How to Curate and Lead a 21-Day Equity Challenge

Here are the tools; join us if you like!

I am proud to share the work of my colleagues, Max MacMillan and Michael Muniz, who exemplify our employee-driven momentum and commitment to building a more diverse, equitable, and inclusive workplace at Alley. In collaboration, they designed and led a company-wide Equity Challenge over 21 days. I am excited (and honored!) to share it with you with hope that you’ll be inspired to follow suit.

This format was based on the work of Dr. Eddie Moore, Jr., Debby Irving, and Dr. Marguerite Penick-Parks to provide a framework for people to study, question, and communicate around topics of racial equity and social justice. Each day, folks choose from curated resources to challenge how they think about equity in different arenas of life, including housing, food stability, intersectionality, education, employment, and healthcare.

Motivated by the momentum of our company-wide workshop—“How to become an Antiracist,” facilitated by Nadia Jones, founder of Culture Cipher—Max and Michael curated a comprehensive curriculum, built an arc of learning, and devised a strategy for engaging Alley’s internationally distributed team in conversations about how inequity and racism affect our lives and community. Folks from across roles, teams, and interests at the company came together to share and discuss their experiences. As Max shared:

“It was a very intimate conversation to ask people to have, to be vulnerable in this way. It brings forth aspects of people’s personality that you don’t always get to see. There were many small victories. It was a new experience to struggle together around non-work-related or client-related ideas. And we really came from a place of humility and spirit as facilitators. We’re not experts—we are all considering different lines of questioning together.”

Michael also spoke to cultivating this type of unique space for sharing within Alley:

“We were ready to make our rumbling visible. No guilt or judgement. We tried to make it as accessible as possible. And the group gave us a treat by giving us access to different perspectives. We made this visible and said, here are the tools, join us if you like.”

“We made this visible and said, here are the tools; join us if you like.”

At this point, we can imagine you are wondering, how do I lead my own 21-Day Equity Challenge? I know you will learn as much as I did from Max and Michael’s processes and what they saw as the core successes and challenges of the 21-Day Equity Challenge described next.

Step 1: Decide the WHAT.

Determine the focus of the challenge.
- Borrow existing resource lists. Many trusted scholars have already curated complete collections of resources that you can choose from without additional research. We recommend the work of Dr. Eddie Moore and Debby Irving.

Curate your own resource list. Poll your community in a survey to understand what they want to learn about. Alley folks voted to focus on the areas of Employment and Equal Pay, Voting Rights and Representation in Government, Intersectionality, Health Care, and Food Security and Nutrition. This adds a level of customization and personalization but isn’t critical to the success of the challenge.

Step 2: Decide the HOW.

Curate a resource list offering a range of ways to engage with each topic. This includes options for reading articles and papers, listening to podcasts, and watching YouTube, thought leader TikToks, and/or movies. This is a great way to honor the diversity of your group—whether it be familiarity with the topic, time availability, or learning style.

Choose a note-tracking tool. This helps folks recall their learnings and takeaways and makes their thoughts visible to each other! We modeled our note-tracking tool from Dr. Debbie Irving’s original 21-Day Challenge Tracking Sheet.

Share a daily Slack reminder to help folks remember what to focus on each day. In the rush of work and home life, an extra reminder is a huge help! [AND a great way to spread awareness for folks not participating.]

Encourage weekly check-ins to allow folks to debrief on what they learned while the thoughts are still fresh. Create a safe space for candid discussions, and you’ll be surprised how vulnerable folks are willing to be.

Structure a final group meeting or retrospective for getting feedback and improving for next time. A retrospective is a powerful way to learn what was successful and challenging from the perspective of the group.

Step 3: Decide on the WHEN.

Offer multiple meeting times to accommodate all time zones and schedules. At Alley, we hosted an 8am PT | 10am CT | 11am ET check-in and a 2pm PT | 4pm CT | 5pm ET check-in. Folks self-organized around those times.

Minimize the time commitment. A 25-minute weekly check-in can be the perfect starting place to begin the conversations, and it allows your participants a 5-minute break before their next meeting. You can always add time next round!

Step 4: Set EXPECTATIONS.

Will you host a kickoff meeting? Kickoffs give folks an opportunity to make sure they understand how the challenge works on a daily and weekly basis.

What norms will you offer the group? Max and Michael borrowed these from the UnitedWay discussion guide.

Stay engaged.
Experience discomfort.
Speak your truth.
Expect and accept nonclosure.
Thread discussions in our #belonging — DEI-focused Slack channel.

Will you co-facilitate or trade-off facilitating sessions? Sharing the facilitator role can balance responsibility, time commitment, and energy spent.

Step 5: Host the CHALLENGE.

Here is an example of a typical day’s activity during the 21-Day Equity Challenge:

ENGAGE with a resource from the Resource List based on the day of the week
1. Monday — Employment & Equal Pay
2. Tuesday — Voting Rights & Representation in Government
3. Wednesday — Intersectionality
4. Thursday — Healthcare
5. Friday — Food Security & Nutrition
6. Saturday/Sunday — Open Ended, Dr. Eddie Moore has an extensive list, select from our list, or choose from the above or your own list of resources.

REFLECT on thoughts and feelings in the Tracking Tool
1. Reflecting and Journaling is a crucial piece of the challenge. Plan to take time every day to reflect on what you chose to do, what you’re learning, and how you are feeling. Difficult emotions such as shame and anger, though uncomfortable to feel, can guide you to deeper self-awareness about how power and privilege impact you and the people in your life.

DISCUSS (optional) in Slack via the daily reminder thread in #belonging or on Fridays during our weekly group check-ins.

Step 6: Reflect on Lessons Learned.

As Alley’s first 21-Day Equity Challenge came to a close, Michael and Max reflected on the following lessons they learned with hope that this will save you time when preparing for your own challenge:

Folks are excited to talk about these topics! Consider increasing the time of the check-ins or else you run the risk of running over your time box.

Select at least one resource that the whole group shares! This will help them engage with one common and specific material per week.

Give conversation a chance to flower. As folks share their notes, let it breathe.

Extend the learning beyond the Challenge participation group. Encourage folks to bring the DEI conversations back to their teams.

Keep the scope; you can always come back to great ideas next round.

If Diversity, Equity, and Inclusion is as important to us as we say it is, make space for people to participate in these learning activities. Whether it means embedding DEI in Professional Development policy or ensuring the Challenge is leadership-endorsed, these are foundational steps toward systemic change.

The 21-Day Equity Challenge is a crucial part of the foundation Alley is laying for our Diversity, Equity, and Inclusion efforts. Our ambitions are audacious, and in order to get there, we’re establishing a baseline of understanding through education, discussion, and becoming more familiar with each other and our differences.

Perhaps most importantly, we’re not passively suggesting folks think about issues of equity. We’re actively organizing opportunities to prioritize it alongside our other work commitments.

We do not see DEI as an extracurricular. I’ve written it before, and I will scream it til’ the end of time: We don’t believe in one-hit DEI wonders. We don’t believe in empty gestures of allyship. We believe in “praxis”—acting and reflecting on the world in order to change it.

And that’s exactly why it’s important to celebrate our Frolleagues—friends and colleagues—like Max and Michael, who are partnering with and motivating others to do just that.

Cover art by @libbyvanderploeg