Wynning Your Way for Senior Leaders

Your Defined Version of Success, Executed

Advanced Leadership Development for Women in Senior Management.

Year-Long. In Person. With Peers. 



Chances are...

Over the last two years (at least) you’ve been sandwiched between the executive team’s strategy and keeping your distracted team engaged while navigating uncertainty in all aspects of life.

More has been asked of you from the top and you’re finding your usual resources on coping, leading, problem solving are no longer giving you the best results.

You’d like to continue to grow in the company, or take on a higher position elsewhere, and you’re wondering how to up your leadership game.

You have high standards and expectations of yourself and that’s been taking a toll on your well-being.

You're Starting To Notice 

  • It’s been a few years since you’ve been offered professional development that matches the level of leader you’ve become.
  • There is a piece of you being held back and you don’t fully recognize it yet.
  • You have scar tissue from past leaders that’s informing how you decide to lead.
  • You sense the rumbling and you’re no longer willing to play small.  

On Top Of That...

You Yearn 

for community and connection on both a professional and human level, especially after the last two years. 

You'd Love

to learn with other women leaders who are at your level.

You Want

new tools and ways to increase your effectiveness as a leader while you also learn how to support your own wellbeing.

... and you know you're NOT going to find this through a networking event.

It’s time to stop giving in to everyone else’s priorities and start redefining what success means to you….


Are you ready to level up your leadership effectiveness, release self-limiting beliefs and champion yourself as much as you champion others?

You're Invited To Apply 

for the ONLY advanced leadership development peer group for senior female leaders 

Apply Today

This Exclusive Annual Membership Is Designed For

next-level women leaders who have weathered the storm of leading through the pandemic and are looking to both rejuvenate themselves and their teams.

Wynning Your Way For Senior Leaders

Is For Women Who 

hold VP, SVP, Director, Senior Director-type positions


have progressed in leadership roles and responsibilities 

report to executive leadership

have a growth mindset

Membership Overview


Wynning Your Way For Senior Leaders is designed for women in mid to upper level management, who have been leading teams for years and are either not getting any professional development or what’s being offered doesn’t match the level of leader they want to be. 


This is an opportunity to elevate your impact as a leader, leverage AND highlight your talents, and prepare yourself to step into roles of greater influence. Along the way you’ll learn more about yourself, how to shift your mindset to align with the type of leader and human you want to be, why you lead, how to get out of your own way, and ways to amplify your voice.


The Wynning Your Way Framework™ merges outward goals of achievement with inward development of being to increase fulfillment and success with less frustration and burnout in business and in life. Each progressive step is infused with high performance teachings to spark deeper self-discovery for direct leadership application while supporting your defined version of success so you’re wynning your way…in your whole life, with your whole self.


You’ll transform into a wynning leader who gets the most out of your team, has greater influence throughout the organization and community, and is centered in a wynning mindset that supports ongoing, sustainable growth for you and your team. This is truly leadership transformation from the inside out.


The annual program begins in September and is limited to 12 women in senior leadership committed to reaching a new level of growth for themselves and others. It’s not a networking group. This is full contact, full transformation of how you lead and live.

Wynning Your Way For Senior Leaders 

September 2022 - August 2023

Exclusive annual membership for a personalized, transformational experience for 12 women in senior management.


The 12 Month Program Includes:

  • Program Kick-off - half-day introduction and working session to set the tone for the year 


  • Nine additional  monthly in-person professional development sessions  (excluding July and December). 
    • Each session is three hours and provides:
      • High performance leadership learning
      • In the moment coaching for socialized learning
      • Community peer support   
      • Facilitated by a master level facilitator and high performance coach 
      • One session to be an experiential mindset outing


  • Subject Matter Experts to lead workshop-style sessions within the monthly group sessions on topics like Money Mindset, Storytelling for Leading, Making a Career Shift Up or Out 


  • Monthly individual leadership coaching sessions - 60 minute virtual coaching each month to support your specific development goals and progress. Deeper application to group topics are explored, resources to current team dynamics provided and individual attention to goals to accelerate outcomes 


  • Monthly members-only newsletter customized to address relevant leadership topics with additional resources to explore deeper learning 


“Michael has mastered the art of listening and understanding her clients and the people around her. Her unique ability to create space for each personality to show up in their own way, then bring it all together to make the team stronger is something that sets Michael apart from other coaches and thought leaders. She creates a safe environment to learn from one another and learn more about yourself.”

