1장
When "Can We Talk" Sends Shivers Down Your Spine
Those dreaded words - "Can we talk?" - have the power to instantly trigger anxiety in even the most seasoned professionals. For Roberta Chinsky Matuson, they changed the trajectory of her career back in 1993 when her boss uttered them after a year of unclear expectations and minimal communication. That awkward, one-sided conversation marked the beginning of the end of her time with that organization. It also sparked her determination to help others navigate these challenging moments more effectively.
Difficult conversations remain an unavoidable reality in workplaces worldwide, yet most of us are woefully unprepared to handle them. According to workplace resource startup Bravely, a staggering 70 percent of employees avoid awkward conversations with bosses, colleagues, and direct reports. This avoidance is costly - each conversation failure costs an organization approximately $7,500 and more than seven workdays of productivity. The result? Declining employee engagement, eroding organizational trust, and skyrocketing workplace stress.
Drawing from decades of executive coaching experience, Matuson developed seven core principles for navigating difficult workplace conversations: Confidence, Clarity, Compassion, Curiosity, Compromise, Credibility, and Courage. Her framework provides a comprehensive approach for transforming these dreaded interactions into opportunities for growth and improved relationships. Whether you're delivering tough feedback, negotiating for resources, or addressing conflict, these principles offer a roadmap for conversations that produce results while preserving relationships.
2장
Building the Foundation: Confidence and Self-Trust
The journey toward mastering difficult conversations begins with confidence - not just in your message, but in yourself. Many of us struggle with self-doubt, especially when facing challenging interactions. We rehearse conversations in our heads, second-guess ourselves, and imagine worst-case scenarios that rarely materialize. This mental chatter creates what Matuson calls the "land of should have, could have, would have" - a place where we endlessly replay conversations with multiple versions: what actually happened, what went through our mind, and what we wish we'd said.
This second-guessing leads to exhaustion and frustration. Consider "Don," who responded defensively when his boss Catherine criticized him for a missing report. Rather than taking responsibility and apologizing, Don made excuses, damaging their relationship. In his "do-over" version, he recognized he should have acknowledged her embarrassment, apologized, and promised improvement - but he didn't trust himself enough to do what was needed in the moment.
Many of us lose our childhood confidence over time and begin trusting others more than ourselves. One client hired her sister, who performed poorly. The client repeatedly second-guessed herself about addressing the problems, eventually having to fire her sister after months of damage to the team. Had she trusted her instincts and confronted the situation early, asking for help and clearly outlining expectations and consequences, she could have avoided what she called "one of the most stressful periods of my life."
To build self-trust, start your day with positive affirmations like "I can do whatever I set my mind to" or "I'm smart and capable." Build confidence gradually by tackling easier conversations before difficult ones. Practice decisive decision-making through a structured process: identify the decision, list options quickly, weigh pros and cons, select the best alternative, and move forward. Replace negative self-talk with positive statements, turning "I'm terrible at that" into "With practice, I could be great."
Trust also forms the cornerstone of all workplace relationships. When trust is absent, we do the minimum required rather than giving our full effort. Matuson introduces the concept of the "bank of trust" - making deposits into relationships before needing withdrawals. Ten ways to build trust include: being honest, helping others before asking favors, keeping promises, supporting colleagues publicly, giving credit appropriately, admitting mistakes, apologizing, and volunteering. This explains why two employees requesting the same time off might receive different responses - the one who previously volunteered during staffing shortages successfully negotiates holiday time, while another who avoided extra work has their similar request denied.
3장
Bringing Focus: Clarity in Communication
Without knowing your destination, you'll never arrive. When handling difficult situations, clarity about your objective is essential before beginning any conversation. Too many workplace discussions leave participants confused and uncertain about what transpired. Whether it's a performance improvement meeting where the manager speaks too quickly or a vague request for assistance from a colleague, lack of clarity causes problems.
Success in challenging conversations is determined before they begin. Too many people simply aim to "get it over with" rather than establishing clear objectives. Before initiating difficult discussions, determine what you want for the relationship - whether to strengthen it or fulfill formalities before termination. Being laser-focused on desired outcomes increases your chances of achieving them.
