Leadership Training That Makes Your Wins Repeatable
Most leadership teams don’t struggle because they lack talented people. They struggle because priorities become misaligned, setbacks keep recurring, and meetings end without clear decisions or accountability.
Gordon Sheppard delivers practical leadership training for executive teams, municipalities, associations, and organizations across Canada. His workshops give leaders practical frameworks they can apply immediately to create repeatable success.Or call Gord: 1-877-609-3628
THE OUTCOMES
What Leaders Walk Away With
The best leadership training doesn’t end when the session does. Leaders leave with practical tools, shared language, and a clearer way to move forward together.
With a background in drama before moving into business, Gord combines storytelling, energy, and audience interaction to create presentations that connect beyond the slide deck.
- Real alignment: Teams move beyond polite agreement and get clear on priorities, expectations, and next steps.
- A better response to setbacks: Leaders learn how to turn challenges into lessons instead of repeating the same mistakes.
- More effective meetings: Conversations become decisions, with clearer ownership and follow-through.
- Less leadership isolation: Executives gain frameworks and perspectives that help them lead without carrying every challenge alone.
THE SYSTEM
Gord's Winning Training Framework
Every session is built around the same five-part lens: Strategy, Work Plan, People, Operations, and Results.
01
Strategy
The vision, mission, values, and goals behind the win.
02
Work Plan
The what, who, and when, plus the major milestones it took to get there.
03
The People
The key stakeholders involved, and their roles and attitudes.
04
Operations
The policies, procedures, software, regulations, and equipment behind the result.
05
Results
How success was measured, qualitatively and quantitatively.
TRUSTED BY
WHAT GORD OFFERS
Leadership Training and Workshop Topics
1/2 day or full day
How exceptional leaders align people, priorities and performance.
1/2 day or full day
How leaders create connection, clarity and performance through storytelling.
1/2 day or full day
How great leaders turn setbacks into strategic advantages.
Full Day or at Corporate Retreats
How senior leadership teams turn the Executive Planning System into a one-page plan they actually use.
3 to 6 months
A multi-month engagement built for leadership teams who want the training embedded over time.
Not Sure Which Session Fits?
RESULTS IN ACTION
A Closer Look at Gord's Training Workshops
Every workshop is designed to create practical change leaders can take back to their teams. Here’s how one of Gord’s sessions helps leaders align, learn, and move forward together.
Winning Together: How Exceptional Leaders Align People, Priorities and Performance
1/2 Day or Full Day
The ‘Winning Together: How Exceptional Leaders Align People, Priorities and Performance’ presentation is for leaders who want to build a positive, productive work culture that gets profitable results.
In this high-impact session, participants learn the ‘Anatomy of a Win’, a proven 5-step system which includes examining the Strategy, Work Plan, People, Operations and Results behind every win.
For example, let’s say a leader was able to get their team to communicate more effectively so they could achieve better results.
That leader can then use the Anatomy of a Win framework to examine the success:
- Strategy – What was the vision, mission, values, and goals behind getting that win?
- Work Plan – Describe the ‘what, who and when’ along with the major milestones it took to get the win.
- People – Who were the key stakeholders and what were their roles and attitudes?
- Operations – What were the operational highlights (i.e., policies, procedures, software, regulations, equipment etc.)
- Results – How did you measure success (qualitative and quantitative)?
Once leaders master this proven framework then they will be able to use it to get more wins in the future.
In addition, participants will also learn how to build an impactful ‘Wins List’ and identify authentic ways to celebrate success.
This session also features inspiring stories from the award-winning Executive Wins Podcast – where senior leaders share their biggest wins, so you can get inspired and grow your business.
Hosted by Gordon Sheppard and available on the Executive Wins YouTube Channel, Apple Podcasts, Spotify and wherever you listen.
Participants will also receive a workbook to help them retain and apply key concepts.
Participants shared impactful wins, wrote their first wins list and shared their best suggestions to authentically celebrate a win at work (and one woman even did her ‘happy dance’ in front of the whole crowd).
Where this session has been delivered.
- University of Calgary (Calgary)
- Municipal District of Greenview (Valleyview)
- City of Leduc (Leduc)
- Edmonton Unlimited (Edmonton)
The Power of a Winning Story: How Leaders Can Create Connection, Clarity and Performance
1/2 Day or Full Day
“The Power of a Winning Story: How Leaders Can Create Connection, Clarity and Performance” is a presentation for leaders who want to learn how to tell compelling stories that inspire their teams and customers.
