Summary
Your first one-on-one sets the tone for your entire leadership journey. Skip the scripts, Dee shows you how to build trust, listen deeply, and start strong as a people-first manager.
So you’ve just stepped into your first management role. Congratulations! I remember how that felt, equal parts thrilling and terrifying. One minute you’re a colleague, and the next you’re expected to lead the same people you were grabbing coffee with last week.
Now you’re probably staring at your calendar with those first one-on-one meetings looming, and you’re wondering: How do I do this without it being painfully awkward for everyone involved?
That first transition from team member to team leader is one of the most significant professional shifts we make. And those initial one-on-ones? They set the tone for everything that follows.
Why First One-on-Ones Matter So Much
In those first moments of leadership, after scheduling that first round of one-on-ones with your the team it’s easy to be tempted to prepare with a detailed agenda, a long list of questions, and a determination to be “officially managerial.”
Ten minutes in to a meeting under those circumstances you’ll both be uncomfortable, it’s inauthentic, and the your team members will sense it immediately. The conversation will be stilted, performative, and not at all useful.
If instead of being focused on being “the boss” you’re in danger of forgetting the most important thing: creating a genuine human connection. For the next one-on-one, scrap the rigid agenda, take a deep breath, and focus on having an authentic conversation. Think about what you’d want from your first meeting with your manager, and operate from there.
This is how you learn that the best one-on-ones aren’t about asserting authority, they’re about building trust and understanding each other as people first, and colleagues second.
Setting the Right Tone from the Start
Here in Australia, we have a pretty egalitarian approach to leadership. We value authenticity and tend to distrust hierarchical posturing. This means your team doesn’t expect (or want) you to suddenly transform into some corporate automaton just because you’ve been promoted. But your cultural context might differ, might value slightly more formality, or less chit chat about what your weekend plans are, or what footy team won (or didn’t) during the week.
The team will be looking for the same qualities that probably got you promoted in the first place: honesty, competence, and a genuine interest in their success.
Your first one-on-one isn’t about impressing your team member with your managerial prowess. It’s about:
- Establishing psychological safety – Creating a space where they feel it’s okay to be honest
- Building connection – Understanding who they are beyond their job description
- Setting expectations – Clarifying how you’ll work together going forward
- Listening deeply – Learning what matters to them and how you can support them
Before the Meeting: Simple Preparation
The best way to reduce awkwardness is to be prepared, but not over-prepared. Here’s what I recommend:
- Schedule enough time – 45-60 minutes is ideal for a first one-on-one
- Find a comfortable space – consider a neutral location like a cafe if your office feels too formal. If meeting virtually, choose a quiet, well-lit space where you won’t be interrupted, and consider turning cameras on to build connection.
- Send a simple agenda ahead of time – Let them know what to expect
- Prepare some thoughtful questions – But don’t treat it like an interrogation
- Check your mindset – Remember, you’re there to serve them, not the other way around
Your agenda doesn’t need to be complicated. A simple email saying:
“Looking forward to our chat tomorrow. I’d like to use this time to get to know you better, understand what’s working well for you, where you might need support, and how I can be a good manager for you. Feel free to bring any topics or questions you’d like to discuss as well.”
That’s all you need to set the right expectations.
During the Meeting: Authenticity Over Authority
When the actual meeting rolls around, here’s how to keep it human and productive:
1. Start with genuine connection
Begin with some light personal conversation. Not the weather, but something that helps you connect as people. Maybe it’s about their weekend, a hobby they mentioned, or something you’ve noticed they’re passionate about.
I always start by asking, “How are you really doing?” and then giving them the space to answer honestly. It’s a simple question, but it signals that I care about them as a whole person.
2. Acknowledge the transition
Don’t pretend there isn’t a shift in your relationship. Name it directly:
“I know it’s a bit different now that I’m in this role. I’m still figuring out how to be a good manager, and I want to make this transition as smooth as possible for both of us. I value our working relationship and want to make sure it stays strong.”
3. Ask powerful questions, then really listen
The heart of a good one-on-one is asking questions that matter, then truly listening to the answers. Some of my favourites for a first one-on-one:
- “What does success look like for you in your role right now?”
- “What parts of your work give you energy, and what drains you?”
- “How do you prefer to receive feedback?”
- “What do you need from a manager to do your best work?”
- “What should I know about you that would help me support you better?”
When they answer, resist the urge to immediately respond or solve problems. Just listen attentively, take notes, and ask follow-up questions that show you’re engaged.
4. Share your management philosophy
Be transparent about how you see your role as their manager:
“I see my job as removing obstacles so you can do your best work, providing the context you need to make good decisions, giving honest feedback to help you grow, and advocating for you and your work.”
Then ask what they need from you specifically.
5. Set clear expectations about one-on-ones
Explain how you envision these meetings going forward:
“I’d like us to meet every [week/two weeks] for about [30-45] minutes. This is primarily your time to talk about whatever would be most helpful to you, concerns, ideas, career development, or just catching up. I’ll occasionally have topics I need to discuss, but I want this to be a space that serves you.”
6. End with clarity and appreciation
Wrap up by summarising any action items or commitments, expressing gratitude for their time and insights, and reinforcing that you’re there to support them.
After the Meeting: Follow Through
How you act after the first one-on-one is just as important as the meeting itself:
- Send a brief follow-up email summarising any key points or commitments
- Actually do the things you said you would do – Your credibility depends on it to build and maintain trust
- Reflect on how it went – What worked? What felt awkward? How can you improve?
- Give it time – Building a trusting management relationship doesn’t happen in one meeting
Common Pitfalls to Avoid
I’ve made plenty of management mistakes over the years. Here are some big ones to avoid in your early one-on-ones:
- Talking too much – Filling silence with nervous chatter
- Turning it into a status update – One-on-ones aren’t for project updates
- Being inauthentic – Trying to act like a “boss” instead of yourself
- Making promises you can’t keep – Be honest about what you can and can’t do
- Avoiding difficult topics – Address tensions directly but compassionately
- Not being prepared – Having no structure at all can make things more awkward
The Power of Vulnerability
One last thought: don’t be afraid to be a bit vulnerable. You’re new to this role. You will make mistakes. Acknowledging that you’re still learning shows strength, not weakness.
I made a good few mistakes in the early years of leading the team, while those stories are for another post, acknowledging those mistakes to the team was the first step in keeping the connection with my reports, but which also paved the way to changing my approach, and resetting to move forward.
A simple, vulnerable admission improves goodwill, and may open the door to honest feedback that helps you improve faster.
Building Your Management Toolkit
As you develop your one-on-one practice, having the right resources and frameworks can make all the difference. At Future of Team, we’ve developed tools specifically for the unique challenges of building culture and leadership.
Our toolkit includes templates for structuring ongoing one-on-ones, frameworks for career development conversations, and resources for creating psychological safety.
The Path Forward
That first one-on-one meeting is just the beginning of your management journey. Over time, you’ll develop your own style and rhythm for these conversations. The awkwardness will fade as you and your team members build trust and get used to your new dynamic.
Remember that leadership, at its core, is about service. You’re there to help your team members thrive, grow, and do their best work. Keep that mindset, and the rest will follow.
The most powerful thing you can do is simply show up as your authentic self, listen deeply, and care genuinely about the person sitting across from you. Do that, and you’ll be miles ahead of most new managers.
So take a deep breath, be yourself, and trust that you’ve got this. Because you do.
