
Scaling People
Tactics for Management and Company Building
Categories
Business, Nonfiction, Self Help, Economics, Leadership, Productivity, Technology, Management, Entrepreneurship, Buisness
Content Type
Book
Binding
Hardcover
Year
2023
Publisher
Stripe Press
Language
English
ISBN13
9781953953216
File Download
PDF | EPUB
Scaling People Plot Summary
Introduction
Building a team that can withstand the tests of time and growth is perhaps the most challenging yet rewarding aspect of leadership. When we look at organizations that have scaled successfully, we find they didn't just add more people—they created intentional systems that allowed their teams to thrive amid complexity and change. The difference between teams that collapse under pressure and those that flourish often comes down to purposeful design rather than chance. The journey of scaling with purpose requires a delicate balance of structure and flexibility, of management and leadership. It demands that we look inward at our own tendencies before looking outward at our teams. Throughout these pages, you'll discover practical frameworks for everything from hiring strategically to providing effective feedback. These insights will help you build not just bigger teams, but better ones—teams with the resilience, clarity, and cohesion to navigate whatever challenges come their way.
Chapter 1: Embrace Self-Awareness as Your Foundation
Self-awareness forms the bedrock upon which all effective leadership is built. It begins with a deep understanding of your own values, work preferences, and capabilities—both natural strengths and developed skills. This foundational knowledge illuminates how you operate, what energizes you, and where your blind spots might be hiding. The story of Eli, a manager at Google, powerfully illustrates how self-awareness transforms leadership. Eli consistently struggled with maintaining appropriate discretion, often sharing sensitive information with his team prematurely. This created unnecessary anxiety and undermined other managers who communicated more carefully. During a management training session led by Stan Slap, Eli shared a profound childhood experience: when he was seven, his mother fell ill with breast cancer, but no one told him what was happening. One day, his stepfather took him to a diner and over pancakes informed him that his mother had died. This formative experience instilled in Eli a deep-seated value of transparency at all costs. This revelation was transformative for Eli. Understanding the connection between his childhood trauma and his current communication style allowed him to address the issue constructively. He began having meta-level conversations with his manager about what information was appropriate to share and when. Rather than seeing discretion as withholding or betrayal, Eli came to understand that thoughtful communication was another way of caring for his team. To develop your own self-awareness, start by examining your core values—what gives you a sense of fulfillment and meaning in your work. Then explore your work style preferences: Are you an analyzer who needs data before making decisions? A director who moves quickly toward action? A promoter who thrives on enthusiasm and relationships? Or a collaborator who values harmony and consensus? Understanding whether you gain energy from interactions or from quiet reflection will help you manage your calendar more effectively. Remember that strengths can become weaknesses when overused. If you're a forceful communicator who excels under pressure, you might need to consciously slow down and listen more in certain situations. Create personal rules, like asking a question before jumping to action, to counterbalance your natural tendencies when they might hinder effectiveness. The most powerful teams are built with complementary strengths. Rather than surrounding yourself with people who think and work like you do, seek diversity in preferences, experiences, and capabilities. This creates a balanced team where different perspectives enhance both decision-making and execution, allowing the whole to become greater than the sum of its parts.
Chapter 2: Design Intentional Operating Systems
Creating effective operating systems for your team isn't merely about establishing processes—it's about building the structural foundation that enables consistent, aligned execution. Think of these systems as the wiring and plumbing of your organizational house: invisible when working well, but catastrophic when they fail. When Claire Hughes Johnson joined Stripe, one of her first questions was about the company's mission. Surprisingly, the company hadn't formally codified one, though an early phrase on their website—"to increase the GDP of the internet"—had organically become their north star. This experience highlighted how founding documents like mission statements, long-term goals, and operating principles provide critical context for employees about why the company exists and what it aspires to achieve. At Google, Johnson witnessed how the company's use of Objectives and Key Results (OKRs) created an effective operating system. Because OKRs were taken seriously at the leadership level and flowed down to teams and individuals, they formed a transparent framework around priorities and forced the resolution of dependencies across teams. The executive team would sometimes delay finalizing company OKRs as they debated priorities—a process Johnson likened to waiting for white smoke from a papal convention. But this deliberation signaled the seriousness with which the company approached its goals. To build your own operating system, start with clear founding documents: a mission that explains why you exist, long-term goals that outline what you hope to achieve, and principles that establish the culture enabling your work. Then create mechanisms for strategic planning, resource allocation, goal-setting, and accountability. Ensure these structures can replicate down through divisions and teams to help clarify priorities and resolve dependencies. Your operating cadence—the rhythm with which your company or team provides progress reports and makes decisions—should be predictable and stable. This might include annual planning processes, quarterly business reviews, monthly all-hands meetings, biweekly one-on-ones, and weekly team meetings. The key is to have a cadence but not get stuck in it. These rhythms will require iteration and should be regularly revisited to keep them relevant and fresh. Remember that good processes should create lightweight checks that solidify alignment and achieve a combination of speed and adherence to best practices. Watch out for defensive processes that exist because people aren't aligned on who owns decisions, and beware of stale processes that people follow by rote rather than with engagement and understanding.
