Tough Conversations: The Real Reason Most Teams (and Relationships) Get Stuck
I didn’t always realize how much was at stake when I avoided “hard conversations.”
Recently, I sat down with Jess Pettitt, a speaker, author, and expert in navigating tough conversations, to talk about what really happens when we skip—or lean into—those moments.
The interview made me look back at all the times I sidestepped a disagreement or let an awkward silence win out over speaking up. I remembered projects that stalled, relationships that felt a little less connected, and teams that drifted into confusion—not because people didn’t care, but because nobody wanted to “rock the boat.”
The truth? Those were missed opportunities for conversations that matter.
Jess put it simply: “We need to get more comfortable being uncomfortable.” That line stuck with me. It reminded me that the best teams and relationships don’t avoid tough topics—they build trust by tackling them head-on.
That’s why I dug into the research and pulled together this post. What exactly is a conversation that matters? Why is it so helpful at work (and at home)? And most importantly, how do you actually start and navigate these talks without everything falling apart?
Below, you’ll find a practical guide—blending insights from my chat with Jess, real-world examples, and research-backed tips—to help you get started. If you’ve ever avoided a tough topic or wished your team could “just talk it out,” this post is for you.
Let’s dive in.
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What’s a “Conversation That Matters”?
A conversation that matters is an honest dialogue about something important.
It’s not small talk or surface-level check-ins. It’s when you say what you really think, feel, or need—even if it’s awkward. Jess described these as “challenging conversations” that unlock real change, trust, and yes—better productivity.
These talks are about showing up as your real self.
Jess told me, “When we hold back, that’s energy we’re not spending on actually getting work done or connecting as humans.” The reality: We’re not meant to agree on everything or avoid all conflict. A conversation that matters is a chance to replace assumptions with clarity and to build connection over distance.
You know you’re having a conversation that matters when you feel both relief and risk.
You might be admitting a mistake, calling out a miscommunication, or just saying, “I need help.” It’s about letting go of needing to be perfect or “right”—and leaning into curiosity and respect. As Jess said, “Trying is trying, because it’s exhausting. But not doing something is also a response.” Progress happens when you try, not when you hide.
Why These Conversations Matter (at Work and at Home)
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Open conversations build trust, speed, and results.
In teams, nothing tanks morale and momentum faster than things left unsaid. Misunderstandings grow. Small problems turn into big ones. Productivity nosedives. Harvard research found the best teams have “psychological safety”—meaning people feel safe to speak up, disagree, or admit a mistake without fear. That all starts with honest talk.
People who talk about what matters are more engaged and happier.
It’s not just a work thing. People who regularly engage in deeper conversations (instead of just small talk) report higher well-being and satisfaction. There’s a direct link between feeling heard and feeling connected, both at home and on the job.
Avoiding tough talks is the hidden productivity killer.
Jess shared a story about a car dealership where two star employees’ performance dropped suddenly. Leadership worried, rumors flew, and culture took a hit. The issue? Both employees were quietly battling chemotherapy and hiding it to “protect” the team. One honest conversation—where they felt safe enough to share—flipped the entire team’s mood, to support, and productivity. “Sales went up. Repairs went up. People showed up for each other. The productivity level was tested—and proved.” That’s the power of a conversation that matters.
How to Start a Conversation That Matters
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Don’t wait for the perfect time or script.
There will never be one. The moment you realize something needs to be said, that’s your signal. Even a simple, “Can we talk about something that’s been on my mind?” is enough to open the door.
Get clear on your “why.”
Before you begin, ask yourself: What do I really want to achieve from this conversation? Understanding? Alignment? A plan for change? Keep that “why” as your anchor.
Lead with curiosity, not accusations.
Jess’s advice: “Lead with a question. Whenever you disagree and don’t know what to say, use ‘Tell me more.’” Curiosity cools defensiveness and keeps things collaborative. Try:
“Help me understand how you see this.”
“Can you share your perspective?”
“What am I missing?”
Use “I” statements and describe, don’t blame.
Focus on your experience and the facts, not character judgments.
Instead of “You always ignore my emails,” try:
“I noticed I haven’t gotten a reply, and I wanted to check in on what’s going on.”
Listen for understanding, not rebuttal.
When it’s their turn, actually listen. Don’t plan your comeback—just absorb. Reflect back what you heard:
“So what I’m hearing is…”
“It sounds like you’re frustrated about…”
Allow for discomfort.
Tough conversations are uncomfortable. That’s a sign you’re doing it right. Jess told me, “You can’t be anxious and curious at the same time.” Focus on curiosity, and the discomfort will ease up.
Don’t get hung up on perfection—focus on progress.
If it gets messy or emotional, that’s okay. It’s better to have an imperfect real conversation than a flawless fake one.
Best Practices for Making Conversations That Matter… Work
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Normalize these conversations in your culture.
At work: Make it a team value to talk about what matters.
At home: Set a weekly “check-in” time for real talk. The more you do it, the less scary it becomes.
Prepare, recognize, and respond.
Jess teaches a three-part framework: Prepare (know your purpose), Recognize (notice what’s really going on—feelings, dynamics, patterns), and Respond (choose your words/actions thoughtfully). You don’t have to get it perfect, but cycling through these three steps keeps you grounded.
Watch your words—always and never are fighting words.
Jess’s tip: “If your sentence starts with ‘always’ or ‘never,’ you’re probably about to get into a fight.” Stick to specifics and the current situation.
Check your motives before giving feedback.
Ask yourself: “Am I trying to help, or just trying to win?” Feedback works best when requested or when there’s real impact—otherwise, sometimes it’s better to listen and support.
Follow up, don’t just drop it.
After the conversation, check in again. Did things improve? Did you misunderstand something? Keep the door open for more dialogue.
Practice. It gets easier.
Like any skill, you get better with use. Each conversation that matters is a step forward—even if the only progress is the courage to start.
The Bottom Line
Conversations that matter are the backbone of great teams, healthy relationships, and your own growth.
They’re not about winning, being perfect, or making everything smooth. They’re about moving forward, together. As Jess Pettitt says, “Do the best you can with what you’ve got, some of the time. That’s literally the definition of ‘good enough now.’”
So the next time your gut says, “We should talk about this,” trust it. Start small, be real, and let the conversation unfold.
You might be surprised how much lighter and more connected things feel—at work and at home.
References / Further Reading:
Harvard Business Review – Research: To Excel, Diverse Teams Need Psychological Safety
Scientific American – Skip the Small Talk: Meaningful Conversations Linked to Happier People
Business Wire – Grammarly and Harris Poll Research Estimates U.S. Businesses Lose $1.2 Trillion Annually to Poor Communication
Productivity Gladiator® – “Conversations That Matter: The Hidden Productivity Killer You're Ignoring” .
I’m Brian. At age 4, I was diagnosed with insulin dependent (type 1) diabetes and told that my life was going to be 10-20 years shorter than everyone else. As a kid I took time for granted, but now as an adult, time is the most precious thing that I have. After spending a career hands-on in the trenches as a leader at all levels, I now train Productivity Gladiators to level up their careers. Graduates wield superpowers in time management, practical leadership, communication, & productivity. If what you’ve seen here intrigues you, reach out, let’s chat!
“Time is the currency of your life, spend it wisely.”