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AIBedtimeStories

(and Boardroom Nightmares)

Why Most Organisations Will Fail at AI and
What the Best Leaders Do Instead

Prof. Alexiei Dingli

Cover of AI Bedtime Stories and Boardroom Nightmares for Business Leaders by Professor Alexiei Dingli
“The meeting ended with the quiet satisfaction of an organisation that believed it had a strategy.”
It did not.

For CEOs, board members and senior leaders

AI failure
is a leadership failure.

AI rarely fails because the board cannot explain how the technology works. It fails because nobody owns the decision, vendors go unchallenged, pilots never scale, risk is discovered too late and people are treated as an afterthought. These six tools help leaders see those failures early and make better decisions before they become expensive.

01

The Myth-Nightmare Matrix

See whether confidence is supported by evidence, or whether the organisation is mistaking activity for readiness.

02

The AI Readiness Ladder

Identify the next capability you must build instead of funding another disconnected pilot.

03

The Governance Triangle

Bring ethics, regulation and accountability into one decision system before risk becomes a scandal.

04

The AI Band-Aid Method

Choose one painful problem, prove value quickly and learn what must change before scaling.

05

The Vendor Credibility Filter

Test evidence, risk and credibility before enthusiasm turns into a contract.

06

The Workforce Transition

Decide which roles to augment, redesign, protect or develop before change is imposed on your people.

The reading experience

Seventeen evenings. Seventeen decisions leaders cannot avoid.

Each evening focuses on one decision that can protect value, reduce risk or stop the organisation from falling behind. The aim is not to turn leaders into technologists, but to help them ask sharper questions and recognise weak answers.

01

The Revolution That Looked Optional

Because treating AI as an optional upgrade gives faster-moving competitors time you will not recover.

02

The Assets Nobody Counted

Because data volume means little if leaders cannot trust it, reach it or turn it into decisions.

03

Saying AI-First While Staying Last

Because announcements, pilots and activity can create the illusion of progress while capability remains weak.

04

The AI Wild West Kicking Down the Door

Because the wrong vendor can lock the organisation into cost, risk and dependency before the board sees the evidence.

05

Hackers with Algorithms and No Sleep Cycle

Because AI allows attackers to scale deception faster than traditional controls and approval routines can respond.

06

When Your Algorithm Becomes the Scandal

Because an opaque algorithm can become a public scandal long before it appears as a technical problem.

07

Regulation Arrives with a Flashlight

Because regulation exposes whether governance is real or merely written in a policy document.

08

The Talent Shortage You Created

Because cutting people before redesigning work destroys the knowledge needed to make AI useful.

09

The Band-Aid That Starts the Surgery

Because the first pilot should solve a painful problem and reveal what must change, not become another demonstration.

10

The First 90 Days of Serious Leadership

Because the first 90 days determine whether AI becomes a governed business priority or another stalled initiative.

11

Spotting an AI Charlatan Before They Invoice You

Because leaders need a practical way to separate evidence from confidence before signing the contract.

12

Training People Before the Jobs Disappear

Because generic AI awareness does not change performance, behaviour or accountability.

13

Ethics as a Competitive Edge, Not a Press Release

Because trust, transparency and fairness influence whether customers, employees and regulators allow AI to scale.

14

When the Smartphone Stops Being the Interface

Because new interfaces can make existing customer journeys and operating models obsolete faster than expected.

15

Websites Are Dying, Agents Are Taking Over

Because AI agents may soon decide which organisations are discovered, compared and chosen.

16

Generative AI: Laziness, Application, or Leapfrogging?

Because convenience creates little advantage unless it develops new capability and better judgement.

17

Business Models That Shed Their Skin

Because the largest AI gains will come from changing how the business creates value, not merely reducing cost.

About the author

Written by Professor Alexiei Dingli.

Professor Alexiei Dingli has spent more than two decades advising governments, boards and senior executives on artificial intelligence, strategy and governance. This book turns that experience into a practical guide for leaders who must make consequential AI decisions without hiding behind technical language or waiting for certainty.

25+years in artificial intelligence
200+peer-reviewed publications
Globalboard and government advisory work

Before publication

The most dangerous sentence in any boardroom is:“We have time.”

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