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Emily Gregory is vice president of design and delivery at VitalSmarts. She is the lead designer for Crucial Conversations, Crucial Accountability, and The Power of Habit and Getting Things Done. Gregory writes, speaks, and consults with Fortune 500 organizations. Her passion is helping people be great at being people.

Emily Gregory

Usually, we find that beneath the surface of persistent problems lies a host of unresolved issues. If we’re not talking about the right issue or the root of the issue, the problem will remain unresolved and may even get worse.

How to Address Repeated Bad Behavior

I was raised in Utah, where a cultural aversion to hard conversations often exists. People value harmony, so hard truths are sometimes softened to the point of marshmallow-like meaninglessness. Other cultures across the US—and throughout the world—have similar aversions.But I’ve learned that avoiding necessary conversations doesn’t preserve relationships—it erodes them. The challenge is not whether to have a conversation, but how to do so in a way that aligns with cultural values. Here’s how you can navigate this.Start With Warmth, Then Add CandorIn cultures that prize politeness, the key to effective conversations is blending truth with warmth. Start with a statement that affirms the relationship before raising the concern. Instead of jumping straight into the problem, say something like:“I really value working with you, and I want to make sure we’re both set up for success. I’ve noticed something I’d love to get your thoughts on.”This approach signals that your intent is not to attack but to strengthen the relationship.Lean On Shared ValuesIn cultures that place a high value on hospitality, kindness, and community, frame your concerns in a way that aligns with these values. For example:“Our team is important to me, and I want to make sure we’re supporting each other as a team. I think if we talk about this openly, we can find a solution that works for everyone.”When you connect the conversation to what people already care about, it feels less like conflict and more like collaboration.Respect the DanceIn some cultures, conversations are direct and quick. In others, they are more like a dance—gradual, measured, full of subtle cues. People may circle the issue before approaching it directly, testing the waters with humor, shared stories, or indirect hints. If you push too hard or move too quickly, it can feel like stepping on toes—disrupting the rhythm of the exchange. If the person you’re speaking with prefers a slower, more indirect approach, let them set the pace. Give them space to process.Silence isn’t always withdrawal—it’s often respect. By honoring the natural flow of the conversation, you make it more likely that both of you will stay engaged, rather than retreating into politeness or passive resistance.Remember: Kindness Without Honesty Isn’t KindnessMany people equate kindness with avoiding hard conversations. But real kindness isn’t about keeping the peace at all costs—it’s about caring enough to address issues before they grow into resentment. The most respectful thing you can do is to be clear in a way that preserves dignity.I have a colleague who grew up in the Deep South. She told me that in her family, disagreeing openly was considered a sign of bad manners. As she got older, she realized something—when people didn’t speak up, problems festered. Relationships suffered. And when someone did finally say something, it often came out in an explosion of long-suppressed frustration.She learned that being honest didn’t have to mean being harsh. She found ways to be clear and warm.Caring isn’t about avoiding crucial conversations. It’s about having them in a way that respects both the relationship and the truth. And when you do that, you’re not just honoring cultural norms—you’re elevating them. 

How to Respect Cultural Differences in Crucial Conversations

It can be hard to interact and meaningfully connect with someone who is different from us. The more we differ, the further apart we are, the harder it is to build a bridge. Why? Because most of our relationship skills are grounded in finding commonalities. When those commonalities are subtle or scarce, we struggle to connect.However, commonalities are not the linchpin of high-performing teams. Amy Edmonson and a legion of other scholars have convincingly shown that the key ingredient for a team coming together well is psychological safety—not liking each other, not socializing, not commonality (although all those factors can help).As Dr. Edmonson defines it, psychological safety is “the belief that work environment is safe for interpersonal risk-taking.” It is “the experience of being able to speak up with relative ideas, questions, or concerns. It is present when colleagues trust and respect each other and feel able—even obligated—to be candid.”One of the interesting characteristics of psychological safety is that it is inherently a team dynamic. It doesn’t exist in any meaningful way at the individual or organizational level. It lives and breathes (and dies) at the team level.So, if you want your team to work together well and you accept that psychological safety is the key, how do you build it? Here are three things to do to get started.Measure When interviewing Dr. Don Berwick, former CMS Administrator and CEO of IHI, he taught me that “a measure is the shadow of your heart.” If we sincerely care about something and want to change it, we will measure it. So, start by assessing where your team is in terms of their level of psychological safety and then decide on what would be a reasonable level of improvement. Continue to measure through regular pulse surveys. This is not a one-and-done. You need to evaluate whether what you are doing is increasing psychological safety (in which case, keep doing it!) or not (in which case, you need to try something else).Choose a Generous ViewAt the very heart of psychological safety is the belief that I won’t be judged negatively for being me. Unsurprisingly, it is the negative judgments we make about one another that, more than almost anything else, destroy psychological safety.To create psychological safety, we need to consciously and consistently choose a more generous view of others. I am not advising that we simply pretend that everyone and everything is great. Rather, I am suggesting that if we can suspend judgment and replace it with curiosity, we will be better able to hold space for the universal contradiction that good people do bad (or even just annoying) things.Insights from the Strength Deployment Inventory (SDI) help people choose to see one another more generously. The SDI provides a framework to help team members look beyond people’s behavior and see how three primary motives (performance, people, and process) are driving that behavior. When we see in this way, it’s easier to choose a generous view because people often have a rational motive even if their behavior is frustrating for us.Maintain Good IntentIn Crucial Conversations, we make this audacious claim: people never become defensive about what you are saying; they become defensive because of why they think you are saying it.Said another way, psychological safety is entirely dependent upon the perception of intent in the conversation. If you want to create safety in a conversation, a relationship, or a team, start by cultivating good intent and then sharing it. Sharing lets them know what your motives and intentions are. It also helps you stay accountable to and connected with that good intent, even when issues pop up that might otherwise irritate or frustrate you.Your team may never become “besties.” But that shouldn’t be your goal. Solid friendships don’t always equal high performance; people may love being on a low-performing team with high comradery. Building a high-performing team that learns together, achieves results, and respects one another is a much more worthy goal and one that is within reach of all teams.

