Can We Talk?

Can We Talk? Plot Summary

Introduction

We've all been there—that moment when your heart sinks as you hear the words, "Can we talk?" Perhaps you're the one who needs to initiate a challenging conversation with a colleague who consistently misses deadlines, or with your boss about a well-deserved promotion. These moments often fill us with dread, causing many to avoid necessary discussions altogether, creating a communication gap that damages relationships and productivity. The ability to navigate difficult workplace conversations isn't an innate talent but a skill that can be developed with the right framework and practice. When mastered, this skill transforms workplace dynamics, builds trust, and creates pathways for authentic connection. Throughout the following chapters, you'll discover seven essential principles that will help you approach even the most challenging conversations with confidence and clarity. These principles aren't just theoretical concepts—they're practical tools that will empower you to speak your truth while respecting others, ultimately creating a more humanistic workplace where meaningful dialogue flourishes.

Chapter 1: Build Trust Through Confidence and Clarity

Confidence serves as the foundation for any difficult conversation. When you approach a discussion feeling self-assured, the conversation tends to flow more naturally and productively. Yet many of us struggle with self-doubt, especially when facing challenging workplace interactions. That little voice in our head whispers things like, "This isn't going to go well" or "What makes you think you're the expert?" This self-doubt often stems from not trusting yourself or the person you're speaking with. Consider Don's experience with his boss Catherine. When Catherine confronted him about a missing report, Don immediately became defensive: "We never received the revenue numbers from you. Therefore, we couldn't finish the report. You also handed us another assignment earlier in the week and instructed us to get that done." Later, Don realized he should have responded differently: "I can certainly see why being called upon by the CEO and not having the information you needed would have been embarrassing. I sincerely apologize for that. I take full responsibility for not coming to you when I first realized we were still waiting on information." Don's initial defensive reaction made a bad situation worse because he didn't trust himself enough to take responsibility. This pattern of second-guessing ourselves often leads to exhaustion, frustration, and regret. One client shared how she delayed firing her underperforming sister for months because she kept second-guessing herself. "I kept telling myself that this week would be the week I'd have this discussion, but the little voice inside my head would tell me to wait," she explained. The situation deteriorated until a long-term employee threatened to quit because they were picking up the slack. Only then did she finally take action. To build self-confidence, start your day with positive affirmations like "I can do whatever I set my mind to" or "I'm smart and capable." Build bench strength by tackling easier conversations first before moving to more challenging ones. Be decisive rather than overthinking every situation—effective decision-making involves considering your past experiences, analyzing the current situation, making a risk-reward comparison, and believing in yourself. Remember that credibility comes from consistency. People judge us by our behaviors, not our intentions. Make daily deposits into your "bank of trust" by doing what you say you'll do, giving credit where it's due, and admitting when you're wrong. When you have a trusting relationship with someone, they're more likely to be receptive when you need to have a difficult conversation.

Chapter 2: Practice Compassion and Curiosity

Compassion and empathy form the heart of productive workplace conversations. When someone reveals personal challenges affecting their work, acknowledging their situation demonstrates that you care about them as a person, not just an employee. People who feel cared for are more willing to openly discuss difficult topics than those who feel no connection to the person addressing them. Matt Androski, a sales executive, learned this lesson the hard way. When addressing performance issues with an employee, he started firmly: "I know you can do this job, but you're falling short in some key areas, which is negatively impacting the team. Frankly, I'm surprised you are struggling." The employee responded with anger: "I have so many balls in the air right now that I don't even know which game I'm playing. One of my parents took ill and I'm now the primary caregiver." Matt expressed sympathy but immediately pivoted to another sensitive topic: "We need to talk about your relationship with your coworker." At this point, the employee completely shut down. Matt's mistake was failing to recognize when compassion required pausing the conversation. After learning about his employee's personal struggles, he should have suggested reconvening later rather than piling on another difficult topic. Showing genuine empathy means putting your ego aside and truly listening to understand the other person's perspective. Building rapport is essential for effective communication, especially before difficult conversations. When you understand what drives people, you'll know exactly what each person needs from you to have a meaningful conversation. Think about how differently you respond to feedback from someone you trust versus someone with whom you have no connection. Rapport makes others more receptive to accepting feedback, which only works if someone is willing to listen. Your nonverbal communication speaks volumes during difficult conversations. When your words don't align with your body language, the listener will likely feel you're being dishonest. To convey compassion, maintain uncrossed arms, lean slightly forward when listening, and use a soothing, modulated voice. Occasional head nods with acknowledgments like "I see" or "I'm sorry to hear that" demonstrate that you're truly listening. Remember that sometimes slowing down actually speeds up resolution. Jan, who led a team of communications professionals, learned this when she hastily confronted an employee about missed deadlines without taking time to understand the situation. "In the last two weeks, you've missed three deadlines. This has to stop," she said, adding, "You do know there are dozens of people who would like your job." The employee immediately resigned. Jan later discovered his spouse had just asked for a divorce and threatened to take his children. Had she slowed down and shown compassion, she might have saved a valuable employee.

