The Leadership League Mastermind 

Claim your space as a leader. Renew your commitments. Find richer rewards.

You’ve got a business, and it’s a beautiful thing. 

You summoned the courage to start something new when there was a far easier path elsewhere. 

You took the risk that there were much greater rewards and impact waiting for you beyond the confines of the status quo.

You made the leap. You did the work. You made it happen. 

Even when it was hard. 

Your effort, perserverance and committment is now paying off. 

You're busy building your body of work and adding value to those you serve, all the while striving to create a better future for yourself and your family. 

You could trot along like this for years, and it would be just fine. Mostly. Probably. 

Except -- you know you're capable of more. Tremendously so. 

You're ready to step out of the shadows and bring a braver, stronger point of view forward. 

It's time to renew your commitment to yourself, your business and the people you serve, in a fundamental way. 

It's time to go beyond the latest strategy-du-jour, beyond marketing, beyond sales, beyond busywork and beyond the next bright shiny object. 

It's time to step up and claim the responsibility you've earned. To get the recognition you deserve. And to ground your work in clear, unwavering PURPOSE. 

What will it take to realize this bolder vision for your business and life? 


Not the stuffy C-suite managment-style version you may immediately think of. 

But instead, your own personal brand of leadership that when activated, positions you to make your highest level of contribution. On your own terms.

And the best way to get there is with others. A community of ambitious, like-minded women on their own leadership journey who get it. 

That's why I created...

Leadership League Mastermind

We begin in...


How the League works:

The Leadership League is one-part leadership training, one-part private coaching, and one-part supportive mastermind community, with the express purpose of helping you level up your leadership capacity so that you can achieve your goals with clarity and confidence, and grow your business.  

This isn't just another business mastermind. We won't be spending our time together focusing on specific strategies related to marketing, sales and development. We might touch on them in our private community when you have a burning question, but that's about it. 

And let's be clear -- you know what to do. That's never been the issue anyway.  

Instead, we'll use this group as a safe incubator for you to explore, practice and hone your personal leadership skills and crystallize your message so that you can show up more bravely and powerfully in your business, and up your impact. 

We’ll run this group under the core values of:

Wholeheartedness -- we will bring our authentic selves to the group, not just the shiny “has it all together” selves. We tell the truth, and we share openly and respectfully. We bring our humanity to the table. 

Resourcefulness -- we will operate from the position that we are smart, capable and able to find the answers we need. We trust ourselves to make the best decisions.

Care -- we will take care of ourselves, and our fellow members so that we can bring our best selves to the experience. If we see someone struggling, we will reach out to offer support. Nobody gets left behind. 

Growth -- we are here to grow and expand ourselves and our businesses. It may not always be comfortable, and we are okay being stretched in service of our own potential. 

Action -- we will endeavour to stay in action, and make meaningful progress on our goals. If we get stuck, we’ll ask for help so we can keep going. 

Together, we will strengthen your:


Tired of feeling unsure and trepedacious about your big ideas and what actions to take? 

We will build your confidence muscles to help you feel stronger and act braver.


There is NOTHING better than feeling the power of crystal clarity - about your message, your mission and how you want to showcase it. 

Together we'll ensure you're focusing on the right things to get the results that are most meaningful to you. 


We all have leadership gaps that hold us back from the results we want to attain.  

Over the course of 10 leadership training sessions and safe, constructive feedback, you'll build the skills required to power a more thoughtful, sustainable version of your company.  


Your caring runs deep and you see business as a catalyst for positive social and economic change (or at least you want to).  

We will help you identify your greatest area for contribution in a way that best serves you and the world.  

Tall order? Maybe. But we know you can do it.  

Develop your leadership capacities and confidence, up your impact and expand your support network 

Kirsten Wreggitt - Leadership League Member

"Being surrounded by a group of strong women who are challenging themselves to show up more authentically, is infectious. Seeing them step more fully into their values, their convictions, and to dare greatly around what matters, gives me courage to do the same.  

The Leadership League Mastermind is less about being taught and more about going deep into truths about ourselves we already know but need help bringing to the surface. Steph creates a space for that exploration as well as a crucible for accelerating our expression of it through action."  

~Kirsten Wreggitt, Author & Opportunity Cultivator 


Here's what to expect. And everything you get:

Enjoy a six-month intimate mastermind experience that will create a container for growth and connection for ambitious, mission-driven entrepreneurs. 

