Tell Me More Words: Dianna's Journey Beyond Right and Wrong
Summary
What if you could approach tense moments not as battles to win, but as opportunities to expand understanding? Dianna Tremblay has spent years learning that the phrase "tell me more words" can transform any situation where you're tempted to pick sides. Instead of getting trapped in who's right and who's wrong, she's discovered how to create new possibilities by getting genuinely curious about what's happening. Her journey from a quiet kid to someone who "makes people uncomfortable in the best possible way” shows us that we don't have to choose between being nice and being real.
What’s in it for you:
You're tired of sitting in rooms where people disagree but no one explores what's actually happening
You want permission to get curious about perspectives that don't match yours without being seen as "difficult"
You're looking for language and examples of how to navigate uncomfortable moments that could lead to deeper understanding
You're ready to stop defaulting to right/wrong thinking when things get tense
Helia’s Perspective
The word "conflict" carries so much weight – someone's right, someone's wrong, someone wins, someone loses. I've realized more and more that when I'm in a healthy place with myself, I suddenly see these moments as opportunities to discuss and explore and understand. It's when I'm struggling that I start to feel tense and move quickly to being defensive and judgmental, and that never leads to good things.
When Dianna and I hopped on what was supposed to be a call about revenue strategies and ended up talking about how she navigates conflict, I was immediately drawn in. She has both a strong sense of self and practical language for moving beyond right/wrong thinking. What struck me most was how Dianna’s words make it so none of this actually feels like "conflict" at all – they transform a tense moment into a moment for expanding possibilities, deepening conversations, and creating understanding. Hearing the specific words she uses and concrete examples can expand the possibilities for all of us who usually default to picking sides.
Me and my rescue pup, Happy. She has an endless supply of licks!
Dianna's Story
This is Dianna's story — co-written with Helia and told from her perspective.
Even as a kid, I was not conflict averse. Not in an "I'm going to fight you" way, but more like, "I know who I am, I know how I feel, and you're going to hear it from me." Which is funny because I was a really quiet kid. Like, really, really quiet.
There are a few things about myself that have always been true: I never lie about anything. I always want to be of service. And I'm fine with being uncomfortable – but that last bit didn't happen until I got older.
I learned early that not all conflict is created equal AND you don't need to wade into all of it, especially if it has a detrimental effect on you as a person. In elementary school, I told the truth when a teacher asked who said a bad word, and the whole class stopped talking to me for almost a month. That taught me about consequences and choosing my battles.
Later, working in e-commerce, I had the highest performing team but held back from healthy exploratory conversations with my boss when I felt like I was getting rolled over. He'd say things like, 'If we had more money, I'd give you a bonus, but I don't have any money.' And I would just say, 'Okay' instead of, 'Let's talk about that. What can we do? How can we work through this?' I wish I could have waded into it, but I didn't have the confidence or experience yet.
Now, as I finish 11 years at the ICA Fund and lots of learning, I'm the connector. I'm the person who pulls things together in tense moments, who can pull two teams together and get to the other side. I love helping people move things forward, and when people are feeling stuck, I help them see all the layers and all the different perspectives.
One of my co-workers says this is her year to make people uncomfortable. I feel like that's been my last two years – diving into healthy conflict. It makes me so happy to do it because I don't like feeling stuck, and I assume other people don't like feeling stuck either.
What she’s learned about expanding conversations
Dianna's approach centers on moving beyond the impulse to determine who's right in a particular moment of conflict and instead getting curious about what's actually happening underneath the surface.
She's learned to scan constantly for what's going unsaid: "I'm always scanning for reactions and how people are feeling. I did a DISC assessment and I'm a pure 'I' – the inspiring/innovator type. Part of my personality is wanting everyone to have as much fun as I'm having, so I’m always reading others to see where they’re at. Most people don't have poker faces, so I can see what's happening.” If their face doesn’t match what they’re saying, there’s a good chance we’ll need to navigate something, so it’s time to ask some questions!
She trusts her body's signals about when to dig deeper: "It's a feeling in my body – this uncomfortable feeling when I'm unsure if a comment is said with positive intent or negative intent. When I can't decipher that, that's when I know to dig deeper."
She's developed specific language that opens rather than closes: "I'm the first one to say, 'Tell me more about that' or 'Say more words.' I don't say 'help me understand’ because that can feel passive aggressive. I want them to actually share more so I can feel out where they're coming from."
She listens for what's underneath the words: "The words between the words, body language, what they're actually trying to say – that’s what will tell you if you need to ask more questions. Were they just not articulate? Are they an external processor working through something? Are they making assumptions because they don't have context? Do they have the context but don't believe it or have a different perception?"
She reflects back before adding her perspective: "People at work say this about me: 'You always do this thing – you say, I hear you, I hear everything you're saying. Then you say, ‘AND,’ and then you say your piece.' Like, ‘I hear you AND I see it differently.’ I want to make sure people know I heard them. I might not agree with you, but I heard you and I respect what you said."
Me, my youngest son, my husband, and my oldest son watching my mom sing at Carnegie Hall this past Summer
Navigating different types of tension
What makes Dianna's approach practical is how she's learned to recognize different scenarios and respond accordingly:
When everyone agrees but something feels off (fake harmony): "This is when everyone just agrees and no one voices any dissent, but everyone knows we didn’t get to the heart of the issue. Sometimes after a meeting like this ends, I'll grab someone and say, 'Hey, can I grab you for a conversation about what just happened?'" Then, in that conversation, I share my observation of them in the meeting (“You seemed to have something on your mind…”), check with them to see if I made an assumption, and then ask what they need to feel comfortable sharing their thoughts with the group, so we can move the work forward.
