The Frontier Leader Show – AI Strategy, Leadership & Decision-Making for Senior Leaders

Eleven and a half years. That was one council’s estimate for sorting 800,000 legacy property files by hand, assuming they could find some poor soul willing to do it.

Sarah Heal, CEO of Information Leadership, helped them get it done with AI in a few weeks. And she’d be the first to tell you the speed is the least interesting part.

Sarah started out at Archives New Zealand and co-founded Information Leadership about 22 years ago, back when a memo could take a week or two to get from the bottom floor to the top floor.

Since then she’s been helping government and enterprise organisations get their information into a state they can trust. Information governance and AI readiness might sound dry but with Sarah, it really isn’t.

In this episode we get into:

• Security by obscurity, and why AI has quietly ended it
• The council job, and what happened once the files were sorted (roughly a quarter can now legally go in the bin)
• Leavers’ OneDrives full of sensitive staff data, and a weekly chore that went from up to two days to under an hour
• What human in the loop looks like when checking every file would put you straight back to doing it manually
• Where to start safely if you’ve been told to “do AI” with no further instructions
• Why Sarah thinks the next decade belongs to the business analyst. I’m married to one, so I’m not arguing.
• How Copilot’s PowerPoint slides went from underwhelming to astounding in about a year
• More sheep than people. Yes, it’s relevant.

If your organisation has twenty years of shared drives and someone upstairs has just asked for an AI strategy, this one’s for you.

Connect with Sarah:

Website: https://informationleadership.co.nz

LinkedIn: https://www.linkedin.com/in/sarahheal/

Book recommendation: "Reshuffle: Who wins when AI restacks the knowledge economy" by Sangeet Choudary

Time Stamps:

00:00 Intro

02:00 From Archives New Zealand to AI

04:52 Working faster, feeling less in control

08:19 Security by obscurity

09:38 800,000 files and an 11.5 year estimate

13:50 The so-what question

15:13 Leavers’ OneDrives and sensitive data

18:43 Where to start without exposing data

19:57 Human in the loop, done properly

22:35 AI adoption in New Zealand

25:20 Copilot at work, Claude at home

29:44 Three takeaways

Get your copy of the Multiply Method ✖️ It’s a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

What happens when an Olympic rower who measured progress in four-year cycles ends up running a tech company where it feels more like four minutes? Steve Rowbotham, Team GB bronze medallist and CEO of Navigator, joins me to talk about leading through that change, and what AI has actually done inside his business.

Steve spent 11 years as a professional rower, competing at two Olympic Games and winning bronze in the double sculls in Beijing. When his career ended at London 2012 he lost the identity that came with it, and he’s honest about how long that took to rebuild. He now leads a team of 35 at Navigator, a London travel audience platform that turns booking behaviour into consumer insight for brands well beyond travel.

In this episode we get into:

• Going from a sport that revolves entirely around you to a business that revolves around 35 other people, and why he loves that more than he expected
• The hard-coded platform Navigator set fire to, and what took its place
• A Fanta brief aimed at neo-hedonists (yes, that’s a real thing)
• Why he refuses to treat AI as a good or bad question, and how a non-technical founder finds the right layer to start with
• What changes when you’re marketing to someone’s AI agent rather than to them
• His three takeaways, including a book he treats as an operating manual
• And the thing he wanted to say before we finished. It might take some pressure off.

Steve’s a non-technical founder running a data business, which makes him a useful person to hear from if AI still feels like someone else’s specialism.

Connect with Steve:

Website: https://navigator.tech

LinkedIn: https://www.linkedin.com/in/steverowbotham/

Book mentioned: No Rules Rules: by Reed Hastings and Erin Meyer 

Time Stamps:

00:00 Intro

02:08 From Olympic rower to founder

04:15 Losing Steve the Olympian

05:26 From selfish athlete to team of 35

06:17 What Navigator actually does

10:46 The Fanta neo-hedonist brief

12:34 Setting fire to the old platform

14:52 AI doesn’t have to be binary

19:28 Licences, guardrails and tokens

22:11 A grant application in hours

23:32 Where the value really sits

27:00 Advertising to AI agents

29:54 Takeaway 1: No Rules Rules

30:45 Takeaway 2: Start with the end in mind

32:15 Takeaway 3: Only know your next step

34:57 Where to find Steve

36:02 Nobody knows what they’re doing

Get your copy of the Multiply Method ✖️ It’s a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

Jay Samit has spoken about AI in dozens of countries, and he says the mood in the room changed about six months ago. People stopped asking what AI can do and started asking what happens to their job.

