How committed is your C-suite to AI transformation?

Supportive - approved budget and give blessing

Interested - want to explore but cautious

Skeptical - need convincing

Not aligned - some oppose or indifferent

Do you have a coalition of influential leaders ready to champion this transformation?

Yes - 5+ leaders across departments aligned

Mostly - 3-4 strong champions identified

Starting - 1-2 champions, need more

Unclear - not sure who would champion

No - would be driven top-down only

>How many other major initiatives are currently underway?

None - we can focus on this

1-2 initiatives - manageable load

3-4 initiatives - getting crowded

5+ initiatives - change fatigue setting in

Constant chaos - always multiple priorities

How clearly defined are your success metrics for this transformation?

Crystal clear - specific metrics with targets

Pretty clear - know what success looks like

Somewhat clear - general direction defined

Vague - "efficiency" or "innovation" goals

Unclear - would figure out as we go

How does your culture typically respond to significant change?

Embrace it - we adapt quickly

Accept it - some resistance but manageable

Mixed - depends on the change

Resist it - change is always hard here

Fight it - major change usually fails

What's your realistic timeline expectation for seeing measurable results?

6-12 months - understand it takes time

4-6 months - willing to be patient

3-4 months - need results reasonably fast

1-2 months - under pressure to show value

Immediate - need quick wins or it dies

How quickly can your organisation make and implement strategic decisions?

How successful were your last 2-3 major change initiatives?

Very successful - delivered on goals

Mostly successful - achieved most goals

Mixed results - some won, some failed

Mostly failed - didn't achieve goals

Failed - abandoned or limped along

How stable and reliable are your core business systems?

Rock solid - minimal downtime or issues

Stable - occasional minor issues

Functional - regular issues but manageable

Problematic - frequent issues cause disruption

Unstable - constant firefighting

How easy is it to integrate new tools with your existing systems?

Easy - modern APIs and architecture

Moderate - possible with some effort

Difficult - requires significant work

Very difficult - legacy systems, limited options

Nearly impossible - locked into proprietary systems

How would you rate your data quality and accessibility?

Excellent - clean, accessible, well-organized

Good - mostly clean and accessible

Fair - usable but needs cleanup

Poor - messy, siloed, hard to access

Terrible - data is a known disaster

What's your level of technical debt?

Minimal - modern systems, well-maintained

Low - some legacy but manageable

Moderate - notable but not crippling

High - significant legacy burden

Crushing - barely keeping systems running

Does your IT team have bandwidth for transformation work?

Yes - can dedicate resources

Mostly - can make it work with planning

Tight - would need to reprioritize

Stretched - already overloaded

No bandwidth - fully consumed with operations

How would you describe the IT-Business relationship?

Strong partnership - aligned and collaborative

Good - communicate well, some alignment

Functional - work together when needed

Strained - frequent miscommunication

Broken - constant conflict or complete disconnect

How well documented are your current processes and systems?

Very well - comprehensive documentation

Well documented - most things covered

Partially - key things documented

Poorly - minimal documentation

Not documented - tribal knowledge only

How would you describe your current financial position?

Strong - healthy cash flow and reserves

Stable - profitable and sustainable

Moderate - breaking even or slight profit

Tight - cash flow concerns

Struggling - financial stress

Do you have budget allocated or earmarked for this transformation?

Yes - budget approved and allocated

Likely - in planning, high confidence

Possible - would need to build business case

Uncertain - budget is tight

No - no budget identified

Can you dedicate key people part-time (20-40%) to this work?

Yes - people identified and committed

Likely - could make it work

Challenging - would need to shift priorities

Very difficult - everyone maxed out

Impossible - no capacity available

How clearly can you articulate the specific problem you're solving?

Crystal clear - can describe it in 2 sentences

Very clear - well-defined problem statement

Somewhat clear - general problem identified

Vague - know something needs to change

Unclear - exploring what the problem might be

What's your expectation for return on investment?

Realistic - 12-18 month ROI acceptable

Hopeful - 8-12 month ROI expected

Optimistic - 6-8 month ROI desired

Aggressive - 3-6 month ROI needed

Unrealistic - immediate ROI required

If this transformation gets difficult, how committed are you to seeing it through?

Fully committed - will push through obstacles

Very committed - willing to work through challenges

Committed - unless major issues arise

Conditionally - depends on early results

Testing - might pull back if it's hard

How aligned is this transformation with your 3-year strategic plan?

Core priority - explicitly in strategic plan

High priority - strongly supports strategy

Aligned - fits with strategy

Somewhat aligned - tangential to strategy

Not aligned - separate from strategic plan