Scaling People

Picture this: You're standing in front of a whiteboard, marker in hand, trying to track your growing team with color-coded names and start dates. Sound familiar? This scenario plays out in countless organizations where passionate leaders find themselves managing rapid growth while desperately trying to maintain the human connection that makes work meaningful.

The challenge isn't just about managing more people—it's about creating systems that scale while preserving the culture and relationships that drive exceptional performance. When you're in the thick of building something important, it's easy to lose sight of the individuals behind the work. Yet the most successful leaders understand that their greatest competitive advantage lies not in their processes or technology, but in their ability to develop people who are excited to tackle ambitious challenges together.

Great leadership begins with a fundamental truth: you cannot effectively manage others until you deeply understand yourself. This isn't about personality tests or abstract self-reflection—it's about building the self-awareness that enables you to create environments where others can thrive.

Consider the story of Eli, a well-intentioned manager who struggled with transparency. His team liked working for him and delivered results, but he had a destructive habit of sharing every piece of information immediately, creating anxiety and confusion. When planning divisional changes, he'd tell his team early, making other managers look uncommunicative. During compensation discussions, he'd share his own stress and uncertainty, undermining confidence in the process before anyone understood its purpose.

The breakthrough came during a manager training session where Eli shared a deeply personal story. As a child, when his mother was battling cancer, his family kept him in the dark about her condition, wanting to maintain normalcy. When she died, he learned the news over pancakes at his favorite diner. That experience shaped his core value: transparency. Understanding this connection between his past and present behavior allowed him to work with his manager to find appropriate ways to share information that supported rather than undermined his team.

To build this foundation, start by identifying your core values and understanding how they drive your behavior. Ask yourself what experiences shaped your leadership style and how your strengths might also be your weaknesses. Create space for regular self-reflection and seek feedback from trusted colleagues about your impact. Remember that self-awareness isn't a destination—it's an ongoing practice that enables you to adapt your approach as you grow and face new challenges.

The most effective leaders combine deep self-knowledge with the courage to say difficult things constructively. They understand when they're managing day-to-day operations versus leading transformational change, and they consistently return to the operating systems that create stability amid chaos.

Every successful organization needs a foundation of clear mission, goals, and operating principles that can replicate across teams as the company grows. Without these foundational elements, you'll find yourself constantly fighting fires instead of building sustainable momentum.

When Claire Hughes Johnson joined Stripe, one of her first questions was about the company mission. Surprisingly, there wasn't a formal one. However, early content on Stripe's website mentioned wanting to "increase the GDP of the internet." Employees and candidates kept referring to this phrase as the mission because it resonated as the most compelling purpose for the company. Sometimes your mission emerges organically, but it must be captured and formalized to guide decision-making at scale.

Your operating system should include founding documents that explain why you exist, strategic planning processes that determine where you're going, and accountability mechanisms that ensure you're making progress. At Google, the use of Objectives and Key Results (OKRs) created an extremely effective operating system. These weren't just planning exercises—they were taken so seriously that sometimes the executive team would delay releasing company OKRs while they hashed out priorities behind closed doors. This delay actually reinforced their importance and credibility.

Begin by documenting your mission and long-term goals, even if they feel obvious. Create team charters that explain each group's purpose and how their work connects to the broader mission. Establish quarterly goal-setting processes and regular review meetings. Most importantly, ensure these systems replicate consistently across your organization—the same language, the same cadence, the same level of rigor. This consistency creates a stable foundation that allows people to focus on their work rather than constantly figuring out how things operate.

Remember that good processes should create clarity and speed, not bureaucracy. If your systems feel heavy or defensive, step back and simplify. The goal is to create predictable rhythms that help people do their best work while maintaining alignment with your mission and values.

The quality of your hiring process directly determines your company's trajectory. When you're growing rapidly, early hires become future leaders, making every hiring decision critical to your long-term success. Yet many organizations treat hiring as a necessary evil rather than a strategic advantage.

Consider the story of Omid Kordestani, Google's 11th employee who built their business operations from the first employees and first dollar in revenue to over 12,000 employees and $20 billion in revenue. When he met with Google's founders Larry Page and Sergey Brin, he quickly realized they were unsure what to ask him. Rather than letting the interview flounder, Omid gracefully said, "You know, if I were interviewing someone for this role, here are the questions I might ask," and proceeded to interview himself. This story illustrates both the challenge of hiring for roles you don't fully understand and the importance of finding candidates who can help you figure it out.

