Glad We Met

Glad We Met Plot Summary

Introduction

Leadership isn't just about making decisions and driving results—it's about connecting with the people who bring those results to life. In today's fast-paced workplace, many leaders find themselves caught in a paradox: they're constantly communicating through emails, messages, and meetings, yet meaningful connections with team members remain elusive. The most powerful leadership tool may be hiding in plain sight: the one-on-one conversation. These focused interactions create space for authentic dialogue that transforms relationships, ignites motivation, and solves problems that would otherwise fester. When approached with intention and care, one-on-one conversations become the foundation for trust, the catalyst for growth, and the bridge between potential and performance. Throughout the following chapters, you'll discover how to elevate these crucial conversations from obligatory check-ins to transformative encounters that both you and your team members will genuinely look forward to.

Chapter 1: Build Trust Through Regular, Meaningful Connections

The foundation of exceptional leadership is trust, and nothing builds trust more effectively than consistent, meaningful one-on-one conversations with team members. These dedicated meetings signal that you value your people enough to set aside time specifically for them—not just for their work output, but for them as whole individuals with ideas, concerns, and aspirations. Consider the transformation at Warner Brothers Discovery, where Senior Vice President Adam Husein implemented regular one-on-ones across his global enterprise data team. Previously, team members felt disconnected from leadership, creating an environment where innovations stalled and turnover increased. By establishing a rhythm of biweekly conversations with direct reports, Husein created safe spaces for honest dialogue. These weren't meetings to discuss status updates—those happened elsewhere. Instead, these conversations focused on understanding each person's perspective, addressing concerns before they became problems, and aligning individual growth with organizational needs. Within months, the team dynamics shifted dramatically. One data scientist who had been considering leaving the company later shared how a conversation about her career aspirations led to a project alignment that reignited her enthusiasm. Another team member finally felt comfortable enough to voice concerns about a process inefficiency that, once addressed, saved countless hours across the department. The regular cadence of these conversations created predictability and security that made vulnerability possible. To build this foundation of trust in your own leadership practice, commit first to consistency. Whether weekly, biweekly, or monthly, the regularity matters more than the frequency. Schedule these conversations as sacred time on your calendar—time that gets postponed only in true emergencies, never simply canceled. Communicate clearly that these meetings belong to your team members, not to you. While you may guide the structure, the content should primarily serve their needs. Create a psychologically safe environment by beginning each conversation with genuine personal connection. Simple questions about weekend plans or family updates signal that you see the whole person, not just the employee. Follow through on commitments made during these conversations, no matter how small, as each fulfilled promise builds trust incrementally. Remember that trust develops at different rates for different people. Some team members will open up immediately, while others may need months of consistent interaction before sharing their authentic thoughts and concerns. Patience and persistence are essential to nurturing these vital connections that transform your leadership impact.

Chapter 2: Ask Questions That Spark Authentic Dialogue

The quality of your one-on-one conversations directly correlates with the quality of your questions. Powerful questions open doors to insights, solutions, and connections that conventional status updates could never reveal. They transform routine check-ins into meaningful exchanges that energize both participants and lead to unexpected breakthroughs. At Boston Beer Company, CEO Dave Burwick transformed his leadership approach by reimagining the questions he asked during one-on-ones. Previously, his conversations focused primarily on metrics and deliverables—important information, but insufficient for truly understanding his team members. During a critical product launch phase, Burwick began asking more expansive questions: "What part of this project energizes you most?" "Where do you see obstacles that I might be missing?" "If resources weren't a constraint, how would you approach this differently?" The shift was remarkable. One senior marketing executive, initially hesitant to voice concerns about market positioning, opened up when asked what kept her awake at night regarding the launch. Her perspective highlighted potential issues that hadn't surfaced in team meetings. This led to crucial adjustments that ultimately contributed to a successful product introduction. The conversation created not only a better business outcome but also deepened mutual respect and understanding between Burwick and his executive. To elevate your questioning technique, start by moving beyond closed questions that elicit simple yes/no responses. Replace "Are things going well?" with "What aspects of this project are working best, and where are you feeling challenged?" Instead of "Do you have what you need?" try "What resources or support would make the biggest difference to your progress right now?" These open-ended questions invite thoughtful reflection rather than perfunctory answers. Practice the art of follow-up questions that gently probe beneath surface responses. When someone says "things are fine," respond with "tell me more about what 'fine' looks like in this situation." Create space after asking a question—comfortable silence often leads to more considered, authentic responses as people gather their thoughts. Balance your questions across multiple dimensions: immediate tasks, long-term aspirations, obstacles, opportunities, professional development, and personal wellbeing. This comprehensive approach ensures your conversations address both urgent matters and important but less time-sensitive topics that might otherwise never surface. The most powerful questions demonstrate genuine curiosity rather than confirmation of what you already believe. Approach each conversation with the assumption that there's something valuable you don't yet know or understand—because there almost certainly is.

