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5.0
Unleash Your Awesome | Background in Tech, Product, Ops | Fractional CxO
Studied at University of Wisconsin - Madison
Works at The People Side
This comprehensive 6-month executive coaching engagement is built for senior leaders, founders, and executives who want to scale their leadership, unlock growth, and lead with greater clarity, confidence, and impact. You’ll partner with your coach in biweekly 1:1 sessions (or a cadence that fits your schedule), supported by asynchronous guidance, goal tracking, and tailored tools. The experience evolves over time to meet your unique context—whether you're leading through scale, navigating complex transitions, or preparing for your next chapter. The engagement also includes a 360-degree leadership analysis, where your coach gathers structured feedback from peers, direct reports, and other stakeholders. This provides a holistic view of your leadership strengths, blind spots, and areas for growth—creating a strong foundation for the work ahead. What you’ll work on: - 360 Feedback Review & Goal Setting: Translate insights into a focused leadership development plan. - Vision & Strategic Thinking: Set direction and align teams around mission-critical goals. - Leadership Style & Self-Awareness: Deepen self-knowledge and adapt your style for maximum influence. - Decision-Making in Ambiguity: Gain tools to lead decisively through complexity and change. - Executive Presence & Influence: Strengthen communication and earn trust with senior stakeholders and boards. - Team Building & Culture: Lead high-performing teams and shape the culture you want to scale. - Stakeholder Management: Navigate dynamics across direct reports, peers, boards, and cross-functional partners. - Burnout & Sustainability: Build systems to lead with energy and balance over the long term. - Career Strategy & Long-Term Growth: Clarify your next step, whether expanding your role, transitioning industries, or building a legacy. This engagement is ideal for executives seeking deep, lasting transformation with a trusted partner who brings structured support, honest reflection, and a focus on measurable impact.
Clearer understanding of your strengths and areas for development as a leader
Stronger executive presence and communication skills
Actionable insights from 360-degree feedback analysis
Confidence navigating high-stakes decisions and ambiguity
Tools to lead high-performing, accountable teams
Improved relationships with key stakeholders and boards
Systems for sustainable performance and energy management
Clarity on long-term career goals and next moves
Trusted thought partnership for real-time leadership challenges
Coaching delivered via live sessions and .
Services included:
Succession Planning
Decision Making
Strategy
Communication Skills
Strategic Planning
Board Relations
Team Management
Leadership Development
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
Get help with Decision Making, Leadership Development, and .
Chris also coaches for Leadership Coaching and Product Management. View all.

Joined December 2025
5.0
Unleash Your Awesome | Background in Tech, Product, Ops | Fractional CxO
Hi there! I'm Chris - an accomplished executive coach (ICF Associate Certified Coach (ACC)) and Certified Team Coach (CTC) with 15+ years of strategic leadership experience in diverse industries. I leverage my entrepreneurial experience and deep background in technology to guide leaders through complex career transitions, executive presence development, and organizational change - but mostly, I help people better understand their work, each other, and themselves. I've completed over 500 hours of ICF-recognized coaching to more than 60 individuals from corporate vice presidents and directors, to educators and entrepreneurs. I'm always looking for ways to give back to the coaching community whether it's through organizing conferences and meetups, teaching in the Center for Coaching in Organizations ECO Coach Training Program, or as a coach supervisor. Let's connect and talk about how coaching can help you can Unleash Your Awesome.
30h–40h of coaching