12 Questions to Ask Your AI About How You Have Been Leading

Severin Sorensen
3 days ago
6 min read

By the middle of any given year, a senior executive has made hundreds of decisions, navigated dozens of difficult conversations, and cycled through enough strategic pivots to fill a casebook. They have also, in all likelihood, spent a significant portion of that time working alongside an AI assistant: drafting communications, thinking through problems, preparing for high-stakes meetings, and processing the complexity of organizational life in real time.

What most executives have not done is turn that relationship around and ask the AI what it has observed.

AI does not observe in the way a human colleague does. What it does have is access to the language you actually used, the problems you chose to bring to it, the decisions you framed and reframed before arriving at a conclusion, and the questions you kept returning to across time. It is a remarkably revealing dataset.

The mid-year AI check-in is a practice built on a simple premise: if you have been honest with your AI over the past six months, it has seen something worth asking about. The questions that follow are designed to help you surface that material that is genuinely useful.

Why the Mid-Year Moment Matters

There is a quality of attention that becomes available at the midpoint of a year that is difficult to access in the daily flow of work. The first half is complete enough to reveal patterns but recent enough that those patterns still feel actionable. The second half has not yet been determined, which means the insights generated now have real leverage.

For most executives, mid-year is also a natural inflection point in organizational life. Performance reviews are either just behind or just ahead. Strategic plans that were set in January are either holding or quietly unraveling. Teams that were configured for one set of priorities may need to be reconfigured for another. The executive who enters the second half of the year with a clear-eyed understanding of how they have actually been leading, as distinct from how they intended to lead, is in a materially better position than the one who simply continues forward on momentum.

The AI check-in does not replace the kind of reflection a skilled executive coach provides. What it offers is something different and complementary: an on-demand, private, low-friction way to examine the evidence that has accumulated in your own words over the preceding months.

How to Run the Check-In

The practice requires one setup step and a willingness to be genuinely curious about the answers. Before asking any of the questions below, brief your AI on the context it needs by inputting the following prompt:

“You are acting as a trusted thinking partner and executive coach for a senior leader conducting a structured mid-year reflection. I am that leader, and I will drive this conversation by bringing you the specific questions I am sitting with—about decisions I have made, patterns I have noticed, places where I feel stuck, or tensions I have not yet resolved. Your role is not to answer my questions for me. It is to help me think through them more rigorously than I would alone. You are not here to affirm my thinking or produce a performance summary. You are here to help me see what I may have stopped noticing including patterns in where my attention has gone, how I have framed difficult choices, and where I may be avoiding something important. When I bring you a question, engage with it directly and with genuine curiosity. Push back where my framing seems too convenient or too settled. Surface what might be underneath the question I am asking, if the real question appears to be somewhere else. Do not soften observations to protect my comfort; respond as a seasoned executive coach who respects my intelligence and expects the same rigor in return. If my answers seem incomplete, overly polished, or self-protective, do not move on. Ask one clarifying or complicating question instead, and wait. Close each of your responses by naming the tension you are hearing in what I have shared, not as a conclusion, but as the next thread worth pulling.”

With that framing in place, the questions below can be asked in any order, though the sequence presented here is designed to move from the concrete to the interpretive, which tends to produce richer material than beginning with abstraction.

The 12 Questions

On How You Have Been Spending Your Attention

Looking at the problems and decisions I have brought to you over the past several months, what do they suggest about where I have been concentrating my attention? Does that concentration seem intentional to you, or does it look more like drift?
What types of problems have I consistently brought to you, and what types of problems seem notably absent? What might that absence suggest?
Have there been moments in our conversations where I seemed to be working through something genuinely difficult, as opposed to simply producing an output? What do those moments have in common?

On Your Patterns as a Communicator

When I have asked you to help me draft or prepare communications, what patterns do you notice in how I think about my audience? Do I tend to lead with their needs or with my own position?
Have there been communications I seemed reluctant to send or decisions I circled back to multiple times before reaching a conclusion? What do those situations have in common?
Based on what I have shared with you about my team, my peers, and my stakeholders, how would you characterize the relationships I seem most comfortable navigating and the ones that appear to require the most effort?

On Your Decision-Making

Thinking about the significant decisions I have worked through with you this year, how would you characterize the way I tend to frame choices? Do I tend to see decisions as trade-offs, as problems to be solved, or as something else?
Have there been decisions where I seemed to reach a conclusion quickly and then look for reasons to support it, rather than genuinely weighing the options? If so, what were those decisions about?
Are there decisions or questions I brought to you early in the year that I never returned to with an outcome? What does that suggest?

On What the Year Has Cost You

Based on what I have shared with you over the past several months, what would you say has been most demanding of me personally, as distinct from professionally? Do those two categories seem related or separate in how I talk about them?
Have there been periods in our conversations where my energy or clarity seemed notably different from other periods? What was happening during those times?
If you were to describe the version of me that shows up in our conversations at my best, and the version that shows up when I am at my most constrained, what would distinguish them?

What to Do With What You Hear

The value of the mid-year AI check-in is not in the AI's answers. It is in what the executive does with those answers in the weeks that follow. The executives who find this practice most useful tend to do three things after completing the check-in:

They identify one pattern that surprised them or that they found themselves wanting to dismiss, and they sit with it long enough to understand what the resistance is about.
They share at least one observation with a trusted colleague or coach and ask whether it tracks with what that person has observed from the outside.
They make one concrete change to how they are allocating their attention in the second half of the year, based specifically on what the check-in surfaced.

One concrete change is the operative constraint. A single, specific, well-chosen change is more likely to hold than a list of intentions that gradually compress back into existing habits under pressure.

The mid-year moment does not last long. The executives who use this window well do not do so because they had more time than their peers. They do so because they made a deliberate choice to treat their own development as something worth the same rigor they bring to everything else they lead.

A Note on What AI Can and Cannot See

AI sees only what the executive brings to it. A leader who has been guarded or self-editing in AI conversations will find that the check-in surfaces a curated version of their leadership rather than an honest one, and AI has no visibility into the meetings, conversations, and decisions that never passed through a chat interface, which remains the majority of leadership work.

What it can offer, used honestly, is a record of how an executive thinks when they are working something out, before the polish of a final position and after the uncertainty of an initial instinct. That window is genuinely valuable and genuinely partial. The executive who approaches this conversation with curiosity about what the partial record reveals will get considerably more out of it than one who expects it to tell the whole story.