Live. Learn. Lead.

Alison Geskin

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MANAGEMENT
UPDATED BIWEEKLY

Alison Geskin talks with some of the most successful leaders from around the globe. She discovers what they're doing, why they're doing it, and what impact they've made.

12/17/2025

The Keynote Blueprint for Inspiring Leadership with Tamsen Webster

What’s the most effective way to communicate our big ideas and share them with clarity? On today’s episode we’re joined by sought-after message designer and speaker Tamsen Webster. Tamsen helps organizations (including Johnson & Johnson and Harvard Medical School) craft meaningful messages that inspire long-lasting change. She reveals to us the importance of messaging and the secrets to creating impactful messages that spark action. Topics discussed in this episode include: Why Tamsen describes herself as a situational extrovert and how it influences her work.The odd pattern that plays out with many of Tamsen’s clients.What Gall’s Law is and how it relates to each individual’s perspective.What the “curse of knowledge” says and how it impacts the way we share our ideas.Why explaining our multi-dimensional ideas is difficult (and is not a personal failing).What Tamsen had to unlearn about her own voice to put herself on stage.Why you can’t perfect your ideas on paper.Seeing feedback as a gift, and how to frame failure as a part of learning.What it means to strategically design internally motivated action.How to apply the Overton window to the strategy of expanding ideas.Tamsen’s take on the high occurrence of failure in strategic change.Why logical and simple frameworks are your friend when crafting messaging.The framework Tamsen is working on now and how it supports message creation. Tamsen’s website: https://tamsenwebster.com The Art of Strategy: https://www.theartofstrategy.ca Alison on LinkedIn: https://www.linkedin.com/in/alisongeskin

57 min
11/24/2025

Legacy of Leadership: A Journey of Courage, Truth, and Joy with A'Lelia Bundles

Why is honest storytelling so important, and how does it intertwine with history? Our guest today is A'Lelia Bundles, a journalist, author, historian, and more. A'Lelia fell in love with writing at a young age, quickly realizing the power and potential for impact in weaving a story. A'Lelia opens up in our conversarion about the most significant moments in her career, the lessons she’s still realizing today, and the role storytelling has played throughout her life. Topics discussed in this episode include: The throughline that connects the various chapters of A’Lelia’s life together.Her parents’ encouragement to do what she loves and why it made a difference.What it was like being a female journalist when it was much less common.The doors other women had to open so A'Lelia could walk through them.How an experience at graduate school inspired her to share her family’s story.Why empowering others is so critical in leadership and what that actually looks like.The gifts her mother and father shared with others and the ripple effect it had.Why she doesn’t 100% approve of the production created about Madam C.J. Walker.Her new book, The Joy Goddess, and what it’s all about.How joy rises out of difficulty and pain, and how that has played out in history.What A'Lelia hopes people are paying attention to and working on now. A’Lelia’s website: https://aleliabundles.com A’Lelia on Instagram: https://www.instagram.com/aleliabundles The Art of Strategy: https://www.theartofstrategy.ca Alison on LinkedIn: https://www.linkedin.com/in/alisongeskin

58 min
11/04/2025

How Hillberg & Berk Went from Kitchen Table to Nationwide Success with Rachel Mielke

What’s the secret to bringing a jewellery brand with such small beginnings to be this impactful? Today we are joined by Rachel Mielke, the Founder of Saskatchewan-based jewellery company Hillberg & Berk. Rachel’s experience of entrepreneurship has been all about taking risks, from taking her business full-time to appearing on Dragons’ Den. But perhaps even more importantly, her journey has been about connection, and that’s been her secret to successfully utilizing the support and community she already had. Topics discussed in this episode include: What it was like for Rachel to launch a brand from her kitchen table. The catalyst that led to her truly seeing the potential in her business.Her experience on Dragons’ Den and the moment she got lucky on the show.The promotional event that led to a flop—and how it led to her best pivot ever.How she leaned into a strategy of building relationships in order to scale.Why she says success is 100% the team you build around you.Her secret to finding those people who are the right fit for the business.The values that have shaped how she shows up as a leader.Why it’s important to leave your ego behind when you’re building a team.How balancing work and motherhood doesn’t get easier (but it’s worth it).How building a stable business earns you the right to say “no” more often.Why she is excited for the next generation and how they view the world.What Rachel sees next for her business and her brand almost two decades in. Hillberg & Berk: https://wwwhillbergandberk.com Rachel on Instagram: https://www.instagram.com/rachelmielke101 The Art of Strategy: https://www.theartofstrategy.ca Alison on LinkedIn: https://www.linkedin.com/in/alisongeskin