In this episode, Jay Samit joins me to talk about his new book, The Second Act Advantage, and why he thinks decades of experience are worth more than most people give them credit for. He's a serial entrepreneur and former chairman of an AI company, and Wired once described his job as the coolest in the industry.

It's an optimistic conversation with the odd blunt moment, and a useful listen if you lead people who are wondering where they fit.

We get into:

✳️ The compliance professional who started posting on LinkedIn, and what landed in his account on day one

✳️ Retirement made sense when life expectancy was 70. Jay's case for what comes next

✳️ Where Jay thinks AI's blind spot is, and why it favours people with a few miles on the clock

✳️ The top ten iPhone apps from year one, and why two of them shape his optimism

✳️ His take on regulation, including the rules Jay says early AI researchers set themselves and what's since happened to them

✳️ A one-question investing quiz where the answer isn't Apple or Google

✳️ And a Ford training film with a deliberate mistake in it

Jay also writes a free Substack where he asks what figures from history would have made of AI. All links below.

Connect with Jay:

Website: https://jaysamit.com/

Substack: https://jaysamit.substack.com/

LinkedIn: https://www.linkedin.com/in/jaysamit

Instagram: https://www.instagram.com/jaysamit

YouTube: https://www.youtube.com/@jaysamitChannel

Book: The Second Act Advantage

Time Stamps:

00:00 Intro

01:28 Who is Jay Samit?

02:47 The mood in the room has changed

06:46 Is work really going optional?

12:08 What happens to middle management

15:05 How this compares to past disruptions

17:54 The best time to start

20:33 The tech company quiz

23:06 Does culture decide who wins?

29:07 Should AI be regulated?

35:54 What scares Jay about AI

38:27 Bespoke news and the misuse of AI

40:31 Art, risk and a painting a day

44:26 What the first iPhone apps tell us

46:14 Where to find Jay

Get your copy of the Multiply Method ✖️ It's a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI. www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

He holds two Guinness World Records for artificial intelligence. So why won't he put his own medical records anywhere near it?

In this episode, I'm joined by Dr Jonathan Schaeffer, the AI researcher whose checkers program Chinook beat the best humans alive and earned him a place in the Guinness Book of World Records twice over, for checkers and for poker.

Forty years into the field, he's now building something that runs against almost everything the big AI labs are selling: a private AI that lives on your own desktop and never sends your files anywhere.

We get into:

• Why he thinks the word "hallucination" is doing AI's PR for it
• The Star Trek computer that shaped how he's thought about AI for forty years, long before ChatGPT existed
• What actually happens to your data the moment you ask a chatbot a question, even if you never upload a file
• How Kind, the desktop AI he built, only answers from your own files and says "I don't know" rather than guessing
• The trillion dollar data centre race, and why he thinks most of it is solving the wrong problem
• And a shelf of 1990s book catalogues that Google can no longer find anywhere on the internet, but his laptop still can

Key takeaway: Jonathan's case for treating AI as augmented intelligence, an apprentice you're in charge of rather than an oracle you defer to, and why that distinction gets harder to hold on to every year AI gets better at sounding certain.

