Sacha Connor v2: Self-Advocacy in the Age of AI | Work 20XX Ep42

Jeff Frick
May 14, 2025
11
 MIN
Listen this episode on your favorite platform!

Sacha Connor returns to Work 20XX and asks, how do you self advocate, make sure the right people see and are familiar with your accompaniments, skills, and potential, when the most important factor when being considered for that next promotion or fresh opportunity is an AI agent preparing a list of candidates for consideration.

Are you on the agent’s radar? What digital persona is assembled by the AI after consuming the knowledge management system data, presentations, actions plans, meeting notes, agendas, project summaries, IMs, emails, meeting transcripts, and more digital exhaust? How does it compare to others?

Please join me in welcoming Sacha Connor back to the Work 20XX podcast at Running Remote, 

As Founder and CEO of Virtual Work Insider, Sacha has long been a leading voice and resource for building distributed team success for years. 

In this episode, we explore how in today’s AI world, people must signal their value to not just their managers and people who make decisions, but the AI agents that create the nominations based on a wide swath of internal systems communications data. 

Recorded April 29, Fair Market, Austin
Special Thanks to Liam Martin, Egor Borushko, Ana Maria Bennett & Team Running Remote

Episode Transcript

Sacha Connor v2: Self-Advocacy in the Age of AI | Work 20XX podcast with Jeff Frick Ep42 at Running Remote

English Transcript

© Copyright 2025 Menlo Creek Media llc.

Cold Open:
Check, check.
One two. One two.
That's your water. A
ll right. So we are good to go
in three, their lining up at the food trucks.
in three, it’s going to start smelling really good
in three, two, one.

Jeff Frick:
Hey welcome back everybody Jeff Frick here. Coming to you from not the home office. Not the home studio I'm in Austin at Running Remote Work 20XX on the road. We're excited to work with the great folks at Running Remote to come down and talk to, I don't know, could be the biggest collection of remote work experts ever assembled in a single place, at least since Portugal last year. And what's really critical here is that these skills are applicable whether you're fully remote, fully in the office, hybrid or some combination in between. So there's a lot of great lessons, and I’m excited to have our next guest. She is Sacha Connor She is the CEO and Founder of Virtual Work Insider. Sacha, great to see you.

Sacha Connor:
Great to see you in person finally.

Jeff Frick:
Absolutely it’s so fun. You know so many of these people. We have such a great community online. So to actually get to come together and meet face to face is a real treat.

Sacha Connor:
Yes, yes.

Jeff Frick:
So one of the things is as we talk about that and being on LinkedIn, and we often think about that in terms of promoting our own personal brand outside of organization. We think about trying to make sure everybody knows who Sacha is and who's Jeff is and why what we say is maybe interesting. You've talked about the challenges now inside, how do people promote their skills and development and blow toot their own horn a little bit when they're in a distributed world and no one's necessarily looking over their shoulders it’s a little harder to, to promote your goodness.

Sacha Connor:
One of the key skills, but hardest skills to get when you are working in a distributed organization is raising your profile. So gaining exposure to other people and then influencing others because you don't get that organic, you know running into each other at the water cooler, at the coffee machine, in the elevator, in the parking lot. And so one of the skills that we teach at Virtual Work Insider is how to build that exposure and influence across distance. And I learned that firsthand from my experience at Clorox in 2010, I went remote, and I was in the remote minority at the time. There was, you know, less than 5% of the company that was working remotely. And I realized that one of the most important things I needed to do on a daily basis was make my presence felt across 3,000 miles, three time zones away. And so in the workshop that we give, on building exposure and influence, we go through a five step process in terms of building your own personal virtual exposure and influence plan. So thinking first about who are your key stakeholders, who are those people that you need to gain exposure to and to influence? And a lot of times you might not know who that whole, you know, map of, of sphere of influence is because you, you only know your known networks. You also have to think about that unknown network. Who were the people that you need to get introduced to in order to build that exposure

Jeff Frick:
Do people even realize maybe it's you just get older and you realize the importance of this. But early on in junior people about how important it is to know who those people are, not only not external that you don't know, but even internal. It seems like a lot of people, if you ask them, you know, who are the 25 most important people in your business world, your business life? They've never thought that through. So? It's so critical for your career.