50 min
10/23/2025

Why An Open Door Policy Isn’t Enough: Cultivating a Speak-Up Culture with Stephen “Shed” Shedletzky

How can leaders create a positive speak-up culture in the workplace? Stephen “Shed” Shedletzky is a keynote speaker and author of Speak-Up Culture. When it comes to cultural leadership, Shed has seen and lived the importance of serving and leading from the inside out. He shares some fantastic tips for soliciting feedback and encouraging honesty from your team so that you can live up to a high standard of leadership. Topics discussed in this episode include: What Shed’s first work experience out of business school taught him about leadership.Why all leaders are followers and why servant leadership matters.How living up to the standard of great leadership isn’t easy in practice.The personal experiences that taught Shed about speak-up culture. Why having an open-door policy in the workplace simply isn’t enough.How workplace culture isn’t like a family (and shouldn’t be presented as such).What it means when you solicit feedback and your team doesn’t speak up.Why it’s important to get curious, disagree, and come out on the other side.How to create a workplace where people feel comfortable with honesty.What not to do if you want honest feedback from your team.Tips for leaders to spot and nurture moments of courage.Why cultivating a diverse, respectful environment is key.The true test of whether or not you’ve created a speak-up culture. Shed Inspires: https://www.shedinspires.com Shed on LinkedIn: https://www.linkedin.com/in/stephenshedletzky The Art of Strategy:https://www.theartofstrategy.ca Alison on LinkedIn:https://www.linkedin.com/in/alisongeskin

53 min
08/21/2025

Heart and Craft: Reviving a Dying Industry Through Love with Tova + Josh Matchett

What does running a successful business as a married couple look like? On this episode of Live Learn Lead our guests are Tova and Josh Matchett of Timeless Furniture. The motivation for their business came from a desire to create a higher level of freedom in their growing family, and they’ve learned a lot through their business journey—which has included a service pivot, a rebrand, the creation of their own upholstery academy, and a new location. Topics discussed in this episode include: How Josh and Tova feel about the work they do.The three words that sum up the essence of Timeless Furniture as a business.Why, as a married couple, they felt drawn to starting a business together.Who Josh’s first customers were and what that experience taught him.What happened when they decided to pivot and rebrand their business.Their inspiration for starting their own furniture line and how it’s going now.What it took to find the right talent in their industry.The qualities they look for in right-fit team members and why it matters.How they deal with those inevitably imperfect days in their business.How being in business together has actually strengthened their relationship.What advice they would give to couples who are starting a business together.The personal mantras that help them in business and in life. The Art of Strategy:https://www.theartofstrategy.ca Alison on LinkedIn:https://www.linkedin.com/in/alisongeskin Timeless Furniture: https://timelessfurniturecorp.com/

