The Leadership League Mastermind 

Claim a braver, bolder business

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. 

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

A Leadership Accelerator for CEOs on the Rise

We begin in...


It starts with claiming your Bold-Ass Move (a.k.a BAM) 

Inside every one of us is a stirring of possibility. It might be an idea, a spark, a project, a business, a book, a pivot or a whole-scale change. But it's there, making noise, wanting you to pay attention and make it happen. 

In the Leadership League Mastermind, we call this your Bold-Ass Move (or B.A.M. for short). And it's the crux of our time together -- creating the space, support and loving push to help you rise up and claim a bigger, bolder vision for your business trajectory. 

You stepping up as the leader your business needs you to be. 

To facilitate this, the Leadership League is one-part leadership training, one-part coaching, and one-part supportive mastermind community, with the express purpose of helping you level up your business by focusing on that one big, exciting B.A.M. that would seriously change the game.

Want to know what's possible? Here's some of what our last cohort of Mastermind members took on for their B.A.M.'s: 

  • Claimed her role as CEO, expanded her business from Canada into Mexico, and lead a new, growing team forward while keeping their values intact 
  • Published her first book and took on 100 acts of promotion and outreach to spread the word
  • Grew her business to the point where she could quit her full-time job and focus solely on her company's growth
  • Moved from being the world's best behind-the-scenes worker bee, to claiming her rightful place in the spotlight as a leader in HR recruitment
  • Revamped her entire business ecoystem to streamline operations, learned to say no to opportunities that pulled her away from her zone of genius work, and ultimately went from underbooked to fully booked in a matter of months
  • Moved beyond her fear of sales conversations/pitching to having close to 20 discovery calls and closing a number of new clients
  • Launched a 30-day free Planning Program to bring in new members for her Membership Community 
  • Stepped out from behind, and created five + acts of bold visibility (public speaking, interviews, guest posts etc) to claim her expertise and build her authority
  • Took on 100 acts of outreach to connect with potential partners, referrers, clients and influencers 
  • Went after her first five clients in a brand-new business venture 

The mastermind kicks off with some foundations-level work to ensure you are set up for success. Next, we'll narrow in your own personal B.A.M. -- why it's so crucial right now, and develop your action plan to realize it. 

Then you'll be off to the races, engaging in daily acts of micro-bravery and bold action to bring you closer and closer toward that goal. 

You'll be joined and championed by up to seven other ambitious, courageous women every step of the way (who know exactly how you're feeling!). 

The program will conclude with each member giving a short presentation to the group about their project (another great way to deepen and strengthen your voice) and finally with a wrap-up and celebration session at the very end of our time together. 

By the end of the Mastermind, you will be able to reflect on a period of significant action, bravery beyond what you'd likely do alone, and an attitude of 'I can do this!' along with the tangible results you'll achieve from making your B.A.M. a reality. 

And even better? You'll have made new friends who have your back and are committed to your success.

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 gaps that hold us back from the results we want to attain.  

We'll ensure you have the tools, skills and capacity to see your project all the way through by addressing any barriers or roadblocks up front.

Join a group of ambitious, high-performing women ready to claim a bigger vision for their work. 

"Being surrounded by a group of strong women who are also challenging themselves to step things up, made a huge difference to my own motivation. Seeing other people being brave, boldly trying things, and stretching themselves, gave me to the courage to do the same. I know they inspired me to do more than I would have on my own.  

The value of the Leadership League Mastermind for me was about a group of women who wanted my success as much as they wanted their own. I had a cheering squad for my accomplishments, a quiet space to rest when I got tired, and even a place to cry over the failures. 

Steph is a skilled facilitator and created the safe place for all of us to share. She is also a skilled coach and asked me the tough questions to help me change my own patterns. If you have a bold move you need to make...join. It is so much better to reach for your bigger dreams with women who are reaching for their dreams too!  

