When two priorities both matter, why do leaders feel such pressure to choose one? The day-to-day work needs attention, but so does the future. A team needs room to act, but it also needs direction.

Wendy Smith has spent more than 25 years studying these recurring tensions. She joins me to explore why an either/or decision can feel so satisfying in the moment, yet leave leaders facing the same problem again.

We look at what both/and thinking asks of us in practice, including the conversations that become possible when different teams see a challenge from different sides. Wendy brings examples from organisational change, strategy and AI, and challenges the idea that holding two priorities means settling for a halfway compromise.

In this episode, we explore:

• Why old and new priorities continue to compete as organisations change
• The four common organisational paradoxes Wendy studies
• How to spot the either/or question hidden in a difficult decision
• Why both/and thinking asks for more than meeting in the middle
• How listening reveals what each side actually needs
• The tension between business as usual and future strategy
• What AI reveals about fear, emotion and human judgement
• How to separate competing demands before connecting them
• Why a shared goal matters across organisational divides
• How guardrails and measures help sustain two priorities
• What Wendy means by balancing rather than finding a fixed balance

Wendy offers a practical starting point: name the tension, explore each side properly, then ask how you might accommodate both. It will not produce an easy answer to every decision. It can open up options that a quick choice would have kept out of view.

If your team keeps circling the same choice, this conversation may help you ask a better question.

Resources mentioned:

• Both/And Thinking by Wendy Smith and Maryanne Lewis
• Barry Johnson’s Polarity Map

Explore more leadership and team conversations: https://www.youtube.com/@thrivingculture

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#Leadership #BothAndThinking #ThrivingTeams

What separates a meaningful team conversation from another meeting where people simply exchange information?

In this Best Of episode of the Thriving Leaders Podcast, I revisit a standout moment from my conversation with Grant about the five skills behind better team conversations.

We explore why the quality of a conversation matters more than the amount of talking taking place and how greater presence, listening, courage and intention can help teams move beyond transactional exchanges.

You’ll hear us explore:

• Why more meetings do not necessarily lead to better communication
• What prevents people from being fully present
• The skills that create greater depth and purpose in team conversations
• Simple rituals that strengthen trust and connection
• How hybrid teams can bring more humanity into the way they work

If your team talks frequently but does not always reach the clarity, honesty or depth it needs, this Best Of episode offers a practical place to start.

Subscribe for more standout insights from the Thriving Leaders Podcast and practical ideas for creating stronger leaders, healthier cultures and high-performing teams.

Learn more about my work at Thriving Culture: https://thrivingculture.com.au

#teamcommunication #leadership #highperformingteams

Why do so many strategies sound compelling in the boardroom but struggle to shape what people actually do?

In this episode of the Thriving Leaders Podcast, I speak with Alicia McKay, an Aotearoa New Zealand-based writer, speaker and strategist who has spent 15 years advising leaders on strategy, change and leadership. She is also the author of From Strategy to Action, You Don’t Need an MBA and Local Legends.

In this direct and thought-provoking conversation, Alicia and I challenge familiar assumptions about strategy, leadership and collaboration. We also examine what may be lost when judgement and decision-making are increasingly handed to automated systems.

If you have ever watched a strong strategy lose momentum after the planning session, this conversation will give you a different way to understand why—and what you can do about it.

In this episode, we cover:

• How strategy is different in local government and the public sector than in corporate organisations
• Why strategy often loses momentum after the planning process
• How strategic thinking shows up in everyday leadership
• What leaders may misunderstand about people and change
• The transition from subject-matter expert to strategic leader
• What gets in the way of cross-functional collaboration
• How organisational systems influence behaviour
• The relationship between trust, agency and accountability
• What automation could mean for human judgement

Watch the full episode to hear Alicia’s refreshingly direct perspective on what it really takes to turn strategy into action.

About Alicia McKay

Alicia McKay is a writer, speaker and strategist based in Aotearoa New Zealand. She works with executive and elected leaders to improve strategic thinking, decision-making and leadership in complex environments.

Alicia is the author of:

From Strategy to Action: A Guide to Getting Shit Done in the Public Sector

You Don’t Need an MBA: Leadership Lessons That Cut Through the Crap

Local Legends: How to Make a Difference in Local Government

Resources and links

• Alicia McKay’s website
• About Alicia McKay
• Alicia McKay’s books
• You Don’t Need an MBA
• From Strategy to Action

Subscribe to the Thriving Leaders Podcast for practical conversations about leadership, team performance and creating thriving workplace cultures.

Why do capable people find it so difficult to ask for help?

Leo Bottary argues that strong teams treat asking for help as an act of resourcefulness—not an admission of weakness.

In this Best Of episode of the Thriving Leaders Podcast, Leo and I explore the connection between psychological safety, feedback and shared accountability. We discuss why team members can struggle to speak up, how a simple change in language can make asking for help feel more inviting, and what happens when feedback becomes everyone’s responsibility.

Leo also shares a memorable team exercise that demonstrates how difficult it is to improve when we are effectively working blind.

You’ll hear us explore:

– Why successful people view asking for help differently

– How to turn a request for help into an invitation

– Why teams need consistent feedback loops

– The role of trusted intent when giving and receiving feedback

– How preparation and shared expectations support teams under pressure

Leo Bottary is an author, speaker, facilitator and the founder and managing partner of Peernovation. His work explores how peers help one another learn, perform and achieve more together.

Watch the full conversation: https://youtu.be/DJa8pzThdjc

I’m Claire Gray, leadership and team facilitator, executive coach, keynote speaker and author of Thriving Leaders and Thriving Teams. Through the Thriving Leaders Podcast, I share practical ideas for building stronger leaders, healthier cultures and high-performing teams.

