On the Subject of Leadership

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

1. A brief for a new chief executive is very often the last leader's failings, inverted.
2. A search can fail because the board never agreed on what it needed.
3. Psychometrics help against bias, but a director who hides behind them has abdicated part of the office.
4. Information about candidates is abundant; judgement is now the scarce thing.
5. The hardest thing for any board to see is its own behaviour.

Chapters

• (00:00) - Highlights, a note before we begin, and the introduction

Guest Links & References

• Malcolm Duncan on LinkedIn
• The Insight Group
• Kestria

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.

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Credits

Recorded remotely via Riverside

Music: The Hidden Thread by Roberto Prado / Artlist

In 2007 the directors of Centro approved accounts that classified some $1.5 billion of short-term liabilities as non-current. They had a chief financial officer, a finance team, and PricewaterhouseCoopers as auditors, yet the Federal Court found that they had failed in their duty of care, because the reading was the one task the law would not let them hand to anyone else. A survey by OnBoard, a vendor of board software, now reports that 92 per cent of directors use AI for board work, and the obvious use—having a model digest the pack—hands that reading to a machine. In this essay, released in audio format, I argue that an AI summary is the newest proxy for a director’s judgement, and that the remedy is an order of operations rather than abstinence.

In this article:

• The Corporations Act protects a director’s reliance on employees, advisers, fellow directors, and board committees, yet a language model is not on that list.
• Machine summaries attend unevenly to long documents, and their errors are likeliest where board packs tend to keep their bad news.
• Delegating the reading erodes the very sense of the company that a director needs in order to notice when something in the pack is wrong.
• A director who reads the pack and then asks a model what was missed is testing a judgement already formed, whereas one who asks the model to read it has surrendered that judgement.
• Uploading a board pack to a consumer chatbot may put at risk not only the company’s confidences but its legal privilege.

A thought to sit with: ‘Using AI well means questioning it after the reading, not before it—much less in place of it.’

Further reading:

• Lisanne Bainbridge, Ironies of Automation (1983)
• Raja Parasuraman and Dietrich H. Manzey, Complacency and Bias in Human Use of Automation: An Attentional Integration (2010)
• Nelson F. Liu et al., Lost in the Middle: How Language Models Use Long Contexts (2024)

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

1. An organisation that cannot say who may approve a decision optimises for non-decision, and the waste that follows looks like activity.
2. Running people at full utilisation produces gridlock rather than output; in trying to do more with less, organisations end up doing less with more.
3. Where goals are used for control, teams set deliberately low bars and get on with the work they believe matters.
4. 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.
5. 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

Guest Links & References

• Tim Newbold on LinkedIn
• OKR Quickstart
• Strategy Candy 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

LinkedIn: dr-robert-winter

X: @DrRobertWinter

Instagram: DrRobertWinter

Mastodon: social.winter.ink/@robert

YouTube: @OnTheSubjectOfLeadership

Credits

Recorded remotely via Riverside

Music: The Hidden Thread by Roberto Prado / Artlist

Australia’s National Microcredentials Framework obliges a provider to disclose fifteen things about a short course, down to the learner’s hours spent reading and on assessment, yet depth of learning—the mastery a learner actually reaches—is merely recommended, and may be estimated. The hours are compulsory; the mastery is optional. In this essay, released in audio format as the first in The Gate and the Room series, I argue that a certificate records the completion of a process rather than the formation of judgement, and that organisations which appoint on it have mistaken a legible signal for the thing it was meant to signal.

In this article:

• A certificate records that a defined process was completed to a defined standard on a defined day, which is useful to know but is not the capacity to exercise judgement.
• An executive who cannot assess a field personally reaches for the most legible signal available, which is rational for the individual yet corrosive for the institution.
• Credentials inflate to track demand for position rather than the difficulty of the work, until they record little beyond a fee paid and a process endured.
• Burke and Hume both treat judgement as something built by practice and comparison, which means it can be neither transferred nor purchased.
• A short course adds most to someone who already has a practice in which it can take root; the failure lies in sending someone without one and reading the certificate as proof that the gap is closed.

A thought to sit with: ‘You do not have judgement. You do it, repeatedly, usually in front of someone who will tell you when you have got it wrong.’