~Kirsten Wreggitt, Author & Opportunity Cultivator 


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

Enjoy an 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 focus for the duration
  • > 2x/monthly live Mastermind & Leadership Trainings via Zoom (15 in total)
  • > 1x/monthly live Hot Seat Coaching & Office Hours (optional)
  • > 4 additional private 1:1 coaching sessions with me 
  • > A 3-hr group planning session to position you for growth in 2019 (held in Dec 2018 or Jan 2019)
  • > 1, 10-minute live class taught by YOU about your B.A.M. so you can showcase your growth and highlight your learnings (it's powerful, trust me)
  • > Private community for connection, questions and accountability 
  • > Weekly Leader Work & Prompts (aka homework) to help you dive deeper and apply your learnings directly to your life and business  

Private 1:1 Strategy Session with Stephanie 

Personalized, private support from me to help kick-start your journey

Mastermind Roundtable  

Bi-monthly meetings with a group of powerhouse women ready to challenge and champion you 

Leadership Trainings

Build your leadership capacities and skills through live training sessions 

Business Office Hours & Hot Seats

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 

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). 

And I want to help you step up and claim our place too - to be bold, be brave and realize your biggest business aspirations. 

Claim a braver, bolder business. 

Tuition & Application Details:

The Leadership League Mastermind is a high-touch program designed to help you go after that one bold move that would make all the difference (you know the one...)

The League runs from October 30, 2018 to June 18, 2019. can 

Investment: Nine payments of $450 CAD or one payment of $3750 CAD. 

  One partial scholarship is available on an as-needed basis. 

To be considered for a scholarship spot, fill out the application below 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 $450 to hold your spot, and then you'll receive all program details. 

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

 What results you can expect: 

  • Step up as the CEO of your business and feel the confidence that comes from your leadership position
  • See your most important project all way through - from idea to completion 
  • Take bolder, braver action toward the projects and ideas that matter most 
  • Increase your income, impact and influence 
  • 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 
  • 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 
  • 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 


Talk to me about attendance. Is it mandatory?  

Essentially, yes. Of course I know that things might come up over the course of our time 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.  

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 B.A.M. -- 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. 

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 and your particular B.A.M. 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, and I will ensure we have the right mix of women in our group.

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, 10-minute presentation to the whole group around your B.A.M. This may be something specific that you can teach (i.e. an area of expertise), or it may be the lessons you've learned along the way. We’ll have lots of time to get ready for this (we do presentations in December) and I'll ensure you 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 make significant progress quicky. And I'll vet each member ahead of time to make sure the group the just-right mix of personalities, aspirations and business stage. 

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:  

  • Make bold, brave action toward a project that will catapult your business forward
  • 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.  

You need to have a desire to be in motion and stay in motion. If you're in a season of business focused on slowing down, simplifying and taking a breather, this is absolutely NOT the right program for you (at least right now). While I am very mindful about staying out of overwhelm and making sustainable plans, the Leadership League Mastermind is about action and bravery first.  

And, 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. We begin October 30, 2018.  

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 $450 deposit and from there you’ll get an email with more details. 

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

ore questions? 

Kerry Worth

"The Leadership League Mastermind experience has given me so many things. Motivation, focus, a group of like-minded entrepreneurs who understand the daily challenges and opportunities of running your own business.

I feel like this group is my pack - we run together - spurring us onward and supporting each other when one or more of us is faltering. We move at different speeds in different industries, yet we also move as a group, propelling each other forward to be our best selves.  

As an employee, I have been in leadership positions before. But as a new business owner, the challenges are different. The focus is so broad; there are so many different elements clamoring for your attention. 

Learning to be a leader in my own business has been challenging and I am grateful for the structure, camaraderie and shared assignments the Leadership League provides - pushing me to lead in this new way.  

Stephanie is an expert facilitator. She knows just what assignments and questions will draw out our sticking points. She shines a kind yet strong light on the challenges and offers different ways of looking at your goals - to get you there with just the right amount of discomfort to know your goal is worthwhile. 

When you choose your BAM, you feel daunted. And yet it is amazing to watch yourself and your fellow Leaguers move through those BAM goals and do more than they thought possible."

~ Kerry Worth, Worthwhile Nutrition