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_{What we’ll learn in today’s Newsletter}

• How to be fully present and create space for real conversations.

• Powerful questions to move beyond surface-level updates.

• Why listening to understand, not just to fix, builds trust.

• The role of vulnerability and authenticity in leadership conversations.

• How to make meaningful conversations a regular habit, not a one-off event.

• The importance of following up and acting to show your team their voice matters.

As leaders, we often focus on strategy, execution, and results. But there’s one critical element that quietly underpins all of these: the quality of our conversations with our team. Meaningful conversations — the kind that go beyond checklists and KPIs — are what build trust, unlock potential, and create genuine engagement.

Yet, in the rush of meetings, targets, and deadlines, it’s easy to let conversations become transactional. So how do we break that cycle and create space for meaningful dialogue that truly moves the needle? Here are some key principles I’ve learned (and continue to work on) when it comes to having impactful conversations with your team.

1. Start with Presence, Not an Agenda

The foundation of any meaningful conversation is being fully present. It sounds simple, but how often do we enter a 1:1 already thinking about our next meeting or mentally writing an email?

When you sit down with a team member — whether virtually or in person — clear your mental clutter. Silence notifications. Close the laptop if you’re in person. Let them know they have your full attention.

Instead of diving straight into "tasks" or "updates," start by asking how they are — and actually care about the answer. A simple, "How are you really doing?" (and giving them time to respond) can shift the entire tone of the conversation.

2. Ask Questions That Go Beneath the Surface

If you want a meaningful conversation, ask meaningful questions. Here are a few powerful ones I’ve used:

• "What’s one thing that’s going well for you right now?"

• "What’s been your biggest challenge this month?"

• "What’s something you wish I knew about your work or experience here?"

• "If you could change one thing about your role or how we work, what would it be?"

These types of questions invite reflection and honesty — and often lead to insights you wouldn’t get from a standard status update.

3. Listen to Understand, Not to Fix

As leaders, we often fall into the trap of wanting to solve problems on the spot. But sometimes, what people need most is simply to be heard and understood.

When a team member shares a frustration or challenge, resist the urge to jump in with a solution. Instead, listen deeply and ask follow-up questions like:

• "Can you tell me more about that?"

• "How did that make you feel?"

• "What do you think would help in that situation?"

By giving them space to process and articulate, you often help them find their own answers — and you gain richer insight into what’s really going on.

4. Be Vulnerable and Human

Meaningful conversations are a two-way street. If you want your team to be open with you, you need to model that vulnerability.

This doesn’t mean oversharing, but it does mean being real about your own challenges and mistakes. Saying things like:

• "I’ve struggled with that too."

• "I don’t have all the answers, but let’s figure it out together."

• "That feedback is hard to hear, but I really appreciate you sharing it."

When you show up as a human, not just a boss, you create a safe environment where people can speak candidly — and that’s where real growth happens.

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5. Make It a Habit, Not a One-Off

One of the biggest mistakes leaders make is treating meaningful conversations as special events — something that happens once a quarter or when there’s a problem.

To build trust and connection, these conversations need to be regular and consistent. Make time for recurring 1:1s that aren’t just about project updates but about them as people — their growth, goals, and wellbeing.

Even a 10-minute meaningful check-in can be powerful if done consistently. And when people know they’ll have a regular space to be heard, they’re less likely to bottle things up.

6. Follow Up and Act

Finally, for conversations to be meaningful, they need to lead to something. That doesn’t mean you have to fix every issue right away, but it does mean acknowledging what was said and following up.

If someone shares a concern, check in later to ask how it’s going. If they offer feedback, let them know what you’re doing with it — or explain transparently if you can’t act on it right now.

When people see that their voice leads to real consideration and action, trust grows — and so does their willingness to engage in future conversations.

Final Thought: Conversations Are the Culture

At the end of the day, the conversations you have (or don’t have) shape your team’s culture. If people feel heard, valued, and safe to speak up, you’ll unlock creativity, loyalty, and performance.

So take a moment to reflect:

• Are your conversations with your team meaningful or mechanical?

• Are you creating space for honest dialogue — or rushing through to-dos?

• What’s one thing you could do this week to deepen a conversation with someone on your team?

Because leadership isn’t just about decisions and strategy — it’s about human connection. And that starts one conversation at a time.

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