Connect with Jonathan:

Website: https://kind.synsira.com/

LinkedIn: https://www.linkedin.com/in/jonathan-schaeffer-phd-frsc-aaai-fellow-3318015/

Book: "The Games that Computers (and Humans) Play" https://link.amazon/B01308A4V

Time Stamps:

00:00 Intro

02:22 40 years watching AI evolve

04:06 The night ChatGPT changed everything

06:12 Star Trek's model for AI

08:38 The privacy trade you don't read

12:21 Kind vs Notebook LM

16:11 It's not just sensitive data

19:33 Fact checking his own book

25:10 Kind Shared, coming this fall

28:15 Why trust is AI's real problem

35:53 Three takeaways

Get your copy of the Multiply Method ✖️ It's a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: https://www.theaileaderlab.com

LinkedIn: https://www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

If you're weighing up whether hybrid working is worth the hassle, or how far you can actually push AI into your own operations, this episode was made for you.

Andy Firth, owner of Leeds digital agency Ascensor, joins Martin to talk through both changes at once. He took his business fully remote and rebuilt the whole business around Claude.

They get into:

• Why "three days in the office" quietly became three or four people in a 10,000 square foot building most Fridays, and what that was costing Ascensor in recruitment
• Claude going from a personal experiment to what Andy calls an additional member of the team, wired into HubSpot, Teamwork, Slack and N8N
• A BCG stat on the gap between what leaders say about AI and what their business actually does.
• The apprentice who built an AI driven World Cup results tracker running through Slack. Yes, really
• What made Andy stick with Claude over ChatGPT and Gemini, and why he thinks tool choice gets stickier the longer you leave it
• Why GEO and AEO matter more than SEO now, in Andy's view, and what "agentic commerce" could do to the way people buy things
• And Andy's three takeaways, including a book on how much of what we call decision making might not actually be up to us

Resources mentioned:

• The Brain by David Eagleman https://link.amazon/B0hQsDSDB
• Luciqo, the AI marketing intelligence platform Andy's involved with www.luciqo.ai

Connect with Andy:

Website: ascensor.com

LinkedIn: linkedin.com/in/andrewjfirth

Time Stamps:

00:00 Intro

01:20 Meet Andy and Ascensor

04:26 Why hybrid stopped working

09:13 Staying connected, remote

12:59 Claude as the tool of choice

15:44 The BCG alignment stat

20:15 Balancing freedom and safety

21:41 Why Claude over ChatGPT, Gemini

25:26 What clients make of it

29:11 GEO, AEO and agentic search

34:29 ChatGPT ads in conversations

35:51 Three takeaways

44:26 Find Andy and Ascensor

Get your copy of the Multiply Method ✖️ It's a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

One person in your business builds twenty AI agents and is accountable for everything they produce. Proud, or terrified?

Amanda spent two decades in workforce advisory, built and sold Newance, a US recruitment and people operations consultancy, and now writes on Substack about what's shifting underneath the headlines in companies and the people who work in them. Her argument is that the job is no longer the smallest unit a business gets organised around. The workflow is. And because that reclassification happens inside the same job titles, the employment numbers don't show it.

We get into:

• Why "will AI replace jobs" is the wrong lens, and what's actually being reclassified underneath it
• Cog work versus marquee talent. Same title in the same company, and a completely different deal underneath
• The OpenAI finding that 43.5% of job-specific ChatGPT tasks fall outside the person's own role, and what that does to accountability
• Whether the CTO and the CHRO end up being the same person
• A client who still keeps paper files, and why adoption is running slower than the model releases suggest
• What acqui-hiring actually means, and why trust is the thing some companies are now trying to buy back
• Grief. Not a word I expected in a conversation about workforce data.

Amanda's takeaway for the week is one I've been chewing on since we recorded: check the weather, not the headlines.

Connect with Amanda:

Website: https://www.amandadaering.com

Substack: https://amandadaering.substack.com

LinkedIn: https://www.linkedin.com/in/amandadaering/

Time Stamps:

02:26 Amanda's background

04:15 Jobs vs workflows: the atomic unit

05:33 Cog work and marquee talent

07:35 Scope creep and the 43.5% study

09:41 Twenty agents: proud or terrified?

12:18 Should the CTO and CHRO be one job?

