I was surprised by, how quickly people really got on board. People really understood and they really wanted this. They needed this resource. And so they bought in and they supported it, and they put their information in it. And they started using the search tool. It was kind of glorious. - “JJ” Jessica Reeder
Jessica “JJ” Reeder was there, with Darren Murph, at GitLab, early pandemic, when suddenly the entire world was interested in their masterpiece, the GitLab Remote Work handbook. When the world was thrown into remote and distributed work over a weekend in Spring 2020, and answers to many of the questions were contained in the tens of thousands of words, and thousands of pages in the GitLab remote work playbook.
As JJ recently reminded, that work started a decade ago. She and Darren are no longer at GitLab, and the Pandemic is 5 years removed and fading in the new rear view mirror. Good news, eyes on the future.
The future is AI-powered. Good news, the same behaviors, attributes, and best practices that powered success in distributed teams, are the same required to increase team AI adoption.
The long held dream of a high functioning organizational knowledge platform, is finally, almost here?
Please join me in welcoming “JJ” Jessica Reeder to the Work 20XX podcast.
JJ and team are implementing said knowledge platform in her new role at Upwork. As we discuss in this interview, it’s about the hard work, and everyone doing their part, that builds the buy in, and the data base, to dramatically improve the chances of success, wide spread adoption, and a significant reduction in the time spent searching for information.
Thanks again, JJ.
Editor’s Note:
Recorded 2025-April-29 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and the entire Running Remote team for collaborating with Work 20XX to capture these in-person interviews with the top minds shaping the future of work.
"JJ" Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX podcast with Jeff Frick, Ep40 from Running Remote
English Transcript
Cold open:
Okay, great.
So, I'll count us down,
and then we'll go
Wonderful
In three, two, one.
Jeff Frick
Hey, Welcome back everybody. Jeff Frick here. Coming to you not from the home studio, but Work 20XX is on the road, and we're down here in Austin, Texas. Working with the great folks at Running Remote to do a couple of special episodes down here if you weren't able to make the trip. And so it's been an amazing show, they've got a back to back. think two stages are going constantly every ten minutes,. Some new expert telling you more about remote work that you didn't know before. So we're excited to have our first guest. She's JJ Reeder. She is now the Director of Remote Organizational Effectiveness at Upwork JJ great to see you.
JJ Reeder:
Great to see you too.
Jeff Frick:
Effectiveness I don't know that I've ever seen effectiveness in somebody's title, I like it.
JJ Reeder:
It is a title. It is, it does exist. Org effectiveness is a thing. But remote org effectiveness is really what brings it to that next level. It's, not just about how to have an effective organization, but also how to do that in a distributed environment.
Jeff Frick:
Right So you've been doing this for a long time. We all know you back from the day when you and Darren were writing the original remote work playbook that we all use and share, and has been widely distributed. But your presentation just now, I thought it was going to be on playbooks, but you really kind of went a different direction on knowledge management. So how does knowledge management and leveraging AI and getting that information that's out of the company. How does that tie back to playbooks?
JJ Reeder:
Well, honestly, I mean if you look at the evolution of the company handbook, what GitLab was doing when GitLab and those companies really innovated the handbook. That was about ten years ago when they really reinvented what the concept of the handbook was. And it has been continuing to evolve ever since then. So what it's evolved into is a digital knowledge system. This is a living system of knowledge that's a key company asset, represents the knowledge of the entire organization. And so as we continue to have this conversation and as AI enters the picture, knowledge becomes a key company piece of infrastructure almost as an asset. And so we have to start thinking about it in new terms.
Jeff Frick:
Right. So I was just at the Atlassian show a couple weeks ago and they talked about 30% of people's time is basically looking for information, whether it's I know I have it someplace or I don't know if I have it, I’m trying to find it. And speaking about inefficiency, you recently posted about 47 million. Was it hours lost to searching for information?
JJ Reeder
This is a stat from 2018, actually from Panopto. They estimated that large businesses lose $47 million per year per business on average through poor knowledge sharing. And that was 2018. So that is pre-pandemic, pre-AI That's like ancient history for us. I'm sure that that number has gotten bigger.
