Emerging Leaders Series: Navigating Challenging Conversations
Wednesday, May 27, 2026
University Center of Lake County
Presenter: Orla Castanien of Leaders Roadmap
8:30 a.m. - Networking
9:00 - 10:30 a.m. - Program
Program Description
We all have a voice or a feeling in our gut that tells us when we need to have a crucial conversation. We often view these conversations as challenging or difficult. We can either move towards the conversation despite our trepidation and angst or avoid it, which usually creates even more duress in our relationship. Given the importance of building trust and rapport with our colleagues, we all need to learn how to successfully “go there” to resolve our concerns. In this interactive workshop, we share strategies and techniques for holding crucial conversations. We look at the role of both mindset and behavior in ensuring a successful outcome to hard conversations and provide practical tools to help you prepare for and practice a real crucial conversation. This workshop will teach you how to transform challenging conversations into opportunities for building trust, performance improvement, setting expectations and moving forward with clarity and commitment.
Meet our Presenter
Orla Castanien is an executive coach, facilitator, and speaker who helps leaders align teams, navigate conflict, and lead through change with clarity and confidence. With more than 20 years of leadership experience in finance, operations, and strategy, she previously trained at Deloitte and served as CFO of Unicare Pharmacy Group, helping grow the organization from start-up to Ireland’s first national pharmacy chain. She now works with leaders across industries, from startups and nonprofits to Fortune 500 companies to address challenges and drive meaningful progress.