In this unique session, participants learn a proven 5-part storytelling system called the ‘Anatomy of a Win’.
It includes helping them learn how to cover the key parts of any work story by knowing how to talk about hightlights from the Strategy, Work Plan, People, Operations and Results.
Once they master the Anatomy of a Win, they will also learn how to effectively use their voice and build the confidence they need effectively communicate a work story in every setting from the office, to networking to doing presentations and more.
This session also features inspiring stories from the award-winning Executive Wins Podcast which is hosted by Gordon Sheppard (your session instructor).
The Executive Wins Podcast features interviews with senior leaders who share their biggest wins so that other leaders can learn from them.
Participants will also receive a workbook to help them retain and apply key concepts.
Participants become confident storytellers who can inspire their teams and build a work culture that gets highly profitable results.
Loneliness in Leadership: How High-Performers Win By Staying Grounded and Connected
1/2 Day or Customizable
“Loneliness in Leadership: How High-Performers Win By Staying Grounded and Connected” is a presentation for leaders who want to learn how to effectively deal with isolation so they can have a healthy work/life balance.
In this high EQ driven learning session, participants learned how to:
- Define leadership loneliness
- Understand what they can and cannot control
- Take action to build reslient connections and more
They also learned a proven 5-part system called the ‘Anatomy of a Win’ – an objective framework that helps them to get more connected by understanding the Strategy, Work Plan, People, Operations and Results behind loneliness.
This session also features inspiring stories from the award-winning Executive Wins Podcast which is hosted by Gordon Sheppard (your session instructor).
The Executive Wins Podcast features interviews with senior leaders who share their biggest wins so that other leaders can learn from them.
Participants also receive a workbook to help them retain and apply key concepts.
Participants were able to learn how to be vulnerable to the right level while they learned a practical framework to help them successfully deal with leadership isolation in the workplace.
Where this presentation has been delivered
- Plenary – CMHA Conference 2025
Turning Losses Into Wins: How Great Leaders Turn Setbacks Into Strategic Advantages
1/2 Day or Full Day
“Turning Losses Into Wins: How Great Leaders Turn Setbacks Into Strategic Advantages” is a presentation for leaders who want to learn how to objectively learn from past losses, so they can get more wins in the future.
In this high-impact session, participants learn the ‘Anatomy of a Loss’, a proven 5-step system which includes examining the Strategy, Work Plan, People, Operations and Results behind every win.
For example, let’s say a leader almost bankrupted their company 5 years ago.
That leader can then use the Anatomy of a Loss framework to examine the what went wrong:
- Strategy – What did we miss in terms of vision, mission, values, and goals?
- Work Plan – What did we miss along the timeline in terms of ‘what, who and when’ which caused the loss.
- People – Who were the key stakeholders and what were their roles and attitudes that cause this loss?
- Operations – What were the operational problems (i.e., policies, procedures, software, regulations, equipment etc.) that caused this loss?
- Results – What was the outcome from this loss (qualitative and quantitative)?
Once leaders master this proven framework then they will be able to use it to examine past losses, learn from them, and avoid them in the future.
In addition, participants will also learn how to build an impactful ‘Losses List’ and identify authentic ways to celebrate failures.
This session also features real stories from the award-winning Executive Wins Podcast – where senior leaders share their biggest wins and losses, so you can get inspired and grow your business.
Hosted by Gordon Sheppard and available on the Executive Wins YouTube Channel, Apple Podcasts, Spotify and wherever you listen.
Participants will also receive a workbook to help them retain and apply key concepts.
Participants learn an objective way to deal with past losses – so they can learn from them and use the lessons learned to make their organizations more profitable in the future.
Winning Meetings: How To Lead Productive Conversations That Drive Results
1/2 Day or Customizable
The ‘Winning Meetings: How To Lead Productive Conversations That Drive Results’ presentation is a highly interactive session for people who want to grow their confidence and skills so they can run more productive and profitable meetings.
Based on the proven 10-Step System in Gordon Sheppard’s best selling book titled the ‘Meeting Leadership Solution’, in this workshop you’ll learn:
- How to calculate the actual cost of a meeting
- How to become an outstanding facilitator
- How to build an effective agenda
- How to manage conflict in meetings
- How to connect your meetings to your strategy
- How to follow up FAST and be more accountable
- How to get inspired and take action!
This workshop is suitable for senior leaders, managers and front line workers who want to improve their meetings.
