Lead by Design

Dev Singh

Conversations about leadership, design, agility, innovation, and many things in between. leadbydesignshow.substack.com

Episodes

  1. 22/08/2025

    Scarcity, control, and the future of leadership systems with Rossco Paddison (#008)

    In a special episode of 'Lead by Design,' Rossco Paddison and I explore metaphors of team dynamics using gardening as well as the concepts of entropic and syntropic systems. We delve into scarcity, uncertainty, the illusion of control, the power of coordination over competition, and the future trajectory of organisational dynamics. I’m releasing this episode over a year after it was recorded, after reflecting on this impactful conversation I had during a rough mental period to find powerful and relevant wisdom I initially overlooked. This conversation is deep and sometimes comically convoluted, and intertwines personal insights, professional experiences, and philosophical ideologies, highlighting the significance of embracing complexity and facilitating growth through interconnected and adaptive systems. Rossco and I have both grown and evolved a lot since this conversation, and Rossco is on fascinating new adventures these days. Here’s a bit about him you should know: Rossco Paddison helps entrepreneurs transform their genius into operational systems teams can run flawlessly (without drift), at scale. Having impacted 300,000+ people across 23 countries, he blends AI, systems thinking, and regenerative design to turn founder intuition into infrastructure. As creator of A Player Brains™ workshops, Rossco equips teams to break through bottlenecks and scale without burnout, fast! 07:39 Introducing Rossco Paddison 20:05 Team Dynamics and Metaphors 26:43 Scarcity and Uncertainty 33:15 Monothinking vs. Systems Thinking 44:01 Defining Entropy and Syntropy 45:06 Human Perception of Order 46:04 Onboarding and Organizational Order 48:06 Living Entropically vs. Syntropically 54:58 Future Perspectives on Control 01:01:03 Media Narratives and Economic Decisions 01:05:55 Debt and Scarcity 01:10:35 Coordination and Innovation 01:18:03 Nature's Self-Healing and Biodiversity 01:25:07 Concluding Thoughts on Design and Leadership --- https://linkedin/in/devsinghnethttps://leadbydesignshow.substack.comhttps://undermyturban.com https://rossco.co This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leadbydesignshow.substack.com

    1h 28m
  2. 10/05/2025

    How to reconnect with yourself and find passion without doing more with 3X world record holder Josh Stinton (#007)

    In this episode, I sit down with Josh Stinton, business design expert, international keynote speaker, and bold charity adventurer known for his larger-than-life personality, unparalleled authenticity, and wacky world-record breaking escapades. We delve into the profound influence of (and what led him to) his impactful adventures for children's charities, and what it means to live a life by design. Josh shares his early inspirations, especially the formative lessons from his grandfather, emphasising that helping others is not just an opportunity but a responsibility. We navigate through his transition from corporate environments to becoming a global adventurer, and the importance of self-leadership. We also explore key themes like the essence of deep focus, the importance of creating space to connect with oneself, and how inspiration, motivation, and empowerment interplay in personal and professional growth. This episode is a truly fun and insightful deep dive into leading a fulfilling life, breaking away from the fast-fun mentality, and genuinely connecting with our core passions and responsibilities - without becoming anxious and overwhelmed at the thought of trying to do that. You can also watch the video version of this episode on YouTube: Selected links from the episode * Josh’s website * Josh on LinkedIn * Extraordinary Measures, 2010 film starring Brendan Fraser * Fishburners * Feel the Magic (Australian charity helping children dealing with grief) * Deep Work by Cal Newport About Josh Josh Stinton is a globally experienced adventurer, keynote speaker, and business design facilitator. Originally from Colorado now living in Norway, he earned his degree in Australia and honed his expertise with Big 4 firms, mastering complex business challenges and redefining conventional thinking. On stage, his dynamic storytelling transforms business dilemmas into breakthrough moments. Whether unicycling down mountains or cycling across oceans, Josh pushes boundaries to uncover the secrets of meaningful engagement. His high-energy keynotes inspire audiences to OWN IT—challenging the status quo and unlocking new possibilities in both business and life. About me Over the past 16 years I’ve led and coached teams across Government, tech, education, non-profit, finance, construction, small business and start-up sectors. My work has shaped multimillion-dollar initiatives, redefined leadership strategies, and built high-performing teams in fast-moving and complex environments in places all over the world like Australia, New Zealand, Asia, Europe, UK, North America. These days you can most easily find me and my musings on LinkedIn or subscribe to my newsletter, Under My Turban.Connect with me Website: https://www.devsingh.netLead by Design podcast: https://leadbydesign.showUnder My Turban newsletter: https://devsingh.substack.comLinkedIn: https://linkedin.com/in/devsinghnet This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leadbydesignshow.substack.com