Sacha Connor:
And we talk about in that five step process, one of the steps is the why why do you need to gain exposure, influence those people. And sometimes it's about the career progression, right. Who are the people that you need exposure to based on what your career objectives are? And sometimes it's about the work itself. How do you get exposure to other ideas, innovative ideas, other function silos within the company? But what is really interesting to me these days is thinking about. You know, I used to frame it around the humans that we need exposure to and to influence. But now with AI, we need to think about how we build our exposure to the AI tools that our companies are using to catalog our skills. Because what's happening as companies move into this kind of skills based organization is they're starting to catalog those skills and are using that information to consider for succession planning, to consider for how they put people together on teams, depending on what the team goal is.  And if you haven't thought about what is the way in which the AI is now determining my skill set or empowered to edit that on your own behalf then you might be getting left out of opportunities.

Jeff Frick:
So have they added AI aficionado as an official category of skills that people are being ranked on and judged cause let's face it, a lot of people have jumped in with both feet. I interviewed this guy, Charles Corley. He's used ChatGPT every day since November of 2022. He just decided to jump in, where other people have still never even tried it at all. So I would imagine in terms of a specific skill, being able to manage, work with, understand and leverage AI has got to be a pretty important one going forward.

Sacha Connor:
I think that will become one of the things that is being developed. I heard recently that, Microsoft is launching something as part of Copilot called, I think it's called People Skills. Okay. Where it is doing this cataloging, and I think it's looking across all of the communication in Outlook, in SharePoint in Microsoft Teams chats and channels. It probably is looking at the use of Copilot itself, Right and through what it's, what it's viewing within that those interactions. Then it is creating the skills profile for you. Right. Beyond just your use of AI, but you know, your communication skills the different types of tasks that you're working on.

Jeff Frick:
And then, you know, Henrik [Jarleskog] just posted on LinkedIn his whole team his 12 [member] AI team which was classic, ChatGPT, I mean, more I didn't even know there was that many AI applications out there. So in terms of thinking about team level agreements a really key piece to success here. Where does AI and all my AI assistants and my little gaggle of people that I bring with me now or my AI start to fit in within team level agreements and how that changes, because I would imagine you know different people are going to have different sizes of of virtual staffs if you will, and then everybody else.

Sacha Connor:
Yeah, this has been a really fun and interesting thing for me to think about, because part of what we do at Virtual Work Insider is help teams at mostly large enterprises think about building their team working agreements. So how do they work? Mostly in cross-functional teams and and get to clarity on their team goals, get to clarity on their communication rituals and their communication norms. But a piece of this, too is what is the role of each of each of the team members on the team. And so as you brought up, we now need to think about what is the role of AI as a team member. And each team is going to be at a different stage in where they are in terms of using AI. And so a lot of the teams that we’re working with in large enterprises haven't yet thought about this at all. They're using AI very tactically, you know, maybe to help them on the side with, you know, writing an email or, you know, some sort of marketing copy. But now, like, if we start to get really intentional and say, okay What is the role of the AI on this team? Right. It gets really interesting. So anything from for example, when I work with a team, I have someone on the cross-functional team who becomes the team effectiveness lead, the person who is responsible moving forward for the effectiveness of that team based on the agreements that they've made. Well, now you could use AI, a GPT, or an agent as you think about, feeding it the information from the team working agreement. And using it as a coach. So a team effectiveness lead coach for the team based on the norms that they've co-created. So that could be one example of how they're using AI as a teammate

Jeff Frick:
So one of your favorite topics is talking about bias, because one of the big challenges with remote is it's all information sharing. And JJ [Reeder] shared on the keynote this morning that we spend so many hours, you know, trying to look for information and with remote that used to be I could just tap you over the shoulder, over the top of the cube and say, hey, you know, Sacha, I have a question. Are you seeing kind of the way that the teams interact Because I don't necessarily know, maybe I'm going to go to AI for that quick tap on the shoulder answer first? So it starts to change what those interactions are. Or has it not really percolated down that far yet?

