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Leadership in the future of work isn’t about preserving traditional structures — it’s about intentionally designing how work gets done.

In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Cindy Machles, Co-founder and CEO of Glue Advertising and Public Relations, about the leadership decisions required to build flexible, skills-based organizations in a rapidly changing professional landscape.

Cindy shares the pivotal moments that led her to leave a large agency, take a personal and professional leap, and launch Glue with a fundamentally different business model. She explains why senior-level thinking, trust, and strong project management are essential to leading effective teams — particularly as fractional talent, technology, and personalization reshape professional services.

The conversation also explores what leaders must do to stay ahead of industry change while keeping people, outcomes, and long-term relationships at the center of how their organizations operate.

In This Episode

00:30 – Introduction to Cindy Machles and Glue
03:18 – Leaving a large agency and taking a leadership leap
05:34 – Designing a different agency model
13:34 – Fractional talent and building flexible teams
16:16 – Why project management is a leadership skill
19:19 – Leadership and thinking ahead of industry change
22:30 – Personalization, AI, and the future of work
27:16 – Skills-based leadership and outcomes over titles
31:46 – What the ideal client-leader relationship looks like
37:35 – Advice Cindy would give her younger self about confidence and leadership