    1h 33m
  3. 29/03/2025

    Building thriving organisations with Caidyrn Roder and Olivia Burmester at ProSocia (#006)

    In this episode of Lead by Design I welcome Caidyrn Roder and Olivia Burmester, co-founders of ProSocia, a consultancy focused on improving organisational collaboration and effectiveness. They discuss their backgrounds, the founding of ProSocia, and the importance of people-centric leadership. The conversation delves into topics such as collaboration, the impact of leadership, the differences in organisational culture between Scandinavia and Australia, and the challenges and rewards of starting a new business. We also go off on some fun philosophical tangents to reflect on prosperity, purpose-driven work, and continuous improvement beyond work into personal life. You can also watch the video version of this conversation on YouTube right here: About ProSocia ProSocia is a consultancy that specialises in operating model and culture uplift to help organisations drive sustainable growth with a focus on increasing productivity and effectiveness. Olivia and Caidyrn started ProSocia with the vision of a world where ‘people first’ is the cornerstone of sustainable, thriving organisations About Olivia Burmester Olivia has a wide range of Management consulting experience from Europe and Australia across various industries such as Health, Travel, Finance, Marketing, Tech and Education. She brings learnings from Scandinavia to help people and organisations reach their full potential. With a background in sociology, international business and international politics she is passionate about the interactions between the individual, organisation and society and particularly how we can shape organisational culture to help people and organisations thrive. She is a mentor with the Minerva Network and Sydney Techstars where she mentors tech start-ups. Olivia teaches regularly at UTS and UNSW in psychological safety, collaboration and continuous improvement. Olivia wrote her thesis on corporate sustainability management in relation to the Sustainable Development Goals (SDGs) in collaboration with ATP (The Danish Mandatory Pension) and IFU (The Danish Investment Fund for Developing Countries). About Caidyrn Roder Caidyrn has over 20 years of experience helping people and organisations thrive. In this time he has come to believe that the best way for organisations to be successful is to focus on their people. The role of leaders is to set clear purpose and direction, create an environment that supports growth and wellbeing, and make it easy for their people to do their best work every day.With extensive experience in both executive and team coaching, Caidyrn specialises in empowering leaders and teams to achieve sustainable growth. His expertise lies in designing and implementing operating models that support people to deliver tangible business outcomes. He has a deep understanding of how value flows through organisations, which he applies to help organisations improve productivity, predictability and effectiveness.He is skilled in designing and facilitating impactful workshops, providing structure and guidance that supports effective collaboration. He has trained thousands of people in collaboration, effective leadership and agile principles and practices. He supports leaders and teams to sustain growth and adaptability in an ever-changing business landscape.He delivers talks at conferences and meetups, is a regular guest lecturer at both UTS and UNSW, and he is passionate about doing work that has a positive impact. Selected links from the episode * What I learned about prioritisation at the ABC by Caidyrn Roder * Why Shared Understanding Matters for Collaboration by Olivia Burmester * The Agile Disease by Luke Halliwell * Punctuated Gradualism * Prosperity Without Growth by Tim Jackson * Design Processes for Humans by Caidyrn Roder About me Over the past 16 years I’ve led and coached teams across Government, tech, education, non-profit, finance, construction, small business and start-up sectors. My work has shaped multimillion-dollar initiatives, redefined leadership strategies, and built high-performing teams in fast-moving and complex environments in places all over the world like Australia, New Zealand, Asia, Europe, UK, North America. These days you can most easily find me and my musings at www.undermyturban.com.Connect with me Website: https://www.devsingh.netLead by Design podcast: https://leadbydesign.showUnder My Turban newsletter: https://devsingh.substack.comLinkedIn: https://linkedin.com/in/devsinghnet This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leadbydesignshow.substack.com

    1h 32m
  4. 04/06/2024

    Stuart Waters on how to facilitate powerful collaboration and effortless leadership (#005)

