Contracting
That first 1:1 can go in a dozen different directions. Sometimes, you click immediately. Conversation flows, ideas bounce, and off you go. Other times… it’s more like two people silently wondering who’s going to break the awkward pause first.
There’s no universal playbook for how someone will show up in that first meeting. Cultural background, previous management experiences, personality—it all shapes the dynamic. And if you’re brand new to the company, you’re still figuring out how formal or casual things should be. Too stiff? You might seem unapproachable. Too laid back? That might feel off, depending on the culture.
If you’ve been promoted from within, there’s an extra layer—navigating the shift in dynamic with teammates who were just your peers (and maybe close friends). It’s a lot to navigate.
So how do you cut through all that and build real alignment from the start?
There’s a tool for that. It’s called contracting.
What is contracting?
Contracting is a lightweight but powerful exercise that gives you and your direct reports space to talk openly about expectations—on both sides. It sets the tone for your working relationship and helps establish trust early.
At your first 1:1, explain that you’d like to walk through a quick set of questions to better understand how you can support them. You can share the questions in advance if you want, or just dive in live—whatever feels more natural.
Here are the five core questions I use when contracting. Feel free to adapt them to your own style or team.
1. What areas would you like support with?
This is intentionally open-ended. It could be technical growth, navigating team dynamics, building confidence, or something else entirely.
Your job here? Listen. No jumping in with solutions, no steering. Just take notes. You’ll come back to these themes in future 1:1s, giving you continuity that goes beyond surface-level status updates.
2. How would you like to receive feedback and support?
People process feedback in different ways. Some prefer direct, real-time commentary. Others need time and space to digest things.
If they don’t give a clear answer, help them think it through with scenarios:
- Imagine you’re leading a whiteboard session—would you rather I call out a concern in the moment, or talk privately after?
- Do you prefer feedback face-to-face, via email, or through comments in a doc?
The goal here is to figure out the best way to deliver feedback so that it lands—with impact and empathy.
3. What could be a challenge in us working together?
This is about surfacing potential friction early. Maybe there’s a technical gap—your background is in JavaScript and theirs is Java. Maybe they’re introverted and worry about pushing back in group settings. Maybe they feel intimidated. These are all valid feelings.
Talk them through. If needed, think creatively—like looping in a senior engineer to provide more targeted mentorship.
4. How might we know if the support I’m offering isn’t working?
This question is about spotting breakdowns early. Maybe interactions feel tense. Maybe feedback isn’t resonating. Maybe coaching just isn’t helping.
Also: how do each of you respond to conflict? Some people shut down. Others escalate quickly. It’s worth discussing how frustration, disappointment, and disagreement show up—for both of you.
And if something’s not working? Agree upfront that it’s okay to say so. That gives you both room to adjust, or even bring in other support as needed.
5. How confidential are our conversations?
1:1s often surface sensitive topics—like concerns about a teammate’s performance.
So it’s worth asking: how confidential is this information in their eyes? Would they be okay with you acting on it? Would they be uncomfortable if it was traced back to them?
Walking through a few examples can help clarify their expectations.
In Summary
Contracting is a simple but meaningful way to break the ice, set expectations, and lay the groundwork for a healthy manager-report relationship.
It’s not just useful at the start—it’s something you can revisit periodically as your relationship evolves.
Best of all, it gives you plenty of meaningful topics to explore in upcoming 1:1s. And speaking of those—next time, we’ll dig into how to make your regular 1:1 meetings genuinely valuable (for both of you).