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May 8, 2025 16 mins

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 podcast with Jeff Frick 20XX Ep40 from Running Remote 

YouTube - Click Here 

https://www.youtube.com/watch?v=WmpI_FOdyyo&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt

Transcript and Show Notes - Click Here 

https://www.work20xx.com/episode/jj-jessica-reeder-scaling-knowledge-evolution-operations-work-20xx-ep40

 

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Okay, great. So,
I'll count us down,
and then we'll go,
Wonderful
In three,two, one.
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 specialepisodes down here.
If you weren't able to make the trip.

(00:21):
And so it's been an amazing show.
They've got a back to back.
I think two stages are goingconstantly every ten minutes.
Some new expert telling you more about remote work
that you didn't know before.
So we're excitedto have our first guest.
She's JJ Reeder.
She is now the Director of Remote Organizational Effectiveness
at Upwork
JJ great to see you.
Great to see you too.

(00:42):
Effectiveness I don't know thatI've ever seen effectiveness
in somebody's title, I like it.
It is a title.
It is it does exist.
Org effectiveness is a thing.
But remote org effectiveness
is really what brings itto that next level.
It's, not just about how to havean effective organization,
but also how to do thatin a distributed environment.

(01:03):
[Jeff] Right
So you've been doing thisfor a long time.
We all know youback from the day
when you and Darren were writingthe original remote work playbook
that we all use and share,and has been widely distributed.
But your presentation just now,
I thought it was goingto be on playbooks,
but you really kind ofwent a different direction
on knowledge management.
So how doesknowledge management
and leveraging AI and
getting that informationthat's out of the company.

(01:26):
How does thattie back to playbooks?
Well, honestly,I mean
if you look at the evolutionof the company handbook,
what GitLab was doing
when GitLaband those companies
really innovated the handbook.
That was aboutten years ago
when they really reinvented whatthe concept of the handbook was.
And it has been continuing to evolve ever since then.
So what it's evolved intois a digital knowledge system.

(01:46):
This is a living system of knowledge
that's a key company asset,
represents the knowledgeof the entire organization.
And so as we continueto have this conversation
and as AI entersthe picture,
knowledge becomesa key
company piece of infrastructurealmost as an asset.
And so we have to startthinking about it in new terms.
Right.

(02:06):
So I was just at the Atlassian showa 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 someplaceor I don't know if I have it,
I’m tryingto find it.
And speaking about inefficiency,
you recently posted about 47 million.
Was it hours lost to searching for information?
This is a stat from 2018,actually from Panopto.

(02:29):
They estimated that large businesses
lose $47 million per year per business on average
through poorknowledge sharing.
And thatwas 2018.
So that ispre-pandemic, pre-AI
That's like ancient history for us.
I'm sure that that numberhas gotten bigger.
[Jeff] Right.
So the vision of a unified knowledgebase has been around forever.

(02:50):
Information locked in, in silos,whether that's departments
or laptops or PDF documentsor presentations
that I'm carrying around on my phone,
have been around forever.
How is itchanging now,
both as acombination
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 allthose different data sources.

(03:11):
Well, that's the thing.I think that's it.
It's the different data sources.
And that's really thechallenge right now is that,
knowledge can no longer be keptin a bunch of different places.
You have to have a single sourceof truth more than ever before.
And we were talking about thisback in the handbook days, but
but humans were ableto sort of make decisions about,
you know, which version of somethingwas probably most correct.

(03:32):
Or they could ask one another.
As AI enters the sceneand as we work faster and faster,
it's really no longer possibleto 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 agentgood information to work from?
That means we needa single source of truth.
We need to practice good information management.

(03:54):
We need to know that it's up to date and accurate,
because the risks arestarting to compound
the loss of effectivenessand efficiency is starting to grow.
And more andmore companies
that don't have their information locked down
are going to beleft behind.
Right? Right.
Because of speed right,speed of decision making,
speed of moving forward,

(04:15):
speed of operation, speed is so critical.
Yeah.
You talked about rollingthis out at Upwork
and trying to help peopleget the information
not only in thedepartmental silos,
but again, off their laptops,where a lot of information lives.
And that's why attachments on emails are
one of the manyreasons they’re so bad.
How did you kind ofget a process going?