Chapter 3: Master the Art of Active Listening and Empathy

The most transformative element of one-on-one conversations isn't what you say—it's how you listen. Active listening transforms these interactions from obligatory check-ins to meaningful exchanges that build connection, uncover insights, and demonstrate genuine respect. When leaders truly listen, team members feel valued, understood, and more willing to contribute their best thinking. Jennifer Fisher, Chief Well-being Officer at Deloitte, discovered the power of this approach during a challenging organizational restructuring. One senior team member, Marcus, had grown increasingly withdrawn during team meetings. Rather than making assumptions about his disengagement, Fisher created space in their one-on-one for authentic listening. She began by acknowledging the organizational changes and simply asked, "How are you experiencing all of this?" Then, crucially, she remained silent, maintained eye contact, and focused completely on understanding his perspective. What emerged surprised her. Marcus wasn't resistant to the changes themselves but had significant insights about implementation approaches that could better support team cohesion during the transition. His withdrawal stemmed from previous attempts to share these thoughts in settings where he didn't feel fully heard. Fisher's attentive listening not only rebuilt their connection but also led to valuable adjustments to the change management approach. By the following quarter, Marcus had become one of the most engaged advocates for the new structure, partly because he felt his perspective had been genuinely considered. To enhance your active listening skills, start by eliminating distractions. During one-on-ones, close your laptop, silence notifications, and position yourself to maintain comfortable eye contact. These physical signals communicate your full attention. Resist the temptation to formulate your response while the other person is speaking—instead, focus completely on understanding their message, both spoken and unspoken. Practice the powerful technique of reflective listening by periodically summarizing what you've heard: "So what I'm understanding is..." This demonstrates your attention and creates opportunity for clarification. Notice your ratio of speaking to listening—in most one-on-ones, the team member should be speaking significantly more than you are. Develop your empathic listening by tuning into emotional content beneath the words. Statements like "That sounds really challenging" or "I can see why you'd be excited about that opportunity" acknowledge feelings without judgment. These empathic responses create psychological safety that encourages further openness and honesty. Remember that listening isn't passive—it's an active choice to temporarily set aside your perspective to fully understand another's. This investment of attention is perhaps the most meaningful way to demonstrate respect for your team members, and it consistently yields insights that would remain hidden in more superficial exchanges.

Chapter 4: Transform Feedback into Growth Opportunities

Delivering feedback effectively is perhaps the most challenging aspect of one-on-one conversations, yet it's also where their greatest value often lies. When approached thoughtfully, feedback conversations become catalysts for development rather than sources of anxiety or defensiveness. They transform potential performance issues into opportunities for growth and deeper connection. Tasha Eurich, an executive at Meta (formerly Facebook), faced this challenge when onboarding Elizabeth, a talented but sometimes abrupt engineering leader. Initial feedback about communication style delivered in team settings had created defensiveness rather than change. Recognizing the sensitivity of the situation, Eurich restructured their one-on-one conversations to create a foundation for more productive feedback exchanges. She began by establishing psychological safety—explicitly acknowledging Elizabeth's technical strengths and the value she brought to the team. In their one-on-ones, Eurich asked questions about Elizabeth's career aspirations and what support she needed, demonstrating genuine investment in her success. Only after several conversations that built this foundation did Eurich introduce specific behavioral feedback, framing it as an opportunity to enhance leadership impact rather than criticism of personality. The approach transformed what could have been a contentious relationship into a developmental partnership. Elizabeth began to see Eurich as an ally in her professional growth rather than a critical supervisor. Within months, team members noted positive shifts in Elizabeth's communication approach, and she herself reported greater satisfaction in her role as she developed new interpersonal skills alongside her technical expertise. To elevate your feedback conversations, establish a regular cadence for these discussions rather than saving them for problems or formal reviews. When feedback becomes an expected part of your one-on-ones, it reduces anxiety and defensiveness. Balance constructive feedback with recognition of strengths and progress—research suggests a ratio of at least three positive observations for each developmental area maintains receptivity and motivation. Focus feedback on specific behaviors rather than personality traits: "When you interrupted Sam during the presentation" rather than "You're too dominant in meetings." Connect the behavior to its impact: "This made it difficult to hear his complete perspective and might have discouraged future contributions." Then collaborate on potential adjustments: "How might we ensure everyone's ideas get fully expressed in our discussions?" Create mutual accountability by inviting feedback on your own leadership. Questions like "What could I do differently to better support your success?" model openness to growth and demonstrate that feedback flows in both directions. Document agreed-upon development areas and action steps, then follow up in subsequent conversations to acknowledge progress and refine approaches. Remember that effective feedback in one-on-ones isn't about fixing people—it's about creating conditions where talented professionals can recognize opportunities for growth and feel supported in pursuing them.

