Every one of us has faced moments when the stakes were high, emotions ran strong, and the outcome mattered deeply — in other words, a crucial conversation. These are the moments that can make or break relationships, careers, and even organizations. If you think back to the most difficult conversations in your life, chances are you can still recall how they felt — and how they shaped what came next.
I’ve left this topic to the final chapter in The Communication Project for a reason. The skills required to successfully manage crucial conversations demand all the skills covered in Chapters 1 to 6 — and then some. Crucial conversations are never easy; our emotions often get in the way, and our brains can feel ‘short-circuited.’ Too often, only with hindsight do we realize — after the damage has been done — that if we had been more thoughtful and applied the skills from earlier chapters, we could have avoided much of the harm caused when we let our emotions run out of control.
An Important Warning for Leaders:
As a leader, you usually hold much more power than your subordinates. You influence their compensation, career prospects, the respect they receive from others, and ultimately, you could fire them. For these reasons, subordinates are often very cautious in how they communicate with you.
It’s only through exemplary communication skills that you get the truth you need — rather than just “lip-service” or overly deferential behavior that is all too common in many organizations. Without it, decisions can be based on incomplete or distorted information, which can cost the team and the organization dearly
This chapter draws on and is inspired by the work of Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler in their best-selling book Crucial Conversations (McGraw-Hill, 2002). While the original concepts originate with them, I have adapted, summarized, and extended their ideas with my own examples and frameworks (such as TEA: Trust, Empathy, and Active Listening) to support everyday communication development.
This material is used under fair use for educational purposes.
Let’s begin with a tragic real-life example from Crucial Conversations — one that shows what can happen when people fail to speak up, whether from fear, uncertainty, or hierarchy, right when communication and courage matter most.
A woman checked into the hospital for a routine tonsillectomy. Instead, the surgical team mistakenly removed a portion of her foot.
How could this possibly happen? Is this a rare anomaly or something more prevalent than we might expect?
The book notes that nearly 98,000 hospital deaths each year are due to human error — and a large part of that is caused by professionals failing to speak their minds. In high-stakes environments, even seasoned experts often stay silent rather than risk conflict or challenge authority.
These statistics are frightening. But consider this: in Canada, approximately 40% of marriages end in divorce. How many more couples stay together but live in fear, silence, and misery?
In the July–August 2025 issue of Harvard Business Review, an article titled The Conflict Intelligent Leader reports on the scale of workplace discord—and the costs are staggering:
“It’s perhaps inevitable that in this time of growing discord, conflict at work would increase too. A recent Society for Human Resource Management survey of 1,602 workers showed that 76% had witnessed acts of incivility in the past month, with 21% experiencing it personally. Nearly half said they encountered it weekly, and 13% said they experienced it daily. Forty-four percent believed incivility would worsen in 2025, and 26% said they were likely to leave their job because of it.
With employee engagement at a low, contentious interactions at work are estimated to cost businesses more than $2 billion a day in productivity losses and absenteeism.”
- Professor Peter T. Coleman, Columbia University (Morton Deutsch International Center for Cooperation and Conflict Resolution)
A less dramatic — but deeply personal — example occurred in my own life.
I’ve shared this story before in an earlier post. It’s a case study in a series of conversations both avoided and poorly handled—by myself and the other party—that ultimately led to me being fired. I survived the episode, but not without considerable emotional pain. And since I was 55 at the time, it effectively ended my corporate career.
The silver lining: I went on to form my own company, which I ran for 20 years before selling it. It brought many challenges, but also many rewards.
If you're interested, I invite you to come back to this post after reading the full chapter: Silence Is Not Always Golden.
A conversation becomes “crucial” when three elements are present:
When these three signals are present, pause and recognize: this is no longer a casual conversation. It has become crucial — and the consequences are serious if not handled with care and skill.
Most people fall into one of two unhelpful patterns: Silence or Violence.
