Yosi Kossowsky

Executive Leadership Architect

I help VP+ technical and functional leaders reclaim agency and build a leadership identity that works beyond their original domain.

Portrait of Yosi Kossowsky
Format
Hybrid
Style
Direct and action-oriented
Engagement
6 to 12 months
Positive Intelligence by Shirzad ChamineNew York · English
01 · About

About Yosi

Yosi coaches VP, SVP, EVP, CTOs, and CIOs who excel as domain experts but are now required to lead far beyond that expertise. With 25+ years in technology leadership, 10+ years leading global development at Cisco across 13+ countries, and 150+ leaders coached, he brings PCC, Marshall Goldsmith, and Enneagram credentials — and has lived this exact transition himself.

02 · Challenges

Your old playbook stopped working — and you're not sure who you are as a leader now

You've built an exceptional career as a domain expert. Now the skills that got you here feel like a liability. Your 360 feedback doesn't match your intent. You've inherited a resistant team. You're one of the most senior leaders in the room and quietly feel like a fraud. You tell yourself you should be able to figure this out alone — but the cost of not doing so keeps rising.

03 · Outcomes

Leading through others — with confidence, clarity, and a style that's genuinely yours

You leave with a named leadership identity that replaces the expert-and-doer model, practical tools for emotional regulation under pressure, a communication framework your stakeholders respond to, and a delegation system that actually works. Self-doubt doesn't disappear — but it stops running the show. The goal is the moment it all feels natural, not performed.

Improved Communication Skills

Enhance your ability to communicate effectively with stakeholders at all levels.

Enhanced Leadership Development

Develop stronger leadership capabilities to inspire and motivate your team.

Increased Team Effectiveness

Build more cohesive and productive teams that achieve exceptional results.

04 · Approach

To help elite technical leaders become the leader their role now demands

At 10, I was placed in a different school for learning difficulties. I spent years feeling broken — watching others live normally. Through therapy and deep study I discovered that self-doubt is universal, and that the fears we carry can fuel growth rather than stop it. I spent five years studying behavioral neuroscience while working as a systems engineer. I left technology leadership in 2022 to coach full-time because developing human systems matters more than building technical ones.

05 · The coaching

See, Shift, Sustain™ — a structured path from domain expert to deliberate leader

Signature 1:1 engagement

7–8 months of 1-on-1 coaching with full stakeholder integration. Includes 10 coaching hours, 3–4 hours of live shadowing, bookended 360s with up to 10 stakeholders, three 45-minute stakeholder meetings, and Executive Access Support. $20,000.

  • Enhanced Communication Skills
  • Stronger Organizational Leadership
  • More Effective Teams
06 · Credentials

Training & memberships

Find Yosi elsewhere
Ready when you are

Curious if Yosi could be your coach?