FlexOS | Future Work

Remote Work: From Debate to Design, Finally

May 10, 2025
Briefing
#
137
Remote Work: From Debate to Design, Finally

Your Weekly Must-Read Briefing on Future Work

Work is evolving fast—AI, automation, and workplace shifts are transforming how businesses operate. With endless information out there, I cut through the noise to deliver what it means and provide actionable insights that truly matter.

Join my weekly newsletter for execution-focused takeaways and a deep dive into the biggest conversations shaping the future—straight from Future Work Experts.

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THE FUTURE OF HR ROUNDUP

Your Weekly Must-Read Briefing on Future Work

Work is evolving fast—AI, automation, and workplace shifts are transforming how businesses operate. With endless information out there, I cut through the noise to deliver what it means and provide actionable insights that truly matter.

Join my weekly newsletter for execution-focused takeaways and a deep dive into the biggest conversations shaping the future—straight from Future Work Experts.

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FlexOS | Future Work

Remote Work: From Debate to Design, Finally

May 10, 2025
Issue
#
137
Remote Work: From Debate to Design, Finally

Last week, our team took a brief pause for Reunification Day here in Vietnam (known locally as their "National Concert" 🇻🇳)—and for me, that meant a reset with family in Milan 🇮🇹.

Now we’re back, and last week’s highlight is a special one: our partner event, Running Remote 2025, took the future of work conversation from debate to design. We’re finally shifting from if remote work works to how to make it truly perform.

Here’s what else stood out this week:

  • AI Already Took Your Job — Now What? 12.6% of U.S. jobs face high AI risk, but the real opportunity lies in upskilling and redesigning roles, not resisting change.
  • Where’s Your Innovation Really Happening? Sophie Wade debunks the watercooler myth, showing how engineered serendipity and virtual tools now fuel deeper collaboration.
  • Real Estate vs Robot Friends: Antony Slumbers argues that in a world of AI companions, real spaces must become sanctuaries for embodiment, ritual, and community.
  • What We Still Get Wrong About Work: Phil Kirschner calls out five blind spots—from poor documentation to broken culture metrics—keeping organizations stuck in legacy mode.
  • The Two AI Paths Changing HR: Anthony Onesto maps HR’s path to lead AI transformation through efficiency (automation) and alpha (revenue enablement), backed by McKinsey and SHRM data.

Let’s get into it 👇

Your Weekly Must-Read Briefing on Future Work

Work is evolving fast—AI, automation, and workplace shifts are transforming how businesses operate. With endless information out there, I cut through the noise to deliver what it means and provide actionable insights that truly matter.

Join my weekly newsletter for execution-focused takeaways and a deep dive into the biggest conversations shaping the future—straight from Future Work Experts.

Join over 42,000 people-centric, future-forward senior leaders at companies like Apple, Amazon, Gallup, HBR, Atlassian, Microsoft, Google, and more.

Unsubscribe anytime. No spam guaranteed.

🔥 Insights from Running Remote 2025: Remote Is Set. Now Design.

At Running Remote 2025, one thing became clear: The remote work debate is over. What comes next is design.

Held in Austin, the event gathered the brightest minds in distributed work, from Stanford economists and HR futurists to real estate strategists and AI pioneers. Across mainstage moments and hallway conversations, leaders agreed: it’s no longer about if remote works, but how to build systems that actually make it work better.

Brian Elliott reminded us to stop obsessing over desk time and start rethinking coordination. Jessica “JJ” Reeder dropped a now-viral truth: “AI cannot search your brain”—documenting knowledge is the foundation of effective AI. Meanwhile, Phil Kirschner framed the big unlock: “Clarity is the new cultural currency.”

The big five insights?

  1. Results Trump Rituals: Forget RTO compliance. Design hybrid workflows that serve how your team actually collaborates.
  2. AI Needs Human Clarity: AI isn’t magic—it amplifies what’s already clear and codified. Without structured documentation, it fails.
  3. Inclusion Is a Daily Choice: Remote work can replicate inequity if not intentionally designed. Rituals like rotating facilitation and async norms matter.
  4. Culture Lives in the Margins: Skip the big offsite buzz. Culture is shaped by everyday interactions, quiet habits, and deliberate feedback loops.
  5. Leadership Is a Repeatable Practice: Great leaders build consistency. Think: weekly standups, peer recognition, and purpose-driven check-ins.