Chapter 3: Find Common Ground Through Compromise

Compromise forms the backbone of productive workplace conversations. It's an agreement reached by each side making concessions, which sounds reasonable in theory but proves challenging in practice. The key is achieving mutual respect first, as people who respect each other are more likely to compromise than those who don't. Consider this scenario: you're having a heated discussion with a coworker whom you respect about different approaches to designing a new product. Your colleague listens to your suggestion and acknowledges its merit, then says, "You know, Ron, that's an interesting way to approach this project. You raise some great points. What if we took this one step further and involved the marketing team while we are still in the product development stage?" While you may not completely agree, you respond with a counterproposal: "I hadn't thought of bringing in the marketing team this early. What if we wait just a bit and bring them in after we've completed the prototype?" Your colleague agrees, and both parties feel good about the outcome. One executive shared how finding common ground helped her navigate a potentially career-ending situation. "I was hired for a new customer service manager role and was enjoying my job until the company changed hands and I was assigned a new boss. My requests for previously promised staff were denied and meetings with my manager became less frequent." After some sleepless nights, she decided to address the situation directly. Her boss admitted, "We already have someone doing some of the job functions you've been assigned. We're trying to figure out if we have redundancies." Instead of becoming defensive, she took a moment to compose herself and said, "I get that the job I was hired for may not be the job I'm in after integration. If needed, I'm willing to work under this other person." Her boss was relieved and offered her a different role leading customer experience initiatives. When seeking compromise, focus on the "why" behind the conversation. Why is it vital that you come to an understanding? When everyone understands why something needs to be achieved, there's a foundation to find common ground. Keep your eyes on the prize—don't try to win every battle, but focus on the big picture. Be open to alternatives and try to understand the other person's perspective. The "you cut, I'll choose" approach can be particularly effective. This childhood method of fairly dividing cake—where one person cuts and the other chooses—applies perfectly to workplace compromises. For each relationship to prosper, both parties must get something and feel they're being treated fairly. When someone makes a request that seems unreasonable, look for a workable solution: "I could take on this task, but you'd need to be flexible on the deadline." Remember that influence is asking for something in a way that allows the other person to say yes. Make your requests specific, think about what's in it for them (WIIFM), and ensure you have a trusting relationship first. Without that foundation, attempts at influence may come across as manipulation.

Chapter 4: Establish Credibility Through Consistent Actions

Credibility isn't something you're born with—it's earned through consistent actions and is crucial for productive workplace conversations. Without credibility, your words carry little weight, making difficult conversations nearly impossible to navigate successfully. Early in her career, Roberta was promoted to senior management at age twenty-four. She mistakenly thought credibility came with her director title, similar to being crowned royalty. She quickly discovered this wasn't the case. Her peers, who were decades older, still viewed her as an inexperienced kid. "I was the poster child of a leader with zero credibility," she recalls. "Only at the time, I didn't know it." After enrolling in an MBA program, she noticed people started treating her differently. While she gained knowledge, the most significant change was in how she showed up every day—projecting an aura of confidence that made others perceive her as credible. Credibility is about being trusted and perceived as believable. It starts with believing in yourself. No one will believe in you when you don't believe in yourself. As demonstrated in The Wizard of Oz, the Scarecrow, Tin Man, and Cowardly Lion all discovered they already possessed what they were searching for. Similarly, your confidence in yourself directly impacts how others perceive you. To establish credibility, be well-read about your field and the topics you'll be discussing. One client recalled a tough conversation with her boss about introducing a new employee benefit that appeared costly. "I arrived at our meeting with facts in hand and was glad I did. He pushed back hard. I didn't back down, presented him with the facts, and eventually he said yes to my request. I had proven to him that I had done my homework." Consistency is equally important. A manager named Judy performed brilliantly some days and poorly others. Despite several discussions about this, she "consistently performed inconsistently," which cost her a promotion. Her boss couldn't trust she would succeed in a more demanding role. Remember that behaviors matter more than intentions—if what you say doesn't align with what you do, people won't trust you. Owning your mistakes also builds credibility. No one expects perfection, but they do expect accountability. One executive coach client apologized to his team for a business decision that cost them unpaid overtime: "Ultimately, the buck stops with me. I misjudged how long it would take for the supplier I chose to deliver. I should have come to you when I realized we'd all have to work nights and weekends. I know better now and can assure you I'll be more communicative going forward." His sincere apology demonstrated accountability and inspired similar behavior in his team. Perception plays a powerful role in credibility. People judge us based on their understanding, which is why it's critical to be aware of how others perceive you. If your credibility begins to decline—people no longer confide in you, you're no longer seen as the "go-to" person, or you're passed up for promotion—take immediate steps to rebuild trust through consistent, ethical behavior that aligns with your words.