Chapter 3: Master the Art of Strategic Hiring
If you believe talent is everything, then your hiring process should also be everything. Your goal is to find people who will thrive and have the most positive impact at your company at every level. This requires a comprehensive approach that balances the need to hire quickly with the need to hire the most successful person for the role. When Johnson interviewed at Google, her final interview was with a director who tested whether she could handle the work environment and fit with the culture. Near the end of the conversation, he challenged her: "So, what's your real career ambition?" She quickly replied, "To undermine the superstructure from within." Though she was shocked by her own candor, this honest answer aligned with Google's disruptive mission and likely helped her secure the job. The story illustrates how authentic interactions during the hiring process can reveal cultural fit in ways that standard questions cannot. Hiring starts with clarifying what success looks like for a given role. Consider the Venn diagram of ideal employees: those who are good at their work, have great impact on the company's progress, and love what they do. Study the people at your company who fit this profile and identify what qualities they share. Then design your job descriptions and hiring process to entice prospects who might be a good fit and discourage those who might not be. For leadership roles, determine whether to promote from within or hire externally. For early-stage companies growing quickly, about one-third of promotions should come from within, one-third from outside, and the final third depends on the company's growth rate and ability to develop internal talent. When hiring externally, be aware that only about 25-50% of outside hires, especially senior ones, are successful. During interviews, test for self-awareness by asking candidates how their colleagues would describe them. If they only mention positive traits, probe what constructive feedback they've received and what they've done to improve. Watch for how much they use "I" versus "we" in their responses. Too much "I" may signal a lack of humility or collaboration, while too much "we" might obscure their specific contributions. Always check references, even when you're eager to make an offer. Ask specific questions like: "Where do you see this person in three years?" "When was the last time you didn't see eye to eye?" and "How would you rate the candidate on a scale of 1-10? You can't say 7!" These questions will reveal more than generic inquiries about strengths and weaknesses.
Chapter 4: Cultivate Teams Through Deliberate Development
Building effective teams requires intentional design and ongoing cultivation. It's not enough to hire talented individuals—you must create an environment where they can collaborate effectively and grow together as a cohesive unit. At Stripe, Johnson observed that management appeared to be a new concept when she joined. Their first employee engagement survey revealed that satisfaction with team-level management was among their lowest-scoring areas. They had promoted many people into management internally to reward high performers and build company scaffolding, but hadn't invested enough in giving these new managers the resources and support they needed. After recognizing this gap, they worked hard to help managers improve their skills. Within just a few years, satisfaction with team-level management became one of the top three highest-scoring categories on the survey. Team development begins with clear structure. Every team should have a mission that ladders up to the division's mission, which in turn ladders up to the company's mission. Teams also benefit from creating a charter—a document that articulates the team's purpose, long-term goals, and what others can expect from them. This clarity helps teams understand their role within the larger organization and enables smoother collaboration across departments. As teams form and evolve, they go through predictable stages of development. Your role as a leader is to guide them through these transitions, helping them establish norms, build trust, and develop effective communication patterns. This includes setting expectations around how decisions will be made, how conflicts will be resolved, and how feedback will be shared. One critical aspect of team development is assigning clear ownership. Without defined accountability, teams can fall into finger-pointing and political jockeying. Make it explicit who is responsible for what work and what outcomes. For collaborative efforts that span multiple teams, be granular about task ownership: "Eve is going to write the product requirements document by the end of this week, and Tim is going to build the prototype by the end of the month." Remember that teams become mirrors of their managers. If you don't recognize that your strengths need to be matched by other people's strengths in other areas, you'll create vulnerabilities. Build a portfolio of people with diverse preferences, experiences, skills, and capabilities. Then arrange their assignments to make optimal use of each person's work style and strengths.