Jeff Frick:
Right. So the vision of a unified knowledge base has been around forever. Information locked in, in silos, whether that's departments or laptops or PDF documents or presentations that I'm carrying around on my phone, have been around forever. How is it changing now, both as a combination of thinking about a playbook perspective as well as now we've got AI, and for AI to be most effective, it needs access to all those different data sources.
JJ Reeder:
Well, that's the thing. I think that's it. It's the different data sources. And that's really the challenge right now is that, knowledge can no longer be kept in a bunch of different places. You have to have a single source of truth more than ever before. And we were talking about this back in the handbook days, but but humans were able to sort of make decisions about, you know, which version of something was probably most correct. Or they could ask one another. As AI enters the scene and as we work faster and faster, it's really no longer possible to have information in a bunch of different places. And the new conversation is really about how do we make sure that we are giving an AI agent good information to work from? That means we need a single source of truth. We need to practice good information management. We need to know that it's up to date and accurate, because the risks are starting to compound the loss of effectiveness and efficiency is starting to grow. And more and more companies that don't have their information locked down are going to be left behind.
Jeff Frick:
Right? Right. Because of speed right, speed of decision making, speed of moving forward, speed of operation, speed is so critical. You talked about rolling this out at Upwork and trying to help people get the information not only in the departmental silos, but again, off their laptops, where a lot of information lives. And that's why attachments on emails are one of the many reasons they’re so bad. How did you kind of get a process going? What was your process to start to transfer some of that information to where it's more accessible? Well, so First of all, I think that Upwork was in a really good place compared to a lot of organizations because they had really done some of the foundational work to transform transfer the organization to digital operations. And so people were having a good practice of documenting things. But really, what was missing was a way to organize the information. So stuff was in just all of these different places. We had an LMS, we had a project management tools, we had a handbook, we had a playbook, we had all sorts of different things. And so really it was about we need to create a single place where there's reliable information. And then to do that, we had to decide what information was going to go into it. So we started just thinking about what information are people going to need to understand that we had to ask We went and had to ask every person at the company, what do you actually need? You have to make decisions about what information belongs and what information doesn't. It's a long process, but by working bottom up and actually getting that buy in and getting people to really understand what this system would do for them, that really empowered the transition. It made it possible, and it made it so that people were really ready to support it, ready to engage with it, ready to fill it with great information.
Jeff Frick:
Right. So it wasn't a new system, right? Was it? Did you pick one as kind of this is going to be the source of truth we're going to move it into or did you have, you know, better APIs into some of the other systems? How did you approach that?
JJ Reeder:
We picked a new system.
Jeff Frick:
Because you don't want another system or did you?
JJ Reeder:
No. We picked a new system.
Jeff Frick:
Okay.
JJ Reeder:
We deprecated old systems.
Jeff Frick:
Well good.
JJ Reeder:
So we picked a new system that had the features and functionality that the team was asking for. We did all of the research first. We said, what do you need? Then we found something that would hit as many of those boxes as possible. And then we deprecated the systems that were no longer serving us, moved all the information over, compiled it, fixed it, cleaned it up got people the information, the permissions and the access that they needed. And then we got rid of the old stuff.
Jeff Frick:
What was the biggest surprise in the process? What was the biggest surprise? Positive or negative I mean, because the other part you talked about is access. And in your presentation just now, you talk about some companies aren't real access friendly and there is governance and there is kind of a need to know type of basis depending on what the project is. So how did you how did you, what was some of the learnings when you were making this move?
JJ Reeder:
Tons of learnings. There's always learnings. You know, I think, actually, I'll tell you something that wasn't really what I expected but it was like a pleasant surprise, which was I, you know, I had come from in the past kind of having to talk to the legal team and the trust and safety team and really make the case for, like, why we need this new tool and why we're going to fill it with all of this company information, which could be a liability. And I was actually really surprised that they already understood at that point they were bought in and they were totally supportive and they just were like, whatever you need, we will run the safety checks on it, but we're ready to go. We understand the importance of this for the company, because what they understood is that the bad information is more of a liability than having your good information someplace where the wrong person might be able to see it. Having bad information out there is more of a risk to the company.
