Dig Deeper

About Dig Deeper

There's no one way to lead. Yet we need to find a way. Our own way. And it can be hard to get right. As we find our way to lead it can be useful to listen to how others found theirs. Each fortnight, I’ll share a rich, unhurried conversation with someone who’s leaned into and learned from the challenges of leadership, change, and life while staying true to themselves. You'll get to experience me doing what I do best: asking the surface-piercing questions to help people see what they couldn't see before. Including you. Learn more about my courses and get more resources at https://www.digbyscott.com/ And follow me on LinkedIn here: https://www.linkedin.com/in/digbyscott/

Publisher

Digby Scott

Category

business · business · education

Language

en

Explicit

Yes

First episode

3 Sept 2024

Latest episode

12 Oct 2026

Latest episodes

90 episodes in the feed.

1. 

   12 Oct 2026

   Gloriously Messy Humans, Honest Feedback, and Getting Out of the Way | Celena Harry

   Have you ever found out that something you were doing to help was actually getting in the way? You had good intent, and knew exactly what you were trying to do for your team. Then someone told you, in much kinder words, to get out of the way. This episode is about the gap between what you intend and what people actually experience (and, what to do when you find one of those gaps in your own leadership). Celena Harry and I get into how to go looking for that feedback without making a production of it, why the best work a leader does is often the work nobody sees, and what it takes to stop telling yourself the worst version of the story. You’ll learn: Why your intent matters far less than your impact, and how to tell the difference Three questions that close the gap between the impact you want and the impact you are actually having How to ask for feedback in a way that gets you something useful back Why the best work a leader does is often invisible, and how to get comfortable with that How perfectionism shows up as an inner critic, and what it costs the people around you How to work out whose opinion genuinely matters to you Celena Harry is Chief People Officer at Ando Insurance and previously held the same role at Mitre 10. She has spent more than two decades helping organisations grow through great leadership, strong culture, and a healthy dose of pragmatism. Away from work, Celena is a mum of two and stepmum of three talented young adults, and cat mum to a feline who has very clear views on household leadership. Proud to hail from West Auckland, she’s built her career on keeping things practical, people-focused, and refreshingly free of corporate jargon. Whether she’s talking leadership, culture transformation, or what it takes to create a fantastic workplace, Celena believes the best conversations are honest, human and grounded in real life. And if those conversations happen to be accompanied by a 90s rock soundtrack, even better. Timestamps: (00:00) - Introduction (02:22) - The feedback that changed how she leads (03:48) - What getting in the way actually looked like (05:17) - Handing over the stage, and what happened next (07:00) - Wind beneath my wings: the work nobody needs to know you did (09:34) - Why people are led by their leader, not by HR (11:59) - Getting braver, and what changed when she went contracting (15:38) - What Playcentre taught her about the human condition (17:57) - Separation, redundancy and Dare to Lead in 2020 (20:37) - How to catch the story you are telling yourself (22:57) - Dual awareness, and finding language for your own state (28:25) - Perfectionism, and who is actually in your arena (33:53) - Leading for impact when your impact is indirect (36:54) - The three questions that close the intent and impact gap (38:48) - A practical way to find out how you are landing (42:13) - Gloriously, beautifully messy humans (45:21) - Reflections You can find Celena at: LinkedIn: (https://www.linkedin.com/in/celenaharry/)https://www.linkedin.com/in/celenaharry/ (https://www.linkedin.com/in/celenaharry/) Check out my services and offerings (https://www.digbyscott.com/)https://www.digbyscott.com/ (https://www.digbyscott.com/) Subscribe to my newsletter (https://www.digbyscott.com/subscribe)https://www.digbyscott.com/subscribe (https://www.digbyscott.com/subscribe) Follow me on LinkedIn (https://www.linkedin.com/in/digbyscott/)https://www.linkedin.com/in/digbyscott/ (https://www.linkedin.com/in/digbyscott/)

2. 

