Skip to main content

August 2025: The First 90 Days: Setting New Hires Up for Success

Use this resource to learn ways you can set new hires up for success on Cloverleaf.

Jason Miller avatar
Written by Jason Miller
Updated yesterday

The Cost of Generic Onboarding

Gallup finds that only 12% of employees strongly agree that their organization does a great job onboarding new employees. This failure gets in the way of the formation of an emotional bond between the new hire and the company, a connection that can make or break retention, especially if a team is virtual. Generic onboarding can also fail at helping to acclimate employees to a new team environment.

Why Personalization in Onboarding Matters

  • Helps new hires integrate faster and feel like they belong.

  • Builds trust and engagement early, reducing first-year attrition.

  • Creates clarity about how to communicate and collaborate effectively.

How Cloverleaf Helps

  • Layered assessments (DISC, Enneagram, 16 Types, VIA Strengths, Culture Pulse) to reveal strengths and blind spots.

  • Automated, in-the-flow coaching tips in Slack, Teams, Calendar, and email.

  • Team dashboards & Thinking Style Comparisons to visualize dynamics before the first meeting.

  • NEW Discover coaching feature for supporting in depth coaching for individuals and teams to help a new hire acclimate faster and with more intentionality.

Using Discover for Onboarding

Discover Overview

Discover offers personalized coaching based on who your people are and what they’re facing. Discover taps into individual strengths, blind spots, and context to respond with relevant coaching for the moments that matter. Whether it's prepping for a tough conversation or navigating a stressful day, your team gets guidance they can use, right when they need it.

  • Lets you ask Cloverleaf questions or make reflective statements about yourself, a teammate, or your team.

  • Generates bite-sized, actionable insights for faster connection and alignment.

  • Turns curiosity and reflection into coaching moments, ideal for new hires, managers, and peers.

Examples

  • Manager: Uses Discover to plan the first 1:1 with a new hire.

  • New Hire: Uses Discover to understand team norms before their first project.

  • Peer: Uses Discover to adapt communication and accelerate trust.

Onboarding Discover Prompt Library

Prompts can be written as questions or emotional/reflective statements to Cloverleaf that trigger meaningful insights.

Prompts for New Hires

  1. I want to understand how to make the best impression on [team name].

  2. What is my biggest strength in [team name’s] dynamic?

  3. I’m nervous about giving feedback to [teammate name].

  4. Which teammate on [team name] is most likely to help me succeed in my first project?

  5. I feel unsure about how [team name] makes decisions.

  6. How does [teammate name] prefer to communicate under pressure?

  7. I want to avoid unintentionally frustrating [team name.]

  8. What is one blind spot I should watch for as I integrate into [team name]?

  9. I feel energized by collaboration and want to know who on [team name] thrives on it too.

  10. When is the best time of day to collaborate with [teammate name]?

Prompts for Managers of New Hires

  1. I want to recognize [new hire name] in a way that feels meaningful.

  2. What might motivate [new hire name] the most in their first 90 days?

  3. I’m concerned about where [new hire name] might experience friction on [team name].

  4. How does [new hire name] prefer to receive feedback?

  5. I want to support [new hire name] during moments of stress or uncertainty.

  6. Which team members on [team name] will naturally collaborate best with [new hire name]?

  7. I want to make sure [new hire name] gets an early win to feel successful.

  8. What is one area where I should adapt my communication to help [new hire name] thrive?

  9. I feel responsible for helping [new hire name] feel included quickly.

  10. Where could misunderstandings happen between [new hire name] and the [team name]?

Prompts for Peers of New Hires

  1. I want to build trust with [new hire name] quickly.

  2. How does [new hire name] like to communicate during projects?

  3. I’m excited to collaborate but unsure what support [new hire name] needs most.

  4. What motivates [new hire name] to do their best work?

  5. I want to avoid doing something that makes [new hire name] feel excluded.

  6. What’s the easiest way for me to give feedback that lands well with [new hire name]?

  7. I feel curious about which of my strengths will be most helpful to [new hire name].

  8. What is one habit I should adapt to work best with [new hire name]?

  9. I want to connect on a personal level without overstepping.

  10. What conversation starter could help [new hire name] feel included in [team name] dynamics?

A 90-Day Roadmap for Cloverleaf Onboarding

Personalized onboarding is most effective when it moves beyond policies into real relationships and team integration.