Learn more: https://thrivingculture.com.au

Subscribe for practical conversations about leadership, psychological safety, accountability and creating teams where people can do their best work.

#PsychologicalSafety #HighPerformingTeams #Leadership

How can teams disagree without damaging trust or making the conversation personal? Claire Gray and Dr Kaye Monk-Morgan explore how leaders can create healthier conflict and make honest challenge less risky.

In this Best Of episode of the Thriving Leaders Podcast, Kaye explains why people sometimes need explicit permission to disagree, why challenging an idea is different from challenging authority, and how shared language can help teams work through difficult conversations.

You will hear practical insights on:

– Inviting healthy challenge within a team

– Separating an idea from the person who raised it

– Avoiding groupthink without creating unnecessary conflict

– Using curiosity and shared language to depersonalise disagreement

– Creating courageous spaces for honest feedback

Dr Kaye Monk-Morgan is President and CEO of the Kansas Leadership Center. Claire Gray is a leadership and team facilitator, executive coach, speaker and author of Thriving Leaders and Thriving Teams.

Explore leadership programs, team development, coaching and more: https://www.thrivingculture.com.au

Subscribe for practical conversations about leadership, high-performing teams, psychological safety, accountability and workplace culture.

#HealthyConflict #PsychologicalSafety #Leadership

How can leaders build team trust when people think, communicate and work differently? Understanding different working styles helps teams turn potential friction into stronger performance.

In this Best Of conversation, I speak with Claire de Carteret from Gallup about the relationship between strengths, leadership bias and trust within teams.

Claire shares the example of a fast-paced leader who unconsciously judged candidates according to how quickly they walked and spoke. Recognising this bias helped her appreciate what a slower, more deliberative person could bring to the team, including deeper analysis and greater awareness of risk.

In this Best Of, we discuss:

- Why different working styles can create tension in teams

- How a leader’s strengths can become a source of bias

- Why cognitive diversity makes teams stronger

- How to identify complementary strengths and partnerships

- Why strengths-based leadership makes difficult conversations easier

- Why focusing on strengths does not mean ignoring weaknesses

Claire de Carteret is a leadership expert from Gallup. In this conversation, she shares practical insights into strengths-based leadership and how leaders can get the best from people whose natural approach differs from their own.

I’m Claire Gray, a leadership and team facilitator, executive coach, speaker and author of Thriving Leaders and Thriving Teams. Through Thriving Culture, I help leaders and teams unite, align and achieve.

Subscribe for practical conversations about leadership, high-performing teams, workplace culture, psychological safety and accountability:

https://www.youtube.com/@thrivingculture

Watch the complete conversation with Claire de Carteret:

https://youtu.be/wZFFB0NBVrM?si=X01gmOieAFenLIOD

Chapters

00:00 How to build trust quickly

01:00 The hidden bias towards speed

02:00 Seeing different working styles as advantages

03:00 Why differences strengthen teams

04:00 Leveraging strengths and team blind spots

05:00 Finding complementary partnerships

06:00 Strengths and difficult conversations

07:00 When feedback feels punitive

08:00 Strengths don’t mean ignoring weaknesses

#teamtrust #strengthsbasedleadership #highperformingteams

Most meetings are designed around content. Someone presents, everyone else listens, and contribution is invited at the end with: “Any questions?”

By then, it may be too late.

Chad Littlefield believes connection is not the warm-up before the real work. It is part of the work — particularly when leaders need people to think together, speak honestly and collaborate beyond their usual teams.

Chad is the co-founder and Chief Experience Officer of We and Me, a TEDx speaker, and the co-author with his late partner, Will Wise, of Ask Powerful Questions and How to Make Virtual Engagement Easy. He also created the We! Connect Cards, which are used in more than 80 countries.

We explore how leaders can invite contribution earlier, create connection without resorting to awkward or unrelated icebreakers, and design meetings that feel more purposeful from the moment people arrive.

We also talk about a challenge I see frequently in organisations: leaders may have strong relationships within their own functions, yet struggle to build the horizontal connections needed to deliver strategy. Chad shares a practical idea for helping those relationships continue after an offsite or senior leader forum — rather than leaving everyone with good intentions that disappear once they return to work.

In this episode, we cover:

• Why connection shapes the quality of the work that follows
• What changes when leaders design for contribution rather than passive listening
• How Chad’s Contribution Method rethinks the flow of a meeting
• Why “connection before content” is different from an icebreaker
• How a simple shift in format can change the energy in a room
• Why teams need the right amount of connection — not necessarily more
• How to extend cross-functional relationships beyond a one-off event
• The question Chad believes can keep a team learning

If you lead meetings, bring large groups together or want stronger collaboration across boundaries, Chad offers a different way to think about the time people spend together.

And he leaves us with a question that is worth returning to — as leaders, as teams and as human beings.

Chapters

• 00:00 – Why connection is part of the work
• 03:00 – Chad Littlefield’s work and why connection matters
• 04:20 – Where Chad’s interest in connection began
• 09:00 – Positive social risks and Chad’s first speaking opportunity
• 12:00 – Why small groups are the units of transformation
• 16:00 – The five-part Contribution Method
• 20:00 – Connection before content
• 23:00 – Designing content for contribution
• 27:00 – How to close a meeting with energy
• 29:00 – Applying the method in everyday meetings
• 40:00 – The minimum effective dose of team connection
• 45:00 – Making cross-functional connection continue after an event
• 48:00 – The question that keeps a team learning
• 49:30 – AI, speed and the value of slowing down
• 51:00 – Being purposeful about time away from work

Links and Resources:

• We and Me / Chad Littlefield
• We! Connect Cards
• Ask Powerful Questions by Will Wise and Chad Littlefield
• How to Make Virtual Engagement Easy by Chad Littlefield
• Explore more leadership resources from Thriving Culture