   28 Sept 2026

   [Solocast] Answer the Question, Not the Brief

   When one of your people brings you work that's accurate, well researched and clearly argued, and it still goes nowhere, where do you look for the reason? At the decision maker who ignored the evidence? Or at what your person couldn't see from where they were sitting? In this solocast, I start with a CFO placement I lost early in my career as a recruitment consultant. I had the strongest candidate on the shortlist and still missed, because I'd answered the brief without asking what the client was really trying to solve. From there I look at research from Gerald Ferris and colleagues showing that intelligence and the ability to read a room are separate capabilities. That's why context is something you need to teach your people rather than hope they pick up. You'll come away with three things to keep in front of your people, and a question that might change what you hand over next. You'll learn: Why a strong shortlist still lost the CFO role, and the three questions that would have changed the outcome Why clever and savvy are separate capabilities, and what the research says about which one predicts performance How most people actually learn context, and why neither route counts as a development plan The three things your people need to weigh up to get an idea across the line: content, circumstances and consequences How to walk alongside your people while the work is still taking shape, rather than after it's failed Why handing over context does more for your people than handing over corrections The question to ask yourself about what you know and haven't said out loud Timestamps (00:00) Introduction (00:10) The CFO placement I got wrong (01:52) Answering the brief and missing the real question (02:09) When great work isn't enough (02:52) Clever people and astute people (03:38) Context is taught (04:25) Content, circumstances and consequences (05:22) Giving context rather than the answer (05:46) A question for you Check out my services and offerings https://www.digbyscott.com/ (https://www.digbyscott.com/) Subscribe to my newsletter https://www.digbyscott.com/thoughts#subscribe (https://www.digbyscott.com/thoughts#subscribe) Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/ (https://www.linkedin.com/in/digbyscott/)

3. 

   21 Sept 2026

   [Interview] Leading a City for Lasting Impact | David MacLennan

   What if the most powerful thing you can do to lift your team's performance isn't to add more, but to remove what's getting in the way? And what does a sheep meat trade ban in Mexico have to do with how one CEO is building a high-performing city? In this conversation, David MacLennan and I get into what 15 years of diplomacy teaches you about leading without authority, a trade crisis that became his most formative leadership moment, and a framework he's built his entire organisation around. We land somewhere worth sitting with: the job of a leader might be less about what you add and more about what you remove. David MacLennan is the CEO of the City of Vincent in Perth, Western Australia, named the second most livable city in Australia last year. He spent 15 years as an Australian diplomat with the Department of Foreign Affairs and Trade, with postings to Papua New Guinea, Mexico City, Lima, and London. Before joining local government, he was a senior leader in the Western Australian Department of Planning. He holds a Bachelor of Arts and a Master of Management from ANU, has been at the City of Vincent for seven and a half years, and has been a coach for 30 years. We get into: How a trade ban on Australian sheepmeat became the leadership lesson David still draws on today Why the CEO's job is best understood as pain management: finding and removing what stops people doing their best work How the City of Vincent gave a whole community permission to lead their own streets, and what that says about leadership at scale What it looks like to get an entire organisation into flow state, and how David accesses his own Why the problems in your work life never go away, and what that actually means for how you grow Timestamps: (00:00) - Introduction (01:40) - From small-town WA to diplomat: David's unlikely career arc (06:52) - The Mexico sheep meat crisis, and what no one saw coming (11:55) - The lesson that stayed: step up when no one else will (17:24) - Clever, creative, courageous: running a city with limited resources (21:11) - Town Teams and giving a whole community permission to lead (24:52) - Performance equals potential minus interference (29:41) - Getting an entire organisation into flow state (30:56) - How David accesses his own flow state (32:30) - From individual performance to a culture of high performance (37:44) - Reflections and where to find David You can find David MacLennan at: LinkedIn: https://www.linkedin.com/in/david-maclennan-35724334/ (https://www.linkedin.com/in/david-maclennan-35724334/) Check out my services and offerings https://www.digbyscott.com/ (https://www.digbyscott.com/) Subscribe to my newsletter https://www.digbyscott.com/subscribe (https://www.digbyscott.com/subscribe) Follow me on LinkedIn https://www.linkedin.com/in/digbyscott/ (https://www.linkedin.com/in/digbyscott/)

Who has been a guest on Dig Deeper

Names identified in recent episode analyses. Showing up to five guests.

• Kirsten Patterson
• Antonia Milkop
• Jennifer Garvey-Berger
• Jodi Willocks

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Spotify

5.0 / 5

13 ratings

Podcast Authority Score: 48 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

75

Social presence

0

YouTube

0

Engagement

51

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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