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Technology Leadership Newsletter

Most AI projects fail before the first prompt

15 May 2026

Most AI projects fail before the first prompt

In a recent Expert session, Umbar Shakir, a Partner and EMEA Lead for AI at Gartner Consulting, made a point that stuck with us:

The number one reason AI initiatives fail is the problem statement.

Not the model, prompt, vendor, or the team's enthusiasm.

It is the problem statement.

That may sound oversimplified, but, as you will soon see, it explains a lot because organizations have a hard time distinguishing between problem statements and proposed solutions looking for a problem .

So, in today's featured guide, we bring you:

  1. The hidden danger of moving too fast
  2. What weak AI problem statements look like
  3. A simple AI problem statement template
  4. Weak vs strong: a practical example
  5. Five questions every AI problem statement should answer
  6. A leadership rule of thumb before funding AI work

Did you know

Many AI initiatives are approved before anyone has clearly defined what success would actually look like.

That is where the trouble starts, because everybody automatically assumes that AI underperforms. The real issue is that it performs against the wrong problem.

Therefore,

Before you build with AI…

Guide

Learn How to Define a Problem

This guide shows how senior technology leaders can turn vague AI ideas into sharper, testable business use cases. It also provides a practical problem statement template that your team can use before approving the next pilot.

Learn more →

Recommended reading

Book

What Business Leaders Still Get Wrong About Technology

Understanding technology is only half the challenge. The harder part is understanding the people who build it. Bridging the Gap is a practical guide for business leaders who want to work more effectively with technical teams, make better decisions, and reduce the misunderstandings that slow projects down.

Get your copy →

Academy News

Over the past few months, an increasing part of our work at CTO Academy has involved supporting senior leadership teams as they navigate the growing overlap between business strategy, technology, and AI.

Across industries, organisations are investing heavily in technology, but many leadership teams still lack the shared digital fluency needed to align decisions and unlock full value from those investments.

Alongside the continued growth of our Digital MBA, we’re excited to be developing a new generation of executive and corporate programmes focused on leadership capability, transformation, and AI-driven decision-making.

Visit our corporate page and/or get in touch to find out more.

Visit Corporate

Fresh from the Community Slack

Daryl is concerned about Google pushing local AI capabilities into Chrome automatically without opt-in. He wonders how this interacts with the governance policies of other members.

Sanjay has a contact seeking beta testers for a Kubernetes offering.

Nati is blown away by interaction models that move beyond turn-based AI interfaces by handling multimodal, real-time collaboration natively across audio, video, and text.

Franz posted about the npm package that was compromised, which is now spreading through other packages.

UPCOMING EVENT:

We're back in Amsterdam next month for an informal meetup with CTO Academy members and friends. Details and reservations here.

Join us

Watch our podcasts here or listen on Apple & Spotify

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