Introduction: What You’ll Learn
This simulation walks through your first 1:1 with a new team member. It’s your opportunity to build rapport, understand their goals and working style, and set expectations for how you’ll work together.
You’ll practice:
- Starting a 1:1 in a welcoming, open tone
- Asking thoughtful questions to get to know them
- Communicating your role and expectations clearly
- Setting up future 1:1 rhythms and psychological safety
Step-by-Step Simulation
Scene 1: Opening the 1:1
You (Manager):
"Hey, glad we could finally sit down! How’s your first week going so far? Anything surprising or confusing?"
New Direct Report (Taylor):
"It’s been good! A bit overwhelming, but everyone’s been nice. I’m still figuring out where things live and how the team works day-to-day."
You:
"Totally normal — onboarding is a lot. If anything feels unclear or stuck, just flag it. I want to make sure you feel supported."
(Optional: check your watch or calendar briefly to acknowledge time)
"We’ve got around 20 minutes — enough to get the ball rolling. We’ll take our time in future 1:1s too."
Scene 2: Establishing Trust and Learning About Them
You:
"I’d love to hear more about how you like to work. Do you prefer structure or more flexibility? Heads-down time or lots of collaboration?"
Taylor:
"I like clarity — having clear goals helps me focus. I don’t mind working independently but I like bouncing ideas when I get stuck."
You:
"Good to know. I’ll make sure we’re aligned on goals regularly, and I’m always around if you need to brainstorm or unblock something."
You (continued):
"What kind of work really gets you excited or motivated? Anything you’re hoping to grow into here?"
Taylor:
"I’m really into frontend design systems. I’d love to own something like that one day, and I’m hoping to build more leadership skills too."
You:
"Love it — sounds like a great growth path. I’ll make a quick note so we can revisit that in our next check-in."
Scene 3: Sharing Your Style and Expectations
You:
"Thanks for sharing that — super helpful. Quick bit about me — I’m big on clear communication and making sure we’re aligned on goals. I’ll always be upfront with you, and I hope you’ll feel comfortable doing the same."
You (continued):
"I like to use these 1:1s for whatever helps you most — whether it's venting, goal setting, or career coaching. Sometimes they’re structured, sometimes just a check-in. How does that sound?"
Taylor:
"Yeah, that sounds great."
You:
"Cool — let’s make this a recurring weekly meeting, and adjust if needed. I’ll usually have a few topics, and you can bring anything too."
You (continued):
"One more thing: most of the team communicates async via Slack and Notion. If that ever feels noisy or unclear, just flag it. We’ll make it work for you."
Mini Roleplay Challenges
Challenge 1:
Taylor is very quiet and gives short answers.
- Best Response: Gently ask open-ended questions like:
“I know it’s early, but what kind of projects do you usually enjoy the most?”
Challenge 2:
Taylor asks directly: “How do I get promoted here?”
- Best Response: Be transparent and positive:
“Great question — let’s explore that together over time. I’ll share the promotion criteria and we can work backward from there.”
Challenge 3:
You’re tempted to skip 1:1s during a busy week.
- Best Response: Don’t. Your first 1:1 sets the tone. Prioritize it, even if shortened.
Optional Curveball Mode
- Taylor mentions past micromanagement trauma — practice active listening.
- They express doubt about their skills despite good onboarding progress.
- They ask for immediate ownership of a high-impact project.
Reflection Checklist
Building Connection
- Did I show curiosity and empathy?
- Did I learn something personal or professional about them?
Setting Foundations
- Did I explain what to expect from our 1:1s?
- Did I share my style and invite feedback?
Support and Growth
- Did I ask about their goals or interests?
- Did I create a sense of safety and openness?
Common Mistakes to Avoid
- Talking too much and not listening enough
- Overloading them with information or structure
- Being vague about how 1:1s will work going forward
- Skipping the personal aspect — it's not just about work