AI Readiness Assessment

Most leadership teams have a gut feeling about AI. This gives you a score.

Answer 12 questions written for your seat. Get an honest read on where your organization actually stands on AI — and exactly what to do about it.

5 minutes12 questionsInstant scoreConfidential

Practitioners, not theorists. Show and Tell builds and runs its own AI — the tools behind this assessment included. We advise from what we ship, not from a slide.

Which seat are you in?

How clearly defined is your organization’s AI strategy, and who is accountable for it? We have a stated AI direction but it lacks a named owner, budget, and timeline
We have informal discussions but no documented strategy or accountable owner
We don’t have one. AI decisions happen reactively as situations arise
We have a board-endorsed AI strategy with an executive owner, dedicated resources, and a 12-month roadmap

How well do you understand how AI is reshaping competitive dynamics in your sector? We have a documented competitive AI intelligence picture that feeds directly into our strategy and planning
We haven’t formally assessed AI’s impact on our competitive position
We’re tracking it loosely but haven’t built it into strategic planningWe have a working view and it’s informing some decisions at the leadership level

How confident are you that your full leadership team — not just individual champions — can lead AI adoption in their functions? A few leaders are engaged but the majority are not equipped or accountable
Most of my leadership team has limited AI literacy and no mandate to build it
My full leadership team has a shared AI framework and each function has a clear adoption mandate
We’re building capability but it’s uneven — some functions are well ahead of others

Has your organization made a deliberate investment in AI literacy at the leadership level? We’ve done a one-off leadership session or brought in a speaker
Some leaders have done self-directed learning but it’s been informal and uncoordinated
We have a structured, ongoing AI leadership development program tied to our strategic roadmap
No, we’ve left it to individuals to figure out on their own

How would you rate your organization’s data readiness to support enterprise AI initiatives? Our data is fragmented across systems with no governance model. We couldn’t build reliable AI on it today
Data exists but quality and accessibility issues would slow any serious AI deployment
We have reasonable data infrastructure but gaps in governance and AI-specific tooling remain
Our data is governed, accessible, and structured to support AI deployment across the organization

Does your organization have a formal AI governance policy covering risk, ethics, data use, and vendor accountability? We have informal guidelines that have been communicated but are not formally enforced
We recognize this is a gap but haven’t prioritized it yet
We have a board-reviewed AI governance policy enforced across all functions and vendor relationships
No, we’re managing AI tools on a case-by-case basis with no enterprise policy

How consistently is AI being applied across your organization’s core functions, not just in pockets? AI use is absent or entirely ad hoc with no organizational coherence
AI is deployed consistently across our core functions with defined workflows and cross-functional coordination
A few functions or individuals are active but most of the organization hasn’t started
Several functions have meaningful AI adoption but it’s uneven and not coordinated centrally

When your organization decides to adopt an AI tool or initiative, how does that decision get made? Decisions are made by individual functions without central visibility or coordination
We have an informal review process but it lacks consistent criteria and executive oversight
There’s no process. Decisions happen informally or by whoever has budget
We have a structured AI investment and adoption process with executive sign-off and cross-functional input

Are you measuring the business return on your AI investments in terms your board would find credible? We’re not tracking AI outcomes in any systematic way
We have a sense of the value but couldn’t quantify it for a board conversation
We report AI ROI to our board against defined KPIs including revenue impact, cost reduction, or quality improvement
We track some metrics but they’re activity-based rather than tied to revenue, cost, or quality outcomes

Has AI generated a documented, material business outcome for your organization in the past 12 months? No, nothing I could point to with confidence
Not yet — our investments are still in early or infrastructure stages
Yes, multiple AI initiatives with documented ROI that has been presented to our board or investors
Yes, one or two wins I could describe though not fully quantified

How would you characterize your organization’s overall readiness to change the way it works as AI capability grows? It’s mixed. Some parts of the organization are open, others will be difficult to move
There’s significant resistance or inertia. People are protective of existing ways of working
We have high organizational readiness. Leadership models AI adoption and change management is embedded in how we operate
There’s general openness but we haven’t done the change-management work to translate that into action

As the senior leader, how actively are you signalling that AI capability is a strategic priority? I actively champion it, it’s embedded in our strategic plan, and leaders are accountable for AI adoption in their functions
I speak about it regularly and it’s on our leadership agenda, but haven’t tied it to performance or accountability
I haven’t made it a visible priority yet. There are more pressing demands on my attention
I’ve mentioned it in a few settings but haven’t made it a consistent or accountable expectation