Chapter 5: Create Clear Action Plans and Follow Through

The true measure of effective one-on-one conversations isn't how they feel in the moment—it's what happens afterward. Without clear action plans and consistent follow-through, even the most insightful discussions eventually lose credibility and impact. Converting conversation into meaningful progress requires intentional structure and mutual accountability. This principle became evident at Johnson & Johnson when Robin Cohen, Head of Talent Management, identified a pattern across departments: productive one-on-one conversations weren't translating into consistent improvement. In particular, a promising marketing director named Priya repeatedly discussed the same development areas with her manager without measurable progress. Upon closer examination, Cohen discovered the conversations lacked specific action commitments and accountability mechanisms. The solution was implementing a simple but structured approach to concluding one-on-ones. Each conversation now ended with both participants clearly articulating: "What specifically will each of us do before our next meeting?" These commitments were documented in a shared format, with defined metrics for success and specific timeframes. At the beginning of each subsequent one-on-one, they briefly reviewed these commitments before moving to new topics. The results were remarkable. Within a quarter, Priya's progress accelerated dramatically as vague development discussions transformed into concrete skill-building activities with clear feedback loops. Her manager reported more satisfaction with their interactions, and the approach spread throughout the department as its effectiveness became apparent. To implement this practice in your own leadership, reserve the final five minutes of each one-on-one for action planning. Resist the temptation to rush this step even when time runs short—without it, the value of your conversation diminishes significantly. Ensure actions are specific and measurable: not "work on communication" but "prepare talking points before the next three team meetings and solicit feedback afterward." Balance accountability with support by identifying potential obstacles and resources needed for success. Ask questions like "What might get in the way of completing this?" and "What support do you need from me to make this happen?" This proactive troubleshooting significantly increases follow-through. Document commitments in a shared format—whether a collaborative document, email summary, or dedicated software. This creates clarity and provides a reference point for future conversations. Be disciplined about reviewing previous commitments at the start of each one-on-one, celebrating progress and addressing barriers where actions weren't completed. Follow through on your own commitments impeccably, no matter how small. When leaders model accountability by honoring their promises, it creates a powerful expectation for reciprocal reliability. This consistency builds trust that extends beyond individual conversations to strengthen your overall leadership influence.

Chapter 6: Balance Personal Connection with Practical Problem-Solving

The most effective one-on-one conversations achieve a delicate balance between building personal connection and addressing practical business needs. Leaning too far toward relationship-building without addressing work challenges can feel pleasant but ultimately unproductive. Conversely, focusing exclusively on tasks and problems without personal engagement misses opportunities to build the trust that fuels collaboration and commitment. This balance was skillfully demonstrated at Radio Flyer, where CEO Robert Pasin noticed a gap in effectiveness between different leaders' one-on-one approaches. Some managers created warm relationships but struggled to drive performance improvements, while others addressed business issues directly but missed opportunities to build deeper engagement. The most successful leaders integrated both dimensions into their conversations. One production supervisor, Carlos, exemplified this balanced approach with his team. Each one-on-one began with a few minutes of genuine personal connection—asking about family updates or weekend activities that mattered to his team members. These moments weren't perfunctory; he remembered details from previous conversations, demonstrating authentic interest in their lives beyond work. After establishing this connection, Carlos would transition to work challenges with questions like "What's one thing that's been challenging you this week?" or "Where could you use some support?" A team member later described how this approach helped him navigate a difficult production issue: "Because we'd built that relationship, I felt comfortable admitting I was struggling with the new equipment configuration. In a different environment, I might have tried to handle it alone to avoid looking incompetent." The personal connection created safety for problem-solving, while the focus on practical challenges ensured the conversations delivered tangible value. To achieve this balance in your own leadership, intentionally structure your one-on-ones to include both elements. Begin with genuine personal connection, allocating at least the first few minutes to topics beyond immediate work tasks. Show that you remember details from previous conversations, demonstrating that your interest is authentic rather than formulaic. Create a natural bridge to practical matters with transition questions: "What's been on your mind this week regarding our projects?" or "Where should we focus our attention today?" Allow the conversation to flow between relationship and task domains naturally, recognizing that personal insights often emerge during problem-solving discussions, and business solutions frequently arise from moments of personal connection. Pay attention to patterns in your one-on-ones. If you notice they consistently tilt toward social conversation without addressing work challenges, introduce more structure to ensure practical outcomes. Conversely, if your discussions feel transactional and task-focused, intentionally create more space for understanding your team members as individuals. Remember that this balance may look different with different team members. Some people naturally share personal information easily, while others prefer more professional boundaries. Respect these differences while still ensuring both dimensions are present in appropriate proportions for each relationship.