  • > A private 1:1 session with me immediately upon acceptance to set your goals and leadership focus for the six months
  • > 2x/monthly live Leadership Trainings & Open Forum Discussion via Zoom (10 in total) + a Welcome Session and a Celebration Session  
  • > 1x/monthly live Hot Seat Coaching / Office Hours session 
  • > 1, 20-minute live class taught by YOU to practice your leadership skills in a safe environment (don't worry - we'll work up to this) 
  • > 3, 45-minute private coaching sessions with me 
  • > Private community for connection and questions 
  • > Bi-monthly Leader Work (aka homework) to help you dive deeper and apply your learnings directly to your life and business  

Private 1:1 Coaching with Stephanie 

Personalized, private support from me to help you navigate the road ahead 

Mastermind Roundtable  

A monthly meeting with a group of powerhouse women ready to challenge and champion you 

Leadership Trainings

Build your leadership capacities and skills through 10 live training sessions 

Business Office Hours

Get direct business support as you implement your new leadership skills

Idea to Action 

Bring your leadership skills to life with a special showcase session with the entire group

Tight-knit Community

Make deep, lasting relationships with a group of like-minded, thoughtful and strong women 


 Leadership training to grow your capacity:

As leaders, we have a responsiblity to ourselves and those we impact to ensure we strengthen our capacity to lead. While I'm all for delegation, there are critical leadership skills that can't be passed off. That's why we'll be exploring a new leadership capacity each month, equipping you with the tools and insights to level up your leadership. 

Leadership Training #1: Leadership Redefined

~ In this session we'll unpack what it means to be an entrepreneurial leader, and why it's more important than ever to step up. You'll begin to formulate your own definition of leadership to support your values and your growth plan. 

Leadership Training #2: The Aligned Leader  

~ We feel our best and our businesses flourish when we operate in alignment. In this session we'll identify gaps and create a personalized plan and credo to help you build the business you actually want to run. 

Leadership Training #3: Everyday Acts of Leadership 

~ Think leadership only looks like being a extroverted 'thought leader' speaking to the masses? Think again. In this session we'll identify all the small, but significant ways you can bring more leadership to your day-to-day operations.

Leadership Training #4: Women, Leadership & Power  

~ Power is a loaded term for many women. We've been taught to play small, people-please, and avoid seeming too ambitious. Yet that cultural conditioning holds back our deepest potential and value. In this session, we'll work with the idea of 'power with' vs 'power over' and help you elevate with grace.

Leadership Training #5: Amplify Your Leadership Voice 

~We need your leadership. And that means we need to hear your voice. Clear. Strong. With conviction. If you know that you have a message to share, but fear taking the 'stage,' this session will help you crystallize your message and share it more powerfully with the world.  

Leadership Training #6: Money, Marketing & Meaning

~ As a leader, you have an opportunity and dare I say, an obligation to market your business and make great money from it. When you do (in a totally ick-free way), you position yourself to make a deeper contribution and shift the balance of economic power for the better. 

Leadership Training #7: The Contribution Connection 

~ What difference do you want to make through your business? If you've ever wondered how to use your business as a platform for good, this session is for you. We'll explore different ways you can infuse more care and contribution into your business model.  

Leadership Training #8: A special class taught by YOU! 

~ That's right, you'll put your leadership skills into practice in a safe, caring space. This will be an incredible opportunity for you to shine and grow. 

Leadership Training #9: Navigating the Cycle of Overwhelm & Rest

~ Tired of riding the ups and downs of entrepreneurship? In this session, we'll create a sustainable model for keeping your momentum up while not sacrificing your well-being in the process. Critical for every leader!

Leadership Training #10: Step out of the Shadows and Do Brave Things

~ In our final session, we'll identify one big, bold project or idea for you to lead in the months ahead. This will be your opportunity to put everything you've learned into action and 10x your leadership capacity and confidence. Game changer!  


Each virtual training session will be live (there will always be a recording) and we'll have a discussion and Q&A afterward. We will then identify one meaningful action you can take to put this skill into action.

Powered by care & caffeine

Your League Leader

Stephanie Pollock

Hi! I’m Stephanie Pollock. 

I'm a Leadership Coach, Podcaster, and Writer, and I'm committed to helping women claim their greatness and level up their leadership. 

I’ve always been a natural leader. Mayor of my grade six classroom, captain of my field hockey and soccer teams, Vice Chair of the Board of one of our city’s biggest non-profit, steering committee member and organizer for the highly successful Women’s Leadership Forum, and head of numerous non-profit committees. 

I’ve been recognized as a Top 40 Under 40 changemaker in my region. I’ve been profiled and spotlighted in national media. I’ve completed an elite Leadership Training program, and received kudos from the governor general for my business prowess. 

Women’s leadership is at the heart of what I do. I believe that as business owners, whether we're a company of one or 100, we are all leaders (even if you've never considered yourself that before). 