Your hiring process should balance speed with quality, involving multiple perspectives while maintaining high standards. Create clear job descriptions and assessment rubrics that focus on capabilities, not just experience. Train your interviewers to ask consistent questions that reveal how candidates work with others, get quality work done, and demonstrate learning aptitude. Most importantly, make hiring everyone's responsibility—when people feel ownership over their future colleagues' selection, they're more invested in those colleagues' success.

Start by analyzing your most successful employees to understand what they have in common beyond technical skills. Look for patterns in their values, work styles, and growth trajectories. Use these insights to refine your hiring criteria and interview questions. Create a candidate experience that reflects your values and gives people a realistic preview of your culture. Remember that every interaction, even with candidates you don't hire, shapes your reputation in the talent market.

The goal isn't just to fill roles but to build a team that's greater than the sum of its parts—people who challenge each other, complement each other's strengths, and share a commitment to your mission.

Creating a culture where people can do their best work requires ongoing feedback, coaching, and performance management. This isn't about annual reviews or formal processes—it's about building an environment where people know where they stand, understand how to improve, and feel supported in their growth.

The most effective approach is what the author calls "hypothesis-based coaching." Instead of waiting for problems to become obvious, great managers form hypotheses about their team members' development needs and test these through targeted conversations and assignments. They separate the person from the task when giving feedback, focusing on specific behaviors and outcomes rather than character judgments.

One powerful technique is to ask team members how their colleagues would describe them, then probe for constructive feedback they've received and what they've done to improve. This reveals self-awareness and learning orientation—two critical predictors of success. Watch for the balance between "I" and "we" in their responses; too much "I" might indicate ego issues, while too much "we" might obscure their actual contributions.

Establish regular one-on-one meetings focused on both immediate work and longer-term development. Create individual development goals alongside work objectives, ensuring people are building capabilities for future challenges, not just completing current tasks. Remember that in high-growth environments, the skills that got someone to their current level won't necessarily carry them to the next level.

When performance issues arise, address them quickly and directly. Have clear expectations, provide specific feedback, and create improvement plans with measurable outcomes. Celebrate high performers publicly and ensure they have challenging work that matches their abilities. For your steady middle performers, focus on development opportunities that help them grow. The goal is creating an environment where everyone can succeed while maintaining high standards for the team's collective performance.

The most important person in your management journey is you. Without taking care of your own development, energy, and relationships, you cannot effectively support others' growth. This requires intentional choices about how you spend your time, what relationships you cultivate, and how you continue learning.

Great managers understand that their primary job is to work themselves out of a job by developing others who can handle increasingly complex challenges. They resist the temptation to be the hero who solves every problem, instead focusing on building systems and capabilities that can operate without their constant intervention. This requires letting go of work you enjoy or feel you do better than others—a difficult but necessary transition.

When the COVID-19 pandemic forced Stripe to rapidly transition to remote work, their response demonstrated masterful change leadership. Rather than waiting for perfect information or a comprehensive plan, leadership began taking immediate actions to protect both employees and business continuity. They communicated transparently about uncertainty while taking decisive steps, such as having half the leadership team work remotely to reduce risk. They provided daily updates, created resource pages, and maintained clear guiding principles throughout the transition.

Develop a personal operating system that includes regular self-reflection, feedback from trusted advisors, and clear boundaries around your time and energy. Identify your own development areas and create plans to address them, just as you would for your team members. Build relationships across your organization and industry that provide different perspectives and support your growth.

Pay attention to your energy levels and what activities drain versus energize you. Structure your work to maximize time spent in areas where you add unique value while delegating or systematizing everything else. Remember that sustainable performance requires recovery and renewal—model the behaviors you want to see in your team regarding work-life integration.

Most importantly, stay curious and maintain a learning mindset. The challenges you face will continue evolving, and your effectiveness depends on your ability to adapt and grow alongside your organization.

Building great teams isn't about having all the answers—it's about creating environments where talented people can do their best work together. The frameworks and principles outlined here provide a foundation, but your unique leadership style will emerge through practice, reflection, and continuous learning. As one leader reminds us, "Leadership is disappointing people at a rate they can absorb"—it requires the courage to drive change while maintaining the trust and support of your team.

The path forward is clear: start with yourself, build systems that scale, hire thoughtfully, provide ongoing feedback and development, and take care of your own growth along the way. These aren't one-time activities but ongoing practices that compound over time to create extraordinary results. Your next step is simple but powerful: choose one area from this guide and commit to improving it over the next month. Whether it's conducting more effective one-on-ones, refining your hiring process, or developing better self-awareness, small consistent actions will build the leadership capabilities that enable you to scale your impact and create lasting value for everyone you have the privilege to lead.