Chapter 5: Implement Effective Feedback Mechanisms
All companies, regardless of stage or size, need to orient their culture around providing feedback that fosters improvement. This doesn't need to be complicated, especially at the beginning. It's far better to start with a basic system and build on it as you go than to try to run a company with nothing in place. When Johnson sent out Stripe's first employee engagement survey, satisfaction with team-level management was among the lowest-scoring areas. This highlighted a critical gap: they had promoted many people into management internally but hadn't invested enough in giving these new managers the resources and support they needed to be effective. After identifying this issue, they worked hard to help managers improve their skills through better feedback mechanisms. Just a few years later, satisfaction with team-level management became one of the top three highest-scoring categories on the survey. Effective feedback begins with creating a culture where saying the thing you think you cannot say becomes normal. During a quarterly business review at Stripe, Johnson noticed people talking around a significant blocker: one team was dependent on another team doing similar work. She stopped the meeting and said, "It feels like we're not talking about the big issue. Is there or is there not a challenge with this other team?" This direct approach allowed them to address the real problem and make a plan to resolve it. As they left the meeting, an engineer commented, "Well, that was refreshing." To implement this approach in your own teams, start by sharing your feelings in a measured way. If you say, "We didn't hit our targets, and I'm worried about the impact this will have on our team and the business," people will immediately understand the gravity of the situation. Also, separate the person from the idea or task. Instead of saying "That presentation was terrible," try "What did you think of the presentation? I was disappointed in aspects of it and would love to hear your thoughts." Formalize feedback through regular one-on-ones, team meetings, and performance reviews. Ensure that no one is ever surprised by the feedback they receive by providing it consistently and constructively. Develop a hypothesis-based coaching approach where you observe behavior, form a hypothesis about what might be causing it, and then test that hypothesis through conversation with the person. Remember that feedback is a two-way street. Create mechanisms for your team to provide feedback to you and to each other. This builds mutual awareness and strengthens the team's ability to learn and adapt together, creating a virtuous cycle of continuous improvement.
Chapter 6: Lead with Clarity Through Change
Leading through change requires exceptional clarity and communication. As organizations grow and evolve, leaders must guide their teams through transitions while maintaining stability and focus on the mission. When Google acquired YouTube, Johnson was the operations leader for Google Video. You can imagine the questions and confusion that arose on her team when news of the acquisition broke. Although she didn't have complete insight into the future strategy, she wrote a short note to her team explaining that she thought it was a smart acquisition that would ultimately make them stronger. She also mentioned that she was part of the YouTube integration team and would keep everyone informed as plans became clearer. This simple act of communication showed empathy and transparency, which bought her time and trust with the team as they solidified plans for the acquisition. In times of uncertainty or change, communicate more than you think is reasonable, even when you don't have all the answers. A personal message or email sharing your reflections can provide reassurance that the company is taking the situation seriously. When communicating about difficult changes, find the Goldilocks zone: sharing too soon creates uncertainty and anxiety, but sharing too late stokes anger and resentment. Change management also requires distinguishing between management and leadership. Management is about creating stability, while leadership is about driving change. As Marty Linsky, co-author of "The Practice of Adaptive Leadership," puts it: "Leadership is disappointing people at a rate they can absorb." This means helping your team abandon the stable and familiar in favor of an uncertain—but exciting—new direction. When implementing change, be clear about what will stay the same and what will be different. People need anchors of stability to hold onto as they navigate new territory. Create a consistent operating cadence with regular check-ins, updates, and opportunities for feedback. This provides structure amid the chaos and helps people feel more secure. Remember that change is emotional as well as practical. Acknowledge the feelings that arise—fear, excitement, resistance, anticipation—and create space for people to process these emotions. By addressing both the practical and emotional aspects of change, you'll help your team move forward with greater confidence and commitment.
