The Enduring Human Element
Week One - The 1:1 Meeting
The Generative Moment has become all-consuming. We’re trapped obsessively debating the good, bad and potentially earth shattering elements of this period.
At Operating by John Brewton we’re massively inspired by all of this and we also care very much about all of us humans. Selfishly, we want to understand what work will look like for people moving forward. So over the next week, we're examining one of management's most human tools, a practice that has survived every technological revolution: the one-on-one meeting.
The 1:1 meeting represents something no algorithm can replicate: trust-building, individual development, and strategic alignment through structured conversation. No technology can supplant the empathy, context, judgment and new understanding between colleagues, leaders and direct reports that make these meetings transformational when properly executed.
Companies need teams of autonomous contributors that are able to run with the projects their given, squash the fires that arise, and deliver on the unique needs of the most trying customers.
Managers and leaders struggle to maintain focus on priorities and are often overwhelmed by the deluge of delays and speed bumps that become entirely new projects when trying to get the biggest objectives to the finishline. This is where the 1:1 meeting becomes so critical.
But many questions must be answered well for the sessions to succeed:
How frequently should the 1:1 session be placed?
Should the timing be the same for all of your direct reports?
What about your director reports, direct reports?
How do you keep scope creep from filling your company’s entire calendar with meetings?
What should and should not be discussed during these meetings?
What’s the difference between a standing meet and a 1:1?
We’re aiming to answer all of these questions, using our hard won personal experience and plenty of research as the guide.
We’re not being sentimental, we’re being strategic. Organizations with highly engaged workforces hold 1:1 meetings regularly at a rate of 86%, compared to just 50% of disengaged organizations. Employees who receive twice the number of one-on-ones are 67% less likely to be disengaged. In an era where human capital optimization is at its most critical, mastering this practice is a requirement, not a nice to have.
Okay, since we love history here at Operating by John Brewton, lets start with a historical deep dive on the topic. We hope the nerd in you enjoys what we’ve put together.
The Century-Long Evolution of Individual Management
The one-on-one meeting isn't a Silicon Valley innovation. It's the systematic application of principles that have guided leadership for over a century, adapting to each era's economic realities while addressing the human need for individual attention and development.
Industrial Foundation: Command and Control (1900-1930)
The first formal 1:1 meetings emerged from Frederick Taylor's Scientific Management principles, introduced in 1911. Taylor's approach emphasized observation, measurement, and individual instruction as core management functions. While focused on productivity and control, this era established the precedent for formal manager-employee check-ins with structured purposes and systematic follow-up.
The early 20th-century foreman was trained in scientific management to measure, monitor, direct, and control the manufacturing system. Though their methods were autocratic, they recognized that organizational success required individual attention and systematic communication between supervisors and workers.
Military Influence: Structured Communication Systems
Military hierarchies institutionalized briefings and debriefings, structured one-on-one conversations that inspired corporate management systems, especially during and after WWII. The military briefing became an accepted staff procedure to save time for the senior officer, enable questioning and clarification, and facilitate rapid response.
The military's systematic approach to individual communication provided structural discipline that influenced civilian management practices. The emphasis on clear objectives, systematic preparation, and documented follow-up established templates that continue to influence 1:1 meeting design across industries.
The Human Relations Revolution (1930-1960)
The human relations movement emerged following Elton Mayo's Hawthorne studies, which discovered that workers were responsive to attention from managers and the feeling that managers cared about their work. This shifted from treating workers as replaceable parts to recognizing them as complex individuals with different motivations and needs.
Chester Barnard's 1938 work "Functions of the Executive" focused on managing individuals in organizations rather than managing organizations themselves, emphasizing the psychological need of individuals to meet their goals. This philosophical foundation would underpin the coaching and development focus of modern 1:1 meetings.
Knowledge Worker Management (1960-1990)
Peter Drucker recognized that "the knowledge worker cannot be supervised closely or in detail. He can only be helped". This insight shaped how individual meetings should function in knowledge-based work environments, shifting from control and compliance to development and empowerment.
Douglas McGregor's Theory Y reframed employees as intrinsically motivated individuals rather than passive workers, highlighting the motivating role of job satisfaction. This created the foundation for collaborative, coaching-oriented individual meetings.
Andy Grove's Systematic Revolution
Andy Grove's 1983 book "High Output Management" explicitly advocated for weekly 1:1s as a way to catch small issues before they became large ones and ensure both parties shared the same context.
