Barry AI

Leadership in the age of AI

Think better.
Decide better.
Lead better.

Turn AI into a thinking partner. Strengthen your judgment, create space to lead, and build an organization that performs better.

Keynotes, workshops, and executive coaching designed by Barry O’Reilly, plus a practical approach to measuring what improves because of AI.

Explore ways to work together Start with the book

For CEOs, executive teams, senior leaders, and founders navigating consequential decisions.

WORK TOGETHER

Build decision advantage.
Choose your starting point.

Inspire a new perspective, work through a live challenge, change your leadership habits, or understand the outcomes of your AI investment.

01 / Keynotes

A new perspective
on leadership.

Give your audience a new perspective on executive effectiveness. Barry shows how combining human and machine intelligence can create thinking space, strengthen judgment, and reshape how decisions move through an organization.

  • Build better judgment, speed, and results with human and machine intelligence
  • Move from personal productivity to leadership performance
  • Build decision advantage and lead the change yourself

For conferences, leadership events, and executive offsites.

Book Barry for a keynote

02 / Workshops

Put better thinking
to work.

Bring a live leadership challenge. In a facilitated executive lab, your team will frame the decision, use AI as a thinking partner, and pressure test the recommendation before making a commitment.

  • A decision brief with evidence, alternatives, and trade-offs
  • A clearer allocation of human and AI responsibilities
  • A workflow experiment with an outcome to measure

For executive teams ready to learn through real work.

Discuss a workshop

03 / Executive coaching

Change how you
think, decide, and lead.

Work directly with Barry, individually or in an executive cohort. Across five sessions, redesign how you work, think, communicate, and build capability in others. Test the changes in real work between sessions.

  • A personal leadership system built around your strengths
  • Repeatable decision and communication practices
  • A 90-day plan to carry new behaviors into your team

For leaders who want lasting changes in how they work.

Explore coaching programs

04 / Measure AI Outcomes

Know what’s
getting better.

Connect the AI conversation to organizational performance. Explore an assessment and research pilot focused on changes in work, decisions, leadership capacity, and business outcomes.

  • Establish a meaningful baseline
  • Identify observable changes in performance
  • Use evidence to decide what to change next

For leaders accountable for the value of AI investment.

Explore Measure AI Outcomes

Productivity · Performance · Presence

Less friction.
More effective leadership.

The capacity you create matters when it changes the quality of your decisions and how you show up for people.

Productivity

Create thinking space.

Reduce searching, reformatting, and repeatedly rebuilding context. Reinvest that attention in work where your judgment matters.

Performance

Make stronger decisions.

Frame choices clearly, distinguish evidence from assumptions, and examine the strongest case against your preferred option.

Presence

Show up ready to lead.

Arrive prepared, listen closely, coach with better questions, and bring clarity to consequential conversations.

The work behind the shift

Make AI part of your
leadership practice.

Better thinking becomes valuable when it changes what happens before a decision, in the room, and after people leave.

Before

Arrive ready to decide.

Clarify the choice. Retrieve the context that matters. Test the assumptions most likely to fail and prepare for the questions you need to answer.

During

Be present for the work.

Focus on judgment, challenge, and trade-offs. Make the recommendation, evidence, and uncertainty visible so others can assess your thinking.

After

Turn decisions into learning.

Preserve the reasoning, ownership, and next steps. Connect what you learned to the next conversation, and revise your approach as evidence changes.

Real Leaders. Real Shifts.


“Artificial Organizations is a practical guide for leaders who want AI to improve performance—not just productivity. Barry’s sessions create clearer judgment, better decisions, and stronger organizations.”
John Marcante Former CIO, Vanguard U.S. CIO in Residence, Deloitte

“The Artificial Organizations program helps leaders like me unlock our true potential in a psychologically safe environment that promotes true learning by doing!”
Misty Shafer Sterne VP, Commercial Technology American Airlines

“Artificial Organizations gives technology executives a practical blueprint to turn AI into sharper decisions, stronger teams, and real operating leverage at scale.”
Stephen Franchetti CIO, Samsara Former CIO, Slack

“The real shift wasn’t adopting new tools. It was changing how leaders made decisions. Speed came from clarity—not control.”
Pete Anevski CEO, Progyny; former CFO, WebMD

“This book changed how I prepare, how I decide, and how I show up in the boardroom.”
Secil Tabli Watson NACD Board Member; former EVP & Head of Digital for Commercial Banking, Wells Fargo

“AI scales best when leaders start with themselves—using it to think better, not just work faster. Artificial Organization shows how to do exactly that.”
Andrew Phillips Chief Technology Officer, Skyscanner

Trusted by leaders at Fortune 500s and fast-scaling startups.