1 / 12

How does your leadership team talk about AI in your marketing strategy? Identified as a priority but not resourced properly
Mentioned but treated as a tool decision, not strategy
It hasn’t come up strategically
A named pillar with executive ownership and budget

Do you have a view on how AI is changing your market and what competitors are doing? We haven’t looked at this
Noticed things but haven’t formalized our read
Documented competitive intelligence briefed to leadership regularly
Informal view shared across marketing leadership

How AI-capable is your marketing team right now? Most people have no practical AI experience
Several use AI tools regularly but without shared workflows
A few individuals experiment on their own
Trained staff, defined workflows, and consistent use across the team

Has your organization invested in formal AI training for marketing? A few have done self-directed learning
Ongoing learning program tied to marketing AI adoption goals
No, nothing offered or funded
We’ve run a one-off session or workshop

How well-organized is your content and campaign data for AI-assisted work? Scattered across tools, drives, and inboxes
AI-ready: structured, tagged, and integrated into our tools
Organized asset libraries but not connected to AI workflows
We have data but it’s not clean or accessible enough

Do you have governance standards for AI-generated content? Formal AI content policy with review gates and brand compliance standards
Aware we need this but haven’t built it
Informal guidelines in use within the team
No, anyone can publish without review

Where is AI actively used in your marketing operations today? Some workflows use AI for content drafting, image gen, or analytics
Embedded across multiple functions with documented workflows and measured output
A few people use consumer AI tools personally
Nowhere in any structured way

How does your team evaluate and adopt new AI marketing tools? Loose evaluation without consistent criteria
Informal research and manager approval
Structured evaluation covering fit, brand risk, ROI, and integration
No process, individuals install what they want

Are you tracking the business impact of AI on marketing performance? We know we should but haven’t started
Not tracking anything AI-specific
We track activity like prompts run or time saved but not business outcomes
We measure against marketing KPIs: cost per lead, content velocity, conversion rates

Has AI delivered a measurable marketing outcome in the past 12 months? Yes, documented ROI on AI-assisted campaigns shared with leadership
No, nothing we could point to
Yes, one or two wins we can describe
Not yet, still early

How does your marketing team respond to AI adoption? Generally positive but waiting for direction
Skeptical or resistant — concern about quality and job security
Mixed — some enthusiasm, some fear
Excited and experimenting within a structured framework

Who drives AI adoption within your marketing function? Enthusiastic individuals without mandate
A named role or working group with leadership backing
No one owns it — ad hoc or absent
A person or small group has informally taken ownership

1 / 12

How does your sales leadership talk about AI in the context of revenue growth? Seen as a priority but not built into go-to-market plan
Embedded in sales strategy with defined use cases, ownership, and resources
Mentioned but treated as a CRM feature, not strategy
Not on the sales leadership agenda

Do you have a view on how AI is changing buyer behaviour in your market? Observed changes anecdotally but haven’t formalized anything
Actively track how AI affects buyer journeys and have adjusted our approach
Informal perspective shared across sales leadership
We haven’t looked at this

How AI-capable is your sales team right now? Several reps use AI tools for outreach, call prep, or CRM but inconsistently
A few top performers experiment on their own
Most reps have no practical AI experience
Full team trained with defined AI playbooks and consistent use

Has your organization invested in formal AI training for sales? No, nothing offered
Done a one-off enablement session or workshop
A few have done self-directed learning
AI is part of ongoing sales enablement with clear skill targets

How clean and accessible is your CRM and pipeline data for AI-assisted selling? Data exists but too messy or siloed for AI insights
Poor hygiene — incomplete, inconsistent, not trusted
Clean, consistently maintained, and integrated with AI tools that surface real insights
Reasonably clean but not connected to AI tools

Do you have governance standards for AI use in outreach? No, reps can do whatever they want
Aware this matters but haven’t addressed it
Informal norms exist within the team
Formal guidelines covering brand, compliance, and personalization standards

Where is AI actively used in your sales process today? AI tools embedded in parts of the process like prospecting or call summaries
Nowhere — reps work the same way they always have
A few reps use consumer AI tools on their own
Woven into the full sales workflow with documented plays and measured impact on conversion