Jeff Frick:
Right
JJ Reeder:
So that was a really cool surprise, you know, and then I think I was surprised by, how quickly people really got on board. You know, I'm so used to living in this world where I'm talking about these things that seem kind of abstract. You know, it's very dry knowledge management systems, like, come on, like nobody's interested in this. But people I, you know, they really understood they really wanted this. They needed this resource. And so they bought in and they supported it, and they put their information in it. And they started using the search tool. And it was kind of glorious.
Jeff Frick:
That's great. So, one of the things that that Darren used to always talk about, one of my favorite lines of his was that all remote forces companies to be good at things that all companies should be good at. And knowledge sharing and the lack of the ability just to tap somebody on the shoulder to get the answer to a question is, is one of the great examples. And you talked about in your talk really digital first. And really it's another way to kind of think of that being digital first. Now with AI and the acceleration of AI, it makes a big difference in your position to go forward. If you are already maybe digital centric, maybe you're not quite digital first, but talk a little bit about how digital first is such an important component to being successful in this next couple of years is because of this is crazy AI thing.
JJ Reeder
Well, this is why I think that remote first companies as a group are going to be leading actually in the next wave of AI adoption because remote first companies didn't just embrace remote work or in order to embrace remote work, they had to also embrace digital communication, digital collaboration, digital connection. And they wrote everything down, and they figured out systems to transfer information and get it flowing throughout the company. And that is something that I think a lot of companies are still really catching up on, which is a lot of what I talked about in my talk just now. I think that remote first companies have this massive potential to really have a head start on AI implementation, and what I think we're going to start to see that come to fruition really quickly as these companies, certain ones, start to just leave the pack.
Jeff Frick:
So another great line Brian Elliott likes to use from formerly Future Forum Now doing his own thing is, is that the same management philosophies, practices, attitude that enable people to successfully implement distributed work, hybrid work, remote work are the same things that enable people to enable AI adoption. And we know right now one of the big enterprise challenges is AI adoption. Everyone knows they want to use it, they're trying to use it. But it's really interesting I thought that Brian pointed out because it's about agency, it's about risk taking. It's about getting outside the box, and it's actually the same behaviors that are going to support, AI utilization AI, you know, trial.
JJ Reeder
Absolutely. That's absolutely right. And it's more than that. It's not just about risk taking. That's a very important part of it. It's not just about thinking outside the box, though. It's being willing to do the hard, dry work that actually supports the execution. So you can have the big idea. But unless you do, what it takes to actually execute on that idea it’s just an idea. And I think that some of these companies really understand it is hard to run a company remotely. It is not easy. And so I think that some of these companies have already built the muscle that they need to sustain the effort to really move ahead in the AI adoption phase.
Jeff Frick:
Do you think the change in attitude is just because of the reaction of something like a ChatGPT to know that now I can actually like I can have a conversation with a computer and extract information that way versus kind of old school queries. And the complexity of trying to get information is that change the acceptance or excitement or willingness to invest in the senior team into finally the the dream of knowledge management that we've had forever and ever.
JJ Reeder:
You know what? I think that's so much a part of it. I think you're absolutely right on about that. And I actually had never really heard it put that way. So thank you for bringing that up. Yeah, I do they It is transformative, even for me to be able to have a conversation [Jeff] Right with ChatGPT And like have a discussion and share ideas and get feedback. And I think throughout the industry and throughout many industries, I think executives are really leaning into AI, which means that they're trying stuff. They are conversing with ChatGPT, and once they start to reach that level where they're having that transformative experience I think absolutely it starts to make sense. It starts to click. You start to see, okay, this is what I can do. But I also think that it's really easy for us to just accept what an AI tells us such as ChatGPT and to not really be super concerned about the quality of the answer that it's giving us. And there's a risk to not having good information underlying that answer. So it's a yes and no thing. I think that yes, it drives adoption, but I'm still concerned about that rigor that we actually need to have good knowledge inside of an organization.