    Stuart Waters, one of Australia's most experienced and renowned collaboration specialists and the owner of Twyfords, one of Australia's most reputable collaboration consultancies, joins us on Lead by Design to share his journey of becoming one of Australia’s most sought-after facilitators, and his passion for helping organisations tackle complex problems through effective collaboration. On this episode, you can expect to learn about: * systems thinking * the challenges of pitching collaboration * the importance of facilitation skills for leaders and executives * practical advice for leaders transforming organisations * and much more! You can also watch the video version of this conversation on YouTube right here: Selected links from the episode * Twyfords * Cynefin framework * Power vs Force by David R. Dawkins * Systems thinking * A Tale of Two Forums by Stuart Waters About Dev Singh:Dev Singh (@DevSinghNet) has over a decade of experience working with established and aspiring organisational leaders to build stronger & more strategic business foundations, and to lead with greater impact and influence.Besides working with organisations all over Australia in over a dozen sectors, Dev has coached and consulted for entrepreneurs and executives in places as varied as Eastern Europe, Scandinavia, UK, Southeast Asia, North America, and Singapore.Dev has designed and delivered keynotes and workshops for hundreds of organisations worldwide on entrepreneurship, business strategy, leadership, branding & marketing, communication, influence and innovation, across a range of industries and sectors including Government, Financial Services, Retail, Professional Services, Non-Profit, Education, Technology & start-ups.Connect with Dev Singh:Lead by Design podcast: https://leadbydesign.showUnder My Turban newsletter: https://devsingh.substack.comLinkedIn: https://linkedin.com/in/devsinghnetTwitter: https://x.com/devsinghnet This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leadbydesignshow.substack.com

    1h 14m
  5. 08/01/2022

    Joseph Merz on serial ethical entrepreneurship, creating your own advisory board, influencing social behaviour, and some hope for our deteriorating planet (#004)

    Joseph founded his first business at sixteen years old. He has gone on to launch a number of organisations since. He is still involved with a few of these organisations: Sterning Group, which is a licensing group of ethical and sustainable recruiters, and the Merz Institute, a data-driven conservation organisation with a broad mission that ensures continual relevance in a world where the only constant is change. Joseph is passionate about solving big issues from consumerism and energy to insect biomass decline and the climate crisis. You can learn more about the Merz Institute at https://merzinstitute.org/ and you can connect with Joseph on LinkedIn at https://www.linkedin.com/in/josephmerz. Show notes: https://devsingh.net/joseph-merz-004Some of the questions I ask Joseph in this conversation What is an ethical and sustainable licensing group business? How did you decide what kind of businesses to set up to drive your mission forward? How did your dad’s experience as a monk influence your business and leadership mindset? How did you recognise you were unfulilled? What is your goal setting system that’s different to larger organisations? How do you cultivate an essentialism mindset? How can you tune into seeing how things really are? What can move the needle faster to deal with our biggest planetary problems? How do you keep moving forward in the face of pessimism about success? How do you design and build an advisory board? How to make the most of your available advisers? About Dev Singh:Dev Singh (@DevSinghNet) has over a decade of experience working with established and aspiring organisational leaders to build stronger & more strategic business foundations, and to lead with greater impact and influence. Besides working with organisations all over Australia in over a dozen sectors, Dev has coached and consulted for entrepreneurs and executives in places as varied as Eastern Europe, Scandinavia, UK, Southeast Asia, North America, and Singapore. Dev has designed and delivered keynotes and workshops for hundreds of organisations worldwide on entrepreneurship, business strategy, leadership, branding & marketing, communication, influence and innovation, across a range of industries and sectors including Government, Financial Services, Retail, Professional Services, Non-Profit, Education, Technology & startups. Dev has a Bachelor of Business and a Bachelor of Medical Science, with a particular interest in Organisational Psychology and Behavioural Neuroscience. He’s also certified in Agile Coaching and Agile Leadership.   Connect with Dev Singh: Newsletter: https://devsingh.substack.comLinkedIn: https://linkedin.com/in/devsinghnetTwitter: https://twitter.com/devsinghnet This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leadbydesignshow.substack.com

    2h 11m
  6. 21/11/2021

    Brendan Marsh on the shadow-side of being ex-Spotify, the strengths and weaknesses of the Spotify model, and the secrets of excellent product leadership by design (#003)

