Six self-assessments. Start with the one that sounds like you.

Where are you right now?

• You've been told to "figure out AI": without a clear runway

  The board, the CEO, or a peer has handed you AI as a mandate. The expectations are real but unspecified. You're being measured on speed, but the call you're being asked to make is mostly about judgement, and the people around you don't have any more clarity on what "AI leadership" means than you do.

  1. Start here

     Are You Actually Ready for Coaching?

     Before you commit to a direction, it helps to know whether what you actually need is a sparring partner, a sounding board, or something else. Forty senior leaders have taken this self-assessment; the question it's good at: what kind of help would actually move you forward right now?

     4 to 12 minutes.

  2. Also worth considering

     Map Your Real Support Network

     AI mandates fail more often because of stakeholder misalignment than because of the technology. Mapping who's actually with you, who's quietly sceptical, and who you've been assuming wrongly about (before you commit publicly) is some of the highest-leverage work you can do this quarter.

     4 to 12 minutes.

  3. Also worth considering

     How You Decide With (And Without) AI

     If AI is reshaping your decisions, it's worth knowing what your default decision-making pattern was before AI arrived, and how that pattern is interacting with the tool. The self-assessment surfaces both. Particularly useful if you're noticing yourself either over-trusting or under-using the AI output you're seeing.

     4 to 12 minutes.

• Your function is being restructured, and AI is in the room

  You run a team or function that's about to look meaningfully different. Headcount, scope, tooling, and the work itself are all in motion. The headline question is operational; the questions underneath it are about people, politics, and what success now looks like for you and for them.

  1. Start here

     Map Your Real Support Network

     Restructures live and die by the stakeholder map. The audit forces you to name (privately) who's actually with you, who isn't, and where you've been operating on assumptions you haven't tested. Most leaders find at least one surprise.

     4 to 12 minutes.

  2. Also worth considering

     Eleven Thinking Traps. Find the Two Costing You the Most.

     Restructures tend to amplify cognitive distortions, especially the AI-relative ones ("if I don't move on this, a competitor will" / "the vendor's analysis must be right"). The spotter surfaces the two patterns most likely to be shaping your reads of this situation.

     4 to 12 minutes.

  3. Also worth considering

     The Shape of Your Success

     If the function changes, the work changes, and that often changes what success means for you personally. Worth pulling that thread before the restructure crystallises what your role looks like for the next several years.

     4 to 12 minutes.

• You're a senior individual contributor weighing what's next

  Your ladder has run out of useful rungs, or it hasn't but the rungs are starting to look the same. You're considering moving into management, a different function, or something adjacent, and the AI-era changes to your craft are part of the calculus, whether you've named that or not.

  1. Start here

     The Shape of Your Success

     The most useful place to start is what success actually means to you now, and what you want it to mean a decade from now in a world where the work itself will have moved. The audit takes three minutes and routinely surfaces something a senior IC hadn't said out loud.

     4 to 12 minutes.

  2. Also worth considering

     Eleven Thinking Traps. Find the Two Costing You the Most.

     Pivots are where the stories you tell yourself get the loudest. The spotter names the two distortion patterns you're most likely to be running: useful before you make a call that's hard to reverse.

     4 to 12 minutes.

  3. Also worth considering

     Are You Actually Ready for Coaching?

     If the next step involves working with someone else (a coach, mentor, or advisor), it helps to know what you'd actually use them for. The readiness self-assessment answers that.

     4 to 12 minutes.

• Your team is splitting over how to adopt AI

  Two factions, or three. The arguments sound technical but the energy underneath isn't. People who used to agree on adjacent things now disagree on this one, and the way they're disagreeing is starting to colour the rest of the work. Your call as the leader is overdue.

  1. Start here

     Map Your Real Support Network

     Most AI-tooling team conflicts are stakeholder problems wearing technical clothing. Mapping the actual influence and support patterns (including each person's AI stance) usually changes what the right intervention looks like.

     4 to 12 minutes.

  2. Also worth considering

     How You Decide With (And Without) AI

     The most common pattern: a team where the leader's default decision-making style and the team's are diverging because AI is reshaping one but not the other. The self-assessment surfaces your own pattern; you can then read the rest of the team against it.

     4 to 12 minutes.

  3. Also worth considering

     Eleven Thinking Traps. Find the Two Costing You the Most.

     Conflicts also amplify your own distortions about the people involved ("she's just being difficult" / "he doesn't get it"). Useful to surface those before you make the call.

     4 to 12 minutes.

• You're sitting with a big decision and can't quite put it down

  A role change, an exit, a redirection. The numbers are in front of you. The pros and cons are catalogued. And yet the decision keeps coming back, which usually means something underneath it hasn't been named: what you want, what you can live with, or what the next decade is actually for.

  1. Start here

     Are You Actually Ready for Coaching?

     Big personal decisions are exactly the kind of moment where talking to someone outside your immediate circle helps. The readiness self-assessment answers a sharper question: what kind of help would actually be useful? A sounding board, sparring partner, decision-coach, or something else?

     4 to 12 minutes.

  2. Also worth considering

     Eleven Thinking Traps. Find the Two Costing You the Most.

     Recurring decisions almost always have a distortion running through them. The spotter names the top two patterns shaping how you're reading this. Frequently the read that comes back is one you wouldn't have predicted.

     4 to 12 minutes.

  3. Also worth considering

     Your Leadership Resilience Wheel

     Big decisions land differently depending on the foundation underneath them. The resilience wheel shows where your foundation is currently strong and where it's thin: useful context for deciding whether to move now or shore up first.

     4 to 12 minutes.

• What "success" used to mean to you doesn't quite fit anymore

  Not a crisis. Just a quiet noticing that the version of you who set the targets you're hitting now isn't the version of you doing the hitting. Maybe you've reached the things you set out to reach. Maybe the work is shifting around you. Maybe both. The question worth sitting with is what the next definition of success actually is.

  1. Start here

     The Shape of Your Success

     The clearest entry point: three rounds, five factors, eleven points each. Designed specifically for the shift you're describing. Most senior leaders who take it find that their drift across past, present, and future tells them something they hadn't said out loud.

     4 to 12 minutes.

  2. Also worth considering

     Your Leadership Resilience Wheel

     If your definition of success is shifting, the foundation under that shift matters. The wheel surfaces where your reserves are full and where they're thin: useful for deciding which moves you can make from strength versus depletion.

     4 to 12 minutes.

  3. Also worth considering

     Are You Actually Ready for Coaching?

     If sitting with the question is starting to feel worth doing properly, the readiness self-assessment tells you what kind of support would actually help. Worth knowing before you book anyone's time, including your own.

     4 to 12 minutes.

Or choose by topic

All six, in order. Choose any of them to start.

• Are You Actually Ready for Coaching?

  Is coaching right for you now? A short, honest check.

  4 to 12 minutes.

• Your Leadership Resilience Wheel

  8 signs of how well you are coping with pressure in the age of AI.

  4 to 12 minutes.

• How You Decide With (And Without) AI

  How do you make decisions, and how is AI changing that?

  4 to 12 minutes.

• Map Your Real Support Network

  See who supports the change you are making, and who does not.

  4 to 12 minutes.

• Eleven Thinking Traps. Find the Two Costing You the Most.

  Find the thinking habits that cost you the most, including thoughts about AI.

  4 to 12 minutes.

• The Shape of Your Success

  What did success mean to you 10 years ago? What does it mean now? And in 10 years?

  4 to 12 minutes.