Jeff Frick:
Right. Because there's the rigor, as you said before, garbage in, garbage out. And then there's the rigor in terms of the appropriateness of the return answer. I had a great interview with a guy, Charles Corley works for a company called M Moser and Associates, and their attitude is treat everything that comes back from ChatGPT as a junior colleague. A really smart junior colleague, a really fast junior colleague, one that never complains or takes time off. But you know, but I was like Charles, what about hallucinations? And he’s like, you have to check the work. So use it, as you said, as a thought partner. But at the end of the day, before you sign on the dotted line, you got to check the work.
JJ Reeder:
Absolutely. And I'm so concerned that that's not necessarily happening because it just feels so organic. You really feel like you can trust this answer. And I think that's another muscle that we now have to build.
Jeff Frick:
Yeah, it's really tricky if it's in an area that you don't know because if it's an area that you know not only can you see the hallucinations, but more importantly, you know the value of the hallucination is it material or immaterial. But if it's something you have no clue about and you just take it as gospel, you know, you can really get yourself in big trouble.
JJ Reeder:
That’s true.
Jeff Frick:
Okay, so last question. One of the hardest things and it wasn't directly in your talk is driving engagement with distributed teams, remote teams how should people think about, approach engagement. Because we know engagement retention is so so important. What's this. What's some of the secrets to keeping good engagement with remote teams?
JJ Reeder:
You know what I'm actually going to talk about this tomorrow.
Jeff Frick:
Oh, good. A little preview for all the local folks.
JJ Reeder:
It’s part of a session tomorrow It's going to be about engagement
Jeff Frick:
Dang, I didn't study my notes on that.
JJ Reeder
It’s like a lightning round of two minute talks. With a whole bunch of people.
Jeff Frick
Okay Um so. Well, you could take more than two minutes here. So go ahead
JJ Reeder:
So my quick spiel on it is that we for the past several years and maybe for a while now have been thinking about culture and engagement as something that is layered on top of the work that we do, right? So we think you go do your work, and then you go to an all hands or you go to a retreat and you connect with your team. But the reality is that's like less than 1% of the time that we spend at work. And actually we are collaborating with people in every moment that we work and If you don't think that's building culture, then you are wrong. So I think we need to really start thinking about building engagement and culture in the day to day work. For me, what that means is making work easy. If we have good systems that empower people to be effective at their work, then they start to enjoy their work and they start to enjoy the people that they work with because they're relaxed, they're showing up as more confident. They feel more possession of their results. And they start to really believe that it's possible to have a good work experience to do their work. They start to feel proud and pretty soon this is producing engagement.
Jeff Frick:
Love it. Well, JJ, it was so great to finally meet you in person. We've been LinkedIn buddies for a long, long time long time it’s great to meet you.
JJ Reeder:
Absolutely
Jeff Frick:
And thank you for the insight. Really, useful stuff. And finally, you know, is finally the dream of a unified knowledge management system in the organization Is finally almost here it sounds like
JJ Reeder:
I love it, I love it. Yeah. There's so much potential. Thank you so much.
Jeff Frick:
Thank you. All right. She's Jessica. Excuse me. She's JJ, I'm Jeff, you're watching Work 20XX on the road from Running Remote in Austin, Texas. Thanks for watching. Thanks for listening on the podcast. Catch you next time. Take care.
Cold Close:
We're out.
Thank you.
How fun Yeah.