14:38 Paper files and fifth-generation CEOs

17:39 Start with the business model

20:58 Decks to desks: the coexistence era

24:40 Anxiety, grief and AI-native ensembles

26:25 What acqui-hiring actually means

30:21 The orchestration layer and $10m PMs

32:47 Checking the weather

35:22 The deal underneath the job title

37:05 How Amanda uses AI

40:14 Takeaways

Get your copy of the Multiply Method ✖️ It's a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

Dubai has given its entire private sector a two year deadline to adopt agentic AI. No pilot phase.

Meanwhile, the honest answer to "what does your AI tool actually do for you" can often be a shrug, or three minutes of enthusiasm that never lands on anything specific.

That is where this conversation with Jeff Ross lives. Jeff has spent 25 years being sent into businesses that had come loose, hotel groups, retail chains and service organisations across three continents, with stints at Starwood, St Regis, Swissôtel, TUI and Apple Retail.

These days he runs Nexus Point Project Management from Dubai, helping owners across the UAE, the GCC and Southeast Asia get the important things done once growth has outpaced what the founder can hold in their own head.

We get into:

• Why Dubai's two year agentic AI mandate is different from every AI strategy document sitting in a drawer elsewhere
• The one line test Jeff uses on leaders: if you can't explain how your AI tool helps you, you're not ready for anything bigger
• What a post-acquisition integration between two of the biggest players in a Swiss market could look like with today's tools, instead of the manual pattern recognition it took at the time
• Why employees quietly resist big AI rollouts long before the rollout is even announced
• What Jeff still believes only a human leader can do, whatever the tools end up being capable of
• And a story about self-driving taxis, his 14 year old son, and why he trusts the cars more than some of the human drivers

The mandate is arriving whether leaders are ready or not. Readiness starts with being able to explain, in one sentence, what the tool in front of you is actually for.

Connect with Jeff:

LinkedIn: https://www.linkedin.com/in/jeffrossme/

Website: https://www.nexuspoint.me/

Timestamps:

00:00 Introduction to Leadership in an AI World

03:30 Jeff Ross: A Journey Through Hospitality and Business

05:46 AI Implementation in Dubai: A Bold Mandate

09:33 Challenges in Leadership and AI Adoption

12:05 Change Management: Lessons from Experience

16:33 Utilizing AI Tools for Business Efficiency

17:17 Transformative Potential of AI in Past Projects

19:07 Leveraging AI for Process Improvement

20:11 Embracing Technology in Education

22:03 Generational Perspectives on AI and Employment

24:10 Leadership in the Age of AI

27:54 Knowledge Retention in Organizations

30:43 Client Engagement and Ideal Partnerships

33:45 Leadership Ethos and AI Implementation

Get your copy of the Multiply Method ✖️ It's a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

Ask most businesses who actually owns AI and you get a pause, followed by a name and a caveat about how it isn't really that person's job. Jim Spignardo reckons that has about twelve months left to run.

Jim's the Director of Cloud Strategy and AI Enablement at ProArch, a global IT services and consulting firm, and he's the person doing that job inside his company.

He reports an assisted value figure of AI to his executive team every single month. It's gone from a few thousand dollars a month to somewhere around $75,000, across 160 licensed users in a company of roughly 400.

In this episode we get into:

• Why the twelve month clock, and why that person doesn't have to be a new hire or a full time role
• How he builds the baseline that makes a monthly ROI number possible, when nobody has ever measured what the work costs today
• Why governance is there to protect the organisation and not shackle it, and who belongs on the council
• The one toggle in agent builder that Jim tells everyone to switch off before anything else
• Why archived and untouched data quietly drags down the quality of what Copilot hands back
• What happened at ProArch when free Cowork credits became paid ones. He uses the word "riot"

Jim's book, The AI Turning Point, came out in March and there's a second one on the way.

Share this with whoever in your business has quietly been doing the AI job without the title.