Chapter 5: Summon the Courage to Speak Your Truth

Courage forms the backbone of difficult workplace conversations. It's the determination to move forward despite fear—not just a mindset or emotion, but a principle of action. When you muster the nerve to do something frightening, you demonstrate "the courage of your talent." Andrea Nation experienced this firsthand during an international conference she was managing. When she discovered her trusted employee had made a critical error with arrival dates affecting 600 attendees, Andrea lost her temper: "I started screaming in the lobby, 'This is not a good sign starting off the program like this!' I kicked a plant and almost broke a glass table—I just lost it." She told the employee to pack her bags and return to California immediately. Two hours later, the employee found Andrea and asked, "Can we talk?" With tears in her eyes, she said, "This is the hardest conversation I've ever had, but after this trip, I don't want to work for you anymore. I value your friendship way too much." Andrea apologized, acknowledging she could be difficult to work with. Years later, Andrea reflects, "Now in my sixties, I realize there is no perfection in life, and I thank this employee, who has become a lifelong friend, for opening my eyes to this." Getting comfortable with discomfort is essential for having courageous conversations. Many people think avoiding action helps them avoid discomfort, but inaction is a decision that can result in things remaining the same or worsening. Peter Rinnig, a business owner, faced this reality during the pandemic when he had to lay off seven of his nine employees. "It was the hardest thing I had to do in nineteen years of owning QRST's," he shared. "No one had done anything wrong. These folks showed up on time, did their work, and were a pleasure to have around." Despite the discomfort, Peter gathered his team and directly addressed the situation. "I've looked at our business from all angles, and the only way I can see this business still standing when this pandemic is over is for me to reduce the payroll." Three and a half months later, he brought everyone back, and their return was covered by a major Boston television station as a story of hope and survival. Office politics represents one of the most challenging areas requiring courage. Whether requesting additional headcount, firing someone you don't want to fire, or securing a promotion, these situations demand political savvy and courage. For example, when asking for more staff, politically astute employees focus on how their request benefits their boss: "I know website security is one of your top priorities given the recent security breach at our competitor. To fix this and keep our systems safe, I'd like to bring on a chief security officer." This approach is more likely to succeed than simply stating, "I'd like to hire another person for our team." Sometimes the most courageous act is standing up for yourself. Aileen Amor-Bautista demonstrated this when applying for a senior executive position. After her boss dismissed her request saying, "I don't see you as being the right fit," she followed him to the elevator and even to the parking area, persisting in making her case. The next day, her boss said, "After much thought about our conversation, I've changed my mind. I'm going to endorse you for the senior vice president position." Today, Aileen is the President and CEO of the company. Remember that courage comes in many forms. Ask yourself: "If I don't speak up now, might I regret my decision later? Am I giving away my power by remaining silent? Do the pros of speaking up outweigh the cons?" The more you practice, the more comfortable you'll become handling situations you previously avoided.

Chapter 6: Navigate Office Politics with Strategic Finesse

Office politics is one game played in every organization, regardless of whether you work for a nonprofit, government agency, or private company. Ignoring it means doing so at your own peril. Political conversations require strategic finesse and careful navigation to achieve your goals while maintaining relationships. The most politically charged conversations often revolve around resources, promotions, and organizational changes. For instance, when competing for limited headcount, politically savvy employees frame their requests in terms of how they benefit leadership: "I know cybersecurity is your top priority given our competitor's recent breach. To address our vulnerabilities, I'd like to bring on a chief security officer." This approach connects the request directly to the leader's priorities rather than simply stating, "My team needs more staff." When facing a situation where your boss asks you to fire someone you believe shouldn't be let go, you must decide if this battle is worth fighting. In one scenario, an employee approached this delicately: "Your message said you wanted to talk about Bob. I've been meaning to talk to you about him." When her boss mentioned the VP of sales wanted Bob fired for poor performance, she revealed critical information: "Bob's been going through some personal issues, which he seems to have recently resolved. Before all this happened, he was one of our top sales reps. If we fire him now, our biggest account may go with him." She then proposed: "Give me a few months to work closely with him; I think we can get his sales numbers back to where they were." This strategic approach preserved both the employee's job and the manager's relationship with senior leadership. Securing promotions represents another highly political situation. Rather than approaching it with entitlement ("When is it my turn for a promotion?"), politically astute employees highlight their contributions and readiness: "Over the course of my employment, I have consistently offered out-of-the-box ideas that have helped us expand our customer base and improve customer retention. I've developed strong relationships with several managers who head up our key accounts." When told another regional manager was pushing for someone else, this employee pivoted strategically: "I've been working on new initiatives regarding the customer experience. How about if you let me present this at next week's management meeting?" Not every battle is worth fighting, however. Choose wisely when deciding which conversations to pursue. Skip the conversation when you've already decided to leave the company, when a situation will likely resolve itself, when timing is wrong (like asking for a raise right after poor earnings are reported), or when dealing with someone who is never going to change. Ask yourself: "Based on what I know about this person and our relationship, how likely is this conversation going to change anything? Do I have sensible solutions to offer? Am I the problem here and not them?" Taking your power back requires courage and strategic thinking. Aileen Amor-Bautista demonstrated this when applying for a senior executive position. After her boss dismissed her, saying, "I don't see you as being the right fit," she followed him to the elevator and parking area to continue making her case. The next day, her boss changed his mind and endorsed her. Today, she is the President and CEO of the company. Her persistence shows the importance of advocating for yourself when the stakes are high. For those uncomfortable with confrontation, start with low-risk conversations, create a brief script, practice delivery, and schedule the conversation. With each successful interaction, your confidence will grow, allowing you to tackle increasingly challenging situations with strategic finesse.