Ron's example shows how conversations can derail when objectives aren't precise - he discussed commitment and presence when the real issue was lack of follow-through affecting the team. When you're clear on what specific behavior change you need, you can be more direct in addressing problems.
Before initiating difficult workplace discussions, determine if you're simply venting or genuinely seeking relationship improvement. Consider whether you want recognition for contributions or behavior change from colleagues. Without proper consideration of purpose, conversations often go nowhere or somewhere unexpected.
Your approach should vary based on your relationship history and the communication style of the other person. The author shares an example of a client with a direct "New York" style struggling to connect with "Californian" colleagues who prefer casual chitchat before diving into business. By recognizing these differences and adjusting accordingly, you can prevent misunderstandings and build stronger relationships.
Timing and location are equally crucial factors. The author emphasizes considering when the other person will be most receptive rather than focusing on your own convenience. For example, scheduling a challenging discussion immediately after your boss finishes back-to-back meetings is unwise as they'll likely be distracted and exhausted. Similarly, where you hold difficult conversations is as important as what you say - the author describes witnessing a manager firing an employee at Starbucks, where conversations are easily overheard.
When the pandemic forced global remote work, managers had to quickly adapt to virtual conversations without proper training. Remote conversations require special consideration of time zones, privacy settings, and the importance of having cameras on when appropriate. Rather than sending potentially misinterpreted emails, scheduling video calls for sensitive matters shows respect and prevents unnecessary stress.
4장
The Heart of Connection: Compassion in Conversations
Compassion requires understanding others' perspectives, even without similar experiences. Early in her career, Matuson lacked empathy as a young manager when employees called out for sick children, focusing on deadlines rather than their challenges. Only after having her own children did she truly understand these situations.
We often want compassion when receiving criticism but fail to extend it when delivering it. This happens because our egos take control or we let personal biases cloud judgment. When confronted about mistakes, responding defensively escalates tension, while acknowledging the other person's frustration builds connection.
Having difficult conversations without established rapport significantly reduces effectiveness. Rapport signals genuine care and creates receptivity to feedback that would otherwise be dismissed. When you understand what drives people, you can tailor conversations effectively. For example, using knowledge of your boss's family situation during a promotion discussion creates an emotional connection that makes a potentially difficult conversation easier.
Communication extends beyond words to nonverbal cues that often speak louder than what's said. When verbal messages don't align with body language, listeners perceive dishonesty, undermining compassion. Facial expressions must match your spoken message - people quickly detect inconsistencies like saying you're interested while rolling your eyes.
For difficult conversations, practice with a trusted colleague or coach to identify misaligned visual cues. If maintaining eye contact is challenging, focus just above the bridge of the nose. Posture matters too - uncrossed arms and leaning forward signal openness, while occasional head nods acknowledge the speaker. Voice modulation conveys sincerity; a soothing, concerned tone demonstrates genuine compassion even in challenging situations.
In today's high-speed business environment, there's pressure to establish instant rapport and think steps ahead of everyone else. Counterintuitively, slowing down and taking time to build relationships is the fastest path to resolving difficult issues. When people trust you, they share information that facilitates smoother conversations.
Jan, a type-A pharmaceutical communications leader, learned this lesson when she harshly confronted an employee about missed deadlines without knowing his spouse had just asked for divorce and threatened to take his children. Her failure to establish a relationship where he felt comfortable sharing personal struggles resulted in his immediate resignation. Had she slowed down and noticed his behavior was unusual, she might have preserved a valuable team member.
Multitasking might work for routine activities but proves disastrous during high-stakes conversations. The author witnessed a boss firing a long-term employee while simultaneously shuffling papers looking for a file needed in her next meeting. This divided attention visibly agitated the employee, demonstrating how behaviors matter more than intentions.