(04:35):
What was your processto start to transfer
some of that informationto where it's more accessible?
Well, so
First of all, I think that Upworkwas in a really good place
compared to a lot of organizations
because they had really done
some of the foundationalwork to transform
transfer the organizationto digital operations.
And so people were having a goodpractice of documenting things.

(04:57):
But really, what was missing wasa 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 sortsof different things.
And so reallyit was about
we need to create a single place
where there's reliable information.

(05:18):
And then to do that,
we hadto decide
what information was going to go into it.
So we started just thinking about
what information arepeople going to need
to understand that we had to ask
We went andhad to ask
every personat the company,
what do you actually need?
You have tomake decisions
about what information belongs
and what information doesn't.

(05:38):
It's a long process,
but by workingbottom up
and actually getting that buy in
and getting people to really understand
what this system would do for them,
that really empoweredthe 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.
Right.
So it wasn't a new system,right? Was it?

(05:59):
Did you pick one as kind of this is going to be
the source of truthwe'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] We picked a new system. [Jeff] Because you don't want
[Jeff] another system or did you?[JJ] No.
We picked a new system.
Okay.
We deprecated old systems.
Okay. Well good.
So we picked a new systemthat had the features
and functionality thatthe team was asking for.
Right. We did all of the research first.

(06:20):
We said, what do you need?
Then we found somethingthat would hit
as many of those boxes as possible.
[Jeff] Right.
And then we deprecated the systemsthat 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 accessthat they needed.
And then we got rid of the old stuff.

(06:40):
What was the biggestsurprise in the process?
What was the biggest surprise?
Positive or negative
I mean, because the other partyou talked about is access.
And in yourpresentation just now,
you talk about some companiesaren'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 youhow did you,
what was some of the learningswhen you were making this move?

(07:03):
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 talkto the legal team
and the trust and safety team
and really make the case for, like,
why we need this new tool

(07:24):
and why we're going to fill it
with all of this company information,
which could bea liability.
And I was actually really surprised
that they already understood
at that pointthey 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

(07:45):
than having your good information someplace
where the wrong person might be able to see it.
Right.
Having bad information out thereis more of a risk to the company.
Right?
So that was a really coolsurprise, you know,
and then I think I was surprised by,
how quickly people really got on board.
You know, I'm so used toliving in this world where

(08:06):
I'm talking about these thingsthat seem kind of abstract.
You know, it's very dry
knowledge management systems, like,
come on, like nobody's interested in this.
[Jeff] Right, right
But people I, you know,they really understood
they really wanted this.
They needed this resource.
And so they bought inand they supported it,
and they put theirinformation in it.
And they startedusing the search tool.
And it was kind of glorious.
That's great.

(08:26):
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 allcompanies should be good at.
And knowledge sharing and the lack of the ability
just to tap somebody on the shoulder
to get the answerto a question is,
is one of thegreat examples.
And you talked about in your talk really
digital first.And really

(08:47):
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 differencein your position to go forward.
If you are alreadymaybe digital centric,
maybe you're not quite digital first,
but talk alittle bit about
how digital first is such an important component
to being successfulin this next
couple of years is becauseof this is crazy AI thing.

(09:08):
Well, this is why I think that remote first companies
as a group
are going to be leading actually
in the next waveof AI adoption
because remote first companies
didn't just embraceremote work
or in order to embrace remote work,
they had to also embracedigital communication,
digital collaboration, digital connection.
And they wrote everything down,

(09:29):
[Jeff] Right
And they figured out systemsto transfer information
and get it flowingthroughout the company.
And that is something thatI think a lot of companies
are still really catching up on,
which is a lot of what I talkedabout in my talk just now.
I think that remote first companieshave this massive potential
to really have a head starton AI implementation,

(09:50):
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.
Right, right.
So another great lineBrian 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

(10:11):
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 enterprisechallenges is AI adoption.
Everyone knows they want to use it,they're trying to use it.
But it's really interesting I thoughtthat Brian pointed out
because it's about agency,it's about risk taking.
It's about getting outside the box,

(10:32):
and it's actually the same behaviors that are going to support,
AI utilization AI, you know, trial.
Absolutely. That's absolutely right.
And it's morethan that.
It's not just about risk taking.
That's a very important part of it.
Right?
It's not just about thinking outside the box, though.
It's being willing to do the hard, dry work