Tracy Call, CEO Media Bridge Advertising


A Wynning Leader


  • Stops playing small and steps into her greatness 
  • Becomes a better leader because she's become better to herself
  • Defines what success means to her now and operates according to her definition, not someone else’s
  • Effectively manages up, down, and horizontally with ease
  • Reaches next level growth and outcomes while maintaining well-being
  • Commits to herself as much as to her team and company
  • Connects and supports the growth of all women leaders because you know there’s room for all of us…and companies benefit when there are more women in higher levels of leadership

Are you ready to become her?


"Michael has the ability to help you uncover life-changing, business-changing insights, and strategies you will use for YEARS.  And she does it in the most playful and easy way…it’s like stumbling over one valuable treasure after another during a lovely walk on the beach." 

Jenny Evans, CEO, Speaker, Author


Who is Michael W Kithcart?


Hi! Technically, I'm a high performance coach, master facilitator, keynote speaker and host of the Champions of Risk podcast.

Fun fact: I love to win, and even more so, I love helping other people win. Winning is such a part of me, it’s even my middle name (Michael Wynne Kithcart)!

But in my pursuit of winning, I’ve also lost plenty...like my health, identity, money, jobs, relationships. In the moment, I thought I was winning in life. On the outside, I came off as successful and accomplished. 

But on the inside I faced years of heightened anxiety and overwhelming pressure that I put on myself.

It was a decades long emotional rollercoaster- one minute at the top of my game and the next feeling like an utter failure. Super confident for periods of time and then questioning everything at other times. Perhaps you can relate.

I spent years searching for solutions. I have my own self-help library, have attended retreats, and leadership conferences. All helped to a certain degree...until they didn't.

Some solutions were more extreme. In an effort to run away from the exhaustion and disappointment, I’d get a new job, move to a new city, or even a different country!

It wasn’t until I stopped running and actually connected with who I wanted to be, and quit operating from a place of exhaustion and challenged myself to take back my power, that the transformation finally happened.

Freedom emerged when I defined what winning looks like for me... regardless of my environment and expectations. It made me a better leader and I became better to myself. 

I created Wynning Your Way out of what has worked for me personally, my clients, and what helped me create high performing teams.

Wynning Your Way For Senior Leaders

Is NOT For Everyone

WYW4SL is NOT for first-time people managers.


WYW4SL is NOT for men.

WYW4SL  is NOT for ghost members who don’t show up for the monthly sessions.

WYW4SL  is NOT for the dabblers and half-assers who aren’t committed to doing the work.

“The takeaways were succinct and actionable. I felt like I made friends with professional colleagues who I could relate to.”

- Beth Knox, Seattle Sports Commission


“Michael has a powerful way of moving people forward.” 

- Cathy Paper, Rock, Paper, Star

I'm so confident in the Wynning Your Way Framework that I offer a 100% Money Back Guarantee.

I’m confident that Wynning Your Way for Senior Leaders is the life-changing reboot you’ve been searching for…

But if you show up throughout the year and you don't excel at a different level, you deserve your money back.

That’s right- you get a whole year to reach a next level of leadership growth. If you show up to the monthly group sessions, participate and do the work for the entire year and you don’t experience transformation personally and professionally, you’ll get a FULL REFUND.

Annual Membership Includes


monthly in-person professional development sessions 


Monthly individual leadership coaching sessions


Subject Matter Expert lead workshop-style sessions within the monthly group sessions


Monthly members-only newsletter with additional resources to explore deeper learning

Membership is limited to 12 senior leaders committed to their growth and wellness.  

What is your current version of success costing you? What would it look like to wyn YOUR way?  

Space is limited to 12 and begins in September