5장
Opening Minds: The Power of Curiosity
Curiosity forms the fourth pillar for handling difficult workplace conversations. When we approach situations with genuine interest, we see things differently and demonstrate to others that we value their perspective. The author, self-described as naturally inquisitive since childhood, explains how asking questions helps move conversations forward and builds relationships.
Adults can learn much from children's straightforward communication and natural curiosity. Children are naturally curious about the world and other people, a trait adults often lose. They're also resilient, bouncing back from stressful situations - a reminder that difficult conversations are rarely as bad as anticipated. Children take risks and view each day as a new adventure, while adults often overthink situations and focus on potential problems.
Despite the cautionary proverb "curiosity killed the cat," curiosity is essential for addressing difficult workplace situations. The author offers a test for readers' "curiosity quotient": find someone with opposing views on a social issue and ask seven open-ended, nonjudgmental questions to understand their perspective without revealing disagreement.
Many leaders claim to value curiosity but unintentionally stifle it in practice. The author offers strategies to encourage inquisitiveness: first, reframe questions as valuable contributions rather than time-wasters; second, recognize curiosity as essential for innovation, citing Henry Ford's failure to adapt the Model T when consumer preferences changed; and third, model curiosity by responding constructively to failures.
Rather than criticizing employees for mistakes, leaders should ask what went wrong, what they learned, and what they'd do differently. The author emphasizes that asking one or two targeted questions is more effective than many unfocused ones, sharing that in her executive coaching practice, she simply asks stakeholders: "What does this person do well?" and "What is getting in their way?"
There's a fine line between curiosity and judgment, with delivery and tone being crucial. Judgmental questions like "Why did you do it this way?" asked sharply can make others defensive. While judgment has its place in solicited contexts, unsolicited judgmental communication stifles innovation and puts people on defense.
Starting difficult conversations is challenging even for CEOs and senior leaders. Instead of using "Can we talk?" which immediately puts people on defense, effective curious conversation starters include: "I need your help with something," "I'd like to understand your feelings better," or "I'm curious. Can you tell me why you chose this direction?"
6장
Finding Middle Ground: The Art of Compromise
Compromise requires each side making concessions to reach resolution, yet achieving this balance is harder than it appears. Unhealthy competition focused on winning at all costs is a losing conflict resolution strategy. True compromise requires mutual respect and willingness to engage in give-and-take. When respect is absent, conversations quickly deteriorate.
Consider two scenarios: In one, you dismiss a disrespected colleague's product design approach without consideration. In the other, you engage respectfully with a trusted teammate, acknowledging their marketing team suggestion while offering a reasonable counterproposal about timing. The second scenario leads to compromise and a better end product.
When facing high-stakes conversations, channel Aretha Franklin's "Respect" - set aside differences, withhold judgment until the other person finishes speaking, and look for elements to build upon. Before salary negotiations, determine your minimum and maximum acceptable outcomes. This prevents emotional reactions that can derail conversations.
Some days it feels like we can only agree that we can't agree. Yet disagreement isn't inherently bad if we can disagree productively. Differing perspectives explain why people hold opposite opinions about political candidates, and those unable to have courteous discussions simply can't see through others' eyes.
To reduce discord and create progress without damaging relationships, focus on the "why" behind your meeting. When everyone understands the purpose, common ground becomes possible, as with Matuson's client who initially faced resistance when suggesting coaching for an employee until she emphasized their shared goal of building peer respect.
The best parenting advice Matuson ever received - "have one kid cut the cake slice and the other choose which piece they want" - applies perfectly to workplace compromise. For relationships to prosper, both parties must feel fairly treated. When approaching tough conversations, consider what's being proposed versus expected. Can you be more generous with your "slice"?
When a colleague makes an unreasonable request, saying no outright might backfire. Instead, look for workable solutions - perhaps taking on the task with a flexible deadline. Explain your logic so they trust you've given their request proper consideration, then ask if they see alternative approaches. We rarely forget when someone makes an effort to meet us halfway.
Some people seem born with the "influencing gene" - a natural ability to convince others to follow their suggestions. Fortunately, influence is a learnable skill, not genetic. Matuson defines influence as asking for something in a way that makes it easy for the other person to say yes - exactly what we want during challenging conversations.
