What I Ask Every Leadership Team in the First 30 Minutes
Most AI conversations start in a similar place. Tools, platforms, capabilities. What’s possible, what’s new, what other organisations are doing.
These are all useful discussions, but they tend to happen before something more important has been made clear……what the business is actually trying to improve.
A Different Starting Point
At the start of an engagement, I tend to approach the conversation a little differently.
The first 30 minutes are not about technology. They are about understanding how the organisation currently operates, where friction exists, and what meaningful improvement would look like.
That initial conversation often reveals more than any technical review.
The Questions That Shape Everything Else
There are a few questions that consistently guide that early discussion. They are simple on the surface, but the answers tend to highlight where clarity exists and where it doesn’t.
The first is about focus.
What are we actually trying to improve in the business?
Not in broad or abstract terms, but in a way that is specific enough to recognise when it has changed. This might relate to time, cost, consistency, or decision-making, but it needs to be grounded in something observable.
The second is about where friction sits.
Where is time being lost? Where are processes slower, more manual, or more inconsistent than they should be? These are often the areas where AI has the most practical impact.
The third is about alignment.
Do different members of the leadership team describe these priorities in the same way? Or do their answers vary?
This is often where the conversation becomes more revealing. A lack of alignment at this stage usually leads to fragmentation later.
The fourth is about measurement.
How would we know if something has genuinely improved? Not just whether a tool works, but what would be different in the day-to-day running of the business if the change was successful.
This is the question that is most often underdeveloped.
What These Questions Reveal
Individually, these questions are straightforward. Taken together, they provide a clear picture of how prepared an organisation is to move forward with AI in a meaningful way.
When the answers are clear and aligned, it becomes much easier to prioritise opportunities, define use cases, and make decisions about where to focus.
When they are not, AI work tends to drift. Ideas accumulate, but direction remains unclear.
Why This Step Is Often Skipped
In many organisations, there is a strong push to move quickly. Teams want to explore tools, run pilots, and demonstrate progress. That momentum is valuable, but it can lead to this initial step being overlooked.
Without clarity on what the business is trying to change, it becomes difficult to determine whether any of that activity is actually making a difference.
From Questions to Direction
Once these questions have been worked through, the rest of the process becomes more straightforward.
Opportunities can be evaluated against clear priorities. Use cases can be defined in the context of real workflows. Success can be measured in a way that matters to the business.
The conversation shifts from what is possible to what is useful.
If AI conversations in your organisation are centred primarily on tools or capabilities, it may be worth stepping back.
Before deciding what to build or implement, take the time to answer a different set of questions.
What are we trying to improve?
Where does that show up in our workflows?
Are we aligned on what matters most?
How will we know if this has worked?
These are not complex questions. But they tend to shape everything that follows.