What to Do When Personality Differences Hinder Teamwork

I once had a nurse manager come to me and ask, “How do I tell a master’s-prepared registered nurse that sleeping at their workstation is unprofessional? In many of my previous management jobs, finding an employee sleeping at their workstation was a fireable offense. In this environment, the employee appears to see no difference between sleeping in a designated break room and sleeping at their workstation.”While it may not always be an employee sleeping on the job, managers in all sectors need to address a variety of unacceptable behaviors. But how can you do so without causing drama?When I ask people what feeling comes to mind when I use the phrases “talk about a problem” or “address an issue,” the most common response is “Ugh!” – which isn’t really an emotion, but you probably get the idea. So, first tip: recognize this as a simple gap between what you were expecting and what you are observing. Your job as their manager is to describe the gap and partner with the person to close it. Here are three suggestions for how to do that:Master Your StoryYou will be far more effective at holding this conversation if you can suspend judgement. For example, even if you believe everyone should know that sleeping at the workstation is unprofessional, hold open the possibility that maybe this person was trained or taught differently. Or maybe, just maybe, they slept at their workstation all through school and no one ever got up the courage to give them feedback about it. After all, it is easy to mistake silence for approval.Catch It EarlyThe time to talk about the bad behavior is the first or second time it happens. Imagine how easy it would be, the first time a new employee falls asleep at their workstation, to gently shake them awake and kindly say, “We want all our nurses to sleep in the breakroom, not their station. Let me show you where it is.” When you catch it early, you are kindly onboarding a new employee and making sure they know what they need to be successful.When you let the poor behavior go on for a while without addressing it, two things happen. First, your own irritation likely builds, fueling your negative story. Second, you make the issue bigger. Now it is not just once or twice that this has happened but months’ worth of bad behavior. When you make the issue bigger through delay, you are more likely to create embarrassment and subsequent defensiveness in the other person.Have and Share a Good IntentIf you use the first two tips, it will be much easier to use the third one. Before any gap conversation, stop and ask yourself: what do I really want for this person? For them, not from them. Asking and answering this question will require you to flip your perspective 180 degrees. After all, we step up to gap conversations because the gap is causing a pain or problem for us. We are acutely aware of how their behavior is affecting us. The question you must ask is: How is it affecting them?What do you want for them and how will sharing this help? It can be as simple as, “I want you to be successful here and that is why I want to talk to you about this.”When you care about someone, and they know you care about them, gap conversations become about improvement, not reproof.

3 Tips for Addressing Unacceptable Behavior in the Workplace

At Crucial Learning, we offer a course around Crucial Conversations—how to communicate when opinions vary, the stakes are high, and emotions run strong. But how do you know when to disengage and walk away from a personal or professional relatio

When Is It Okay to Leave a Relationship?

How do you talk with an employee doing the bare minimum and expecting great rewards? First, try reframing your question: How can you help an unready or underserving employee learn and grow into the promotion or appraisal they seek?

Responding to Underachieving Employees Who Want a Promotion

Managers of both people and projects are often called upon to make tough choices. Use these tips from Crucial Learning’s Crucial Conversations for Accountability course to start holding people accountable.

Should You Hold People Publicly Accountable?

Here are five tips to help managers successfully provide L&D that both improves employees’ professional and personal lives and helps their organization stay productive and profitable.

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