How many meaningful conversations are you having each week with your leader, team, or peers? Life and work are busy, our calendars fill up, notifications distract us, and it’s easy to lose sight of what matters most: understanding ourselves and others.

That’s where Cloverleaf Discover comes in. It’s not another task, it’s a way to make your existing conversations more meaningful by:

Highlighting your strengths and growth opportunities.
Offering insights into how your teammates think and communicate.
Helping you act on what you learn to collaborate better.
Building awareness for yourself and your team at the same time.

Why a Challenge & What is It?

If you want to strengthen a muscle, you work it regularly. If you want to strengthen your team’s collaboration, you need regular reflection and practice.

The Cloverleaf 30-Day Challenge is a micro-learning development experience that helps teams build awareness and collaboration through short, consistent reflection. Over one month, you’ll use Cloverleaf Discover 2–3 times a week to learn, reflect, and apply learning, creating small, steady shifts that lead to stronger teamwork and better results.

Use Cases & Positioning

Team kickoffs or onboarding - build trust faster through shared insights.
Post-reorg or leadership changes- establish alignment and shared language quickly.
Teams experiencing friction - improve how people understand and respond to one another.
After completing assessments - (DISC, Enneagram, 16 Types, etc.) — move from “awareness” to applied learning.
Prepping for a high-stakes quarter- help people communicate better and avoid conflict under pressure.

How a Leader Can Position the 30-Day Challenge

This is a way for our team to build stronger communication and collaboration through small, consistent reflection.
It’s not tons of extra work - it’s a way to make our current work better.
We’ll each take 5–10 minutes a few times a week to reflect using Cloverleaf Discover.
The goal is to grow self-awareness and learn how to work better together.
We’ll tie these reflections to real situations - like feedback, meetings, or problem-solving.
At the end of the month, we’ll reflect as a team on what we’ve learned and how it’s impacted our work.
You don’t need to prepare anything - just show up with curiosity and a willingness to try.

How it Works

In a team meeting, challenge your team to engage with Cloverleaf Discover 2–3 times per week for the next month, to intentionally build self-awareness and improve communication and collaboration.

You can access Discover insights from your Cloverleaf Dashboard once you log in to Cloverleaf via your Daily Coaching email.

To help the team stay consistent:

Create a team calendar reminder 2–3 mornings a week for a 10-minute reflection block.
Or, ask everyone to schedule 10 minutes on their own calendar within the first two hours of their workday on those days.

When to Use Cloverleaf Discover

Encourage team members to use Discover insights in the flow of their real work, especially when preparing for or reflecting on common workplace scenarios such as:

Having a Challenging Conversation
- Check your Discover insights before a difficult conversation to understand your stress triggers and communication tendencies.
- Ask: “How might my style impact how feedback is received by [team member]?”
Preparing for a 1:1 or Coaching Conversation
- Review your own insights or your teammate’s profile to tailor your communication.
- “What motivates [team member], and how can I communicate in a way that resonates?”
Sharing an Idea or Giving Feedback
- Reflect on your approach to persuasion, collaboration, or risk-taking.
- Ask: “How can I adjust my communication style to ensure my message lands effectively with [team member]?”
Planning or Leading a Meeting
- Use insights to anticipate how different team members might approach problem-solving, planning, or decision-making.
- Ask: “What’s the best way to engage the thinkers, doers, and collaborators in this meeting with the marketing team?”
Reflecting After a High-Stakes Situation
- Use a post-event Discover session to explore what went well, what challenged you, and what you learned about yourself or others.
- Ask: “What can I do differently next time to create a better outcome with the compliance team?”

Team Integration (Weekly or Biweekly)

During team meetings or 1:1s, invite members to share:

An insight or reflection that influenced their behavior or mindset that week.
How they applied a Discover insight to a real scenario (i.e. a challenging conversation, idea pitch, or team collaboration).

Ask discussion questions like:

“How did using Discover change how you approached that situation?”
“What surprised you about your reaction or your teammate’s?”
“What action or adjustment did you make as a result?”

End-of-Month Debrief (20–30 minutes)

Use these questions for your final group reflection:

How did engaging with Discover 2–3 times a week impact your work or relationships?
Which scenarios did you find most valuable to pair with Discover?
What’s your biggest insight about yourself or the team?
How do we want to continue using Discover as a team moving forward — and why?
What might change over the next 6–12 months if we maintain this practice?

OR Create a Custom Challenge with Your Team

You don’t have to use the full 30-day structure, your team can co-create a challenge that fits your rhythm. This can be a quick, 10–20 minute discussion during a team meeting.

Facilitate the conversation with these steps:

Start with purpose - Ask: “How would our team benefit from more self- and team-awareness?”
Share examples- Invite teammates who’ve used Cloverleaf successfully to speak to the impact.
Position Cloverleaf as a practical tool - Remind the team: Development doesn’t need formal training—this takes just a few minutes a few times a week.
Demo Discover- Show a prompt or two to illustrate how quick and valuable the experience can be.
Identify real use cases - Ask: “When would Discover be most useful in our day-to-day?” Think feedback, meetings, tough conversations.
Set a cadence- Ask: “What’s a realistic number of days per week we can commit to using Discover?” Agree on a timeframe.
Plan for reflection - Decide how you’ll assess impact. Use questions like:
- What did I learn about myself or my team?
- What action did I take, and what changed?
- What do we want to keep doing?
Reconnect to the “why” - Close by restating the benefit of this commitment—and revisit it regularly to maintain momentum.