Grove saw great value in one-on-ones, writing that "Ninety minutes of your time can enhance the quality of your subordinate's work for two weeks, or for some eighty.”
Grove's contribution was making the business case for systematic 1:1 meetings, positioning them as strategic investments rather than administrative obligations. His framework synthesized decades of management thinking into a practical system that addressed the challenges of knowledge work.
Grove's model was influenced by military briefing structures and earlier management theories, but adapted them for the realities of technology development and knowledge worker management. The subordinate owns the meeting and prepares the agenda, which should cover KPIs, current problems, and potential problems, even if it's currently just a hunch.
Grove emphasized that "the subordinate must feel that there is enough time to broach and get into thorny issues," noting that "heart-to-heart" topics tended to emerge around the 20 to 30 minute mark. This insight about timing became foundational to meeting design.
Silicon Valley Adoption and Network Effects
"High Output Management" became a cult classic within Silicon Valley and is frequently praised by tech founders such as Mark Zuckerberg of Meta, Evan Williams of Twitter, Brian Chesky of Airbnb, and Ben Horowitz of a16z. Grove's credibility as an iconic CEO with engineering expertise gave his recommendations authority among Silicon Valley's leadership.
With the decline of manufacturing and the rise of the knowledge economy, especially in tech and consulting, the nature of work changed. As workers were paid more for thinking than doing, interpersonal communication became a management imperative. Grove's systematic approach provided scalable solutions for managing technical teams during rapid growth.
As Intel alumni and Grove disciples moved to other companies, they carried these practices throughout the technology ecosystem, creating network effects that spread weekly 1:1s across the industry. The practice became a competitive advantage signal, companies that adopted systematic 1:1 practices could attract talent from organizations lacking structured individual development approaches.
Contemporary Validation and Strategic Importance
Gallup research found that employees who have regular one-on-one meetings with their manager are almost three times as likely to be engaged as those who don't. Microsoft's research shows that employees who receive little to no one-on-one time with their manager are four times as likely to be disengaged.
Nearly half (47%) of all workplace meetings are one-on-ones, yet despite their massive presence in modern organizations, these conversations remain understudied. This gap in understanding one of management's most enduring practices represents a gap in understanding.
The Human Advantage in an AI World
As artificial intelligence transforms how we work, the human elements of management become more valuable, not less. 1:1 meetings represent something no algorithm can replicate: trust-building, individual development, and strategic alignment through purposeful conversation.
While AI can analyze performance data, predict outcomes, and suggest optimizations, it cannot provide the empathy, context, and judgment that make individual development conversations transformational. The ability to read nonverbal cues, understand emotional context, provide psychological safety, and adapt communication styles to individual needs remains uniquely human.
The evolution of 1:1 meetings demonstrates that while tools and techniques have advanced, the fundamental purpose, helping individuals achieve their potential while advancing organizational goals has remained consistent across more than a century of management practice.
What's Coming This Week
Over the next week, Operating by John Brewton will explore 1:1 meetings from different practical and historical angles each day, helping you design and improve your implementation of this practice. We'll examine:
The strategic architecture of high-impact 1:1 meetings, optimal timing frameworks, and how to construct the optimal agenda
Integration with performance management systems and technology platforms
The psychology of trust-building and why consistency matters more than perfection
Common pitfalls that destroy value and how to avoid them
Advanced techniques from leading organizations and academic research
Each piece will combine historical insights with practical frameworks, providing both inspiration and actionable guidance for optimizing this human management tool.
The one-on-one meeting represents our ongoing attempt to balance organizational efficiency with individual development, a balance that remains as crucial today as it was when Frederick Taylor first began systematizing worker-supervisor interactions over a century ago. In an age of artificial intelligence, mastering this irreplaceable human practice is essential.
Tomorrow, we'll dive into the strategic architecture of peak-performance 1:1 meetings, exploring the frameworks that transform routine conversations into competitive advantages.
As always, thank you, your time and attention mean a great deal.
John Brewton documents the history and future of operating companies at Operating by John Brewton. After selling his family’s B2B industrial distribution company in 2021, he has been helping business owners, founders and investors optimize their operations ever since. His frameworks have generated over $500M in enterprise value. He still cringes at his early LinkedIn posts.
Well researched and beautifully written, John!