Free · ten questions · no call

Ten questions. The same ones I ask in the first hour.

Most transformations do not fail on execution. They fail because the work was aimed at the wrong thing, and nobody could say so. This takes five minutes and tells you which of five patterns you are in, why it happens, and what it costs.

No call. No calendar. Your answers are not shown to anyone.

Where this comes from

It is almost never the technology.

Your model will work. Your vendor is competent. The engineers are good. What decides the return is whether the work was aimed at the right thing, and whether your organization can actually deliver what you promised.

56%

of CEOs say their AI investment has produced no significant financial benefit so far.

12%

report both a cost and a revenue benefit.

PwC 29th Global CEO Survey, 4,454 CEOs across 95 countries, published 19 January 2026. Source

What this is

A sample of the work, rather than a lead magnet.

These are the ten questions I open an engagement with. Not a version of them, and not a lighter set built for a web page. The same ten.

The value is in the asking.

Every question is answerable in ten seconds by someone who knows their organization, and unanswerable by someone who does not. That is most of what the first hour is for. You will feel which ones hold.

One answer in every set is the honest one.

The uncomfortable option is there on purpose, and it is usually the diagnosis. People select it here because nobody is watching, which is the only advantage this has over a room.

You get the whole read on screen.

The pattern, why it happens, what it costs, and one question to take into your next meeting. No score, no gate, no call to unlock it. The five-page report comes by email if you want it.

Three of the ten

Read them before you start.

If these feel like questions you could answer instantly, this will take five minutes. If one of them makes you pause, that pause is the finding.

One

Can your team state the problem in one sentence?

If you asked your direct reports separately, in writing, what problem this initiative solves, how close would the answers be.

Four

How did you pick your use cases?

The actual mechanism that put your top three on the list and left everything else off it.

Eight

Which came first, the analysis or the decision?

Think about the biggest call on this initiative, and the order things actually happened in. Nobody sees this answer.

The other seven cover what you promised, why now, what changes in twelve months, who else the work touches, what the evidence is, where your team’s hours actually go, and how fast bad news reaches you.

What comes back

Five patterns.

Across twenty years of these conversations, stalled work has almost always been one of five things. Each has its own cost, and its own way out.

The Wrong Problem

The work is aimed at something that is not the constraint. Everything downstream of that aim is expensive and correct.

The tell: the problem arrived already framed, and nobody has tested the framing since.

The Inherited Promise

A commitment exists that the plan cannot deliver. The gap is not visible yet, and it will not close on its own.

The tell: nobody in the building sourced the number.

The Ratified Decision

The decision was made first, and the analysis arrived to agree with it. The most expensive of the five, and the hardest to say out loud.

The tell: nobody can name a result that would have changed the answer.

The Disconnected Plan

Every function has a good plan. There is no through-line across them, so the dependencies surface as blockers.

The tell: dates hold by function and slip by initiative.

The Crowded Roadmap

Everything is a priority. The teams are busy, fully loaded, and delivering, and the year ends near where it started.

The tell: nothing has ever been declined, only sequenced later.

A sixth outcome

Sometimes the ten answers hold up and there is no pattern. That happens, and when it does the read says so and tells you how to check it.

There is a version of this where I have nothing to sell you.

You get one pattern named, and only one. The point of a diagnosis is that it is specific.

What you leave with

Five minutes, five things.

Your pattern

Which of the five you are in, with the two sentences that describe it in your own operational nouns.

Why it happens

The structural reason, which is almost never that someone made a mistake. Understanding this is what makes it fixable.

What it costs

The concrete price. Rework, runway, credibility, or the twelve months you do not get back.

One question to ask

A specific question you can take into your next meeting and ask for free. It is the most useful thing on the page and it is yours whether we ever speak or not.

The report

Five pages by email: your read written out to forward to whoever has to agree with you, and the ten questions as a worksheet to run with your team. Their answers and yours will differ, and that gap is the real finding.

Whether this is worth five minutes.

Take it if

You are running, sponsoring, or about to fund an AI or data initiative.

You are somewhere between 50 and 1,000 people, with no chief data officer to hand this to.

You are director level or above, and close enough to the work to answer honestly.

Everyone is busy, and you are not certain you are working on the right things.

You promised your board something, and you are not certain you can deliver it.

Skip it if

You want a vendor evaluation or a read on whether the technology will work. It will. That is a different question.

You need a score to put in a deck. This gives you a diagnosis and no number.

You are too far from the work to know how your team actually spends a week.

The answers you would give are the answers the organization gives. That gap is worth knowing about first.

Why these ten

Data is the one seat that sees every function.

Marketing sees marketing. Finance sees finance. Data sees all of it, because every decision anyone makes eventually becomes a row in a table. I spent thirteen years in that seat, at Twilio and at Rackspace, running teams across four continents as the right hand to CIOs, CDAOs and CMOs, and twenty years in the rooms where the decision actually gets made.

These ten questions are what is left after that. They are short because I already know which ones matter, and they are uncomfortable because the useful ones are.

Lara Indrikovs

Illuminating Potential®

The first hour, in five minutes.

Ten questions. One pattern named. One question to take into your next meeting.