Led by Gordon Sheppard, a highly experienced Facilitator and Executive Coach, in this workshop you’ll get:
- A wonderful team building opportunity
- The Meeting Leadership Workbook
- The Meeting Leadership Book (186 pages)
- Professional Development Credits
- Certificate of Completion
And once you’re done you’ll be able to lead more effective meetings!
Where this session has been delivered:
- Association for Professional Engineers and Geoscientists (APEGA) – 10x
- APEGA Nexxus Conference
- City of Chestermere
- Dialog Architects
- AICPA Conference
- APC Conference and more
Executive Winning System Masterclass
Full Day or at Corporate Retreats
The ‘Executive Winning System Masterclass’ is for highly motivated leadership teams who want to profitably transform their organizations.
This Masterclass is a great investment for Executives who want a more profitable business.
In this workshop participants learn the Executive Planning System, a proven 5-step approach that includes:
- Strategy
- Work Plan
- People
- Operations
- Results
Each area has specific sections. For example, under Operations you’ll find the Human Resources section.
Each section also contains detailed questions that an Executive Team can answer to optimize each part of of their business.
It all rolls up into a one-page Executive Plan Dashboard that helps senior leaders achieve their goals.
The result?
- No more silos on your Executive Team because each leader will have a solid understanding of what the other leaders are working on
- Your team will develop an integrated thinking approach that will help you make better decisions
- The plan can be referred to on a regular basis to help you achieve your goals
In the end senior leaders that use the Executive Planning System are happier and have more successful companies.
Led by Gord Sheppard, a highly experienced Management Consultant and Executive Trainer with 25+ years of experience, in this workshop you’ll get:
- A terrific team-building opportunity
- In-person or online
- Executive Team Planning System Workbook
- Professional Development Credits
- Certificate of Completion
Municipal Wins Leadership Program
3 to 6 Months
The “Municipal Wins Leadership Program” is for municipal leadership teams that want to build a winning work culture.
In this high-impact session, participants learn:
- How to get the most out of past wins and losses
- The Executive Winning System, a proven approach to optimize your entire organization
- The Anatomy of a Win/Loss – which includes examining the Strategy, Work Plan, People, Operations and Results behind every win and loss.
For example, let’s say a leader almost bankrupted their municipality 5 years ago.
That leader can then use the Anatomy of a Loss framework to examine the what went wrong:
- Strategy – What did we miss in terms of vision, mission, values, and goals?
- Work Plan – What did we miss along the timeline in terms of ‘what, who and when’ which caused the loss.
- People – Who were the key stakeholders and what were their roles and attitudes that cause this loss?
- Operations – What were the operational problems (i.e., policies, procedures, software, regulations, equipment etc.) that caused this loss?
- Results – What was the outcome from this loss (qualitative and quantitative)?
Once leaders master this proven framework then they will be able to use it to examine past losses, learn from them, and avoid them in the future.
In addition, participants will also learn how to build an impactful ‘Wins/Losses List’ and identify authentic ways to celebrate successes and failures.
This session also features real stories from the award-winning Executive Wins Podcast – where senior leaders share their biggest wins and losses, so you can get inspired and grow your business.
Hosted by Gordon Sheppard and available on the Executive Wins YouTube Channel, Apple Podcasts, Spotify and wherever you listen.
Participants will also receive a workbook to help them retain and apply key concepts.
Visit https://executivewins.com/municipal-wins-leadership-program/ for more details
Participants learn an objective way to deal with wins and losses – so they can learn from them and use the lessons learned to build a winning work culture in the future.
Click the link for details.
Municipal Wins Leadership Program
THE PROOF
Why Executives Hire Gord
FAQ
Common questions from organizations looking for leadership training and workshops.
Most sessions run half a day or a full day, depending on the topic. The Executive Winning System Masterclass runs a full day, or can be delivered as part of a corporate retreat. The Municipal Wins Leadership Program is the exception, a longer engagement that runs three to six months.
No. Gord delivers training in person because the sessions are built around interaction, discussion, and group participation, things that work best in the room.
Yes. Loneliness in Leadership and Winning Meetings are both offered in customizable formats, and the Municipal Wins Leadership Program was built specifically for municipal leadership teams. Ask Gord about tailoring a session to your team’s situation.
Gord’s training client list spans government, higher education, professional associations, and municipalities, including the Government of Alberta, MacEwan University, University of Alberta, APEGA, and the City of Chestermere.
SEE GORD IN ACTION