Further reading:

• Michael Spence, Job Market Signaling (1973)
• Randall Collins, The Credential Society: An Historical Sociology of Education and Stratification (1979)
• Gilbert Ryle, The Concept of Mind (1949)
• Leesa Wheelahan and Gavin Moodie, Gig Qualifications for the Gig Economy: Micro-Credentials and the ‘Hungry Mile’ (2022)

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

Guest Links & References

• LinkedIn — 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

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

LinkedIn: dr-robert-winter

X: @DrRobertWinter

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Mastodon: social.winter.ink/@robert

YouTube: @OnTheSubjectOfLeadership

Credits

Recorded remotely via Riverside

Music: The Hidden Thread by Roberto Prado / Artlist

Mintzberg’s diary work found half of observed management episodes concluding inside nine minutes, and later research shows that people compensate for interruption by working faster, at a price in stress, frustration, and effort that throughput never records. A manager or board watching only velocity therefore sees no problem at all. In this essay, released in audio format, I argue that the person who takes on eight things and ruins all eight is following the organisation’s specification rather than indulging a personality, because busyness is legible whereas judgement is not.

In this article:

• The cost of overload lies not in the tasks but in the switches between them, where the residue of unfinished work degrades whatever comes next.
• The interruptions that fragment a manager’s day are a product of how the work is designed, not of the appetites of the worker.
• What an organisation’s decision-makers attend to is, in effect, its strategy, which makes the calendar a more honest strategic document than the one on the shared drive.
• An executive carrying forty live commitments has not been overloaded by a strategic choice but spared one, and given the theatre of having made it instead.
• The number of consequential decisions a manager can make properly is a design parameter that the organisation sets, deliberately or by accident, and not one within the gift of the manager.

A thought to sit with: ‘A decision made in the eleven minutes between two other decisions is not a decision in this sense at all. It is a reflex, dressed in the clothing of authority, and the organisation will not discover the difference for eighteen months.’

Further reading:

• Mintzberg, The Nature of Managerial Work (1973)
• Simon, Designing Organisations for an Information-Rich World (1971)
• Ocasio, Towards an Attention-Based View of the Firm (1997)
• Perlow, The Time Famine: Toward a Sociology of Work Time (1999)

The Commonwealth supplies less than half the revenue of Australia's universities and sets very nearly all of their terms.

We have spent a decade arguing about fees, caps, international student numbers and research funding, and each of those arguments quietly settles the larger question — what universities are actually for — without ever putting it to a vote. Price a humanities degree high enough and you have made a claim about the worth of the humanities. You have simply made it with a spreadsheet rather than an argument.

Professor Alistair Noble has worked inside almost every model this country uses to answer that question: the large public research university, the private specialist college, the regional university, and now a small independent institute. In this conversation he declines the framing I brought him — that universities are becoming trade schools — and offers a better one. Then he shuts the door on his own argument for lighter regulation, and does it honestly.

Takeaways

1. Prestige in Australian higher education is a colonial inheritance wearing the costume of a quality ranking.
2. The question is not whether universities have become too vocational. It is what is being lost that nobody is counting.
3. "Regional Australia" is a category invented in capital cities for capital-city purposes, and a well-funded institution can stifle the culture that was already there.
4. Talent does not reliably out. Someone has to notice it and say so, or it is never converted.
5. Compliance is the price of doing business. It is a floor, not evidence of quality.
6. The case for lighter-touch regulation fails on trust — and the sector's own governance record is why.
7. The part of a university that does not scale is the part that matters.

Chapters

• (00:00) - Introduction

Guest Links & References

• Professor Alistair Noble - LinkedIn

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

LinkedIn: dr-robert-winter

X: @DrRobertWinter

Instagram: DrRobertWinter

Mastodon: social.winter.ink/@robert

YouTube: @OnTheSubjectOfLeadership

Credits

Recorded remotely via Riverside

Music: The Hidden Thread by Roberto Prado / Artlist

Every incentive system that fails is easy to criticise. The difficult ones are those that work.

In the late 1990s David Harvie sold for a firm that ran its Sydney floor as a concentric ring: new arrivals on the outside, moving inward as they succeeded, progressing through a hierarchy of birds toward the falcon. Individual numbers went up twice a day, visible to everyone. He reached the top tier and was flown to New York. He also, some time later, found himself unable to get out of bed. Asked to render a verdict on the system, he does not hedge: it worked.

This conversation follows what a person does with that experience. Harvie leads direct sales at Totality, formerly Saxo Australia, and has built a health venture for time-poor fathers alongside it. He and I studied leadership philosophy together as postgraduates, which makes him one of the few people I can ask which of those philosophies survived contact with a target — and which quietly died.

Takeaways

1. Authority conferred by rank is not the same currency as authority granted by the governed, and the two are not interchangeable.
2. An incentive system can succeed completely and still exact a cost its designers never measured.
3. The disciplines a leader keeps in private are not private; employees and children are both watching the actions.
4. Standards written by the people who must live under them outlast standards handed down — including when those people are five years old.
5. The obstacle to a fuller life is rarely time and usually priority, though that claim is easier to make from some positions than others.
6. Discipline is a mechanism; judgement is the context in which the mechanism is pointed at something.