In my experience, silence is far more common in the workplace — especially when subordinates disagree with their boss. The issue becomes even more pronounced when leaders fail to create psychological safety and instead lean into controlling or dismissive behavior.
At the heart of every Crucial Conversation lies one guiding principle: People will not engage meaningfully unless they feel psychologically safe.
Safety is achieved when two conditions are met:
Together, they form the foundation for open, honest dialogue — even on the most contentious topics.
Even in the most skeptical or polarized situations, applying the principles of mutual purpose and mutual respect can lead to meaningful progress. A compelling example comes from efforts to address teen pregnancy, where two groups with deeply opposing beliefs — pro-life and pro-choice advocates — chose to work together.
Neither side was asked to compromise their overarching convictions. Instead, they agreed on a shared purpose: reducing teen pregnancy and supporting at-risk youth. By committing to mutual respect, each group listened without judgment, sought to understand the other’s perspective, and focused on actionable solutions rather than philosophical debates.
The result was significant: programs and initiatives were developed that combined the strengths of both approaches, reaching teens more effectively than either group could have done alone. This case demonstrates that even when fundamental beliefs differ, mutual purpose provides a common goal, and mutual respect keeps the dialogue constructive, allowing progress where it might otherwise seem impossible.
This section includes:
In short: Begin every crucial conversation by clarifying your motives, staying focused on mutual benefit, and avoiding the trap of anger, fear, or ego.
A note from me: asking for feedback is a skill that often takes practice — and it’s something I’m still learning.
Early action works because:
Contrasting prevents misunderstandings by clarifying what you do mean and what you don’t mean. It’s especially useful when you must give critical feedback to someone you respect.
Bill is a promising team member: hard-working, delivering on goals. But he’s consistently 10 minutes late to monthly management meetings. You’ve raised it before, and it’s now a pattern.
A poor approach (what not to say):
A better approach using contrasting (DO and DON’T):
Contrasting makes your intent explicit, prevents immediate defensiveness, and invites collaboration on a solution.
Below are three scenarios showing STATE in action.
Context: A high-potential subordinate feels she was passed over for promotion because she’s female and “not experienced enough.” She’s disengaged.
Using STATE:
Grounding the conversation in fact and curiosity lowers defensiveness and opens space for genuine explanation and problem solving.
Context: A friend in a regular social group tends to dominate conversation. Others end up zoning out.
Using STATE:
Ask yourself if this truly requires a crucial conversation. In my case, I realised I could soften up and enjoy the stories — we were there to play golf and have fun, not solve the world’s problems. Sometimes changing my behaviour was the better route.
Context: You’ve been investing in creative work and have shared it, but your partner’s lack of engagement makes you feel invisible.
Using STATE:
Optional starter note you could use:
“Hey Brian - there’s something on my mind. I’ve been putting a lot into my blog posts on the “Communication Project”. I’ve shared parts of it with you because I value your opinion. Your silence in responding has made me wonder if the subject matter does not resonate for you or perhaps you’ve simply been swamped with work. I don’t need applause, but as I have said – I value your opinion and would love to hear from you”
Even if you don’t believe you caused the problem, if the other person believes you did, consider apologising — genuinely.
Remember: No apology is better than an insincere one.
When you recognise, you’re in a crucial conversation, do not dig yourself deeper. The brain’s executive function shrinks under stress; impulsive reactions follow.
“It’s true that becoming an empathetic listener takes time, but it doesn't take anywhere near as much time when you're already miles down the road - to redo and to live with unsolved problems.”
- Stephen Covey
“Knowing yourself is the beginning of wisdom”
- Aristotle
If you want to change someone else’s behaviour - first, try changing your own behaviour.
I’ve saved this recommendation for the end, because in my experience, it’s among the most useful practical rules. When we react to another’s behaviour by judging or criticizing, we usually get exactly what we expected: resistance or withdrawal. Instead, try this approach:
Thanks for signing up!
I respect your privacy. Your personal information will never be shared with a third party.