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October 2026: New to the Role: What Actually Changes in Your First 90 Days for Managers and Individual Contributors

How to use Discover, Coaching Topics, and Roleplay to read a new team fast, coach through the shift into leading, and rehearse conversations you don't have formal authority for yet.

Written by Jason Miller

Recording of this webinar will be uploaded here after the broadcast.

What you'll learn

  • How to use Discover to get a working read on a team before you have to make your first real decision

  • How to set a Coaching Topic around the specific shift that comes with newly leading people

  • How to use Roleplay to rehearse a conversation you don't have formal authority to have yet

  • How the same three tools apply whether your title changed or not

Who can do this: All Cloverleaf users.

Who is this guide for?
If you're a manager, this is about leading people who didn't choose you, often direct reports you're responsible for from day one. If you're an individual contributor, this is about leading a piece of work, a project, or an initiative with no title change, working alongside peers and people who outrank you on paper.

This guide is for people already on the team who are newly leading something. If you're onboarding a brand new hire instead, see "The First 90 Days: Setting New Hires Up for Success."

Before you get into the tools
Being new to leading, titled or not, means reading how a team actually operates while the people on it are already watching you do it. That read usually takes months of trial and error. The three tools below compress it.

How do I get a working read on a team before I have to make a decision?
​Discover lets you ask Cloverleaf a question, or make a reflective statement, about yourself, a teammate, or your team. It answers using the specific behavioral makeup of the people involved, not a generic framework.

Open Discover from your left-side navigation.

Manager example: "How does this team make decisions when priorities are unclear?"
Individual contributor example: "Who on this team needs the most context before a change lands?"

Write Discover's answer back in your own words before you act on it. That's what turns an insight into something you'll actually remember in the room.

How do I coach myself through the specific shift that comes with newly leading someone?
A Coaching Topic is ongoing coaching on a goal, a relationship, or something you're actively working through. It has no fixed length and no end date. It runs until you tell Cloverleaf you're ready to move on.

Find Coaching in your left-side navigation, directly under Assessments. Open Manage topics, then Add new topic, and describe what you want coaching on in your own words.

Manager example: a topic around moving from doing the work yourself to coaching someone else through it.
Individual contributor example: a topic around getting buy-in from someone with more tenure than you have title.

How do I rehearse a conversation I don't have formal authority to have yet?
​Roleplay lets you rehearse a difficult conversation with an AI partner before you have it for real, informed by the actual person's behavioral assessment data. Every session ends with a scored evaluation and specific feedback.

Open Roleplay, describe the situation, and pick the person you're practicing with by name. Review their Participant Insights (how they typically receive feedback and handle conflict) before you start.

Manager example: delivering direct feedback to a report in your first few weeks leading them.
Individual contributor example: pushing back on a peer who missed a deadline, with no positional power to lean on.

Where should I start?

If you're a manager:

  1. Run one Discover session on your new team before your first real decision.

  2. Set a Coaching Topic around shifting from doing the work to coaching someone through it.

  3. Use Roleplay to rehearse your first piece of direct feedback before you deliver it.

If you're an individual contributor:

  1. Run one Discover session asking who on the team needs the most context before a change lands.

  2. Set a Coaching Topic around getting buy-in from someone with more tenure than you have title.

  3. Use Roleplay to rehearse pushing back on a peer before the real conversation.

You'll know it worked when...

  • Discover gives you something specific enough about the team that you can restate it without checking the screen

  • Your Coaching Topic shows up in Manage topics with the right focus and starts pacing itself

  • You walk into the real conversation having already heard the hardest version of it once

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