Executive coaching programs

A stronger leader.
A stronger system of work.

Coaching starts with your real responsibilities: the board conversation, the strategic choice, the difficult 1:1, or the work that keeps pulling you away from leadership.

Between sessions, run a leadership experiment and bring back evidence: what you tried, what changed, and what you will keep, adapt, or stop. Assess the effect on your preparation, decisions, communication, and follow-through.

Talk about your leadership goals
  1. 01

    Build your personal leadership system

    Start with how you think best, the work that matters, and the tools that can support it.

  2. 02

    Think better before you decide

    Frame the choice, map the evidence, challenge your preferred option, and define when to revisit.

  3. 03

    Create executive-quality insight

    Turn signals into a recommendation. Adapt the emphasis for boards, peers, and teams while preserving the facts.

  4. 04

    Build your AI leadership operating system

    Eliminate unnecessary work, simplify the flow, and assign human and AI roles with clear review points.

  5. 05

    Lead an Artificial Organization

    Model the behaviors, coach colleagues, and create a 90-day plan with experiments, outcome measures, and an accountability partner.

Measure AI Outcomes

What is getting better
because you’re using AI?

Usage tells you whether people are using AI. To understand its value, examine how work changes and what improves. Start with the outcome you need, establish a baseline, and learn from the evidence.

01

Decision quality

Are alternatives and assumptions tested? Are decisions reopened because something important was missed?

02

Decision velocity

How long does it take to move from a question to a commitment, and from a decision to action?

03

Leadership capacity

Is less effort spent reconstructing context? Is that capacity reinvested in people, customers, and strategy?

04

Organizational learning

Are teams testing assumptions, revising workflows, and sharing practices that work?

05

Customer & business outcomes

What changes in cycle time, quality, customer experience, cost, or risk in the work you are improving?

Build an evidence base for your next investment.

Explore a Measure AI Outcomes pilot. Define the consequential work, agree what should improve, and examine behavior alongside operational evidence. The assessment framework is in development and being tested through expert review and research.

Discuss a measurement pilot

Start with the book · Available now

Artificial Organizations

A practical foundation for how you think, decide, and lead with AI.

Build your personal leadership system, use AI to pressure test your thinking, and turn meetings and conversations into context you can reuse.

Read or Listen it on your own, then bring the ideas into a keynote, workshop, or coaching program.

Get the book

Your partner in the work

Barry O’Reilly

Business leader, executive advisor, and bestselling author of Unlearn and Lean Enterprise.

Barry has spent more than two decades helping leaders and organizations navigate shifts in how work gets done. As cofounder of Nobody Studios, he also works with founders building new businesses with AI.

His approach starts with the leader: how you think, how you make decisions, and how your behavior shapes the organization around you.

Work with Barry

A few useful answers

Start where you are.

Do we need technical expertise?

No. The work focuses on leadership judgment, decisions, communication, and organizational performance. We use AI in the context of your responsibilities and the tools you can access.

How do we choose between a workshop and coaching?

A workshop helps a team work through a shared challenge and practice a new approach together. The five-session coaching program develops personal leadership, decision-making, communication, workflow design, and the ability to coach others, with live experiments between sessions.

Can the sessions be tailored to our organization?

Yes. Start with the decisions, leadership moments, and outcomes that matter to your team. Discuss your audience and goals with Barry to shape the engagement.

Can Measure AI Outcomes help us demonstrate the value of AI in our company?

Measure AI Outcomes has been developed and tested to help companies establish a baseline, identify where targeted interventions can make the biggest difference, and track performance improvements over time.

A pilot gives your company a practical starting point: understand current AI adoption, choose specific improvements to test, and measure changes in outcomes that matter to your business.

The aim is to build credible evidence of value, baseline yourself against the market, and focus on measured operational improvements and financial returns from your AI investment. 

Start a conversation

What would you
like to improve?

Tell us about the audience, decision, leadership challenge, or organizational outcome you have in mind.

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