Published 09 Sep 2025

Why Remote Work Doesn’t Always Work

Talent Sherpa Podcast - Episode 55

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Flexibility & Performance in the Modern Workplace

Remote work has become one of the most polarizing topics in modern business, with passionate advocates on both sides. In this episode, co-hosts Scott Morris and Jackson Lynch engage in a heated debate about whether remote work is a viable long-term solution or simply a temporary flexibility that we’ve confused with sustainable practice. Scott and Jackson explore the statistical benefits of remote work – including 35-40% productivity gains and better work-life balance – while also examining the hidden costs and constraints that few organizations acknowledge. Through their discussion, they demonstrate that remote work effectiveness hinges on one critical factor: whether organizations focus on results over activities, with high performers earning flexibility while underperformers require additional structure and support.

“It is not my job as an executive to create the standards for work-life balance. It is my job as an executive to create the freedom for you to define that for yourself while accomplishing the business goals.”

– Scott Bontempto (quoted by Jackson Lynch)

Three Key Takeaways

  • Remote work requires intentional leadership, not default acceptance – Organizations that succeed with remote work actively shape meeting culture, set clear expectations about camera use and engagement, and create structured touchpoints rather than letting remote practices evolve organically without guidance.
  • Crisis moments and collaboration challenges reveal remote work’s limitations – While remote work suits steady-state operations, pivotal moments requiring intense collaboration, strategic pivots, and crisis management often demand in-person interaction for maximum efficiency and alignment.
  • Performance enables flexibility, not the reverse – The most effective approach treats remote work as a privilege earned through consistent results delivery. High performers gain maximum flexibility, while underperformers lose remote privileges until performance improves through additional coaching and support.

Practical Advice

The CHRO Remote Work Strategy Framework:

1. Develop a Clear Philosophy First

  • Define principles around performance expectations, collaboration needs, and flexibility boundaries
  • Write down concrete expectations rather than leaving remote work policies to evolve organically
  • Build leadership coalition around the philosophy before implementing rules

2. Apply the Performance-Flexibility Principle

  • High performers who consistently deliver outcomes earn maximum flexibility
  • Underperformers lose remote privileges temporarily while receiving additional coaching and support
  • Make this expectation universal and transparent from the start

3. Be Strategic About In-Person Requirements

  • Crisis management and strategic pivots require physical presence
  • Designate specific days for team meetings where everyone attends in person
  • Avoid meaningless office mandates – if people come in, make it purposeful

Key Questions for CHROs:

  • “Are we being intentional about remote culture or just letting it happen?”
  • “What activities truly require in-person collaboration versus convenience?”
  • “How do we maintain talent development and coaching effectiveness remotely?”

Remember: Remote work isn’t inherently good or bad – it’s a tool that requires skilled implementation. Focus on outcomes over activities, and be willing to adjust based on business lifecycle needs and individual performance patterns.

Want More?

  1. Remote: Office Not Required by Jason Fried and David Heinemeier Hansson – The foundational guide for implementing effective remote work practices that focus on results rather than presence
  2. Survey: Remote Work Isn’t Going Away — and Executives Know It – Harvard Business Review analysis showing that despite return-to-office mandates, executives expect both remote and hybrid work to continue growing over the next five years (Harvard Business Review, August 2023)
  3. The Future of Remote Work: An Analysis of 2,000 Tasks, 800 Jobs, and 9 Countries – McKinsey research on which jobs can effectively be done remotely and the long-term implications for productivity, inequality, and organizational design (McKinsey & Company, November 2020)
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