    Brendan has worked in the tech product space for 12 years and has recently returned to Australia, after six years in Sweden. Five of those he spent with Spotify during their hyper growth phase, first as an Agile Coach and then as the Product Manager for Spotify’s desktop client. Brendan has an eclectic mix of skills and experience, having worked as an Agile / Org Coach, Product Manager and Chief Product Officer. He's worked on mature platforms with millions of users (like Spotify for Mac / Windows), blue sky innovation features (like Spotify Running), as well as in the depths of technical infrastructure, with native client architecture and big data. Product Management / Product Ownership Agile and Lean Coaching Product Discovery / Innovation Organisational Design and Culture Leadership Coaching Brendan is particularly passionate about helping individuals, teams and organisations to accomplish their goals through working with and acknowledging the human side of work. Throughout his time at Spotify, Brendan had the honour of giving talks across Europe about Product Discovery and the Agile Coach role, telling stories through the lens of Spotify’s culture. Just prior to joining Organa Brendan worked at a non profit, mental health startup on a mission to bring personal growth to the masses and he joined Organa to bring lessons learned from Sweden to Australia as well wanting to be part of a company that shares the principles and ways of working I've come to love and admire. Show notes: https://devsingh.net/brendan-marsh-on-spotify-and-product-leadership-003/ Some of the questions I ask Brendan in this conversation Is there a shadow side associated with carrying that ex Spotify label? What is SAFE (Scaled Agile Framework) What did Spotify struggle with? What did Spotify get wrong along the way? What do you get asked the most? What do you wish people would ask about more? How, if at all, does the Spotify model foster leadership by design, and what can others learn from it? How do you compete with much larger and more powerful organisations? What do we give up by choosing innovation and product differentiation? Was the culture at Spotify caused by the model or was it just a correlation? Why did you decide to stop being an agile coach and start being a product owner? What was that experience like? Are product owner and product manager two different jobs? In your bio, it says that you’re particularly passionate about helping individuals, teams, and organizations to accomplish their goals. What is your experience in terms of being able to do these things through working with and acknowledging the human side of work, working as a coach and as a product manger? What is the human side of work? What does that mean? Did you experience of going from being a coach to a product owner and product manager mean that you had fewer opportunities to practice mastering yourself in the moment because of the nature of these roles or did it become more important? What are some of the most valuable lessons you’ve brought from Sweden back to Australia that you learned from observing mistakes, whether at Spotify or elsewhere, or making mistakes of your own? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leadbydesignshow.substack.com

    1h 36m
  7. Steven Ma on making work more human, how to fight fear with compassion, designing organisations and leadership for agility, and making the world better for future generations (#002)

    16/08/2021

    Steven Ma on making work more human, how to fight fear with compassion, designing organisations and leadership for agility, and making the world better for future generations (#002)

    Steven Ma lives and breathes agile, and has trained, evangelised, coached and directed Agile across a wide range of industries, both domestically and internationally. He is the Current Chief Purpose Officer at No Moss Co, and his personal mission is to make work more human. Steven co-designs organisations for empathy and agility; emphasising a more human purpose to work. His self-described super-powers are personal grit and endless energy; and he thrives in contexts where leaders desire change and share his agenda of growing people, building purpose and creating environments for incredible business outcomes. Show notes: https://devsingh.net/steven-ma-on-making-work-more-human-002 Some of the questions I ask Steven in this conversation What is the relationship between empathy and agility? Has the popularity of Agile been a good thing for leadership coaching or diluted the value and impact of it? Can you have one without the other (coaching for the benefit of an individual's development vs for the benefit of the organisation) to the extent where it becomes an issue where that lack of integration can start to fester? Why and how did you come up with your title Chief Purpose Officer, and what's your purpose these days? What made Steven a successful entrepreneur despite coming from a vulnerable, refugee background? How can leaders who might be stuck in the rut of risk aversion or attachment to accountability, escape that rut and inspire their own vision and imagination? What does it mean to lead by design? Should you design your organisational system first or your leadership first? How do you bring loving kindness and compassion into the design of your leadership in the face of pervasive systemic racism? About Dev Singh: Dev Singh (@DevSinghNet) has over a decade of experience working with established and aspiring organisational leaders to build stronger & more strategic business foundations, and to lead with greater impact and influence. Besides working with organisations all over Australia in over a dozen sectors, Dev has coached and consulted for entrepreneurs and executives in places as varied as Eastern Europe, Scandinavia, UK, Southeast Asia, North America, and Singapore. Dev has designed and delivered keynotes and workshops for hundreds of organisations worldwide on entrepreneurship, business strategy, leadership, branding & marketing, communication, influence and innovation, across a range of industries and sectors including Government, Financial Services, Retail, Professional Services, Non-Profit, Education, Technology & startups. Dev has a Bachelor of Business and a Bachelor of Medical Science, with a particular interest in Organisational Psychology and Behavioural Neuroscience. He’s also certified in Agile Coaching and Agile Leadership. Connect with Dev Singh: Visit the Lead by Design PODCAST: https://devsingh.net/lead-by-design-podcast Visit the Dev Singh BLOG: https://devsingh.net Follow Dev Singh on TWITTER: https://twitter.com/devsinghnet This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leadbydesignshow.substack.com