“We had finally moved on to focus on how to optimize distributed work rather than endless debate and concern about whether it would last.” — Sophie Wade

Bottom line: remote work has matured. But performance, inclusion, and trust won’t happen by accident. They must be designed.

FROM OUR EXPERTS 🎙️

I keep a close eye on what our Future Work Experts are thinking, saying, and questioning. I break down the key conversations and brainstorm practical steps we can take to move forward.

This week:

WORKPLACE CLARITY GAP

What We Still Get Wrong About Work

  • Despite the maturity of distributed work tools, many organizations are stuck, held back not by technology, but by outdated assumptions and invisible friction. Phil Kirschner identifies five critical blind spots: our reluctance to document, a false sense of connection, fragmented workplace ownership, the dismissal of remote work’s strategic impact, and a shallow understanding of culture.
  • From McKinsey's research on organizational health to live stories from Running Remote 2025, his diagnosis is clear: clarity, not just technology, is the missing variable in transforming work. Until leaders treat the workplace as an integrated product and prioritize behavioral alignment, progress will stay stalled.

⚒️ Prompt: Pick one blind spot. Now imagine explaining it to a confused intern on their first day. If your answer includes “it depends” or “just ask around,” congratulations—you found your friction. Fix that one first.

SERENDIPITY ENGINEERING & TRUST-BASED LEADERSHIP

Where’s Your Watercooler?

Where’s Your Innovation Really Happening?

  • Sophie Wade challenges the myth of the watercooler as an innovation hub, calling it a weak excuse for RTO mandates. Drawing from MIT’s Allen Curve and research by Harvard’s Prithwiraj Choudhury, she explains that physical proximity drives interaction, but in today’s distributed world, serendipity must be designed. Virtual watercoolers like Donut or CultureBot, and engineered interactions (like intern-exec pairings) now outperform hallway chance encounters.
  • Sophie also spotlights “Leadership in 4D”, calling for more emotional intelligence, transparency, and intentional trust-building to foster high-performing, connected teams. According to Deloitte, trust and belonging are the most critical drivers of success through 2027.

⚒️ Prompt: If your most innovative idea came from bumping into a water dispenser, you might need a better system. Try this: set up one random 15-minute virtual match this week, with someone outside your team. Then ask, “What are you working on that’s weirdly cool?”

AI-LED HR TRANSFORMATION

The Two Types of AI Transformation

The Two AI Paths Changing HR

  • Anthony Onesto outlines a strategic blueprint for how HR leaders can lead company-wide AI transformation. He defines two core paths: Efficiency, where AI automates repetitive HR tasks (like recruiting—cutting cost-per-hire by up to 30% per SHRM Labs); and Alpha, where HR powers revenue by enabling AI tools for frontline teams, like sales (boosting productivity by 3–5% according to McKinsey).
  • Anthony introduces a decision framework to guide adoption—aligning AI with business goals, building internal buy-in, and tracking KPIs like EBITDA impact, turnover, and productivity. The message is clear: AI is HR’s opportunity to lead, not follow.

⚒️ Prompt: Grab two sticky notes. On one, write a task you’d love to never do again. On the other, write a revenue number you want your team to help move. Congrats—you’ve just defined your Efficiency and Alpha AI priorities.

HUMAN-CENTERED REAL ESTATE

Real Estate vs Robot Friends

Real Estate vs Robot Friends

  • Antony Slumbers responds to Mark Zuckerberg’s vision of AI-generated “friends, therapists, and girlfriends” with a compelling counterpoint: in a hyper-digital world, real estate becomes the ultimate refuge.
  • As AI begins simulating intimacy and colonizing attention, the built environment can assert its value as the last authentic space—a place for embodiment, community, and ritual.
  • Antony outlines a blueprint for future-proof real estate: algorithm-free zones, multi-sensory design, human-as-a-service models, and even architectural dissent. In an era of synthetic connection, real space becomes the thirteenth friend—the irreplaceable, analog ally AI can’t replicate.

⚒️ Prompt: If Meta offers you 12 AI friends, go build a space to host one real one. This week, design or visit a place where phones go down and eye contact goes up—tag it #WhereRealPeopleMeet.