The foundation of influence is trust. Without a solid relationship, influence attempts may appear manipulative. If you have a stable relationship with someone, they'll likely believe you have their best interests in mind when suggesting changes.
7장
Establishing Authority: Building Credibility
Credibility isn't something you're born with - it's earned daily through consistent actions and is essential for productive conversations. Without it, your words mean nothing. True credibility comes from within; when you don't believe in yourself, others won't either. It's about being trusted and perceived as believable, starting with your own self-confidence.
While education and titles provide initial credibility, it's your consistent behavior, preparation, and willingness to own mistakes that truly establish your reputation as someone worthy of trust. Matuson learned this lesson early when promoted to senior management at 24 - despite her corner office and reserved parking spot, her older peers viewed her as inexperienced. Even with years of work history, perception mattered more than reality. Only after pursuing her MBA did colleagues begin treating her differently, not just because she gained knowledge, but because she projected greater confidence.
The imposter syndrome - doubting your accomplishments and fearing exposure as a fraud - undermines credibility because when you don't believe you deserve something, others won't either. To establish credibility, learn everything possible about your field or discussion topic, especially when anticipating challenges. Matuson once convinced her resistant boss to introduce a costly new employee benefit because she arrived prepared with thorough research. Had she stumbled through his questions unprepared, she would have lost both her request and her credibility.
Inconsistent performance destroys credibility. Matuson once managed Judy, whose work quality varied dramatically day to day. Despite discussions, her unpredictable performance cost her a promotion because Matuson couldn't trust she'd succeed in a more demanding role. Similarly, leaders who say one thing but do another - like announcing across-the-board pay cuts while secretly giving raises to favorites - quickly lose trust.
Admitting mistakes properly increases both credibility and reciprocity. Empty, reactive apologies mean nothing, but taking genuine responsibility shows integrity. One executive coaching client effectively rebuilt trust after a costly business mistake by acknowledging his error, explaining what he learned, and sincerely apologizing for the impact.
Credibility isn't something you can simply put on when needed or pull off a shelf in emergencies - it requires consistent daily effort to establish. While titles like CEO or Doctor carry initial credibility, they alone don't sustain trust. Many high-profile leaders like Kenneth Lay and Elizabeth Holmes fell from grace despite impressive titles.
Building credibility with remote employees requires intentional effort but isn't impossible. The pandemic taught us valuable lessons about connecting virtually. To establish and maintain credibility with remote workers: keep webcams on during meetings to build familiarity and trust; communicate more frequently through regular check-ins; adhere strictly to response times and deadlines; choose appropriate communication channels for different purposes; and show appreciation through occasional gestures like surprise gifts or notes of gratitude.
8장
Taking the Leap: Finding Your Courage
Courage, the final principle for navigating difficult conversations, often requires facing fears and taking action despite them. What requires courage varies by individual - a public speaker might find addressing large audiences easy while a doctor comfortable with treating patients might fear small presentations. Ultimately, courage means moving forward despite fear, making it a principle of action rather than merely a mindset.
Like Matuson's night dive experience in Turks and Caicos, courage often means taking the plunge despite not feeling ready. Sometimes, support from others - even unintentional support - can help ease our fears. We all possess unique talents, but fear often holds us back from utilizing them fully. When facing tough conversations, remember "the courage of your talent" - identify your superpowers, weigh risks against benefits, and take action. The more you face fears, the easier it becomes to do so in future situations.
Over time, we can become more comfortable with situations that once made us uneasy. The author admits it took twenty years to learn to speak up when treated unfairly or when others presented her ideas as their own. Avoiding action doesn't prevent discomfort - it often prolongs or worsens it. Many people get stuck overthinking, claiming they need more research when what they really need is forward movement.
Some of the most courageous conversations happen in politically charged work environments. Many people mistakenly believe they can avoid office politics by keeping their heads down, but politics exists in every organization - nonprofits, government agencies, private companies, and family businesses alike. Politics isn't just about manipulation; it's about using power effectively.