Sacha Connor:
I haven't seen it percolate that far yet. But it could be useful. And what you're bringing up is there's distance bias, our brains natural tendency to put more value in the people, and things that we’re closer to than those that are further away. Or recency bias. The, our brain’s natural tendency to put more value on the people and things that we've heard from or seen more recently. And what you're bringing up is interesting in that if we're in different time zones and we I can't Slack you very quickly or tap you on the shoulder to ask a question, what can I do instead? Well, if you have put that knowledge base into an AI, GPT for example, FAQ, create an FAQ, GPT on something. I could use that as my first line of questioning before maybe, you know, you wake up in your time zone and can answer me back. That is probably an application of where this is going.

Jeff Frick:
So you're leading a star filled panel, tomorrow called Roses and Thorns: Practical advice for work across distance for the folks that aren't going to be able to make it. For our audience that’s not here today. What are some of the little, tips and tricks you look forward to sharing tomorrow? You have Darren [Murph], Lauren [DeYoung], Karrah [Phillips] It's a pretty good, panel. Y

Sacha Connor:
Yeah, we have a great panel. So I love talking about enterprise distributed work. And so we have, from Allstate, 50 over 50,000 person company, 93 year old company to Airbnb and Zillow 7,000 employees each about, you know, 20 year old companies. So we're going to talk about what they've learned, the good, bad and ugly around, communication, collaboration and creating connection and trust and also accountability and decision making. So they're going to share with us the experiments that they've done and what they've learned so far, because I love how they’re iterating and sharing with the community.

Jeff Frick:
Yeah, it should be great. So don't miss that one. Well, Sacha, it is super to, to finally meet in person and catch up and really appreciate the time.

Sacha Connor:
Thanks so much.

Jeff Frick:
All right. She’s Sacha. I’m Jeff. You're watching Work 20XX we’re coming you from Austin, Texas at Running Remote. Thanks for watching. Thanks for listening. See you next time.

Sacha Connor v2: Self-Advocacy in the Age of AI | Work 20XX podcast with Jeff Frick Ep42 at Running Remote

English Transcript

© Copyright 2025 Menlo Creek Media llc.

Links and References 

Sacha Connor v2: Self-Advocacy in the Age of AI | Work 20XX podcast with Jeff Frick Ep42 at Running Remote 

Sacha Connor 

Founder and CEO, Virtual Remote Insider

Virtual Work Insider 
https://virtualworkinsider.com/ 

Virtual Work Insider - Blog and Resources 
https://virtualworkinsider.com/blog-and-resources/

LinkedIn 
https://www.linkedin.com/in/sachaconnor/

Running Remote 
https://runningremote.com/

—---------

People, Articles, Sessions and other items mentioned in the interview 

Running Remote Sessions mentioned in the interview 

Opening Keynote 
Handbooks on steroids: in the age of AI, knowledge management is a make-or-break strategy
Jessica “JJ” Reeder,
Director, Remote Organizational Effectiveness @ Upwork
While the rest of the world was treating company handbooks as nice-to-haves, many digital-first organizations invested in robust, living knowledge bases. Then came AI - and suddenly, companies with a searchable archive are set up for massive gains in efficiency, collaboration, and innovation. Here's what the handbook of the future looks like, and how to invest wisely in yours.

Roses & Thorns: Practical Tactics for Enterprise Teams to Work Across Distance
Darren Murph,
Senior Director, Cloud HQ Experience @ Zillow
Lauren DeYoung, Work Futurist @ AllState
Karrah Phillips, EX Program Manager @ Airbnb
Moderated by: Sacha Connor, CEO @ Virtual Work Insider
This session explores the "roses"—successful practices and tools that foster connection, productivity, and alignment—and addresses the "thorns"—common obstacles such as miscommunication, siloed workflows, and cultural differences. Participants will leave equipped with practical techniques to enhance teamwork, improve communication, and build resilient, high-performing teams in any enterprise environment. Perfect for managers, team leaders, and collaborators looking to thrive in a dispersed workplace.

