A blackboard with a colorful chalk drawing of a soccer field, including game strategy markings, circles, X's, arrows, and numbers, with hands and chalk pieces around.

Winning isn’t random. It’s designed.

We enable business leaders to build high-performance organizations - by aligning strategy, culture, leadership and execution.

Multiple diverse hands holding puzzle pieces coming together in a circle.

When performance stalls, the system is usually to blame.

Leaders aren’t short on ambition or ideas. But without the right operating model - one built to perform - strategy breaks down, execution stalls, and value gets left on the table.

We work with executives and teams who are:

  • Struggling to execute strategy across functions

  • Under pressure to reduce cost or increase productivity

  • Managing complex change or transformation

  • Frustrated by silos, unclear accountability, or slow decision-making

  • Leading underperforming teams or business units

If that sounds familiar, you’re not alone - and it’s fixable.

Diagram with hexagons showing key components for winning: Culture & Values, Structure & Roles, People & Leadership, Metrics & Feedback Loops, Technology & Tools, Processes & Ways of Working, and Define Winning. Caption: "Design the system. Win the game."

We help you design the system to win.

At How to Win Advisory, we use our proprietary framework - The Winning System - to diagnose what’s really blocking performance - and work alongside you to redesign your operating model for clarity, speed, and results.

It’s a practical, principle-based model built around seven critical levers of organizational performance:

Strategy. Culture. Structure. People. Process. Technology. Metrics.

Whether you’re scaling, transforming, or under pressure to deliver more with less, The Winning System gives your team the clarity, structure, and momentum to execute with confidence.

Businessperson in suit touching a digital rising graph with an upward trend, representing data growth or success.

We don’t deliver decks. We enable organizations to operate better and realize their strategy.

Our clients achieve:

  • Sharper focus on what drives value

  • Improved cross-functional execution

  • Lower operating costs without compromising impact

  • More accountable and aligned leadership teams

  • Higher confidence in delivering strategy

About the Founder

  • Smiling man in business suit sitting in office with cityscape view in background.

    Paul Craig

    Paul is the Founder and CEO of How To Win Advisory, a strategist and transformation leader with over 25 years of international experience helping organizations design and deliver winning organizations. A former Strategy and Transformation Leader at Monitor Deloitte, Paul has advised senior executives across industries on growth, innovation, and performance.

    A former national team volleyball player and coach, he has guided national and Olympic-level athletes and brings that high-performance mindset to business. Paul serves on the Boards of Volleyball BC and the West Vancouver Lawn Bowling Club, where he also competes at the provincial level.

    He lives in North Vancouver with his wife, daughter, and two fur-sons.

    Read Bio

Ready to fix what’s holding your organization back?

Whether you’re scaling, transforming, or just not performing at the level you should, we can help you design a system that wins.

Book an exploratory call
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