Connect with Jim:

Website: https://spignardo.com/

LinkedIn: https://www.linkedin.com/in/spignardo/

Jim's Book: https://link.amazon/B0dNQNvL3

Timestamps:

00:00 Introduction to AI Leadership

02:09 Jim Spignardo's Role and Focus

04:06 The AI Turning Point Book Overview

07:18 Challenges of Legacy Systems and AI Integration

09:55 Measuring ROI in AI Adoption

12:47 The Importance of Governance in AI

18:10 Navigating Change in Organizations with AI

18:37 Navigating AI Governance and Strategy

19:27 Data Security in AI Implementation

21:52 Understanding AI Usage and Monitoring

23:19 The Future of AI: Risks and Opportunities

25:23 Public Sentiment on AI: A Complex Landscape

27:53 Key Takeaways for Business Leaders

Get your copy of the Multiply Method ✖️ It's a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

What happens to your AI-powered workflows if the model you built them on disappears overnight?

I'm on my own this week, catching leaders up on what actually happened in AI through July, because it was a genuinely packed month even by this year's standards.

In this episode:

• Why Fable 5 vanishing for two and a half weeks in June still matters even though it's back
• Satya Nadella's "reverse information paradox," and what he says every prompt is quietly costing you
• There's closed weight, and then open weight, and then full open source. All three explained with one car analogy
• China's most crowded month yet for open weight releases, and the distillation row that followed
• A letter fifty companies signed on open weight regulation this week. Anthropic wasn't one of them

Whether you're trying to work out what "open weight" actually means or you're just wondering what your backup plan is if your AI vendor gets cut off tomorrow, this one's for you.

Timestamps:

00:00 Introduction

01:57 Reverse Information Paradox

03:28 Open vs Closed Models

05:46 July Updates

06:54 The Emergence of Open Weighted Models

10:16 Closed or In-house?

12:15 Future of AI: Open Models vs. Frontier Models

Get your copy of the Multiply Method ✖️ It's a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.

AI can generate a thousand polished slides that say absolutely nothing. So what actually makes a leader worth listening to now?

Rob D. Willis went from producing top 10 records in Germany to coaching executives on narrative. He calls himself a strategic story producer, and the parallel holds up. An artist used to walk into his studio with an eight minute song and no chorus, and his job was working out what they were really trying to say. He does the same thing now for leaders at HelloFresh, Moneybox, Salesforce, Babbel and Pfizer.

Rob also hosts the fantastic Chief Story Officer podcast.

In this episode we get into:

• The pronoun pattern in Andy Burnham's first speech outside Number 10
• How to be strategic by answering Kendall Haven's three questions
• Why the investor deck grows from eight slides to forty, and what that says about being too close to your own idea
• What AI is genuinely good at for helping leaders with stories
• Three great things leaders can take away to become better storytellers
• And a scene from Margin Call that does more for executive communication than most presentation training

Key takeaway: the stories you need are already sitting inside your organisation. AI is unusually good at surfacing them but working out which ones matter is still your job.

Connect with Rob:

Website: https://robdwillis.com/

Chief Story Officer Podcast - Apple: https://podcasts.apple.com/gb/podcast/chief-story-officer/id1852972717

Chief Story Officer Podcast - Spotify : https://open.spotify.com/show/1SY7gFeUEMFZz9hCcoCd3G?si=f4ff0a957a1b4967

LinkedIn: https://www.linkedin.com/in/robdwillis/

Instagram: https://www.instagram.com/robdwillis

TikTok: https://www.tiktok.com/@robdwillis

YouTube: https://www.youtube.com/@strategic-stories

Time Stamps:

00:00 Welcome

02:33 From music studio to boardroom

05:32 What Burnham does with pronouns

08:08 When HR and compliance flatten it

10:11 Be strategic before structural

12:07 Eight slides became forty

13:59 Context, direction, action, consequence

16:56 How to open, and how not to

19:11 What AI is good at with stories

23:34 Rob's Obsidian and Claude setup

28:57 Three takeaways

Get your copy of the Multiply Method ✖️ It's a FREE roadmap walking you through how to multiply the capabilities of your people and your business with AI.

www.theaileaderlab.com/roadmap

Connect with Martin:

Websites: www.theaileaderlab.com

LinkedIn: www.linkedin.com/in/martinjwheatley

Subscribe to The Frontier Leader Show wherever you listen to podcasts.