Develop stronger managers through expert leadership coaching, real-world practice, and peer community.
Leadership Coaching. Peer Community.
Leadership Playground is an interactive coaching community where high-potential managers build confidence, sharpen communication, and practice real leadership challenges alongside experienced leadership coaches and improv-trained facilitators and a vibrant peer network. Managers get expert coaching, practical feedback, and meaningful connections with leaders navigating many of the same challenges.
Why Leadership Playground?
Leadership coaching that's tangible, affordable, and ongoing.
As HR and L&D leaders, you know that managers need ongoing coaching, peer support, and opportunities to learn from others navigating the same challenges.
Leadership Playground gives HiPo managers access to expert coaching, practical leadership practice, and a community of peers without the cost of traditional 1:1 executive coaching.
It's leadership coaching that's accessible, engaging, and immediately useful.
Is Leadership Playground Right for Your Organization?
Leadership Playground is designed for organizations that want to:
Develop high potential managers
Provide leadership coaching on a limited budget
Support managers consistently throughout the year
Give leaders practical opportunities to practice
Invest in people without building an internal program from scratch
Every month, members join live virtual leadership coaching and practice sessions focused on the skills and challenges that matter most to managers. With expert coaching from Erin Diehl and experienced leadership development facilitators trained in improv, members build confidence, practice real leadership situations, and learn alongside a vibrant community of peers. Example coaching topics include Effective Communication, Thinking Quickly on Your Feet, Presentation Skills, Leadership, & more!
What Your Managers Will Experience
1 Virtual Leadership Development Training: Learn actionable tools through experiential, improv-inspired exercises designed specifically for mid-level management.
1 Group Coaching & Scenario Practice Session: Guided by experienced leadership development facilitators trained in improv and our “Yes, And” framework, managers work through real workplace scenarios, receive coaching and feedback, and connect to situations they'll actually have with their teams. Each scenario topic is voted on by the community every month based on their real-time challenges.
Peer Learning & Community: Connect with leaders from other organizations, share challenges, exchange ideas, and build your professional network with peers navigating similar leadership challenges. We listen to members in the community to create opportunities for deeper connection and support around their most pressing needs.
Each month includes:
Leadership is built through practice & feedback.
Play creates the psychological safety leaders need to experiment, take risks, fail, and find their confidence. Through experiential, improv-inspired exercises and group coaching, managers practice real workplace conversations, get coached in the moment, and build confidence in a supportive, low-stakes environment before they have them on the job.
Why Leadership Playground Works
An Affordable Solution for
HR & L&D Teams
Give your managers access to leadership coaching, real-world practice, and peer connection without the investment of building a custom program or providing traditional 1:1 executive coaching.
Whether you're looking for leadership coaching for a handful of managers or building a leadership pipeline across your organization, we handle everything from coaching and training to community-building:
Live monthly leadership development training
Group coaching & practice
Participant communication
Learning resources
Cohort experience
Virtual community-building
You enroll your managers
& we take care of the rest.
Pricing
Whether you're investing in your own leadership development or seeking coaching for a group of managers, Leadership Playground offers flexible options to fit your needs.
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Perfect for mid-level managers looking to grow their leadership skills alongside peers from other organizations.
$49.99/month
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Enroll 5 or 10 managers from your organization and save 10% with a prepaid commitment.
5 Managers
3 Months | $675 Total Investment | $135 Per Person
6 Months | $1,350 Total Investment | $270 Per Person
9 Months | $2,025 Total Investment | $405 Per Person
10 Managers
3 Months | $1,350 Total Investment | $135 Per Person
6 Months | $2,700 Total Investment | $270 Per Person
9 Months | $4,050 Total Investment | $405 Per Person
Also Available for Associations
Looking for a valuable member benefit?
Leadership Playground gives associations an easy way to invest in HiPo members.
Purchase a cohort on behalf of your members, and they'll receive ongoing leadership development, community, and practical skill-building throughout the program…all included as part of their membership experience!
About improve it!
improve it! is a professional development company that uses improv comedy to help leaders and teams build connection, confidence, and adaptability at work. Through workshops, keynotes, and experiential learning, improve it! has helped thousands of leaders create more human-centered workplaces.
For years, we've helped organizations develop stronger communicators, more adaptable leaders, and more connected teams through experiential, improv-based learning.
Now, Leadership Playground brings that same engaging approach to experiential group coaching and community, giving HiPo managers a place to practice, grow, and connect.
Ready to invest
in your managers?
Frequently Asked Questions
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Leadership Playground is an ongoing virtual leadership coaching community for HiPo managers. Members build confidence, practice real-world leadership skills, and learn alongside peers from other organizations through experiential, improv-inspired sessions.
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Leadership Playground is designed for HiPo talent and mid-level managers who are ready to strengthen their leadership skills, build confidence, and connect with other managers navigating similar challenges.
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Inside Leadership Playground, you'll get:
One live monthly workshop built around a core leadership skill
One group coaching and scenario practice session, voted on by the community, where you work through the real challenges you're facing right now
A community of peer managers from other organizations working through the same challenges
Access to replays and resources inside Circle
A space to ask questions, practice, and grow alongside people who get it
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Jump in anytime! You’ll get immediate access to everything inside the platform, including past trainings and resources. You can go at your own pace and catch up whenever it works for you.
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On an individual basis-yes, you can cancel anytime. That said, there are no refunds for past payments.
For cohorts joining from the same organization, we cannot refund your package, but you can decide to not renew moving forward. -
Nope! Stay as long as it’s serving you. We hope you’ll stick around, but you’re never locked in.
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Everything happens inside our community platform, Circle. That’s where you’ll access workshops, replays, discussions, and connect with other members. You’ll receive access as soon as you join!
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Our workshops and group coaching & scenario practice sessions are live (because that’s where the magic happens), and replays are available if you can’t make it.
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This program works best when you show up. Each month includes one live workshop and one group coaching practice session, both designed to be practical enough to use the next day at work. We know life happens, so replays are there if you have to miss one, but the real growth (and the reason members stick around) comes from showing up live, practicing with the group, and building momentum month over month.
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This isn’t passive learning. We combine improv-based techniques, real-life scenarios, group coaching, and a vibrant peer community so you can actually practice leadership, get feedback, and grow alongside people who get it.
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Both 😄
We believe people learn best when they feel safe, energized, and engaged. So yes, it’s fun—but it’s also deeply practical and results-driven, with real coaching, practice, and feedback built in. -
Totally normal. Most people are at first.
You can participate at your own pace—whether that’s observing, engaging in the chat, or jumping fully in. This is a judgment-free, supportive space.