In this episode of the Brandon Hall Group™ Excellence at Work podcast, host Rachel Cooke, COO of Brandon Hall Group™, sits down with Angela Ostermann, Senior Manager of Leadership and Organizational Effectiveness at Paylocity, to unpack what it really takes to build a high-performing leadership pipeline before people ever step into the role. Drawing on Paylocity’s award-winning Leading Advantage program, which earned a Gold in Leadership and a Silver in Learning and Development from Brandon Hall Group, Angela brings a practitioner’s lens to one of the most pressing challenges in organizational development today: turning high-potential individual contributors into confident, capable, and strategically aligned leaders.
Angela shares the philosophy behind Leading Advantage, a program purpose-built not for theory, but for real-world application. Designed specifically for Paylocity’s operations group, the company’s largest and most business-critical division, the program brings together high-performing ICs and prepares them for leadership through structured learning, on-the-job activities, professional coaching, and peer mentorship. The conversation also explores how deep business immersion, cross-functional collaboration, and ongoing iteration have made this program a genuine growth lever and not just a training initiative.
To read the Executive Interview with Angela Ostermann, click here.
Key Topics:
- Bridging potential to performance through application-first design: Most leadership programs teach concepts. Leading Advantage builds experiences. By pairing classroom learning with on-the-job assignments completed alongside a direct leader, participants leave the program with real stories to tell in interviews, not just knowledge to recite. The design philosophy is simple: every learner should be able to answer “tell me about a time when” with confidence.
- Professional coaching as a confidence engine: First-time leaders often struggle not with skills, but with self-doubt. Angela describes how each participant is paired with an objective third-party coach who provides a safe space for working through challenges including managing up, navigating ambiguity, and building the self-awareness that formal training alone can’t deliver. Coaching, combined with mentorship from the direct leader, gives emerging leaders the compass they need.
- Immersion in the business as the foundation of great program design: Leading Advantage wasn’t built in a silo. Angela and her team conducted deep focus groups with top-performing leaders inside operations to understand, at a granular level, what competencies and behaviors the role actually demands. That immersion in the business, rather than reliance on generic leadership theory, is what makes the content land. The advice: spend the majority of your time in scoping and planning, and the building follows naturally.
- A leadership pipeline that continues beyond the program: Completion isn’t the finish line. Graduates of Leading Advantage flow into Paylocity’s broader Leading Now program, a continuing education curriculum for all leaders that addresses real-time business challenges including change management and performance conversations. An alumni network keeps the community connected, with former participants mentoring new cohorts and reinforcing a culture of continuous development.
- Anchoring everything in culture and business outcomes: Every element of Leading Advantage, from its content to its on-the-job activities, is tied directly to Paylocity’s values, KPIs, and current organizational priorities. Culture isn’t a module in the program; it’s embedded throughout the entire experience. Angela emphasizes that the best leadership programs aren’t just relevant at launch. They iterate continuously based on learner feedback and evolving business needs.