Here’s a suggested week-by-week progression using Cloverleaf’s tools:

Week 1–2: Connection & Clarity

  • For New Hires: Complete key assessments: DISC, Enneagram, 16 Types, VIA Strengths, Energy Rhythm, Culture Pulse.

  • For Talent Leaders or Managers: Have a talent leader or manager walk the new hire through all the functionality of Cloverleaf as part of the onboarding process.

    • Encourage new hires to explore the Team Dashboard to see roles, personalities, natural collaborators, key team influencers. and team strengths.

    • Invite the new hire, manager and peers to Use DISCOVER prompts to guide intro conversations and team orientation.

    • Introduce daily coaching tips in Slack, Teams, or email to help with first impressions and communication.

    • Encourage new hires to consume their daily coaching tips each day as a way of grounding their day in intentional communication and collaboration. This will also help them ramp up getting to know others on their team, especially if the team is virtual.

Week 3–6: Collaboration & Feedback

  • For Managers: Encourage peers to share coaching tips about working with the new hire.

    • TIP: A Manager might consider conducting a team meeting where you ask everyone PRIOR to the meeting to bring the tip that most resonated with them in the past week OR a tip that called them to action in the past week

    • Invite the New Hire to Use Thinking Styles Comparison to uncover workstyle differences and discuss how to complement each other.

    • Begin early feedback loops:

      • Managers use Discover to identify friction points or motivators.

      • Peers check in on “working well together” moments using Cloverleaf insights.

  • For New Hires: Begin sharing tips from their own assessments or daily coaching to help teammates collaborate effectively.

Week 7–12: Trust & Contribution

  • For New Hires: Transition focus from learning to making meaningful contributions:

    • Review Team Dashboards to identify where the new hire’s strengths fill gaps.

    • Use Discover to guide role clarity and performance reflections:

    • “I want to know where I can contribute more to [my team name’s] success.”

    • “What is one area I can make the most difference in on [team name]?”

  • For Talent Leaders & Managers: Encourage new hires to share insights about themselves with peers to deepen trust.

    • Use daily coaching nudges to reinforce preferred communication, stress responses, and collaboration habits.

    • Conduct a 90-day reflection meeting combining DISCOVER insights, team comparisons, and key learning moments to solidify long-term integration.

Feature Focus: Insights Discovery for Onboarding

Insights Discovery is a psychometric tool rooted in Carl Jung’s psychological theories, designed to enhance self-awareness, improve team dynamics, and foster effective communication in the workplace. It employs a straightforward four-color model to represent distinct personality preferences:

Fiery Red

Characterized by a direct, assertive, and results-oriented approach. Individuals with a preference for Fiery Red energy are action-oriented and thrive in positions of control.

Sunshine Yellow

Denotes enthusiasm, sociability, and a dynamic communication style. Those leading with Sunshine Yellow energy are often persuasive, enjoy collaboration, and seek engaging interactions.

Earth Green

Reflects a focus on values, harmony, and supportive relationships. Individuals with a preference for Earth Green energy value depth in relationships, prefer democratic approaches, and strive for understanding.

Cool Blue

Represents a methodical, analytical, and detail-oriented demeanor. Those leading with Cool Blue energy prioritize accuracy, value independence, and approach tasks with careful consideration.

Why Insights Discovery Accelerates Onboarding

  • Uses simple color energy language to quickly explain preferences.

  • Strengthens psychological safety and makes early collaboration easier.

  • Keeps insights sticky and actionable well beyond the first 90 days.

How to Apply in Onboarding

  • Introduce team color-energy profiles in first team meetings.

  • Use color energy insights to shape early feedback and conflict navigation.

  • Reinforce understanding with Cloverleaf coaching tips in daily tools.

Call-to-Action

Pick three Discover prompts mentioned above to use this week with a new hire, peer, or manager to transform onboarding into a personalized, insight-driven experience.

Did this answer your question?