AI Readiness Assessment — Weymouth Club

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Company & Context

Q1 Company overview

Company Name

Industry

Annual Revenue

Q2 What is your organization's 3–5 year strategic vision?

Q3 How many employees do you currently have?

Q4 What are your primary products or services?

Q5 Is your business in a regulated industry?

No Yes — please specify:

2

Current Operations & Pain Points

Q6 What are your top 3 operational pain points right now?

1

2

3

Q7 Which of those pain points would have the biggest impact if solved?

Q8 What are your organization's top 3 priorities right now? Select exactly 3, then drag to rank them — #1 being the most important.

Available — check 3 to rank

Reducing Costs / Improving Operational Efficiency Growing Revenue Improving Customer Experience Reducing Risk / Improving Compliance Optimizing Staffing / Reducing Labor Costs Modernizing Systems & Infrastructure

Q9 How much time per week do you estimate is spent on manual or repetitive work across your team?

5–10 hours 10–20 hours 20–40 hours More than 40 hours — approximately how many?

Q10 Are there specific workflows where your team feels most bogged down or interrupted?

3

Systems & Data

Q11 What business systems do you currently use?

ERP (e.g. Acumatica, NetSuite) CRM (e.g. HubSpot, Salesforce) Accounting / Finance (e.g. QuickBooks, Xero) Scheduling / Dispatch Other

Q12 How well do these systems talk to each other?

Poorly — mostly disconnected; we move data manually Somewhat — some systems connect; some manual work remains Reasonably well — most systems integrate Very well — data flows smoothly between systems

Q13 Where does most of your operational data live?

4

Willingness to Change

Q14 How comfortable is your team with process automation?

Enthusiastic — we want to try it Open — we see the value Cautious — show us proof first Skeptical — we prefer doing it ourselves

Q15 Are there any specific processes your team would resist automating? Why?

Q16 In an AI-assisted workflow, what's your preference?

AI handles it; we spot-check results AI recommends; human approves (human in the loop) AI handles routine cases; humans handle exceptions Not sure yet

Q17 Have you tried implementing process automation or new systems before? What worked? What didn't?

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Quick Win Potential

Q18 Pick the ONE workflow from your pain points that, if automated, would free up the most time or eliminate the most friction.

What's the workflow?

Who does it today?

How many people do this task?

Their hourly rate?

How often?

Time per instance?

What gets in the way?

Q19 For that workflow, what information needs to be in the final output?

Q20 Do you have examples of past work we could use to test an AI solution?

Yes, plenty Some Not really Not sure

6

Data, Privacy & AI Deployment Preferences

Q21 How sensitive is the data your team works with day-to-day?

Low — mostly internal operational data, nothing confidential Moderate — some employee or customer data, but generally low-risk High — employee PII, financial records, health data, or confidential client information Very high — regulated data (HIPAA, PCI, SOC 2, etc.) with strict compliance requirements

Q22 When AI tools process your business data, how important is it that your data stays within your own infrastructure (i.e. never sent to a third-party cloud)?

Critical — data must stay on our own servers or network at all times Important — strong preference for on-premise or private cloud, but not a hard requirement Neutral — open to either, as long as the vendor has strong security practices Not a concern — we already use cloud tools and are comfortable with that model

Q23 Have you or your leadership team expressed concerns about data leaving your network when using AI tools like ChatGPT or Microsoft Copilot?

Yes — it's a significant concern that has slowed or blocked adoption Yes — we've raised it but haven't let it stop us yet No — we haven't thought about it much yet No — we're comfortable with how those platforms handle data

Q24 If an AI solution could run entirely on your own hardware or private network — with no data ever sent to OpenAI, Microsoft, Google, or any third party — how would that change your interest level?

Much more interested — that's exactly what we need Somewhat more interested — it removes a real concern About the same — data location isn't our primary decision factor Less interested — we prefer managed cloud solutions over self-hosted

Q25 How does your organization currently store operational and employee data?

Primarily in cloud-based SaaS tools (e.g. Microsoft 365, Google Workspace, HubSpot) On-premise servers or local network storage Private or hosted cloud (we control the environment) Mixed — some cloud, some local, varies by department Significant amount still on paper or in local files

Q26 Would your organization be open to deploying AI on dedicated hardware at your location (a small server or workstation running AI models locally) if it meant stronger data privacy and no ongoing per-user licensing fees?

Yes — that actually sounds ideal Open to it — would want to understand the maintenance requirements Maybe — depends on cost, complexity, and IT support needed No — we prefer fully managed cloud solutions with no hardware to maintain

Q27 Does your organization have an IT person or team who manages your infrastructure?

Yes — internal IT team Yes — one internal IT person Outsourced / managed service provider (MSP) No dedicated IT — we handle it ourselves or call someone when needed

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Team & Decision-Making

Q28 Who is the primary decision-maker for this project?

Name

Title

Email

Q29 Who are the primary stakeholders involved in this project?

Name

Title

Email

Department

Q30 Who will actually use any solution we build?

Q31 What's your realistic timeline?

Pilot / proof-of-concept in 30–60 days Exploratory phase — understand options first Later this year Just exploring; no firm timeline

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Weymouth Club — Call Verification & Detail

Weymouth Club only This section verifies key insights from your discovery call and gathers operational detail to support the AI governance plan, leadership productivity initiative, and phone attendant rollout.

AI Phone Attendant

Q32 On our call you mentioned two options for an AI phone attendant — a third-party vendor already in market and Daxko/Club Automation's beta offering. Where are you currently leaning?

Third-party vendor — more developed product Daxko/Club Automation beta — free, native integration Undecided — want guidance on the trade-offs

Q33 Approximately how many after-hours calls come in per week that go unanswered or to voicemail?

Q34 What are the most common reasons members call after hours?

Q35 What would a successful phone attendant rollout look like in the first 90 days?

Leadership Productivity

Q36 On our call you described wanting directors to spend less time on email and admin and more time on the floor. Which director role is the most urgent priority?

Q37 Approximately how many director-level leaders are in scope for this initiative?

Q38 What does a typical director's day look like in terms of time split between admin work and floor/member-facing time?

Admin / email / back-office

/

Floor / member-facing / leadership

Q39 What would the ideal split look like after implementing AI productivity tools?

Admin / email / back-office

/

Floor / member-facing / leadership

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Anything Else?

Q45 Is there anything about your business, team, or situation that would help us understand your needs better?