When your team evaluates a new AI sales tool, what happens? Structured evaluation covering pipeline fit, CRM integration, and ROI
Some evaluation but without consistent criteria
Informal research and a manager approves
No process — whoever has budget buys what they like

Are you measuring how AI affects your sales performance metrics? We know we should but haven’t started
Not tracking anything AI-specific
We track activity like emails sent or time saved but not revenue outcomes
We measure against pipeline, win rate, deal velocity, or quota attainment

Has AI delivered a measurable sales outcome in the past 12 months? Not yet, still in early exploration
No, nothing we could point to
Yes, documented impact on pipeline or revenue presented to leadership
Yes, one or two wins we can describe

How does your sales team respond to AI adoption? Mixed — some see the upside, others are skeptical
Generally positive but looking for clear guidance
Excited — early adopters are sharing wins and pulling others along
Resistant — reps see it as surveillance or a threat to commission

Who drives AI adoption within your sales function? No one — entirely ad hoc
A few high performers experiment independently
A named enablement or ops role with leadership mandate
A sales ops person or manager has informally taken it on

1 / 12

How does your IT leadership engage with AI strategy across the organization? IT is a co-owner of the enterprise AI strategy with a defined governance role
IT is involved in AI decisions but often after the fact
We respond to requests as they come — no proactive stance
We have opinions but aren’t at the table when business units make AI decisions

Does your organization have a formal AI strategy that IT has helped shape? Business-unit initiatives exist but no enterprise-level coordination
No formal AI strategy exists
Board-level AI strategy with IT governance embedded from the start
Informal AI roadmap but lacks executive sign-off and resourcing

How AI-capable is your IT and technical team right now? A few individuals have explored AI tools or done self-directed learning
Several team members have practical AI skills and are applying them
Defined AI capability across the team with clear roles, training, and delivery track record
Limited — most staff have no hands-on AI or ML experience

Has your organization invested in formal AI upskilling for the technical team? No, not funded or prioritized
A few individuals have done self-directed learning
Sustained upskilling program aligned to our AI roadmap with measurable capability targets
Done a one-off training or brought in external support for a specific project

How would you describe your organization’s data infrastructure readiness for AI? Data is siloed with poor governance and no single source of truth
Reasonably clean data and some analytics capability but gaps in AI-specific tooling
AI-ready: governed, accessible, documented, and integrated with the tools that need it
Data exists but quality, access controls, and metadata standards are inconsistent

Do you have a formal AI risk and governance framework? Informal guidelines that some teams follow
No, we handle AI tools case by case with no formal framework
Formal AI governance framework reviewed regularly and enforced across all initiatives
Aware we need one but haven’t built it

How does IT currently support AI adoption across business units? Occasional technical review but no structured support model
Formal AI enablement function with intake, evaluation, integration support, and governance
We don’t — business units source their own tools and IT cleans up after
Informal AI intake and support process but capacity is a constraint

How mature is your process for evaluating and approving new AI tools and vendors? Basic security and procurement review but not AI-specific
No formal process — business units self-approve
Rigorous AI vendor framework covering security, data handling, integration, and TCO
AI-aware evaluation checklist but not consistently applied

Are you measuring the business impact of AI investments IT has supported? We know we should but don’t have the framework or data
We track some output metrics but not business outcomes
Not tracking outcomes — we measure delivery not impact
We measure AI impact against defined business KPIs and report to leadership on ROI

Has an AI initiative your team delivered produced a documented business outcome in the past 12 months? Yes, one or two initiatives with outcomes we can describe
Yes, multiple initiatives with documented ROI presented to executive leadership
No, nothing we could show a CFO
Not yet, still infrastructure and enablement stage

How does your organization respond when IT raises AI governance or risk concerns? Heard, but concerns treated as blockers, not guardrails
Often ignored or overruled — business urgency wins
IT governance respected as a business enabler — pulled in early, not informed late
Reasonable influence but have to fight for it case by case

Who drives AI adoption strategy in your organization, and what role does IT play? No one drives it — entirely reactive and fragmented
Business units drive it independently and IT supports on request
IT is a co-lead with a formal mandate and seat at the strategy table
Cross-functional effort exists but IT is a junior partner

1 / 12

Most leadership teams have a gut feeling about AI. This gives you a score.

Executive / Whole business

Marketing

Sales

IT / Ops