On the Subject of Leadership

About On the Subject of Leadership

On the Subject of Leadership is a series of conversations about how organisations are actually led, managed, and governed—the kind usually held behind closed doors, here held out loud. Each episode, I sit down with an executive, director, founder, or scholar who has carried real responsibility, and we talk through what they have seen: the decisions nobody takes, the frameworks that meet real organisations, the gap between what is said in the boardroom and what is said in the corridor afterwards. The conversations are curious rather than combative, unhurried, and grounded in the research where the research has something to say. The result is a seat in the room for the conversations that shape organisations but are rarely heard. If you lead people, sit on a board, or simply want to know what is said when it matters, this is for you.

Publisher

Dr Robert N. Winter

Category

business · society & culture

Language

en

Explicit

No

First episode

7 Feb 2026

Latest episode

20 Oct 2026

Latest episodes

23 episodes in the feed.

1. 

   20 Oct 2026

   Malcolm Duncan: Reality Versus Aspiration

   Charisma is the most overrated quality in an executive, says Malcolm Duncan, and it is usually confused with leadership. After nearly four decades in executive search, and years spent assessing boards and leadership teams that are not hiring anyone, he explains why a search shows what an organisation would like to be, while an assessment shows what it is. In this episode: Takeaways A brief for a new chief executive is very often the last leader's failings, inverted. A search can fail because the board never agreed on what it needed. Psychometrics help against bias, but a director who hides behind them has abdicated part of the office. Information about candidates is abundant; judgement is now the scarce thing. The hardest thing for any board to see is its own behaviour. Chapters (00:00) - Highlights, a note before we begin, and the introduction (03:27) - What a search shows, and what an assessment reveals (08:38) - The brief describes the last leader's failings, inverted (13:13) - The briefs worth declining (18:30) - Judgement, confidence, and a board that could not agree (26:49) - Psychometrics, references, and the transfer of responsibility (32:07) - From scarce information to scarce judgement (40:10) - Leaders across sectors, and the rise of the professional director (47:46) - What a board cannot see in itself, and why six years is enough (54:29) - What separates a good chair (58:27) - Lightning round Guest Links & References Malcolm Duncan on LinkedIn (https://www.linkedin.com/in/malcolm-duncan-891a01/) The Insight Group (https://www.insightgroup.com.au/) Kestria (https://www.kestria.com/) About the Show On the Subject of Leadership is a series of conversations about how organisations are actually led, managed, and governed—the kind usually held behind closed doors, here held out loud. Each episode is an unhurried conversation with an executive, director, founder, or scholar who has carried real responsibility, about what they have seen: the decisions nobody takes, what becomes of frameworks when they meet real organisations, and the gap between what is said in the boardroom and what is said in the corridor afterwards. The conversations are curious rather than combative, and grounded in the research where the research has something to say. A seat in the room for the conversations that shape organisations but are rarely heard. For people who are sceptical of easy answers. Hosted by Dr Robert N. Winter. Subscribe / Follow Newsletter / Website: robert.winter.ink (https://robert.winter.ink) LinkedIn: dr-robert-winter (https://www.linkedin.com/in/dr-robert-winter/) X: @DrRobertWinter (https://x.com/DrRobertWinter) Instagram: DrRobertWinter (https://www.instagram.com/drrobertwinter/) Mastodon: social.winter.ink/@robert (https://social.winter.ink/@robert) YouTube: @OnTheSubjectOfLeadership (https://www.youtube.com/@OnTheSubjectOfLeadership) Credits Recorded remotely via Riverside Music: The Hidden Thread by Roberto Prado / Artlist

2. 

   6 Oct 2026

   Tim Newbold: Doing Less with More

   Management has a long habit of inventing instruments to turn intention into action, and an equally long habit of watching each one harden into paperwork. When it happens, we blame the organisation rather than the instrument. Tim Newbold, founder of OKR Quickstart, has spent the better part of a decade coaching organisations through Objectives and Key Results, and he has watched more of these rollouts succeed and fail than most people will see in a career. His view is that the tool is rarely the problem. What fails is the organisation around it: leaders who use goals to tighten control, teams run so close to capacity that nothing can improve, and a culture in which nobody will put their name to a decision. From his first internship, writing specifications that never became working systems, to the clients he now turns away, Tim explains why busy organisations get less done, why people set low targets on purpose, and why the most useful thing a manager can give a team is permission to say no. It is a practitioner's account, frank about its own failures, and it leaves open a question worth sitting with: if every failure belongs to the culture, what would it look like for the instrument itself to be wrong? Takeaways An organisation that cannot say who may approve a decision optimises for non-decision, and the waste that follows looks like activity. Running people at full utilisation produces gridlock rather than output; in trying to do more with less, organisations end up doing less with more. Where goals are used for control, teams set deliberately low bars and get on with the work they believe matters. Saying no is a gift a leader can give a team, but only when the team understands the strategy well enough to know what to refuse. Make someone's job depend on hitting a target and the number will be hit, whether by gaming the system or something worse. Chapters (00:00) - Highlights, and why management instruments harden into paperwork (04:48) - Eighteen years of specifications that never shipped (09:57) - Nobody teaches leaders to lead, and tenure shows it (15:31) - Fragile by design: control and the view from the top (21:27) - Lean is not the same as fully utilised (29:49) - Busy work, and the gift of saying no (38:51) - Escalation, borrowed authority, and whose fault it is (48:01) - Making space: problems, capacity and the time audit (53:00) - When a measure becomes someone's job (57:26) - A strategic house is not a strategy (01:08:06) - Lightning round: one objective, Drucker over Grove, and OKR theatre Guest Links & References Tim Newbold on LinkedIn (https://www.linkedin.com/in/timnewbold/) OKR Quickstart (https://okrquickstart.com/) Strategy Candy Podcast (https://okrquickstart.com/podcast/) L. David Marquet, Turn the Ship Around! (2012) Peter M. Senge, The Fifth Discipline (1990) Peter F. Drucker, The Practice of Management (1954) About the Show On the Subject of Leadership is a long-form interview series, with a written companion, on governance, organisational culture, and how decisions are actually made. Guests are challenged rather than affirmed, and the argument continues in writing after the recording stops. For people who are sceptical of easy answers. Hosted by Dr Robert N. Winter. Subscribe / Follow Newsletter / Website: robert.winter.ink (https://robert.winter.ink) LinkedIn: dr-robert-winter (https://www.linkedin.com/in/dr-robert-winter/) X: @DrRobertWinter (https://x.com/DrRobertWinter) Instagram: DrRobertWinter (https://www.instagram.com/drrobertwinter/) Mastodon: social.winter.ink/@robert (https://social.winter.ink/@robert) YouTube: @OnTheSubjectOfLeadership (https://www.youtube.com/@OnTheSubjectOfLeadership) Credits Recorded remotely via Riverside Music: The Hidden Thread by Roberto Prado / Artlist

