Chapter 10: Yeah, But — Advice for Tough Cases
“Good words are worth much and cost little.” — George Herbert
Overview
The general dialogue skills apply to virtually any situation. This chapter addresses 17 tough cases with specific guidance for each.
The 17 Tough Cases
1. Sexual or Other Harassment (Subtle)
Problem: Offensive comments/gestures that are subtle enough you’re unsure HR can help.
Solution: The offender often has less power than you think. Most of these problems go away when addressed privately, respectfully, and firmly. Use Mutual Purpose (“I’d like to talk about something getting in the way of us working together”) + STATE your path with specific observed behaviors, not conclusions.
2. Overly Sensitive Spouse/Partner
Problem: Giving constructive feedback triggers such strong reactions that you retreat to silence.
Solution: Catch it early — don’t let the issue build. Use Contrasting up front (“I’m not trying to blow this out of proportion, just deal with it before it gets out of hand”). Describe specific behaviors. Talk tentatively about consequences. Encourage testing. When they still become defensive, don’t conclude it’s hopeless — think harder about your approach.
3. Failure to Live Up to Agreements
Problem: Team members talk about improving, then don’t follow through on what they agreed.
Solution: In the best teams, every member holds every other member accountable — not just the boss. When you see someone violating an agreement, speak up immediately and directly. Waiting for the boss = allowing the problem to fester.
4. Deference to Authority (Kissing Up)
Problem: Direct reports filter what they say, guess what you want to hear, take no initiative.
Solution: First, diagnose the cause — are you creating the fear (check your Style Under Stress with a peer), or are you dealing with ghosts of previous leaders? Then: reward risk-takers, encourage testing, thank people who disagree, play devil’s advocate, leave the room to give breathing space. Never command people to stop deferring.
5. Failed Trust
Problem: Someone missed a deadline or broke a commitment; you’re not sure you can trust them.
Solution: Trust is topic-specific and degree-specific, not all-or-nothing. Focus on the issue, not the person. State your concern tentatively in the moment (“I get the sense you’re only sharing the good side — I need to hear the risks”). Don’t let mistrust in one area bleed into your overall assessment of their character.
6. Won’t Talk About Anything Serious (Withdrawn Spouse)
Problem: Spouse/partner consistently withdraws from any meaningful discussion.
Solution: Work on yourself first. Start with simple, non-explosive topics. Make safety a constant priority. Watch when they become uncomfortable — back off. Use tentative language. Separate intent from outcome. Build toward the hardest topics gradually. Don’t nag or go to violence (that gives them evidence that crucial conversations cause harm). Eventually invite them to talk about how you talk — sometimes that conversation is easier than the topics themselves.
7. Vague but Annoying
Problem: Nothing blatantly wrong, just subtle behavior that grates on you.
Solution: First, check if the behavior is actually worth discussing (maybe the problem is your tolerance). If it is worth it, retrace your Path to Action to its source — identify the specific observable behaviors, not vague conclusions. Clarify the facts before speaking. STATE with facts, not abstractions.
8. Shows No Initiative
Problem: Team members do exactly what’s asked but stop the moment they hit a barrier.
Solution: Don’t address an instance — address the pattern. Establish new, higher expectations explicitly. Give examples of when they hit a barrier and backed off. Jointly brainstorm what they could have done differently. Examine if you’re compensating (reassigning, following up yourself) in ways that remove their incentive to take ownership.
9. Pattern (Groundhog Day)
Problem: You’ve had the same conversation about the same problem multiple times.
Solution: Stop talking about the latest instance. Talk about the pattern itself — which is a bigger issue about trust and keeping commitments. When you address the pattern, your emotions will be proportionate. When you address only the latest incident while stewing about the whole pattern, your reaction seems out of proportion — and it is.
10. I Need Time to Calm Down!
Problem: You’ve been told never to go to bed angry, but sometimes you can’t calm down.
Solution: Taking a time-out is not silence — it’s healthy dialogue. Agree together to pause: “I need some time to think; can we continue tomorrow?” Then, once calm, have the conversation. Avoid telling others they need to calm down (sounds patronizing) — instead, get to the source of their anger using AMPP.
11. Endless Excuses
Problem: Someone has a new excuse every time they fail to do something.
Solution: Don’t accept the excuse as fixing the problem. Gain commitment to fix the overall problem, not just the stated cause: “So you think a new alarm will help? Good — do whatever it takes. Can I count on you being there tomorrow at 8 sharp?” As excuses accumulate, talk about the pattern, not the latest excuse.
12. Insubordination
Problem: Employees or kids step over the line into disrespect or insubordination during a tough conversation.
Solution: Show zero tolerance immediately, but respectfully. Change topics from the issue at hand to how the person is currently acting: “I’d like to step away from the scheduling issue for a moment… The way you’re leaning in and raising your voice seems disrespectful. I want to help you, but I’m going to have a tough time doing so if this continues.”
13. Regret Saying Something Horrible
Problem: Built-up resentment led to saying something you wish you hadn’t.
Solution: (1) Use STATE skills early before the story turns ugly. (2) If you’ve let it build, don’t hold the conversation while angry — schedule it. (3) If you already said something awful, apologize and then STATE your path. You can’t unring the bell, but you can apologize.
14. Touchy and Personal (Hygiene, Boring, Personal)
Problem: Issues so personal you fear raising them will damage the relationship.
Solution: Silence serves no one — the person may go years without helpful information. Use Contrasting up front (“I don’t want to hurt your feelings, but I do want to share something that could be helpful…”). Establish Mutual Purpose. Describe the problem tentatively and specifically. Move quickly to solutions. These conversations don’t have to be insulting.
15. Word Games
Problem: Children or others exploit technicalities in what you said.
Solution: Talk about both behaviors and outcomes, not just behaviors. “You’re hurting your sister’s feelings when you call her stupid. Please don’t do that, or anything else that might hurt her feelings.” Focus on patterns and results, not instances.
16. No Warning
Problem: Team members surprise you with problems only after it’s too late.
Solution: Clarify the “no surprises” rule explicitly: once assigned, there are only two acceptable paths — complete as planned, or immediately notify you of a problem. The first time someone comes with a legitimate excuse but didn’t warn you early: “We agreed you’d let me know immediately. I didn’t get a call. What happened?“
17. Breaks All the Rules
Problem: Someone violates dialogue principles most of the time.
Solution: “How do you eat an elephant? One bite at a time.” Choose the most grievous and most approachable issue. Establish Mutual Purpose around something they care about. STATE that one issue. Don’t nag or take on everything at once. One element, one day at a time.
Meta-Principle
In all 17 cases, the underlying approach is the same:
- Work on me first (Start with Heart, Master My Stories)
- Make it safe (Mutual Purpose, Mutual Respect)
- STATE your path (facts → story → ask → tentative → encourage testing)
- Address the right issue (usually the pattern, not the latest incident)