    1h 27m
  8. Dr. Anne Stenros on creative leadership, strategic design, the importance of heroes and sheroes and much more (#001)

    04/07/2021

    Dr. Anne Stenros on creative leadership, strategic design, the importance of heroes and sheroes and much more (#001)

    Dr. Anne Stenros on creative leadership, strategic design, the importance of heroes and sheroes, and what it takes to be a future-proof leader in a rapidly changing, complex and chaotic world Show Notes: https://devsingh.net/dr-anne-stenros-on-creative-leadership-and-strategic-design Dr. Anne Stenros (@CasaAnna) is a thought leader and an architect with a doctorate in technology. She has over 25 years of experience in Creative Leadership and Strategic Design. Between 2005 to 2015, she acted as the first Design Director at KONE Corporation, a world leading elevator and escalator company. In 2016 to 2018, she was appointed as the first ever Chief Design Officer CDO of a city, namely the city of Helsinki. She has also had a professorship in Creative Leadership at the Aalto University. She has participated as an expert role in many different EU forums, and she was the member of the World Design Capital WDC 2022 selection committee by World Design Organization WDO. Currently she is speaking, lecturing, writing, mentoring, and catalyzing change. She's curious about the future of cities, architecture, and urbanism. She believes in collaboration, co-creation, and creative collective. Some of the questions I ask Anne in this conversation: • Why do you think that fitting designers into a traditional and strict organizational model will kill their creative capacity? • What is design leadership? How is it different to not design leadership or any other leadership? Is there even a distinction or is every leadership actually design leadership? • What is the difference between design leadership and Creative Leadership? • Should all leaders be creative? And should leadership by default, be creative or is Creative Leadership something different? • Do you think it helped that you were a creative professional before and while there are some fundamental lessons that you got as a designer or as a creative professional that helped you be a better leader? • What can [emerging and aspiring leaders] learn from creative disciplines, or design or service design or strategic design that would help them become a better leader, even if they're not working in a creative field themselves?   About Dev Singh: Dev Singh (@DevSinghNet) has over a decade of experience working with established and aspiring organisational leaders to build stronger & more strategic business foundations, and to lead with greater impact and influence. Besides working with organisations all over Australia in over a dozen sectors, Dev has coached and consulted for entrepreneurs and executives in places as varied as Eastern Europe, Scandinavia, UK, Southeast Asia, North America, and Singapore. Dev has designed and delivered keynotes and workshops for hundreds of organisations worldwide on entrepreneurship, business strategy, leadership, branding & marketing, communication, influence and innovation, across a range of industries and sectors including Government, Financial Services, Retail, Professional Services, Non-Profit, Education, Technology & startups. Dev has a Bachelor of Business and a Bachelor of Medical Science, with a particular interest in Organisational Psychology and Behavioural Neuroscience. He’s also certified in Agile Coaching and Agile Leadership. Connect with Dev Singh: Visit the Lead by Design PODCAST: https://devsingh.net/lead-by-design-podcast Visit the Dev Singh BLOG: https://devsingh.net Follow Dev Singh on TWITTER: https://twitter.com/devsinghnet This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit leadbydesignshow.substack.com

    1h 16m

Ratings & Reviews

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Conversations about leadership, design, agility, innovation, and many things in between. leadbydesignshow.substack.com