The Executive Team Assessment
The Executive Team Assessment helps you discover exactly where your leadership team is winning, where it’s losing momentum, and what to do next.
Every Organization Has Wins But...
Most never stop to understand why they happened.
Inside every successful project…
Every engaged employee…
Every loyal customer…
Every high-performing team…
…are leadership decisions worth repeating.
The Executive Team Assessment by Executive Wins uncovers those patterns.
What This Assessment Will Answer...
- What leadership behaviours create your biggest wins?
- How do your leaders deal with your biggest losses?
- What habits should ever leader adopt?
- How do our leaders talk about wins and losses?
- How will we build a winning culture?
How It Works
The Executive Team Assessment helps leaders understand their wins, losses and what to do about it.

Learn
Through surveys and interviews Gordon Sheppard will find out how your leaders achieve their wins and deal with their losses.

Analyze
Using the Executive Wining System, Gord will decode the patterns and give a practical presentation to help your leadership team gain alignment.

Take Action
Gord will provide a 90-Day Action Plan you can implement it to get more wins!
The Executive Team Assessment
A systematic approach to help your leadership team build a more profitable organization.
Step 1: Learn
Interviews
Gordon Sheppard is an experienced consultant who will ask individuals on your leadership team important questions including…
“Tell me about your biggest wins and losses.”
The answers to this question will reveal:
- Leadership strengths
- Hidden successes and failures
- Team accomplishments
- Culture builders
- Service excellence
- Winning Stories worth sharing
The answers to these questions become the foundation for the assessment.
Document Review
In addition to interviews, Gord will also review your strategic plan, website and any other relevant documents
Step 2. Analysis
Analysis
Gord will do the analysis of your wins/losses using the Executive Winning System,
- It’s a proven 5-Step approach used to examine the Strategy, Work Plan, People, Operations and Results behind every win/loss
Executive Team Report
- All of the results will be recorded in the Executive Team Report – a detailed report that will categorize key information and recommendations to help you get more wins in the future
- It will also show you how to make an impactful ‘Wins List’, along with finding authentic ways to celebrate in the future
Presentation
- Gord will present the findings to your entire leadership team.
- During this interactive session, top wins and losses will be reviewed
- Gord will also facilitate a safe environment where leaders can share openly
Step 3: Take Action!
90-Day Action Plan
- Based on what was discovered, Gord will build a 90-Day Action Plan you can use to get more wins
Follow-Up
- He will also be available to do 2-3 Executive Coaching sessions, to help build accountability and execution of the 90-day plan
Why Work With Gordon Sheppard
Gord brings clarity, energy, and structure to every leadership program 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!
What You Get
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A Highly Interactive Team-Building Opportunity
During this highly engaging process your Leaders will get a chance to share openly and make suggestions that will be recorded and acknowledge. They will also build empathy and trust as they work towards building a positive work culture.
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The Executive Winning System
The Executive Winning System offers a complete organization improvement system for leaders. It includes helping leadership teams master the Strategy, Work Plan, People, Operations and Results behind every win and loss.
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Executive Wins Report
Every participant will receive a copy of the Executive Wins Report. It will contain all findings from the entire engagement.
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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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An Experienced Business Advisor
The Executive Wins Assessment is led by Gordon Sheppard, a highly experienced Business Advisor, Corporate Trainer and Meeting Facilitator who helps leadership teams get more profitable results.
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90-Day Action Plan
Gord will deliver a 90-Day Action Plan that your Executive Team can implement to get more profitable results.
Trusted by Executives and Industry Leaders



























Notable Clients
Case Study
Municipal District of Greenview Leadership Wins Training & Alignment Project
Highlights
- 20 Pre-Interviews to discover ‘wins’
- Interactive 1-Day Training with 43 leaders and a wall of wins
- Municipal Wins Playbook Creation
- CAO featured on the Executive Wins Podcast
- Positive feedback and implementation of key concepts
Erin Klimp, Manager of HR for MD Greenview, hired Gordon Sheppard to deliver the ‘Leadership Wins Training and Alignment Project’.
The project included doing pre-interviews with 20 leaders, providing a full day of ‘Wins’ Training for 43 Managers, Supervisors and members of their Senior Leadership Team, and delivering the Municipal Wins Playbook (14 pages of wins gathered from their leaders throughout the entire procees).
The Process included a before/during/after approach.
Before
- Gord met with Erin Klimp and Nicole Perry to go over the engagement
- Gord conducted 20 pre-interviews leaders to learn about their ‘wins’ at work
- He also built a robust agenda and designed and delivered a customized workbook
- He interviewed Stacey Wabick , MD Greenview CAO, about his big culture win on the Executive Wins Podcast (episode 61)
During
- Gord facilitated a highly interactive full day of training
- Training day highlights included examining wins, losses and learning the Anatomy of a Win
After
- Gord helped to build and deliver the Municipal Wins Playbook, that now contains 14 pages of wins that were gathered throughout the process
- Follow up meetings were held to get feedback and learn about implementation of key concepts
This project was a significant contributor to the overall efforts that MD Greenview is making to build a positive work culture (that now has a retention rate of more than 90%!)
Senior leaders now have a ‘Wins List’ (the Municipal Wins Playbook) that they can refer to, and add onto in the future to drive more positive behaviours.
Some leaders are already implementing the Wins List approach in their departments.
Overall, the CAO and HR team felt that it was worthwhile – and because the process helped to surface really authentic wins, the overall impact of this project was very positive.
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.
What Executives Say
About Working With Gordon Sheppard
Free Download
Executive Team Scorecard
For Executive Teams who want to improve alignment and execution
FAQ
Common questions about the Municipal Wins Leadership Program
Three months including interviews, pre-work, meetings and post-work.
- Executive Teams will understand their current state
- They will also learn how to reverse engineer past wins and losses, so they can pull out best parts to get more wins in the future
- Leaders will also learn how to build a Wins List and how to authentically celebrate wins
- Leaders will gain the tools and confidence to build a winning work culture
CEO, Directors, Managers, Department Heads, Senior Leadership Teams 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 throughout the engagement.
Your leadership team will understand where they are at, and also be able to prioritize wha to do next.
Confidentiality is addressed in our legal contract, and Gordon Sheppard upholds the highest ethical standards.