Chapter 7: Balance Management and Leadership
Understanding the distinction between management and leadership is crucial for scaling a company effectively. Both are necessary, but they serve different purposes and require different approaches. Johnson describes her realization of this difference as a pivotal moment in her career. At Stripe, she finally grew from being a strong manager into a true leader while helping to build a great company. She avoided some of the mistakes made at Google, though she acknowledges making new ones—an inevitable reality when working at a fast pace in a growing organization. Great managers run teams that do the actual building. Management is about human-centric execution: defining goals, setting operational cadences, and helping each report have a clear view of their performance and career aspirations. Teams with great managers have high trust, experience the challenge and reward of hard work, and feel they're making progress both individually and collectively. Great leaders, on the other hand, put forth a vision and set lofty goals that inspire others to forge ahead, even when the path isn't clear. The clarity of their vision keeps everyone focused on the big picture and sustains motivation. Leaders don't have to be managers, but if they aren't, they need to know how to work with and hire managers to build the right teams to execute that vision. Johnson references a framework from "The Practice of Adaptive Leadership" that evaluates technical versus adaptive problems. Technical problems have a solution and an achievable resolution, while adaptive problems are continuously evolving. Managers excel at solving technical problems, while tackling adaptive problems requires leadership. Once you become a great manager, you can get very comfortable. But once you become a true leader, almost every day is uncomfortable. Experienced employees mostly need a leader and just a bit of a manager. If they've reached a certain point in their careers, they're probably good at getting their work done. But they'll look to a leader to lay out the overarching vision and milestones, and to pave the way for progress within the broader organization. Less experienced employees mostly need a manager and just a bit of a leader. They'll benefit from someone who can help them think through tactics, manage their day-to-day work, and help them develop. The most successful organizations have a balance of strong management and visionary leadership. By understanding which role is needed in different situations and with different team members, you can build a company that executes effectively today while preparing for the challenges of tomorrow.
Summary
Throughout these chapters, we've explored the multifaceted journey of building teams that can scale with purpose and stand the test of time. From the foundation of self-awareness to the delicate balance of management and leadership, each element plays a crucial role in creating teams that thrive amid complexity and change. As Marty Linsky wisely noted, "Leadership is disappointing people at a rate they can absorb"—reminding us that true leadership requires the courage to guide teams through uncertainty toward a compelling vision. Your next step is to assess where your team stands today. Choose one area from this book that resonated most strongly with you—perhaps it's designing more intentional operating systems or implementing more effective feedback mechanisms. Start there, making small but meaningful changes that align with your team's current needs and challenges. Remember that scaling with purpose isn't about perfection; it's about continuous, intentional improvement that creates the conditions for lasting success.
Best Quote
“Heuristics for testing your goals Assess your goals using these guidelines: Does your goal start with a verb (“launch,” “build,” “refactor,” etc.)? Then you probably have an action, so reframe it to describe the outcome you want. Often, this takes the form of translating “X so that Y” into “Y via X” (and consider if you need X in there at all). A helpful trick to figure out the proper framing is to read the goal out, ask yourself why, answer that question, then do that a couple of times until the true goal comes into focus. (See Table 2 for an example.) Do you have “engineering goals” and “business goals,” or something similar? Stop it. Are your goals more than one page, more than three to five objectives, or more than three to five KRs per objective? No one will read them—let alone remember them. When you (or your team) look at your goals, do you wince and think, “What about X? I was really hoping to get to that this quarter”? If not, you probably haven’t focused enough, and your goals are not adding value. Could one team member think a goal is achieved and another one completely disagree? Then your goal isn’t specific enough. (By contrast, if everyone feels it’s mostly successful but the assessments range from 60–80 percent done, who cares?) Can you imagine a scenario where the goal is achieved but you’re still dissatisfied with where you ended up? Then your goal isn’t specific enough, or an aspect is missing. Could you be successful without achieving the goal? Then your goal is overly specific, and you should rethink how to define success.” ― Claire Hughes Johnson, Scaling People: Tactics for Management and Company Building
Review Summary
Strengths: The author, CHJ, is experienced and knowledgeable, and the book is well-written with clear and comprehensible advice. The content on everyday work with people, such as hiring and team development, is valuable.\nWeaknesses: The book did not meet the reader's expectations set by the introduction, which suggested a higher-level strategic focus. Instead, it covers more fundamental managerial topics that can be found in other sources. The reader expected more on strategic thinking and creative growth.\nOverall Sentiment: Mixed\nKey Takeaway: While the book offers valuable insights into everyday managerial tasks, it may not fulfill expectations for those seeking advanced strategic guidance from an experienced author like CHJ.
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Scaling People
By Claire Hughes Johnson