🔥 QUICK HITS:

  • [ETHICAL REBUILD] When Creed Collapses, What Remains? // By Jess Von Bank
    Jess Von Bank paints a raw, urgent picture of 2025: a world spinning faster than our values can catch up. As AI accelerates and institutions crumble, we’re operating without a shared belief systema “creed”—to guide ethics, equity, or even truth. She compares our moment to a horse loose in a hospital: chaotic, incoherent, and unnerving. But amid the collapse, Jess sees a rare opportunity: to rebuild systems, redefine leadership as stewardship, and design technology with human dignity as a metric, not a casualty.
    ⚒️ Prompt: Start your own creed. What 3 non-negotiables will you protect in the age of AI? Write them down. Share them. Build from there.
  • [NONLINEAR STRATEGY] If Not Impossible, It Will Happen // By Dror Poleg
    Dror Poleg reframes the modern world through the lens of quantum logic: if something isn't forbidden, it will happen. As digital systems collapse the boundaries of time, space, and distribution, the difference between possible and likely is disappearing. From TikTok virality to financial contagion, nonlinear outcomes are now the norm. In this chaotic, fast-evolving landscape, Dror urges us to shift from prediction to discovery, from optimization to adaptability, and to build systems, both personal and societal, that can sense and scale what works in real time.​⚒️ Prompt: Design one habit or system this week that prioritizes detection over perfection. Ask: how can I spot what's working faster—and double down?
  • [TALENT STRATEGY] Retention = Purpose + Trust + Growth // By Dr. Tracy Brower
    Top talent drives outsized results—outperforming average peers by 400%, according to research from Indiana University. Yet they are the most likely to leave, with 30% departing in year one and up to 21% of high-potential contributors likely to exit. Dr. Tracy Brower outlines three critical retention levers: (1) purpose, which makes people 5x more likely to stay; (2) trustworthy leadership, as 61% don’t trust current leaders; and (3) growth, since lack of development makes top talent 4x more likely to leave. Retention is not a perks game—it’s about clarity, connection, and consistent investment.
    ⚒️ Prompt: Pick one top performer on your team this week. Ask them: “What would make you want to stay and grow here?” Then act on it.

🤖 LEAD WITH AI

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✅ Insights into the 2025 AI job landscape—why AI fluency now pays up to 30% more
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✅ Actionable steps to integrate AI into your daily workflow
✅ Live Q&A with AI leaders using tailored AI every day

Not one-size-fits-all. Just real AI skills that fit your role.

FUTURE WORK ROUNDUP 📰

I track what’s worth your attention—bringing you the news and updates that matter most to how we work, lead, and grow.

This week:

AI IN THE WORKFORCE

Source: Isobel O'Sullivan (Tech.co)

AI Already Took Your Job — Now What?

  • SHRM reports that 12.6% of U.S. jobs—around 20 million—face a high or very high risk of AI-driven displacement. Blue-collar, service, and administrative roles top the list. Companies like Dukaan replaced 90% of support staff with a chatbot, while IBM plans to automate 30% of back-office roles by 2030. Google, Salesforce, Klarna, and MSN are moving ahead with AI-first strategies, focused on cost and efficiency over headcount.
  • But there’s hope: 62.8% of roles are only slightly at risk, because AI replaces tasks, not entire humans. The difference? Upskilling and Reskilling.

In Schools: Train AI Creators

  • More than 250 CEOs, including Satya Nadella and Brian Chesky, are calling for mandatory K–12 AI and computer science education. In China, six-year-olds are learning chatbot ethics. South Korea has trained all teachers and introduced AI textbooks. The U.S. lags: only 12 states require computer science to graduate, and just 6.4% of high schoolers took a CS course last year.
  • AI literacy is the fastest-growing workplace skill, with the potential to lift wages by 8% and create $660 billion in annual economic value, according to LinkedIn and the World Economic Forum.
  • Demis Hassabis, CEO of DeepMind, urges students to build foundational thinking and explore across disciplines. The edge, he says, lies in learning how to spot the right problems at the right time.

In the Workplace: Upskill and Reskill the Core

  • Only 44% of managers have formal training. As AI reduces operational load, coaching tools like LinkedIn’s AI coach, Skillsoft’s CAISY, and CoachHub’s AIMY are helping managers build feedback, decision, and empathy skills through adaptive simulations.
  • At Salesforce, internal tools like Career Agent and Career Connect, integrated into Slack, guide employees to new roles. In early 2025, 50% of positions were filled internally, with over 90% discovered via AI matching.