Chapter 7: Overcome Meeting Fatigue with Purposeful Interactions

In today's meeting-saturated workplace, one-on-one conversations often compete with numerous other demands for time and attention. When poorly executed, they become just another dreaded calendar obligation. However, when approached with intention and purpose, these interactions stand out as uniquely valuable experiences that energize rather than deplete participants. At Zoom Video Communications, Chief People Officer Matthew Saxon confronted this challenge directly during the company's period of explosive growth. With employees spending unprecedented hours in virtual meetings, adding one-on-ones risked increasing already concerning levels of meeting fatigue. Rather than reducing these crucial conversations, Saxon reimagined how they could be structured to provide maximum value with minimal drain. Saxon implemented an approach called "purposeful interactions" across his leadership team. Each one-on-one was designed with three key elements: clear intention, participant preparation, and format variety. Leaders articulated the specific purpose of each conversation in advance—whether developmental coaching, problem-solving, relationship-building, or performance feedback. Both participants came prepared with relevant thoughts and materials. Perhaps most importantly, they varied the conversation format to combat monotony. One manager, Sophia, rotated between traditional desk meetings, walking conversations, virtual "coffee chats," and occasionally even brief voice calls while commuting (for appropriate topics). Team members reported that these varied formats kept the interactions fresh and often matched different conversation modes to different topics—complex problem-solving benefited from whiteboard visualization, while career discussions flowed naturally during more relaxed walking meetings. To overcome meeting fatigue in your one-on-ones, start by clarifying the distinct value these conversations provide that other interactions cannot. Communicate this unique purpose to your team members so they understand why these meetings matter amid competing priorities. Prepare thoughtfully for each conversation rather than approaching them as routine check-ins—review previous notes, consider specific questions, and identify the most valuable focus areas. Experiment with different formats and settings based on conversation goals. Walking meetings stimulate different thinking patterns and energy levels. Virtual backgrounds or location changes can refresh perspective. For appropriate topics, even brief, focused phone conversations can provide connection without the fatigue of video meetings. Be ruthlessly efficient with administrative updates to preserve time for more meaningful exchange. Consider moving status reports to asynchronous formats before the meeting, allowing your face-to-face time to focus on areas requiring dialogue and connection. Start and end on time to demonstrate respect for boundaries in a demanding schedule. Perhaps most importantly, be fully present during these conversations. The quality of your attention—free from distractions, multitasking, or preoccupation with other concerns—transforms these interactions from obligations into energizing connections. When team members experience your complete focus, they're more likely to reciprocate with their own engagement and commitment.

Summary

The transformative power of one-on-one conversations lies not in their frequency or duration, but in the quality of connection and clarity they create. Throughout these chapters, we've explored how these crucial interactions build the foundation of trust that makes all other leadership functions possible. As Peter Bregman of Bregman Partners noted, these meetings may be "one of the most helpful, valuable, practical, and grounded leadership tools" available to modern leaders. Today, take one step toward elevating these conversations in your leadership practice. Whether scheduling regular one-on-ones for the first time, improving your questioning technique, or bringing more intentional structure to your follow-through, start with a single, consistent change. The compounding effect of these improved interactions will gradually transform not only your relationships with team members but the overall culture and performance of your organization. When team members genuinely look forward to your conversations because they consistently leave feeling valued, understood, and equipped for success, you'll know you've mastered one of leadership's most powerful tools.

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Steven G. Rogelberg

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