Chapters

[00:00] Cold Open — Nothing to Do With Time
[01:17] Introduction — The Least Examined Discipline
[03:32] A Method Actor, and a Country Town
[14:01] Where the Texts Met a Feeling Already Held
[21:26] Revising the Model of Self
[26:47] The Thundering Herd — A System That Worked
[31:33] Becoming Coachable, Becoming a Coach
[37:14] Three Pillars an Under-Five Team Wrote
[42:24] The Drive Home That Became DADBODZ
[48:30] The Queue in Which the Father Comes Last
[53:34] Building Without Chevrons
[59:10] Self-Command as the First Plank
[1:08:24] Lightning Round — Alignment, Arrogance, Judgement

Guest Links & References

• linkedin.com/in/david-harvie/
• DadBodz
• Nexus Holistic Health

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

LinkedIn: dr-robert-winter

X: @DrRobertWinter

Instagram: DrRobertWinter

Mastodon: social.winter.ink/@robert

YouTube: @OnTheSubjectOfLeadership

Credits

Recorded remotely via Riverside

Music: The Hidden Thread by Roberto Prado / Artlist

For the better part of a decade the surveys have promised imminent transformation, and for the same decade the earnings impact has stayed flat. Jay Fontanini's argument is that this is not evidence of a fraud but the signature of a general-purpose technology mid-adoption — the dynamo was ready long before the factory was rebuilt around it. The complementary investment that matters most, he contends, is not better software. It is human capital, and at the centre of that, judgement.

Which raises the harder question the conversation works: if the models are now a near-substitute for the quick reasoning and rapid recall that peak early in a career, then the entire human premium falls on the accumulated, seasoned kind of intelligence that cannot be hurried into existence. Jay teaches executives through the structure of the medieval trivium on the principle that no stage can be skipped — and reports that they do not give up at the difficult foundations, but at the middle, where thinking with the tool actually begins.

Takeaways

• The flat productivity number is a phase, not a verdict — but a theory that explains any delay as unfinished co-invention is only honest if the complementary work is actually being done.
• Artificial intelligence substitutes for fluid intelligence, not crystallised. It is cheapest exactly where we were quickest, and no help at all where we were wise.
• Most AI-attributed layoffs are ordinary corporate bloat wearing a new excuse — and they sit in direct contradiction with the efficiency dip that genuine adoption requires.
• Executives do not abandon the learning at the grammar stage. They abandon at the dialectic, and leap to holding forth about a tool they have not learned to think with.
• Judgement is earned rather than learned: cumulative, progressive, and not compressible into a prompt library.
• Friction belongs in the workflow by design. A system may draft anything; it should be permitted to send nothing.
• The engineers built a language model, which puts the humanities on the ground floor of the most technical instrument in the building.

Chapters

Guest Links & References

• Writing and notes: jayfontanini.com
• LinkedIn: linkedin.com/in/jay-fontanini/
• Prediction Machines: The Simple Economics of Artificial Intelligence — Ajay Agrawal, Joshua Gans and Avi Goldfarb (2018). Jay's nomination for the one book to read before touching a prompt.
• From Strength to Strength: Finding Success, Happiness and Deep Purpose in the Second Half of Life — Arthur C. Brooks (2022), the source of the fluid and crystallised intelligence framing discussed in the episode.
• The Diversity Bonus: How Great Teams Pay Off in the Knowledge Economy — Scott E. Page (2017), on complementary skill in problem-solving teams.
• Superintelligence: Paths, Dangers, Strategies — Nick Bostrom (2014)

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

LinkedIn: dr-robert-winter

X: @DrRobertWinter

Instagram: DrRobertWinter

Mastodon: social.winter.ink/@robert

YouTube: @OnTheSubjectOfLeadership

Credits

Recorded remotely via Riverside

Music: The Hidden Thread by Roberto Prado / Artlist

The second essay in the Prior Obligations series, released as articles in audio format, follows a number from birth to dashboard. When a felt condition becomes a score out of one hundred, it acquires an owner, a target, and a budget — everything except a cure — and the question of which way its correlations actually run turns out to matter more than the score itself.

In This Article:

• A score is never merely descriptive; the moment it exists it acquires the apparatus of institutional life, and the apparatus acquires an interest in the condition's persistence.
• When a measure becomes a target it stops measuring; employees who notice their answers have consequences soften the answers.
• The headline correlations run at least as plausibly in reverse: the confident and secure adopt demanding tools, the anxious abstain.
• The score may be measuring the team, not the technology — where interpersonal risk is survivable, the anxieties are conversation topics.
• The exemplars are chosen for the legibility of their numbers, not the durability of their results; the metric nobody dashboarded was quality, and it reversed the flagship strategy when it finally arrived.

A Thought With Which To Sit: "A number is easier to own than a failure, which is why failures are so often converted into numbers."