In fact, I'd go so far as to say that you must be a leader if you're to truly build a business that endures. It's what I call The Leadership Imperative.

Rise without compromise 

Tuition & Application Details:

The Leadership League Mastermind is a high-touch program designed to develop your leadership skills and confidence so that your business is best positioned to grow. 

The League runs from October 26, 2017 - April 19, 2018. can 

Investment: Six payments of $525 CAD (less deposit)  

  Select partial and full scholarships are available on an as-needed basis. To be considered for a scholarship spot, fill out the application below including your request (partial or full) and I'll be in touch to discuss. 

If you are interested, please take a moment to apply. We will then hop on the phone and ensure this is the right fit for you. Once your spot is confirmed, you'll make an initial payment of $250 to hold your spot, and then you'll receive all program details. 

*Please note: this is a six-month active committment, not a membership subscription. You are responsible for the full tuition. 

 What results you can expect: 

  • Make better decisions that align with your values (not just what's in front of you) 
  • Set stronger boundaries with grace to protect your time and your well-being 
  • Take bolder, braver action toward the projects and ideas that matter most 
  • Step into your personal power and fill the gaps where you're currently giving it away 
  • Feel more confident in all aspects of your business 
  • Start (or amplify) using your voice to share your ideas and build your authority 
  • Build a business that aligns with your values, your highest capacity for contribution and how you want to live your life 
  • Use language that lifts your message up (instead of dilutes its impact) 
  • Take action daily in support of your goals (with a renewed sense of clarity and purpose)
  • Have a tight-knit community of women committed to your growth and well-being  
Pepper Makepeace - Leadership League Member

"There's been a huge demystification for me around the concept of leadership. It's no longer tied to ideas of being an "expert" or a "thought leader" which sound icky and ego-based. But instead it's more tangible acts of love and badassery deeply rooted in our core values. 

It's about the courage and clarity required to hold ourselves accountable to those values in all areas of our lives. Looking at leadership this way has opened my eyes to my own behaviors and how much of a dis-service some of these behaviors are to me, my clients, and anything I care about. But also a new awareness to the ways that I am embracing leadership in some areas and that helps build my confidence. 

While it's broadened my view of the concept of leadership, it's also made leadership a more tangible, more actionable, and less daunting aspiration. Because it's the consistent, daily acts that count - not just the big gestures.  

The support I feel from true connection with an amazing group of women is immeasurable. I will be eternally grateful for this opportunity to be a part of this group."  

~Pepper Makepeace, Founder Small Business Sisterhood 


Why is this Mastermind focused specifically on Leadership?  

Because I believe that when you grow your leadership skills, you grow your business. And there just isn’t enough out there helping you do that. There are millions of courses and products designed for specific business tactics, and there are even mastermind groups for getting things done or learning the basics of building a business, but there are very few that focus first on YOU the business owner and who YOU need to step into being.  

So while we’ll use your business as the greater context to explore your leadership development, the core mission of the program is to develop your leadership capacities, confidence and clarity so that you can make the greatest contribution possible.  

Will we be able to ask business-specific questions of you and/or the members?  

Yes! Absolutely. We will have a private community where you can ask any type of business-related question. I’ll be active in this community and will help you get your questions answered.  

We will also have optional monthly Office Hours sessions (1x/month) where you can get mastermind support, hot seat coaching from me or the time to workshop an idea or plan live. 

The key difference here is that we won’t be using our leadership mastermind sessions for this work. In these sessions (2x/month), we’ll be focusing specifically on your leadership work -- helping you navigate this new ground, asking you take risks, get out there and practice and then use the feedback you receive to further refine and stretch. These sessions are designed to grow your leadership, not help you figure out how to use webinar software (for example).  

Bottom line? There’ll be a space and time for both.  

What stage of business should I be at to apply for the League? 

This is a leadership mastermind for entrepreneurs and women leaders, not a business program. So while we will certainly speak to your business, it will be in the context of developing your own leadership capabilities. That means, it's less important what stage of business you're in and more important that you come to the League prepared to contribute, challenge yourself and grow personally and professionally. 

Currently, we have members who are just starting out and others who are 10 years (or more) in. It's been a perfect blend. 

Do I need to run a business to apply for the League? 

Not necessarily. While this is designed for business owners, given the nature of the topic and Mastermind format, having a business isn't mandatory. That said, you'll need to have a body of work you're building, already have demonstrated leadership skills, and have an entrereneurial, take action spirit.  

Talk to me about attendance. Is it mandatory?  

Essentially, yes. Of course I know that things might come up over the course of six months that would prevent you from attending a session. And that’s ok.  

