FOR BUSINESSES
Workplace
Connections
Where Conflict Meets Clarity—and Connection Follows.
Conflict is inevitable—but with the right guidance, it can lead to growth, stronger relationships, and lasting change.
With over 20 years of experience in negotiation, mediation, facilitation, and restorative dialogue, Sheila Maloney Connections helps individuals, teams, and organizations move through challenges with intention and integrity.
Whether you're facing internal workplace tension, preparing for a team retreat, or seeking impactful training in negotiation and communication, our services offer a calm, expert presence and practical strategies for creating forward momentum. Through emotionally intelligent and culturally attuned support, clients are empowered to turn difficult conversations into opportunities for real connection.
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EXPERT GUIDANCE FOR EVERY SITUATION
With over 20 years of experience transforming sensitive disputes into opportunities for growth and collaboration, Sheila Maloney is an expert in negotiation, conflict resolution, facilitation, and community restoration.
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.
In 2018, Sheila and her family embarked on a transformative “Family Gap Year” in Brazil to reconnect with one another and explore her Brazilian heritage. Inspired by this journey, she penned the best-selling memoir Family Gap Year and founded a boutique agency focused on helping singles and couples build meaningful relationships through mindful connection and values-based dating.
Sheila’s facilitation, mediation and restorative dialogue 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 dynamic facilitation, training and retreat practices have helped countless organizations, teams, and individuals achieve transformational outcomes, reaffirming her as a leading voice in negotiation, conflict resolution and community restoration.