3. 

   8 Sept 2026

   Pamela Wyatt: Organisations Don't Change Because They're Criticised

   No organisation matches the brochure. The question is what you do about the gap — and whether you have any right to. International development runs on a settled principle: reform must be owned by the government that enacts it, or it will not survive the funding. The outsider advises. The sovereign decides. Adaptation is the professional virtue and imposition the professional sin. The difficulty is that the sector is also, unavoidably, in the business of changing things. My guest this week has spent a career on both sides of that contradiction — and, in the course of an hour, states a principle of deference and then describes several occasions on which she overruled it. Pamela Wyatt began in Australian retail banking and established ANZ's offshore operations hub in Manila. She spent close to a decade at the Asian Development Bank, six years of it negotiating governance reform with Pacific governments, with private sector work across Central Asia. She led the Bank's Gender Task Force, examining her own employer's record and reporting to its vice-presidents. She is now Head of Business Transformation for Asia-Pacific at DT Global — the delivery side of the industry she once financed. Takeaways Being the outsider is a working method, not a handicap: it licenses the basic question that a room of experts has stopped asking. Seating, titles and forms of address are not the packaging of an institution. They are how it assigns standing — and moving someone to the table is a redistribution, not a courtesy. Not everyone wants the seat you think they are entitled to. Some of the chairs against the wall are protecting the people in them. A quota that is loosest at the most senior levels is not a badly designed instrument. It is a well-designed one, if the purpose is to be seen to have quotas. Organisations do not change because they are criticised. They change when enough people become uncomfortable — which means the report may be the by-product and the interviews the intervention. Growing sustainable change and delivering change are two different things, and funding follows the one that can be measured inside a programme cycle. Adaptability as a leadership style has an exception clause, and everything interesting is in the exception. Chapters (00:00) - The Advice That Sounds Right and Is Wrong (01:19) - A Word Before We Begin (02:02) - Introduction: Leadership Where Authority Runs Out (05:09) - Your Leader Is Part of Your Family (07:33) - A Career That Resists the Box (11:00) - Not Everybody Wants to Lead (15:09) - Imagine the Room Is Empty (17:06) - Sixty-Seven Nationalities and the Pull of Home (21:10) - What the Translator Takes Away (25:30) - No Organisation Matches the Brochure (28:46) - Some People Want the Chair Against the Wall (30:32) - Credibility Is Trust, and PNG Was a Message (37:22) - Tajikistan Is Not Tonga (39:07) - Adaptation, or Normalising What Should Not Be (43:57) - Grow Change, Don't Deliver It (48:35) - The Mouse They Had Never Used (50:46) - Holding the Mirror to Your Own Employer (57:02) - The Pipeline Problem and the Courage of Conviction (00:17) - Hearts and Minds, or Just the Number (01:57) - Lightning Round Guest Links & References LinkedIn — https://www.linkedin.com/in/pamelawyatt01/ (https://www.linkedin.com/in/pamelawyatt01/) On gender-responsive budgeting in Fiji — a short ADB piece in which Wyatt sets out how gender analysis is embedded in the budget cycle. Useful background to the second half of this conversation: https://www.youtube.com/watch?v=cS-z_cF3VUY (https://www.youtube.com/watch?v=cS-z_cF3VUY) About the Show Long-form conversations for people who carry responsibility. No slogans — clear thinking on authority, judgement, coordination, and accountability under real constraints. Hosted by Dr Robert N. Winter. Subscribe / Follow Newsletter / Website: robert.winter.ink (https://robert.winter.ink) LinkedIn: dr-robert-winter (https://www.linkedin.com/in/dr-robert-winter/) X: @DrRobertWinter (https://x.com/DrRobertWinter) Instagram: DrRobertWinter (https://www.instagram.com/drrobertwinter/) Mastodon: social.winter.ink/@robert (https://social.winter.ink/@robert) YouTube: @OnTheSubjectOfLeadership (https://www.youtube.com/@OnTheSubjectOfLeadership) Credits Recorded remotely via Riverside Music: The Hidden Thread by Roberto Prado / Artlist

Who has been a guest on On the Subject of Leadership

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

• Alistair Noble
• David Harvie
• Jay Fontanini
• Brett Raven
• Jarrod Myers

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1 ratings

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