to be something that was looser so that I could fit everything. I was learning into it, and then I needed to kind of remix it again to make it something that people could follow and not just have it be kind of a laundry list of stuff I learned.

Jorge: It sounds like there’s a combination here of you working in your computer — in this kind of digital information environment — and these outlines, the structural constructs for your book kind of broke out of that and literally kind of went out onto your physical environment. And knowing that you have a family as do I and — so you live with other folks — and I’m wondering how your using the physical environment that’s part of your information management strategy played out with your family. Were there issues around that?

Gretchen: Sort of. I mean, I definitely took over half of the dining room table. My husband was a little like, “Okay. When do I get the table back?” You still could have referred to it as my my “pile.” I have piles of stuff there. I also watercolor paint, so I have all of my analog materials sort of taking a part of the dining room table. But I was trying to be pretty considerate of cleaning stuff up the end of the day, both so that everybody didn’t have to live with my total mess but also because I didn’t necessarily want them like messing with it. I think writing a book is an interestingly intimate thing and even when I first sent out a copy for a review, I had to wait until I was ready to do it. You know, one of my maxims is to share early and often for collaboration, and I could found I could only do that with very few people. I just wasn’t ready and even talk to friends about it and it start to give thoughts about ideas they had and I would find myself getting frustrated or upset because I just couldn’t hear it at that time. And so I did try to clean my stuff up at the end of the day and keep things organized. My children were definitely interested in the whole topic. That is one of the things that inspired me also write this book is that they, at their school, are taught to collaborate because the school acknowledges that this is a 21st century skill. So I also spoke with teachers there and but you know, they would come in and say, “Oh, I see a writing about trust mama at school say this” and so it was a dialogue starter. Although I wasn’t always open to that dialogue in the early days.

Jorge: It sounds like a lot of that hinges on the subject of the book. You mentioned as an aside that you don’t know if you’re going to do another one, just because of… I’ve been there, there’s there comes a point close to the end of the work where you’re like “never again!”, you know? And you never say “never again,” right? But the thought that came to mind is you also said that you desperately missed your whiteboard and what I’m reading from that is that if you were to take on writing books as something of a part of your identity and part of your life, perhaps you would want a dedicated physical environment where you could do this or you could take over the place and put your ideas up on the walls.

Gretchen: Yeah. I am a real analog person. Even writing, I find that that motion of the hand is what gets my brain engaged. And so even the first time I make an outline, I’m often doing that by hand. And I love whiteboards because — again, I like to be able to fit everything in one canvas that I can take in at one time. And I don’t think I’m alone in that. I’ve designed robotic surgery suites and I’ve done genetic analysis equipment. Like I’ve done really complicated things, but I think the goal is: you should be able to grok the system in one go. And so, having the dedicated space would be great. I think being able to write from home was nice because I could do it kind of early before my kids were up or I could do it for at least an hour a day and make sure that I did it even if I didn’t go somewhere. Also on the topic of information, I tried something out because I heard people on Twitter talk about dictating their books. So I tried. I would go for a walk and do speech to text on my phone. And that was an interesting way to get a real rough first draft. There were definitely times where I’m like, “Huh, I hope that wasn’t a brilliant point because that got real garbled!” But It was a cool way to generate ideas because your editor brain cannot get involved. You know, you’re walking and talking. It’s sort of natural to just let things flow and then go back and edit that. So there was some virtuality to that but that also led me to, “Did I already say this point?” Because I didn’t have a visual record.

Jorge: It sounds like you’re looking for ways of bridging that analog- digital divide. You mentioned the dictating into the phone and also the the idea of using stickies and white boards, and I’m curious about how you turn that more analog stuff — these brain dumps that you’re talking about — how do you turn them into t ext that you can send to an editor, a publisher? What’s that process like?