“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX podcast with Jeff Frick Ep40 from Running Remote
© Copyright 2025 Menlo Creek Media, LLC, All Rights Reserved
“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX podcast with Jeff Frick, Ep40
Director, Remote Organizational Effectiveness, Upwork
LinkedIn
https://www.linkedin.com/in/jessicareeder/
JJ Reeder dot com
https://jjreeder.com/
Bluesky
https://bsky.app/profile/jjs.business
—--
Upwork Research Institute
https://www.upwork.com/blog/introducing-research-institute
—----
Select appearances
2025-Apr-29
“Handbooks on Steroids: In the Age of AI, Knowledge Management is a Make-or-Break Strategy”
Running Remote Conference Session
https://runningremote.com/ai-handbooks-and-the-future-of-remote-work-written-interview-with-upworks-jj-reeder/
2024-Jun-04
“Cultivating Culture in Distributed Teams with JJ and Charlotte”
Epoch Podcast
https://podcasters.spotify.com/pod/show/epochapp/episodes/Cultivating-Culture-in-Distributed-Teams-with-JJ-and-Charlotte-e2c97vuSpotify for Creators+1Spotify for Creators+1
2023-Sept-28
#171: To Make Remote Work Effective Requires Thinking About Others: Jessica "JJ" Reeder of Upwork
Wise Decision Maker YouTube Channel
https://www.youtube.com/watch?v=CKZSEVgcJ3s&ab_channel=WiseDecisionMaker
2023-Jul-25
“Inspired People, Inspired Places”
Orion Growth YouTube Channel
https://www.youtube.com/live/dk_O9jLvjhY?si=0BUbXg0tf8KRCScyLinkedIn+2Turn The Lens Podcast+2LinkedIn+2
—-------------------------
Other items mentioned in the interview
----------------------------
GitLab’s Guide to All-Remote
https://handbook.gitlab.com/handbook/company/culture/all-remote/guide/
Atlassian State of Teams
https://www.atlassian.com/blog/state-of-teams-2025
Panopto Valuing Workplace Knowledge
https://www.panopto.com/resource/valuing-workplace-knowledge/
2025-April-18
Charles Corley: Culture, Wellness, Visualization, AI Colleague | Work 20XX Ep34
https://www.work20xx.com/episode/charles-corley-culture-wellness-visualization-ai-colleague-work-20xx-ep34
https://www.youtube.com/watch?v=LkNGFqywW7g&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt
https://open.spotify.com/episode/30aXprLp2ccy966Ut3fxbC?si=ztzCBiR_Rh2M7YJEt9rbow
2024-Aug-13
Brian Elliott v2: AI, Experiment, Outcomes, Trust | Work 20XX Podcast with Jeff Frick Ep28
https://www.work20xx.com/episode/brian-elliott-v2-ai-experiment-outcomes-trust-work-20xx-ep28
https://www.youtube.com/watch?v=Iv6SwrHUmJo&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt
https://open.spotify.com/episode/53knlL5u3R5DNOfMCMMwlI?si=PD9FIeBhSfKBC-jsnYolhQ
2023-June-23
Brian Elliott: Connected, Effective, Workplace Future | Work 20XX Podcast with Jeff Frick, Ep15
https://www.work20xx.com/episode/brian-elliott-connected-effective-workplace-future-work-20xx-15
https://www.youtube.com/watch?v=rKiBzaLJ57o&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt
https://open.spotify.com/episode/77vADFHykJG60PgAVn5RRF?si=FGWUr_7jQlCMwNy1S1vEyw
2021-Dec-22
Darren Murph: Remote-First, Asynch Communications, Operating Manual | Work 20XX #01
https://www.work20xx.com/episode/episode-1-darren-murph
https://www.youtube.com/watch?v=2A8J6QTqZaU&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt
https://open.spotify.com/episode/7JksH1BNyNHTjzU6Ihvyje?si=cGZuoRDeSSOZNC1W1BsJCA
2020-May-01
All-remote GitLab offers advice and resources for life away from offices
By Mark Albertson, SiliconANGLE Media
https://siliconangle.com/2020/05/01/all-remote-gitlab-offers-advice-and-resources-as-companies-adjust-to-life-away-from-offices-cubeconversations/
2020-Apr-29
Darren Murph, GitLab | CUBE Conversation, April 2020
SiliconANGLEtheCUBE YouTube Channel
https://www.youtube.com/watch?v=SP7u0gYCHiY&ab_channel=SiliconANGLEtheCUBE
2018-July-16
Inefficient Knowledge Sharing Costs Large Businesses $47 Million Per Year
Panopto Release
https://www.panopto.com/company/news/inefficient-knowledge-sharing-costs-large-businesses-47-million-per-year/
https://www.panopto.com/resource/valuing-workplace-knowledge/
—-------------------------
Thank you Liam, Egor, and Ana and the entire Running Remote team for the collaboration. Running Remote and Work 20XX, goes together like peanut butter and chocolate.
Running Remote
https://runningremote.com/
—------------------------
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