Chapter 7: Create a Drama-Free Work Environment

Workplace drama manifests in various forms—insubordination, backstabbing, office gossip, finger-pointing, and power struggles. Interestingly, some workplaces experience significantly more drama than others, even within the same industry. The difference often lies in company culture and leadership approach. A client whose workplace rarely requires uncomfortable interventions has a CEO who communicates directly and addresses issues promptly. In contrast, another client in the same industry has a people-pleasing CEO who avoids confrontation, allowing problems to fester until they explode. The resulting conversations become far more challenging than if issues had been addressed from the start. Even if you're not at the top of your organization, you can create a drama-free subculture within your team. Start by modeling the behavior you want to see. If an employee isn't pulling their weight, address it immediately rather than letting it slide. If office gossip becomes problematic, gather your team and clearly state: "I've recently noticed there's been a lot of gossiping going on around here. This kind of behavior can be hurtful and is unwelcome. I'm putting everyone on notice that if you are involved in fanning the rumor mills, you will face disciplinary action." Lack of clarity often creates unnecessary drama. When assigning projects, be specific about responsibilities to avoid situations where team members feel unfairly burdened. If such a situation arises, acknowledge your role in the confusion: "When I assigned the project to you and Tom, I failed to specify my expectations. For that, I apologize." Then clarify each person's responsibilities moving forward. Sometimes you'll need to mediate between team members experiencing conflict. One manager faced this when two employees, Beth and Lisa, were clashing over morning responsibilities. Beth complained that Lisa wasn't at her desk promptly at 8:30 AM to cover the phones, while Lisa insisted she arrived on time but stopped for coffee first. Through facilitated conversation, the manager discovered Lisa had new family responsibilities with her stepson living with her part-time. The three worked together to create a schedule that accommodated both employees' needs, with Beth working earlier shifts on some days and Lisa covering others. When difficult conversations arise, stay on track despite attempts to derail you. Common blockers include statements like "That's not how we do things around here" (respond with: "I understand this approach may be different. For now, let's try it this way, and we can reconvene to discuss how things are working"); "Well, X does this too" (respond with: "I'm not here to discuss X. I'm here to talk with you about..."); or emotional responses like tears (suggest a pause and reconvene when emotions have settled). The key to creating a drama-free environment is consistent, clear communication. Address issues promptly, be specific about expectations, acknowledge your role in any confusion, and facilitate productive conversations between team members. By doing so, you'll reduce the need for difficult conversations and create a workplace where people can focus on their work rather than interpersonal drama.

Summary

The seven principles explored throughout this book—confidence, clarity, compassion, curiosity, compromise, credibility, and courage—provide a comprehensive framework for navigating workplace conversations that might otherwise feel impossible. As you've seen through numerous real-world examples, these principles aren't just theoretical concepts but practical tools that can transform how you approach challenging interactions. Remember that "credibility starts with you. No one is going to believe in you when you don't believe in yourself." Your next step is simple but powerful: choose one conversation you've been avoiding and apply these principles. Start with a lower-stakes situation to build your confidence, prepare thoroughly, and approach the discussion with genuine curiosity and compassion. With practice, what once seemed daunting will become second nature, allowing you to speak your truth while respecting others. The workplace becomes more humanistic and productive when we have the courage to connect through authentic, respectful dialogue—so keep talking, even when it feels difficult.

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Roberta Chinsky Matuson

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