Developing Emerging Leaders to Drive Design Excellence at Scale
Coaching five team leads through individualized development journeys to build a scalable, self-sustaining leadership foundation
The Leadership Challenge
Growing Organization, Diverse Leadership Needs
As Paycom's Product Design organization scaled, I oversaw five talented Team Leads at different stages of leadership maturity:
- First-time leaders needing foundational management skills
- Experienced leaders ready for higher levels of influence
- High work volumes requiring balance between delivery and leadership
- Cross-functional challenges with Product and Development partners
Individualized Development Journeys
Team Lead A
From Detail-Oriented to Diplomatically Influential
Challenge
Strong, diligent leader with high standards but communication style was sometimes blunt; needed to expand influence at organizational scale.
Coaching Focus
- • Refining communication: from blunt to direct with diplomacy
- • Shifting from project focus to organizational strategy
- • Building strategic partnerships
Outcome
Became one of the most influential leaders in the department, known for strategic partnerships and consistently delivering high-impact work to the business.
Team Lead B
From Team Unity to Cross-Functional Influence
Challenge
Led the most cohesive team with deep trust, but hesitated to communicate proactively with leaders outside her team.
Coaching Focus
- • Broadening relational scope beyond her team
- • Engaging actively with Product, QA, and Development
- • Stretch assignments for cross-functional exposure
Outcome
Became a stronger presence in cross-functional settings, influencing collaboration across entire product portfolios, not just her own team.
Team Lead C
From Designer to Emerging Leader
Challenge
First leadership role with great design instincts but little formal experience managing projects or people.
Coaching Focus
- • Building foundational leadership skills
- • Project management and Jira planning
- • Balancing delivery with mentorship
Outcome
Emerged as a reliable, organized leader who could keep his team focused and on track without losing sight of design quality.
Team Lead D
From Trusted Team Lead to Strategic Contributor
Challenge
Already mature, adaptable leader with strong business relationships; needed preparation for Manager-level role.
Coaching Focus
- • Refining executive communication
- • Navigating challenging Product relationships
- • Strategic initiative leadership
Outcome
Became a go-to voice in leadership discussions, contributing to hiring strategy and shaping design operations with steady, diplomatic influence.
Team Lead E
From Subject Matter Expert to Cross-Functional Leader
Challenge
Deep expertise in internal tools with strong relationships, but needed skills in conflict navigation and difficult conversations.
Coaching Focus
- • Conflict navigation and collaboration
- • Difficult conversations with partners
- • Maintaining alignment and respect
Outcome
Spearheaded cross-functional modernization efforts, improving performance and creating measurable efficiency gains as an indispensable bridge across departments.
Collective Leadership Impact
Team Scope & Business Contribution
Leadership Bench Strength
Distributed Leadership: 5 leaders managing 30 designers provided stable, distributed leadership across critical product areas during organizational growth
Multiplier Effect: Each mentored leader went on to develop their own team members, cascading leadership principles to 30+ additional designers
Expanded Capacity: Built leadership capacity without external hires, creating sustainable growth from within
Individual Growth
- Each leader developed confidence and independence in their domain
- Improved cross-functional relationships and influence
- Enhanced communication and strategic thinking skills
Organizational Impact
- Design organization became more scalable and collaborative
- Created trusted advocates and reliable Product partners
- Established self-sustaining leadership culture
Leadership Multiplication Effect
Through intentional coaching and empowerment, I cultivated a team of leaders who now lead with confidence, clarity, and character. The ripple effect was profound: our design organization became more scalable, collaborative, and self-sustaining, allowing me to focus on higher-level strategy while knowing our leadership culture was thriving.
Leadership Development Philosophy
Individual Focus
Each leader needs a unique development path based on their strengths, challenges, and career aspirations
Growth Mindset
Coaching for their next role, not just their current one, creates leaders who scale with the organization
System Building
Developing leaders creates sustainable systems that outlast any single person's involvement