Leaders in Conversation Series 2: Facing the uncomfortable side of ourselves.

Simon Cookson
5 min readSep 20, 2020

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What is Leaders in Conversation?

Leaders in Conversation is an online community exploring more human ways to work. Through a thriving Linkedin Group and the live online conversation series, hundreds of leaders around the world share their insights on how to harness our humanness in digitally dominant workplaces.

If we wish to be big hearted leaders who encourage human centred working; what do we do when faced with the messy, chaotic and uncomfortable side of humanness?

Our uncomfortable side is the theme for series 2.

We start with the cost of success and burn out, then in Episode 2 we look at how we might be making things worse when we try to get the best from people. Episode 3 explores defeat, moving on and how exposing that can feel. Then episode 4 is a practical session all about fear and leading when scared.

Episode 5 is a conversation about how copying what others do, trying to mimic the success of others is squashing innovation and success. We then round off the series in episode 6 with a truly unique experience. If you’re looking to lead with authenticity, bring more of your true self to work; then episode 6 will give you a whole new way to explore your authentic self.

Free tickets to join all 6 conversations can be booked in Eventbrite

Being human is complex, this complexity includes those parts of human nature that seem hard to deal with in the workplace. Navigating, managing and overcoming conflict, division and disengagement takes time and energy. These are the things that make the ‘people piece’ of any strategy so awkward and tricky.

Yet we know to lead with integrity and encourage engaged, committed and innovative working we need to embrace our whole selves; grow a human centred, high trust culture. Therefore, we must face the more uncomfortable side of ourselves.

Series 2 has gathered 6 international guests to help us discover what we gain by facing these difficult to manage elements of humanness?

Book your tickets to join us live and take part in the conversation with our wonderful guests.

Episode 1: Get Over Yourself with Dan Kirby

Wed, October 7th, 17:00–18:00 BST

Stop the unhelpful bullshit you tell yourself about leadership and business.

Entrepreneur, founder and innovator Dan Kirby will share his frank and honest reflections on his experiences of leading the Tech Dept; MCing the tech off; and setting up getahead festival. Our conversation will cover the highs of being filmed as his alter ego MC Danimal to the lows of burnout, depression and self-sabotage. Dan will get you thinking deeper about the cost of success and what it really means to be a human at work.

During this live conversation there will be an opportunity to ask Dan questions about his experiences. Expect honesty, strong language and dark humour.

Episode 2: How leaders sabotage success with Dr Terri Simpkin

Wed, 14th October, 17:00–18:00 BST

Discover how the way you manage performance could be sabotaging the success of your teams and business.

Imposter Syndrome is as much an organisational issue as it is an individual one. Processes and procedures around recruitment, objective setting, performance management and feedback exasperate imposter feelings.

Terri has discovered the fail fast, learn fast culture in technology lead businesses; alongside the constant background level of uncertainty in the world is fuelling a perfect breeding ground for the Imposter Phenomenon and strangling innovation and leadership potential.

Episode 3: What’s lost by fitting in with Veronica Fossa

What happens when fitting in drives your decisions & shapes your business?

Wed, 21st October, 17:00–18:00 BST

Veronica Fossa is a multi–passionate entrepreneur who has focussed her work around the food culture at work. Tonight Veronica has agreed to share her experiences of closing down her consultancy business. She will step us though what failure has taught her about herself, her fear of being an outsider and the crucial role moving on plays in every leader’s journey.

This episode will be ideal of those feeling uncertain about the path their business is currently taking.

Episode 4: leading scared

What fear in leadership looks like & how to overcome it.

Wed, 28th October, 17:00–18:00 GMT

During this live conversation with entrepreneur, author and blogger Elizabeth Shassere, you will uncover how fear might be affecting you as a leader and what you can do to regain control over the fears that may be affecting your leadership. There will be an opportunity to ask Elizabeth questions about her experiences and seek direct advice.

A key theme will be how to recognise fear in others; and in particular what practical steps you can take when you recognise that your leaders are struggling with fear.

Episode 5: the uncomfortable truth about success

In this live conversation with founder, strategist & TedX speaker Alex Smith we’ll explore why success comes from trusting yourself.

Wed, 4th November, 17:00–18:00 GMT

Right now our world is packed with challenges that are forcing us to rewrite business strategies and pivot our plans. To help leaders find the answers, there is an army of consultants, a huge library of methodologies and an ocean of data on the market and your competitors.

In this live conversation Alex presents the idea that ultimately none of that matters and true success comes from trusting yourself. Whatever challenge your business is facing, stop trying to mimic what others have done, don’t follow your competition with envious eyes, stop thinking you need to think, act, look a certain way to be successful.

Episode 6: the authenticity challenge

Leadership in the workplace starts with personal authenticity.

Wed, 11th November, 17:00–18:00 GMT

The workplace can force us to fragment who we really are. We cover up our true selves and present an artificial ‘work persona’ so we can fit in or match what’s expected. This impacts connection, as other people sense something is hidden, lowering trust and engagement.

In this live conversation Fateme will share how her innovative use of storytelling, poetry and heART helps leaders and teams tap into their creativity, improve trust and find new ways to to lead with integrity and authenticity.

Who are the hosts of Leaders in Conversation?

Leaders in Conversation is a transatlantic initiative, co-hosted by two leaders who know that people and relationships make all the difference when it comes to solving today’s big business challenges.

Amanda Cookson, UK

Coach and Founder of Northern Value Creators. With over 20 years experience in the creative and Edu-Tech sectors, leading award winning multi-site teams. Amanda combines this experience with accredited coaching practice, helping businesses thrive by focusing on their people.

Ken Blackwell, USA

For 24 years Ken has had the privilege to help leaders and teams from some amazing companies. Those companies range from big to small, in a variety of industries, across the U.S. and around the world. Ken speaks and presents on team and leadership development, coaching, and has appeared as a guest on Comcast Network’s Money Matters and ABC’s Good Morning America.

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