—----

Darren Murph
Senior Director, Cloud HQ Experience, Zillow
https://www.linkedin.com/in/darrenmurph/

Henrik Jarleskog
Head of Future of Work Europe, Sodexo
https://www.linkedin.com/in/henrik-jarleskog-246294/

“JJ” Jessica Reeder
Director, Remote Organizational Effectiveness 
https://www.linkedin.com/in/jessicareeder/

Karrah Phillips
EX Program Manager, Airbnb 
https://www.linkedin.com/in/karrahphillips/

Lauren DeYoung
Workplace Futurist, Allstate
https://www.linkedin.com/in/laurendeyoung/

Proximity or Distance Bias 
https://en.wikipedia.org/wiki/Proximity_bias

Recency Bias 
https://en.wikipedia.org/wiki/Recency_bias

—--------------

2025-May-10
Ryan Anderson v2: Support Rich Interpersonal Interactions | Work 20XX podcast with Jeff Frick Ep41 from Running Remote
https://www.work20xx.com/episode/ryan-anderson-v2-support-rich-interpersonal-interactions-work-20xx-ep41

2025-May-08
“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX podcast with Jeff Frick Ep40 from Running Remote
https://www.work20xx.com/episode/jj-jessica-reeder-scaling-knowledge-evolution-operations-work-20xx-ep40

2025-04
Not one hand went up - Henrik introduces his AI team 
Henrik Jarleskog LinkedIn Post 
https://www.linkedin.com/posts/henrik-jarleskog-246294_futureofwork-superworker-ai-activity-7315400860648284163-Si8V/

Today, I lead as an ultra-effective team, with AI agents deeply embedded in how I think, create, and deliver. Not as tools—but as colleagues:

ChatGPT: My Chief Strategy & Innovation Officer

Claude: Executive Editor-in-Residence

Perplexity: VP of Research & Insights

Gemini: Director of Real-Time Verification

Midjourney: Creative Director of Visual Production

Canva: Head of Rapid Design & Branding

Eleven Labs: Senior Manager of Voice Experience

Notebook LM: Chief Knowledge Curator

Gamma AI: Director of Presentation Development

Otter AI: Chief Meeting Historian

Ambient AI: Chief Workflow Orchestrator

Veed: Director of Video Content Creation

2025-April-23
Microsoft Launches People Skills In Copilot, Altering the HR Tech Market
By Josh Bersin, Josh Bersin dot com
https://joshbersin.com/2025/04/microsoft-launches-people-skills-in-copilot-altering-the-hr-tech-market/

2025-April-23
Announcing People Skills general availability and new Skills agent
By John Mighell, Microsoft 365 Copilot Blog
https://techcommunity.microsoft.com/blog/microsoft365copilotblog/announcing-people-skills-general-availability-and-new-skills-agent/4406364

2025-April-18
Charles Corley: Culture, Wellness, Visualization, AI Colleague | Work 20XX podcast with Jeff Frick Ep34
https://www.work20xx.com/episode/charles-corley-culture-wellness-visualization-ai-colleague-work-20xx-ep34

2024-July-03
Sacha Connor: Learn, Skills, Mindset, Behaviors | Work 20XX podcast with Jeff Frick Ep27
https://www.work20xx.com/episode/sacha-connor-learn-skills-mindset-behaviors-work-20xx-ep27

2021-Dec-22
Darren Murph: Remote-First, Async Communications, Operating Manual | Work 20XX podcast with Jeff Frick  Ep01 
https://www.work20xx.com/episode/episode-1-darren-murph

—------------------------

Disclaimer and Disclosure 

All products, product names, companies, logos, names, brands, service names, trademarks, registered trademarks, and registered trademarks (collectively, *identifiers) are the property of their respective owners. All *identifiers used are for identification purposes only. Use of these *identifiers does not imply endorsement. Other trademarks are trade names that may be used in this document to refer to either the entities claiming the marks and/or names of their products and are the property of their respective owners. 

We disclaim proprietary interest in the marks and names of others.
No representation is made or warranty given as to their content.
The user assumes all risks of use. 

© Copyright 2025 Menlo Creek Media, llc.

Jeff Frick
Founder and Principal,
Menlo Creek Media

Jeff Frick has helped literally tens of thousands of executives share their stories. In his latest show, Work 20XX, Jeff is sharpening the focus on the future of work, and all that it entails.