Gretchen: Well, generally I would just transcribe Post-its into a digital outline and then work through that outline. Something else I learned about writing a book is that it doesn’t happen in a linear fashion. At least it didn’t for me. I would start say, “Okay, my goal in this week is to do chapters 2 and 3” and I would find myself 3/4 of the way through chapter 2 and then jumping into chapter 5 to take some notes and then back to chapter 2 again and then on you know… So it did have like almost like a mini recursive loop running through it. Some advice I got early on from a pretty serious writer friend was, “Hey, just get to the fifth version as fast as possible.” And I remember thinking like, “Fifth version? That crazy!” But if I think back I probably did make five passes through everything. Just not in order.

Jorge: When you say passes you’re talking about like sitting down and writing chapter level text?

Gretchen: And editing. You know, you get one version and then you go back and you turn it into… I thought maybe by my second or third time through, “Okay. Well, this is pretty solid.” And that’s when I shared it and that’s when I realized, “Oh, no, I still have more to go!” And probably went through everything about two more times to get it to a real final state. So it really was about turning that visual map into something that was linear, even if I wasn’t going to work through it in a linear fashion. I think it was actually you who suggested to me that I use Scrivener, which I started to try to use a little too late in the process because they do have a sort of virtual version of my Post-Its. But it just didn’t… I couldn’t quite make it work with the 200 pages I’d already written and importing them and all of that but I think, again, If I did this again — not doing this again! — I might look at a tool like that.

Jorge: Yeah, Scrivener. The reason I suggested it is because you had told me about this wall of stickies thing, and Scrivener has a view of the text that looks kind of like a cork board with index cards that you can move around, and moving them around changes in the structure of the text. So it’s a it’s a way of having your outline and your text kind of together.

Gretchen: Yeah, and that would have been helpful. Because what I did was essentially the cut-and-paste version of that.

Jorge: Did you take any photos of the stickies before you took them off the walls? Or was it just the transcription into an outline?

Gretchen: I just transcribed them. It’s interesting, I probably should have. Note for next time!

Jorge: Well, the reason I’m asking is because I find… When I’m doing stickies, the stickies go into dimensions; you have vertical and horizontal. Whereas the outline is kind of a list that has a hierarchy to it, but it’s a kind of linear list. Is there anything lost in that transcription from a two-dimensional​ matrix onto a linear outline?

Gretchen: Sort of. But because the book was going to end up linear, it was really just the fact that you can’t really see it all once it’s in… You know, I would use Google Docs mostly. They do have an outline view. It was helpful. And I made good use of headings to help me be able to jump around. But I think the hardest part of working linearly is to get from chapter to chapter 9 as a bit of a track. You have to walk for a while in a way that you can kind of just glance over when it’s all mapped out. But at the end of the day because a book is linear, I just force myself to do that and then to make sure I had everything organized against whatever out when I was working against at the time.

Jorge: Having been through this process of working on books a couple of times… For me, I find myself like having to shut off other parts of the world so that I can concentrate on the subject. I’m wondering, to what degree did this project intrude in your ability to remain engaged with other sources of information. Was that an issue at all?

Gretchen: Not really. I mean, I do have a good ability to focus when I want to. W hat I found is I couldn’t do it for more than maybe two hours a day at most. During crunch time, I was getting up into the four or five our range. So that was a real stamina pusher for me; I’m a great starter, not the greatest finisher. But I would say, like many things in my life, I tackle this by… I just make myself do something for some limited amount of time where I can be focused, and then when I’m not focused I take a walk, go to yoga, do some paying work, sit on Twitter, or whatever other things I have to do. And I try not to sweat it so much.

Jorge: So you can mode switch, is what I’m hearing. Do find that helpful to actually getting progress on the project?

Gretchen: I do. Even since college or high school I’ve known this about myself. I can work incredibly hard for some couple or three hours of time and then I’m done until I’ve given myself time and space to reboot.. I’m a real morning person, and so I noticed in college I couldn’t pull an all-nighter. I would get to 10 or 11 o’clock and be like “I got to go to sleep.” I tried it a couple times and was like, ‘I can do more in two hours in the morning than in six hours all night, and it will be higher quality.” So I just tend to take that approach to productivity.