When requesting additional staff during tight budget periods, conversations become politically charged because resources are limited. If two managers want to add staff but there's only budget for one hire, it becomes a zero-sum game where one must lose for the other to win. Success depends on political astuteness and making a convincing argument. The key is understanding what benefit your supervisor would gain by approving your request rather than someone else's.
Not every difficult conversation is worth having. With limited time and energy, be selective about which battles to fight. Four scenarios where silence may be wiser: when you've already decided to leave the company, when a situation will resolve itself (like an imminent reorganization), when timing is poor (like requesting a raise after poor earnings), or when dealing with someone demonstrably resistant to change.
Many people regret not speaking up for themselves in crucial moments. It takes significant courage to advocate for yourself, especially in politically charged situations. Aileen's story demonstrates how persistence can overcome initial rejection. Despite her CEO dismissing her promotion request and literally walking away, she followed him to continue the conversation, ultimately securing not just the promotion but eventually becoming CEO herself. The mere act of standing up for yourself can be life-changing.
9장
Creating a Drama-Free Workplace: Bringing It All Together
Like assembling a complex jigsaw puzzle, handling difficult conversations requires strategy and patience. Start with manageable conversations rather than the most challenging ones - equivalent to attempting a 250-piece puzzle before tackling a 1,000-piece one. This approach allows you to make mistakes and recover more easily when the stakes aren't as high.
The seven principles of "Can We Talk?" function like puzzle pieces that must all connect, regardless of which one you start with. An executive's story illustrates this perfectly: wanting to leave her CEO position with a severance package, she strategically approached her difficult boss by defining clear goals and leverage points. By entering the conversation with confidence, clarity, compassion, curiosity, willingness to compromise, credibility, and courage, she achieved everything she wanted - demonstrating that with careful preparation, anything is possible.
Even in the extraordinary environment of space, leadership challenges persist. NASA Astronaut Christina Koch, who holds the record for the longest continuous time in space by a woman, confirmed that difficult work conversations aren't left behind when leaving Earth. When asked about being the "new gal" on the International Space Station and whether she faced resistance when leading teams, she acknowledged hearing familiar phrases like "We've always done it this way" or "That's not how we do things here."
Difficult conversations rarely end with a single interaction. Following up is essential for rebuilding relationships and ensuring productive outcomes. Start by acknowledging the awkwardness with phrases like "That was a tough conversation" or "Thank you for having the courage to tell me what was on your mind." Then advance the conversation by summarizing what was said and agreed upon, either in person or through a follow-up email that documents next steps and creates a shared understanding.
Workplace drama manifests through insubordination, backstabbing, gossip, finger-pointing, and power struggles - and isn't limited to specific industries. Company culture, defined as shared values and beliefs, significantly impacts these dynamics. When leadership sets clear standards for communication and conflict resolution, others follow suit. Direct communicators tend to create less dramatic environments than people-pleasers who avoid confrontation until issues implode.
Even if you're not at the top of your organization, you can create a drama-free subculture within your team by modeling appropriate behavior. Address performance issues promptly, set clear expectations about unacceptable behaviors like gossip, and provide clarity about project responsibilities to prevent conflict. By taking control and resetting standards, you can significantly reduce workplace drama.
When difficult conversations hit roadblocks, your reaction determines whether you can achieve positive results. To maintain productive dialogue, work on shifting from opposition to partnership by repositioning yourself mentally and physically to focus on solving shared problems. Reframe conversations from convincing to learning by starting with "Help me understand" to genuinely explore others' perspectives. Speak your truth clearly by putting intentions on the table, constructively deconstruct assumptions by asking rather than guessing others' thoughts, and offer sincere apologies when appropriate.
As you apply these seven principles - confidence, clarity, compassion, curiosity, compromise, credibility, and courage - difficult conversations will transform from dreaded encounters into opportunities for growth and stronger relationships. With practice and persistence, you'll find that "Can we talk?" no longer sends shivers down your spine, but instead signals the beginning of productive dialogue that moves both you and your organization forward.