54 min
07/28/2025

The Maverick's Guide to Modern Leadership with Dan McLean

Ever wonder how leadership is different in the world of politics compared to in business? On this episode of Live Learn Lead we’re chatting with Dan McLean, a city councillor for Ward 13 in Calgary since 2021, who has a unique view of leadership through the lens of municipal politics. He discusses his experience as a business owner and how it compares to his life in politics, how he deals with difficult situations and conflict, and the skills that it takes to be an effective councillor. Topics discussed in this episode include: What comes to mind for Dan when he hears the word “leadership.”The values that stand out most in Calgary and what he loves about it.One of the biggest benefits of winning his elected position.Calgary’s unique relationship with the agricultural industry.How Dan fought to get rid of the “ridiculous bag bylaw” (and won).Why he decided to transition from life as a business owner into a life of politics.The importance of having thick skin. How Dan stays in tune with the pulse of the city and why it matters.Why it’s crucial to compromise in conflicting situations. Dan on Facebook: https://www.facebook.com/danmclean4calgary/ Dan on Instagram: https://www.instagram.com/danmclean4ward13/ Dan on LinkedIn: https://www.linkedin.com/in/dan-mclean-1a56b4a8/ The Art of Strategy:https://www.theartofstrategy.ca Alison on LinkedIn:https://www.linkedin.com/in/alisongeskin

47 min
06/25/2025

Family First: A Mother’s Journey of Purposeful Career Choices with Kara Chomistek

What does it take to lead a global brand while also raising a little human being? As a career-focused woman, Kara Chomistek, a Partner at PARK Production House, spent her 20s building that part of her life up. Later, when her daughter came along, she knew she would have to find a way to be a present mom while still pouring energy into her work. Today we get to hear Kara’s life-changing experiences in motherhood, how she maintains healthy relationships as a busy working mom, and how she has still been able to also successfully grow her business along the way. Topics discussed in this episode include: How Kara’s life trajectory differed greatly from her friends and peers.The realization that dawned on her quickly after having her baby.How she handles guilt as a working mom and where it tends to come up the most.Why quality time with her daughter is so much more meaningful than the quantity of time. The health issues she had coming out of her pregnancy and how it impacted her energy.How finding the little joys in life help Kara and her husband connect in busy times.Kara’s secret to maintaining a healthy relationship with her business partner.The experiences that have helped her and her partner run a high-stress business together.The type of clients their business attracts and where they’re growing now.The advice she would have given herself as a new founder if she could go back. PARK Production House: https://parkproductionhouse.com Kara on Instagram: https://www.instagram.com/karachomistek The Art of Strategy:https://www.theartofstrategy.ca Alison on LinkedIn:https://www.linkedin.com/in/alisongeskin

44 min
05/15/2025

Making the Complex Awesomely: Simple A Conversation with John Spence

What are the responsibilities of a great leader, and what do you need to do to embody purpose-driven leadership? Today we’re talking with John Spence, a global business expert and coach, about the greatest lessons he’s learned in his decades of leadership. He is one of the Top 100 Business Thought Leaders in America and has a wealth of experience in advising Fortune 500 companies. During the discussion, he shares his thoughts on most leaders’ greatest struggle, along with how to solve it from the root of the problem. He also gives tips for creating a better culture in the workplace andexplains why employee happiness is key to customer happiness. Topics discussed in this episode include: What John thought he would pursue as a career and why that changed.How he became a CEO at 26 and how it aligned him with a life-changing connection.What servant leadership is and why it’s important to understand.How being clear is kind and why this is a crucial part of leadership.The biggest fear most leaders have and how it presents in their business.The importance of building a people-centered culture, and why culture=cash.How shaping your employee experience impacts your customer experience.What people think drives a company forward versus what actually does.How to remove the friction from your business to support execution.The different ways AI can be used and why you need to know when not to use it.Why John believes that he’s here on this earth and what he’s doing about it. John Spence: https://johnspence.com John on LinkedIn: https://www.linkedin.com/in/johnbspence The Art of Strategy: https://www.theartofstrategy.ca Alison on LinkedIn: https://www.linkedin.com/in/alisongeskin

1h 11m

TRAILER

Live. Learn. Lead. Trailer

Alison Geskin uncovers leadership lessons from some of the most successful leaders from around the globe.

S1

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1 min

Alison Geskin talks with some of the most successful leaders from around the globe. She discovers what they're doing, why they're doing it, and what impact they've made.

Creator

Alison Geskin
Years Active

2021 - 2025
Episodes

23
Rating

Explicit
Copyright

© 2021 The Art of Strategy
Show Website

Live. Learn. Lead.