5 Blind Spots Holding Back Modern Work

‍1. We Still Don't Write Things Down

For this first insight, I ​posted​ a critical piece of background during my time at Running Remote:

The management practices of natively remote companies give them higher levels of organizational health than over 90% of all the companies McKinsey has ever studied with its Organizational Health Index (OHI) survey.

From that ​research​, my former colleagues and I discovered that employees of natively remote companies believe their organizations frequently “document and update knowledge, process, and procedures.” McKinsey calls this management practice “process-based capabilities,” and traditional organizations often struggle with it.

This brings me back to Running Remote, where ​“JJ” Reeder​ said, "poor knowledge sharing is quietly driving return-to-office decisions." Companies with office-based cultures rarely rely on rigorous documentation for ​how work happens​, because workers with questions can just ask the person next to them. JJ knows highly distributed companies must have “search-first cultures,” where employees help themselves before scheduling meetings.

Founder ​Maryam Taheri​ also outlined a clear, executive imperative for better documentation and written, asynchronous communication: leaders who think the knowledge in their head is a single-point of failure risk avoiding vacation and ultimately burning out.

​Darren Murph​ (Zillow) said that writing things down is “simple, but not easy,” while assuring the audience that AI-powered tools are making it easier than ever to surface buried knowledge.

2. We Think Connection Is Easy

Traveling all the way from Lagos for her first speaking engagement in the US, ​Dr. Adora Ikwuemesi​ said that “connection must be designed intentionally.” Darren’s version was that “every great distributed team has a great in-person strategy.”

Proximity doesn't magically create culture, and neither does Slack.

Employees at Airbnb love their flexibility, but internal research identified concerns about connection. ​Karrah Phillips​ said one solution has been large gatherings synchronized with semi-annual product launches, which aligns social connection with ​business rhythms​.

But who funds these moments?​ Lauren DeYoung​ (Allstate) revealed that giving teams connection budgets wasn't enough. It took nearly a year of adding guardrails and training; this illustrates my "​Below the Line​" thesis that resources alone don't create experiences.

Finally, JJ delivered another truth bomb (my favorite of the conference):

No offsite can transform a broken culture. They take up 1% of work time, yet we obsess over them while ignoring daily interactions that truly shape culture.

Human connection can’t just happen quarterly; it must be nurtured continuously and digital-first.

3. We Don't Productize Workplace

The most refreshing quote came from​ Noel McNulty​ (Twilio): "There is no Chief Workplace Officer." Workplace strategy remains fragmented, with real estate, IT, and HR teams navigating politics instead of reimagining employee experience and treating occupants like customers.

Progressive companies also view physical space differently now. ​Izabella Lorenz​ said Zoom now has "Innovation Centers" or “Experience Centers” (not “offices”) with ​clearer purposes​. She even uses a ​cost per visit​ metric to monitor value!

Moderator Brian Elliott published ​a newsletter​ about “the great workplace reset,” that day, including notes from a tour of Atlassian’s office in Austin.

The fundamental insight? The workplace isn't just physical infrastructure; it's a product with users, new experience metrics, and iterative development cycles. Too few building owners and occupiers have restructured their leadership and investments to reflect this reality.

4. We Dismiss Remote Work's Impact

While many with office-centric business models dismiss remote work, presentations by Stanford's​ Nick Bloom​ and Harvard's​ Prithwiraj Choudhury​ showed distributed work's broader positive impacts.

The ability to work from  ("remotely") is a business strategy.

Nick's​ research​ shows firms are expanding hiring geographies, benefiting women and people with disabilities. For economic development, Raj’s new ​book​ says 50+ U.S. communities are replicating Tulsa Remote's ​success​, shared live by ​Justin Harlan​, to attract remote workers to smaller cities.

Though​ Chase Warrington​ showed how power outages in Spain affected Doist's operations, strong asynchronous practices and distributed teams across time and power zones ​create resilience​. The same practices help when execs are stuck on planes without Wi-Fi.

5. We Confuse Culture with Vibes

Several participants showed how people misuse "culture" and mistake time spent together for actions that build commitment and strategic value.

A simple first example was ​Ebony Beckwith​ talking about the costs of miscoding and vague phrases like “end of day” from workers who are not explicit about where they are. She further invoked an “operating system” metaphor to demonstrate how behaviors matter.

​Tiffany Fort​ (Coursera) borrowed Sherlock Holmes' observation that people “see but do not observe,” urging organizations to teach better remote behaviors.​ Sarah Walker​ (The Long-Term Stock Exchange) noted that people value IKEA furniture that they assemble over store-bought pieces. Individual participation matters in culture too.

Chase described an annual, company-wide strategic planning process that engaged every employee directly to create role clarity and autonomy.

JJ summarized it nicely: "Engagement isn't something you layer on top."

Clarity Is the New Cultural Currency

After dozens of conversations at Running Remote, I'm more convinced than ever: Distributed work, hybrid arrangements, AI integration, and new real estate models will all fail to achieve stated goals without behavioral clarity.

It's time to stop waiting for tools, trends, or CEO transitions to fix fundamentally human and organizational gaps.

If you're responsible for workplace transformation, here's your action plan:

1. Document what matters. Create a search-first culture with accessible knowledge. Begin with one critical process.
2. Connect intentionally. Program meaningful interactions rather than hoping for spontaneous culture.
3. Unify workplace ownership. Connect real estate, IT, and HR under a holistic work experience strategy.
4. Embrace broader impact. Leverage distributed work for talent access, inclusion, resilience, and economic growth.
5. Clarify, don't proclaim. Focus on operational practices over superficial cultural statements.

Need help getting started? My frameworks for creating a “​North Star​” vision and mapping “​Forces​” of resistance provide practical tools to begin addressing these blind spots today.

Which blind spot is holding your team back right now? If you're ready to transform documentation practices, design intentional connections, or create a unified workplace strategy, I'd love to help.

- Phil