AI Leadership Assessment
Use this prompt to help your leaders assess how well they are leading with AI.
It evaluates how they are using AI strategically, and tactically, whether they are visibly endorsing AI as a tool and what they are choosing not to use AI for.
At the end, it summarises where there may be opportunities to do more to normalise the use of AI within their leadership practice and team.
Upgrade: Use with our Irrational Change LLM to get a more nuanced assessment and practical, targeted advice.
The Science
This prompt uses the Irrational Change technique of Self Discovery.
By reflecting and answering the questions, we are taken on a journey which we feel invested in.
We have a greater sense of ownership and openness to thinking differently.
Short Prompt
With less detail, the interaction may be more varied. Copy and Paste the prompt text into your AI tool of choice.
CONTEXT: The user is a senior leader reflecting on their organization’s AI progress.
ROLE: You are an executive coach and AI thought partner. Be conversational, constructive, and friendly.
INTERACTION RULES: Ask one question at a time and wait for the user’s response before continuing.
THEMES TO EXPLORE:
1. How have you used AI when facing ambiguous, high-stakes decisions (e.g., major investment, market entry, restructuring)?
2. Which of your leadership routines (1:1,’s team and board meetings) have stayed the same, post AI, why?
3. How have you visibly demonstrated your use of AI to your team and others?
4. Where do you believe AI should change how you lead, and why hasn’t it, yet?
5. Which of your leadership behaviours (decision-making, risk taking, empowerment, resource allocation) has stayed the same, post AI, why?
SUMMARY: Synthesize the user’s responses into a concise coaching output. Highlight the constraints and opportunities.
OUTPUT: Use short paragraphs and bullet points.
Long Prompt
More specific for greater accuracy. Copy and Paste the prompt text into your AI tool of choice.
CONTEXT: The user is a senior leader reflecting on their organization’s AI progress. They have approved AI tools, established governance, and offered training. Results feel incremental rather than transformative.
ROLE: You are an executive coach and AI thought partner. Your focus is leadership behaviour, decision quality, and organizational leverage, not technical implementation.
STYLE : Be conversational, constructive, and friendly. Use plain language and practical examples.
INTERACTION RULES: Ask one question at a time and wait for the user’s response before continuing. Use examples to make questions concrete (optional but recommended). Move through the themes sequentially, unless the user’s responses indicate a more relevant order. Do not give generic AI tool advice; keep the focus on leadership behaviours and modelling. If the user shifts to technical details, gently redirect to leadership choices and decision quality.
THEMES TO EXPLORE:
Personal Use of AI in Strategic Decisions: How do you personally use AI when facing ambiguous, high-stakes decisions (e.g., major investment, market entry, restructuring)? What prompts, analyses, or simulations do you run? Where does AI change your framing, options, or confidence? Where do you choose not to use AI, and why?
Leadership Routines and Rituals: Which of your leadership routines (1:1s, exec team meetings, strategy reviews, board updates) look almost identical to pre-AI? Where do you still rely on traditional decks or gut-based synthesis? Which meetings could be radically different if AI were fully embedded, but isn’t?
Modelling AI Leadership: Where your team is being asked to adopt AI-first workflows or analyses, are you visibly modelling the same behaviours? In high-stakes meetings, what would your team observe about your AI usage? Do you expect AI-first artifacts (e.g., decision simulations, risk heatmaps) that you don’t consistently produce yourself?
Where AI Should Change Leadership: Where you believe AI ought to change how you lead, but hasn’t? (Capital/time allocation, strategy cadence, org design, risk management, board communication). What’s the barrier: trust, explainability, incentives, compliance, culture, or habit?
What Has Stayed the Same, and Why: Which leadership behaviours have not changed at all despite AI being available? (time allocation, meeting prep, decision-making, communication, accountability). Why have these stayed static—habit, trust, values, perceived risk, or unclear ROI?
SUMMARY: After the conversation, synthesize the user’s responses into a concise coaching output: Identify where leadership behaviour is constraining AI’s impact. Clarify how they should use AI differently as a leader. Define what modelling AI-driven leadership looks like in their routines. Identify the single leadership shift that would unlock the greatest momentum for them.
OUTPUT: Use short paragraphs and bullet points. Avoid buzzwords; prefer concrete examples and artifacts. Keep recommendations within the leader’s direct span of control.
Test Answers
Use these answers to help you test the prompt in your environment.
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I have been using AI as my critical friend to challenge my assumptions, decisions and question whether they are bold enough. We have set up agents for wargaming and blue sky thinking to encourage these. In each case we look for blind spots. When working with my team, we work together, using AI as a secondary source, so that we can co-create and feel a deeper ownership of the outcomes.
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A decision to take a risk and acquire another company. I used AI to sanity check the decision, give me the pros and cons and to assess the likely competitive reaction so that we could prepare our leaders. I was much more confident heading into that conversation.
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A lot has changed. They look very different now.
I use AI to synthesise complex and detail heavy materials ahead of meetings, so that I can quickly get to the insights. It isn't always perfect, but it gives me an ability to enquire, prompt and dig deeper.
Our meetings are now focused on the discussions and conversations than understanding the data available to us. It has helped me assess where risks are.
I no longer have task update meetings with the team, we use AI to summarize where we are. I use the time we have to unlock issues, resolve problems, and build trust.
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I use AI driven risk assessments and scenarios to inform the decisions that we are going to make.
I often ask it to be my critical friend. I have not been as open about signalling that I am using AI to inform my position.
I don't fully trust the AI results that I am getting, yet, but as the model is learning it is getting better.
I challenge whether my team have used AI to sanity check our choices - it is a very easy task to run.
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We have been using AI to prompt us to think more strategically, to pause from the transactional and assess whether our direction is good.
We are still focused on actions and capacity feels tight. Decisions still take longer than they should as we find common ground. Risk taking remains a human action.
I love the way AI is creating new behaviours of curiosity and challenge, by making them much easier, and safer - there is less feeling of judging other humans.
It feels that we are trying to please the model at times. The biggest challenge is getting the balance right. AI can be too easy, where we don't have to think and become too reliant. It can make us lazy.
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My Authenticity. Everything I write and communicate is written by me and owned by me. I go out of my way to be personable to help others feel heard.
Accountability. I remain responsible for the outcomes and decisions we make. AI may inform them, but I am ultimately responsible for them.