Human Skills Lead the Way

  • Skills like adaptability, empathy, and ethics remain the toughest to automate. Shannon McKeen calls them essential, not optional. Liberal arts education now delivers the flexibility and moral reasoning needed to complement technical expertise.

At the Executive Level: Close the Gap

  • A Gartner survey of 456 executives shows only 44% of CIOs are viewed as AI-savvy by CEOs. Yet 77% of CEOs say AI is a strategic priority. The top barriers: unclear ROI and limited talent readiness.
  • Executives must lead with fluency, trust, and alignment. AI is now a business imperative.

TL;DR: Don’t Panic—Prepare

  • AI is replacing tasks, not people—yet.
  • Upskill and reskill early, upskill and reskill often.
  • Teach kids to create AI, not just consume it.
  • Build a culture where humans + AI = better together.

MIDDLE MANAGEMENT

Middle Management Isn’t Dead—It’s Evolving

Despite long-standing predictions of its demise, middle management is evolving—not disappearing. Gartner projects that 20% of companies will use AI to eliminate over half of current middle manager roles by 2026, yet research shows these managers are critical to navigating transformation.

Their role is shifting from supervision to facilitation: translating strategy, guiding skill transitions, and humanizing AI. Middle managers drive top-down execution, surface bottom-up feedback, and foster cross-team adoption during digital shifts—while also managing the emotional and psychosocial fabric of teams.

⚒️ Prompt: Ask yourself: Are your middle managers managing spreadsheets—or momentum, emotions, and innovation?

Audit how much of their week is spent on admin vs. coaching, cross-team connection, and culture work. Then shadow one (chainsaw optional) to see what friction you can remove—or where AI can help—so they can get back to translating strategy, not chasing approvals.

MEANINGFUL WORK

How to Make Work Matter

Consultants Wes Adams and Tamara Myles identify three universal drivers of meaningful work: community, contribution, and challenge.

These pillars, backed by research across 25 industries, help employees feel valued, impactful, and continuously growing—whether at Microsoft or Chick-fil-A.

Community builds belonging, contribution connects work to real-world impact, and challenge fuels growth.

In high-stress industries like hospitality, reframing even routine tasks (like polishing forks) through purpose can reenergize teams. Their work shows that purpose is not perks—it’s a mindset leaders must intentionally foster.

⚒️ Prompt: Your employees aren’t craving ping pong tables—they want to matter. This week, ask: Do your people know who they’re helping, how they’re growing, and where they belong? If the answer’s “umm,” it might be time to stop polishing reports and start polishing purpose.

🔥 QUICK HITS:

  • [GEN Z]'s Micro-Shift Revolution: Gen Z is leading the rise of micro-shiftsflexible 6-hour work blocks enabled by AI and driven by economic pressure and lifestyle demands. Women dominate this model, which could unlock $2T+ in labor participation. 45% report better work-life balance. Shorter shifts, stronger retention?
  • [TARIFF] Trump’s UK Trade Deal Still Foggy: The US-UK deal raises car export limits and grants tariff relief for Rolls-Royce and Boeing deals—but keeps 10% tariffs intact. Steel, pharma, and digital tax terms remain vague. With the UK just 2.9% of US trade, the impact is more symbolic than seismic.
  • [COMPENSATION] Amazon Rewards the Long Game: Amazon shifts to a tiered comp model, favoring multi-year top performers: 4 years of excellence = 110% pay; one year = just 70%. Internal “Overall Value” (OV) scores drive decisions, but remain opaque. A clear move toward consistency over spikes.

Your Weekly Must-Read Briefing on Future Work

Work is evolving fast—AI, automation, and workplace shifts are transforming how businesses operate. With endless information out there, I cut through the noise to deliver what it means and provide actionable insights that truly matter.

Join my weekly newsletter for execution-focused takeaways and a deep dive into the biggest conversations shaping the future—straight from Future Work Experts.

Join over 42,000 people-centric, future-forward senior leaders at companies like Apple, Amazon, Gallup, HBR, Atlassian, Microsoft, Google, and more.

Unsubscribe anytime. No spam guaranteed.