top of page

WORKPLACE SERVICES

Facilitation

Thoughtful. Inclusive. Purpose-Driven.

Sheila Maloney is an expert in conflict resolution, facilitation, and community restoration, with over 22 years of experience transforming sensitive disputes into opportunities for growth and collaboration.

After earning her law degree from Northwestern University Pritzker School of Law in 2003, Sheila began her career as a lawyer and mediator, quickly establishing herself as a thought leader in dispute resolution. She returned to Northwestern Law as an adjunct professor of Negotiation, and later served as Assistant Director of the Center on Dispute Resolution. Since then, Sheila has held other distinguished roles, including hearing officer, arbitrator, and Administrative Law Judge for the City of Chicago. She currently serves as Chief Hearing Officer for the City’s Department of Human Resources.

Sheila is the author of the American Bar Association’s acclaimed and practical Guide to Resolving Your Legal Dispute: Inside and Outside the Courtroom, a trusted resource for individuals and organizations navigating conflict.

Sheila’s facilitation practice is rooted in emotional intelligence, practical problem-solving, and a deep commitment to helping people feel seen and heard. Her approach to conflict resolution is defined by creating safe, inclusive spaces that empower individuals and groups to address even the most volatile or sensitive disputes. Sheila’s ability to foster trust and guide participants toward collaborative solutions has been instrumental in helping non-profits, government institutions, and corporations resolve long-standing challenges and restore community harmony.

A Brazilian-American professional working with Chicago’s diverse global population, Sheila brings a unique ability to navigate cultural differences with sensitivity and insight. Her clients describe her as “present,” “emotionally courageous,” and “masterful” at turning conflicts into opportunities for connection and growth.

Sheila’s facilitation and retreat practices have helped countless organizations, teams, and individuals achieve transformational outcomes, reaffirming her as a leading voice in conflict resolution and community restoration.

Why Work With Sheila?

TRUSTED EXPERTISE

With over 22 years of experience, Sheila transforms sensitive disputes into opportunities for growth, collaboration, and restored trust.

LEGAL & ACADEMIC BACKGROUND

Sheila has served as a mediator, arbitrator, Administrative Law Judge, and professor at Northwestern Law, shaping the next generation of conflict resolution leaders.

EMOTIONALLY INTELLIGENT & INCLUSIVE

Sheila creates safe, empowering spaces where all voices can be heard—especially in high-stakes, emotionally charged environments.

CULTURALLY FLUENT & GLOBAL-MINDED

As a Brazilian-American working across diverse communities, she brings a nuanced, culturally aware approach to every engagement.

AUTHOR & THOUGHT LEADER

Her ABA-published guide is a go-to resource for individuals and organizations navigating legal conflict inside and outside the courtroom.

Hear From Sheila's Past Clients:

"I first engaged Sheila as a meeting facilitator many years ago when I was building a nonprofit organization. She built an agenda that set a positive, welcoming tone from the start. She ensured everyone felt at ease and encouraged meaningful conversation about who we were and what we could become as an organization. The result was a day that energized our team, built shared understanding, and deepened investment in our work. 

If you’re looking for a skilled facilitator who brings warmth, structure, and clarity to your gatherings, someone who helps groups connect deeply, stay focused, and move forward with purpose, I can’t recommend Sheila highly enough."

Katrina Pavlik

Founder of Breastfeed Chicago

Board President of Beverly Arts Center

Let’s Plan Your Next Retreat or Strategy Session

If your organization is preparing for an offsite, retreat, or facilitated session and wants to ensure it’s thoughtful, engaging, and results-driven, click below to schedule time on Sheila’s calendar. Let’s build something meaningful—together.

Stay in the Loop

Sign up for our mailing list!

© 2025 Sheila Maloney Connections

bottom of page