When someone says something sideways (simmering tensions): "This is when someone makes a comment and we all look at each other with that cringe 'ooh' moment. I immediately say 'Tell me more words' to understand the intent. Often they just weren't articulate or are missing context I have access to as someone on the exec team. And sometimes, even if the intent was not malicious, their comments may still have had a negative impact. When that happens, I share the impact of those words for those of us in the room or for the clients we serve. It is really important to do that in real time or it just simmers and turns into anger or annoyance and will 100% of the time affect your working relationship with that person.
When people are already going at it (active conflict): "I had two colleagues who could not agree on anything – opposite sides, opposite personalities – and they were actually arguing right in front of me. I said 'Hey y'all, can we pause?' and they said 'No.' I realized that it wasn't my place to create fake harmony – they needed to hash it out, professionally, which they were doing. I've learned not to insert myself into every tension just because I want everyone to be comfortable." Caveat – When these are folks I am managing, I engage more directly. Not to stop the conversation but rather to help them navigate and support, whether changing the timing, location, OR just staying present.
Secret Sauce & Takeaways
"Tell me more words" instead of "Help me understand" – More direct, less passive aggressive, gets people actually sharing instead of defending.
Scan the room constantly – I'm always looking for external cues that someone didn't connect or needs more context.
Use the "I hear you AND" structure – Recap what they said to show you really listened, THEN add your perspective. People need to know they were heard before they can hear you.
Check your own regulation first – My nervous system has to be regulated or I'll enter conflict for the wrong reasons. I do 4-4-6 breathing in meetings (no one can tell) and lots of self-care before big meetings.
Ask yourself: Will this further the conversation or get us in a rabbit hole? – If it furthers the work or strengthens relationships, engage. If not, don't argue for argument's sake.
Your goal isn't to change minds – It's adding a different piece of information that might help them think through a situation differently, or to give them an expanded perspective for the future
Sometimes you need to process afterward – Find a trusted person (work colleague, partner, friend) and ask permission: "Can I share something that just happened and get it out of my body?" Then say you're done and mean it.
Know which conflicts are yours – If it's to move work forward and connect dots, I'm in. If it's personal because I don't like something or I'm annoyed, it's irresponsible to wade into it.
In group settings, scan for who needs support – I'll be in a meeting and see a co-worker who wants to say something but isn't comfortable. If I'm in a different spot in my experience or position, I can say the uncomfortable thing for them.
Questions you might want to sit with
Here are some questions to consider as you think about your own relationship with tense moments:
What's your relationship with moments that feel tense or uncomfortable? Do you avoid them, jump into right/wrong thinking, or find yourself somewhere in between?
When you're in meetings, how much are you scanning for what's going unsaid or unexplored?
What would change if you approached tense moments with genuine curiosity about what's happening rather than trying to determine who's right?
How do you regulate yourself when conversations move into territory that feels uncertain or uncomfortable?
What could your version of "tell me more words" be? What phrase feels authentic to you for opening up exploration?
Want to Try This?
Templates & Guides:
DISC Assessment — Understanding your natural style can inform how you approach difficult conversations. Dianna's "pure I" (inspiring/innovator) helps explain why she wants everyone to have fun and speak up
4-4-6 breathing technique — Dianna uses this in meetings (breathe in for 4, hold for 4, exhale for 6) to regulate her nervous system before engaging
+2 Listening (aka Level 2 Listening) - Being willing to listen deeply for the words not said and be willing to adjust your opinion helps you move from what’s right and what’s wrong
Recommended Reads:
Podcast: This is Uncomfortable - one of my favorite podcasts that uses real life stories to share the uncomfortable parts of being a human being - helps me build a little discomfort reserve
Book: Brené Brown’s “Dare to Lead” - You need so much personal awareness to “wade into conflict” if you’re not vulnerable and courageous you really can’t do it
Book: The 15 Commitments of Conscious Leadership by Jim Dethmer, Diana Chapman, and Kaley Warner Klemp’s - This book was a mirror for me to explore how and why I do things and if I was approaching situations from “above the line” or “below the line” - it helped me not walk into unhealthy conflict at work and at home!
Connections
Connect with Dianna on LinkedIn and mention Helia or email her directly at tremblay.dianna@gmail.com with subject line "Helia Connection" to learn more about her approach to organizational dynamics, team development, and building capacity in constrained organizations.
About the Contributor
Dianna Tremblay is the former Chief Program Officer at ICA in Oakland, where she spent 11 years helping the organization grow and evolve. She's the kind of person who will clean out a closet on vacation (and love it), gets genuinely excited about connecting dots between people and projects, and has perfected the art of being direct and kind at the same time.
When she's not pulling teams together or diving into healthy conflict, she's hanging out with rescue horses (who apparently know exactly where the front door is), traveling to cabins with her family, or working with ChatGPT to make her notes more efficient. Dianna brings the same thoughtful curiosity to everything she does – whether it's board governance, team dynamics, or figuring out how to help people move forward when they're feeling stuck.
Connect with Dianna on LinkedIn and mention Helia.
This article comes from a coffee chat with Dianna in July 2025. These conversations form the heart of the Helia Library – because I've learned the most from doing and from talking with other doers willing to share their wisdom. We don't need to start from blank pages or do everything alone.
As always, take what's helpful, leave what's not, and make it your own.
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