I am a very direct individual. I struggle to work with anyone who is not direct, who is conflict-avoidant, and who does not speak up to ensure we work together effectively. Trying to make it safe for people like this feels like coddling and a waste of time. I think it’s good to learn skills to speak up, but I don’t see the benefit in placating to people who are insecure or introverted or both. Am I missing something?

My 80-year-old dad is experiencing cognitive decline, has had eye surgery on both eyes, and is deaf. One of my siblings says that my dad is a “terrifying” driver. But no one in the family is doing anything about it, probably because they’re all busy raising families. How can I talk to them about my dad’s driving? And how can we talk to our dad, who will not take lightly his car keys being taken by his children?

How can I find the strength to say what I need to say when someone does me wrong? I struggle to tell people when I’m bothered because I believe I will get in a heated argument with them and get lost for words. Sometimes my dad raises his voice at me and I just keep quiet. Sometimes a colleague will speak to me in a threatening voice and I say nothing. Sometimes someone makes my child cry and I still say nothing, and so on. These often feel like life-or-death situations, and afterward I blame myself for being weak. Sometimes I so badly regret not speaking up that I can’t even sleep at night, playing over and over in my head what I should have said. What can I do?

My niece recently turned 18 and is planning to schedule an elective double mastectomy. For the past few years she has identified as non-binary, then she legally changed her name, and more recently she has started taking estrogen blockers that make her voice low. Her dad and mom think that she’s brave and strong. My mom is 100% supportive. I think they’re all insane, and I’ve told them perhaps she’s just confused and that maybe we should encourage her to postpone having body parts surgically removed. They think I’m being intolerant and unsupportive. I haven’t shared my concerns with my niece, but I think I need to try to stop her. Should I keep my mouth shut and watch from the sidelines, or tell her what I really think? If so, how?

What is the best way to respond to someone who has the habit of dominating conversations? My colleague will not let me finish my sentences, interrupts with an opinion or comment, talks at great length, and often repeats what she already said. I feel hostage to her while she hogs the airwaves. What can I do?

A few years ago I was promoted to leadership while my senior colleague who also wanted the role was not. Since then, our relationship has deteriorated. He has said he feels personally attacked by direction I’ve given the team. I have tried to make it safe, contrast, state my path, start with heart, but to no avail. I’ve even given him small tokens of appreciation—a treat or a gift card—but he won’t acknowledge my efforts to rebuild trust or communicate with me. I’ve been through your communication courses and received communication coaching, and I regularly seek feedback from my peers and leaders, and they say they feel safe to communicate openly with me. My manager and VP have said he has a personal issue with me, but none of us has been able to get him to open up. How can I “Make It Safe” for someone who clearly doesn’t feel safe?

Dear Crucial Skills, I have a coworker that I just can’t stand. He is good at his job, but I struggle to get along with him because he is so opinionated and narrow-minded. He has an opinion about everything and can’t fathom any other viewpoint. I’d rather go to the dentist than be in a …

A few months ago, while I was out of town, a colleague aired his grievances against me in a meeting with our new CEO. Two others joined in. This colleague previously reported to me, then was promoted to be my peer. He has been a contentious bully ever since, badmouthing me behind my back. When I returned from my trip, I was called into a meeting with the new CEO and the three who have issues with me. I was blindsided by their allegations. I pushed back very little but have since been stewing to the point of depression. Where should I go from here?

Do you think children could use the skills taught in Crucial Conversations? If so, do you have any suggestions for how I might adapt the lessons for them?