(10:52):
that actually supportsthe execution.
So you can havethe big idea.
But unless you do,what it takes
to actually execute on that idea
it’s just an idea.
Right.
And I think that some of thesecompanies really understand
it is hard to run a company remotely.
It is not easy.
Right.
And so I think thatsome of these companies
have alreadybuilt the muscle

(11:13):
that they need to sustain the effort
to really move aheadin the AI adoption phase.
Do you think the change in attitude is just
because of the reactionof something like a ChatGPT
to know that now I can actually like
I can have a conversationwith a computer
and extract information that way
versus kind of old school queries.
And the complexity

(11:33):
of trying to get information
is that change the acceptance
or excitement or willingnessto invest in the senior team
into finally the
the dream of knowledge management
that we've hadforever and ever.
You know what?
I think that's so much a part of it.
I think you're absolutelyright 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

(11:54):
It is transformative,
even for me to be ableto 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 executivesare really leaning into AI,
which means that they're trying stuff.
They are conversingwith ChatGPT,
and once they startto reach that level

(12:16):
where they're having thattransformative experience
I think absolutelyit 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'sreally 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.

(12:38):
And there's a riskto not having good information
underlyingthat answer.
So it's a yes and no thing.
I think that yes,it drives adoption,
but I'm still concerned about thatrigor that we actually need
to have good knowledgeinside of an organization.
Right? Right.
Because there's
there's the rigor, as you said before,
garbage in, garbage out.
And then there'sthe rigor
in terms of the appropriateness

(12:59):
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 complainsor takes time off.
But you know,
but I was like
Charles, what abouthallucinations?

(13:20):
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 signon the dotted line,
you got to check the work.
Absolutely.
And I'm so concerned thatthat's not necessarily happening
because it just feels so organic.
You really feel likeyou can trust this answer.
And I think that's anothermuscle that we now have to build.
Yeah, it's really tricky if it's in an area that you don't know

(13:42):
because if it's an areathat you know
not only can you see the hallucinations,
but moreimportantly,
you know the value of the hallucination
is it material or immaterial.
But if it's something
you haveno clue about
and you just take it as gospel,
you know, you can really get yourself in big trouble.
Yeah, yeah.That’s true.
Okay, so last question.
One of the hardest things
and it wasn't directlyin your talk is

(14:02):
driving engagement withdistributed teams, remote teams
how should people think about,approach engagement.
Because we know engagementretention is so so important.
What's this.
What's someof the secrets
to keeping good engagementwith remote teams?
You know what I'm actually goingto talk about this tomorrow.
Oh, good.
A little previewfor all the local folks.
It’s part of a session tomorrow
It's going to beabout engagement
Dang, I didn't study my notes on that.

(14:23):
It’s like a lightning round of two minute talks.
Okay.
With a wholebunch of people.
Okay
Um so.
Well, you could take more than two minutes here.
So go ahead
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 workthat we do. Right?
So we think
you go do your work,

(14:44):
and then you goto an all hands
or you goto 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 momentthat we work and
If you don't think that's building culture,
then you are wrong.
[Jeff] Right, right.
So I think we need to really start thinking about

(15:06):
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 thepeople that they work with
because they're relaxed,
they're showing up as more confident.

(15:26):
Right, right
They feel more possessionof their results.
And they start to reallybelieve 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.
Love it.
Well, JJ, it was so greatto finally meet you in person.
We've been LinkedIn buddies for a long, long time
long time it’s great to meet you.

(15:47):
Absolutely, and thank youfor the insight.
Really, useful stuff.
And finally, you know, is finally the dream
of a unified knowledge managementsystem in the organization
Is finally almost here it sounds like
I love it, I love it.
Yeah. There's so much potential.Thank you so much.
Thank you.
All right. She's Jessica. Excuse me.
She's JJ, I'm Jeff,
you're watching Work 20XX on the road

(16:08):
from Running Remotein Austin, Texas.
Thanks for watching.
Thanks for listeningon the podcast.
Catch you next time. Take care.
We're out.
Thank you.
How fun
Yeah.
Hey, Jeff Frick Here
big shout out to the podcast audience.
Thanks for listening in.
You can get show notes and transcripts at Work20XX.com

(16:28):
And that also has links to the videos as well.
Appreciate you listeningin on the podcast
Do reach out
say hello, like subscribeand smash that notification bell.
Thanks for listening.Take care. Bye bye.
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