However, the strength of a mastermind is squarely in the commitment of its members. If only a few people show up each session, everybody misses out on the richness of conversation, feedback and insight that could be possible.  

So do please check the schedule here and see if the dates work for you. If most do, then great. If most don’t, then I’d encourage you to check out the next round.  

I’m nervous about the presentation I need to give. Can you tell me more about this?  

I’m a big believer that we become better leaders by leading, not just by learning. Of course both are important, but it’s in the practice that we actually grow our leadership abilities. When we are stretched to take the stage and receive helpful, supportive feedback, we grow in our confidence and conviction.  

As members of the Leadership League Mastermind, you’ll deliver a short, 20-minute presentation to the whole group on a topic of your choosing. This may be something specific that you can teach (i.e. an area of expertise), or it may be something that you are really passionate about. We’ll have lots of time to get ready for this (we do presentations in February) you’ll have all you need to show up for this and be fully supported.  

Why should I pay for a mastermind? Couldn’t I just create one for free on my own?  

Of course you could! And if this program isn’t the right fit for you, then I do encourage you to do so. I’m all in favour of informal masterminds (I’ve always been part of one).  

The difference here is that I’ve created a very specific, thoughtful container to help you explore an area of personal and professional growth - leadership. That means that on top of regular mastermind meetings, you’ll also have specific trainings and discussions, coupled with topic-specific challenges to engage in the work each month.  

You also have 1:1 coaching sessions with me at a fraction of what I charge normally, and the assurance of a structure, accountability and commitment.  

What will I walk away with at the end of this experience?  

I know this sounds cliché, but you’ll get out of this experience what you’re willing to put in. So bear that in mind. If you show up, engage with the group, stay open to sharing your challenges and your wins, and be willing to test out your learnings, I know you’ll receive a tremendous amount from this Mastermind.  

In particular, you can expect to:  

  • Have a greater sense of confidence in yourself and in your approach to business  
  • Form deep connections with people traveling the same path who can challenge and cheerlead you along the way  
  • Take bolder action in service of your goals  
  • Feel aligned with your business in a way you likely haven’t yet, knowing that your vision, mission, values and goals are lined up in a way that is truest to you  
  • Make better, faster and smarter decisions with a solid framework to guide them  
  • Have clarity around the unique contribution your business can make to the greater good (this will be highly personalized to you and your business)  
  • Be actively using your voice in pursuit of what matters most  
  • Feel less overwhelmed and unclear about what to do and how to do it  
  • Have a clear plan to navigate the ups and downs of entrepreneurship without burning out  
  • Take full ownership for your company as its leader in a way that will position you for the greatest growth and contribution  

Who is this program not a good fit for?  

I tend to dislike these “who is this right for / who is this wrong for” style of questions because the answers feel really judgemental. So I’m going to mostly bypass that trusting that after reading this and everything else, you have a gut sense of whether this is a good fit for you (or let's chat to ensure it is).  

However, I WILL say that there are a couple of things that I do want to highlight as being immediate disqualifiers for the group. This isn’t from a place of judgement, but rather experience.  

If you hold things really close to the chest and really struggle to share what’s true for you (unless it’s bright and shiny) this probably isn’t a good fit for you. Great masterminds require a degree of vulnerability on behalf of each member to really thrive. Does this mean you have to share all your deep secrets? Of course not. But you do need to be willing to come to the sessions ready to share your insights, learnings, challenges and most of all, yourself.  

As well, you must be willing to give and receive feedback openly and respectfully. That means that you’re willing to be generous with your ideas, connections, support and constructive feedback for your fellow members, and be open to receiving this from them. I am not interested in having to work exceptionally hard to draw people out -- I’m looking for people ready to share, be of service and learn. 

And finally, this is not a good fit for you if you dislike online learning environment. We use Zoom (very user-friendly) and all meetings happen over video. If you greaty prefer in-person to online, this may not ideal. 

What are the dates for this round? 

You can find the full list of dates here. Applications close October 19th.  

What are my next steps if I’d like to explore this further?  

If this is speaking to you, I encourage you to apply as there are only 6-8 spots available. Applying does not obligate you to the mastermind. Once I receive your application, we’ll hop on the phone for a quick chat to really make sure it’s a great fit - both for you and the collective group.  

If we’re both a go, you’ll receive an email with a link to submit your $250 deposit and from there you’ll get an email with more details. 

*Applications close October 19th at 11pm MT. We can do our 20-minute chats after this date, but all applications must be in to be considered by this round.* 

BONUS: Secure your spot by September 30th, and get an extra 60-minute coaching session with me.  

More questions? Feel free to email me at and I'd be happy to answer. 

ore questions? 

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