Jorge: You said at the beginning of the conversation and — well, I think you said this — that writing was something of a lonely activity, or it can seem to be that, right? And then there comes a point where you have to share what you’ve done. I’m curious about this idea of sharing what you’ve learned. I know that you recently started writing in Medium as well, and I was wondering if you could tell us about that and if and how the project the writing the book has influenced that decision to start sharing there as well.

Gretchen: I definitely live my life out loud on social media. When I was writing the book, however, I wasn’t doing that. I think I tweeted one day, “Oh my God, I think I’m writing a book!” And Jason Mesut replied, “Oh, you should write it in public!” No, it’s a great way to be motivated and get feedback and I was sort of horrified at the thought of that initially. But I got what he was saying. And so I thought well, I don’t think I could write the book and public — like I’m not going to publish it as I go — but maybe what I will do is publish select parts just so I can do that kind of getting feedback. So I did that. I blogged a few pieces of it and I didn’t actually get as much detailed feedback as I had expected. I mean I was sort of bracing myself and in some ways hoping for people to just come at me with “Oh my God, you’re totally wrong!” And “This is stupid, and here’s why!” Because then I would know those arguments ahead of time and I could defend against them. But instead what I got was kind of more encouragement, which I think Jason also pointed out that I would get. It was a nice motivation. It’s also interesting how much easier it was for me to… You know, I was cutting and pasting a book thing and then turning it into a blog, but there were still some editing I had to do because the tone of a blog is so much different than a book. And it was so much easier for me to write in that “bloggy” tone, where I felt like the expectations are perhaps lower in terms of… It could be more casual and I didn’t feel like I had to have everything footnoted to the nth degree and that sort of thing. So there was sort of a call-and-response there of doing some stuff, getting some feedback, feeling motivated, and then bring it back into the book and moving on at some point. Although I just ran out of energy for that and just said, “I’ve got to write the book and put the blogging on hold.”

Jorge: Do you think you’ll continue doing it when once the book is done?

Gretchen: Maybe. I do… Again, I find myself like, “I’m not going to write a book again.” But like, “Oh, I do have this other thought I want to share. Oh, maybe I should blog that.” Just haven’t actually picked up a pen to do that. But I do this with my paintings; I’ll post the decent ones online as a way to have an audience. I was a performer growing up, a singer and a dancer and an actress, and so there is a part of me that that likes having an audience. So I think blogging is interesting for that in a way that the book audience is so far removed. That’s a completely false construct; they’re not really that different of activities, but in my mind the immediacy of in the audience make a big difference for blogging.

Jorge: I can’t wait to read the final version of the book. When is it coming out?

Gretchen: Should be out in June of 2019. It’s called “Mastering Collaboration” and it’s how to make working together less painful and more productive.

Jorge: This is a very underserved subject in my opinion, and just having read some of the things you’ve written so far, I think it’s going to be really good in a real contribution to this. So where can folks read more about you follow up with you, Gretchen?

Gretchen: I have a personal website at gretchenanderson.com, and that’s got a way to get in touch with me. I’m also gretared on Twitter.

Jorge: I want to encourage everyone to visit your site and follow you on Twitter and be on the lookout for the book. I know I am. Are there any other things you’d like to share with us? Any projects that you’re working on that our audience might be interested in?

Gretchen: Not really. I mean, I’m working on work. I coach people in collaboration and storytelling. So if that’s a need that you have feel free to get in touch with me.

Jorge: They can they can do that through your website as well?

Gretchen: Absolutely.

Jorge: Well, fantastic. This has been a real treat, Gretchen. Thank you so much for your time, and I’m looking forward to reading the book

Gretchen: Likewise. Thank you so much Jorge.