Winning Together:A Leadership Team Review
A facilitated opportunity to help leadership teams assess their current state, optimize decision-making and focus on delivering profitable results.
Why Winning Together Matters
When leadership teams spend too much time putting out fires they can fall into silos – and stop moving their strategic priorities forward.
That’s why working with an experienced facilitator who can lead an objective, off-site meeting, is such a valuable investment.
Not only is it a chance to talk about your wins and losses, it’s an opportunity to:
- Deepen trust and communication
- Focus on your most important issues
- Achieve profitable results and more
Why Work With Gordon Sheppard
Gord brings clarity, energy, and structure to every leadership team review he facilitates.
His style has been described as ‘assertively kind’, which means he helps leaders get to the point quickly and confidently.
The result?
Leaders feel energized and focussed so they can get back to making their organizations more profitable!
The Process
Gord follows a simple Before/During/After framework to ensure your leadership team review is highly productive.
- Before → Pre-interviews with key leaders, co-design of agenda, meeting activity planning
- During → Skilled facilitation that keeps discussions grounded and energized
- After → Debrief to build accountability and keep the momentum going
What You Get
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A Highly Interactive Team-Building Opportunity
In this highly engaging session Executive Leaders will get to know each other at a deeper level. They will also build empathy and trust as they learn to cooperate at the highest possible level.
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A Highly Experienced Facilitator
The Winning Together session is led by Gordon Sheppard, a highly experienced meeting Facilitator who helps leadership teams to focus and rapidly get more profitable results.
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Winning Together Workbook
Every participant will receive a copy of the Winning Together Workbook. It contains customized information, inspiration and the Executive Winning, 5-Step System that your team can use to make your company more profitable.
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Wins/Losses List
Gord will help you build a Wins/Losses List that you can refer to in the future to know what to do - and what not to do to achieve your goals.
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Celebration List
Gord will ask 'how do you celebrate' after a win? He will then help you build your own, authentic celebration list that you can use to acknowledge each other in the future.
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Summary Report
Gord will deliver a brief summary report that you can build on to get more wins in the future.
Trusted by Executives and Industry Leaders



























Notable Facilitation Clients
The Executive Winning System
Gord’s work is based on the Executive Winning System, a proven 5-step approach that will help to fully align your leadership team so they can achieve more profitable results.
Define the vision, mission, values, and goals that will drive your business forward.
Create a clear, action plan to move from strategy to execution.
Bring the right people on board—those with the skills, mindset, and attitude to drive success.
Establish the systems, processes, and policies that enable seamless execution.
Measure the quantitative and qualitative data you need to get more wins in your business.
About Gordon Sheppard
Gord Sheppard is a people-centred Executive Coach, Consultant, and Facilitator with over 25 years of experience and his mission is to “empower Executives so they can positively impact themselves, their teams and their entire organization.
He combines an MBA with a Bachelor’s Degree in Drama, and Prosci Change Management Certification to deliver a unique, people-centred approach that helps leaders to succeed.
He’s helped thousands of leaders grow through workshops, strategy sessions, and coaching – across Canada and the U.S.
Executive Team
Scorecard
Is your Executive Team aligned and executing at the highest level? Download the Executive Team Scorecard to find out.
What Executives Say
About Working With Gordon Sheppard
FAQ
Common questions about the Winning Together Leadership Session.
Half day in-person, and it can be customized as needed
- Leaders will determine whether or not they are on track to carry out their current strategy – or if it has to be adjusted
- Leaders will learn a proven system to help optimize decision-making
- Leaders will be in a better position to achieve their goals
Business Owners, CEO’s, Executive Directors, Board Members, VP’s, COO’s, CFO’s, Non-profit Leaders, Executive Teams, Support Staff and more.
You Facilitator is Gordon Sheppard, a highly experienced meeting leader who has successfully led strategic planning, conflict management, innovation sessions and more
Yes! Because the pre-work interviews and documentation review will surface important issues that will be addressed during the session.
Your leadershiep team will deepen trust, communicated openly and be in a significantly better position to achieve your goals.
Confidentiality is addressed in our legal contract, and Gordon Sheppard upholds the highest ethical standards.
It’s Time To Start
Winning Together
If you want a leadership review that will inspire your team and get profitable results — let’s start a conversation.



