AI Readiness: Quick Win Assessment

For small and mid-size businesses — 20 to 100 employees
⏱ 8–12 minutes 📋 42 questions
1
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?
2
Current Operations & Pain Points
Q5 What are your top 3 operational pain points right now?
1
2
3
Q6 Which of those pain points would have the biggest impact if solved?
Q7 How much time per week do you estimate is spent on manual or repetitive work across your team?
Q8 Are there specific workflows where your team feels most bogged down or interrupted?
3
Systems & Data
Q9 What business systems do you currently use?
Q10 How well do these systems talk to each other?
Q11 Where does most of your operational data live?
4
Willingness to Change
Q12 How comfortable is your team with process automation?
Q13 Are there any specific processes your team would resist automating? Why?
Q14 In an AI-assisted workflow, what's your preference?
Q15 Have you tried implementing process automation or new systems before? What worked? What didn't?
5
Quick Win Potential
Q16 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?
Their hourly rate?
How often?
Time per instance?
What gets in the way?
Q17 For that workflow, what information needs to be in the final output?
Q18 Do you have examples of past work we could use to test an AI solution?
6
Team & Decision-Making
Q19 Who is the primary decision-maker for this project?
Name
Title
Email
Q20 Who are the primary stakeholders involved in this project?
Name
Title
Email
Department
Q21 Who will actually use any solution we build?
Q22 What's your realistic timeline?
Q23 Has budget been allocated or approved for this initiative?
If approved or pending, what's the approximate range you're working with?
7
Anything Else?
Q23 Is there anything about your business, team, or situation that would help us understand your needs better?
8
SecondWind-Specific Call Verifications
SecondWind Water Systems only This section verifies key insights from your discovery call and gathers operational detail to support order-writing, scheduling, and intake optimization.
Order-Writing Bottleneck
Q24 Who writes orders today?
Q25 Approximately how many orders per week?
Q26 How long does a typical order take to write?
Q27 What information must be included in an order?
Q28 Where does customer information come from when writing an order?
Q29 How often are you interrupted while writing orders?
Scheduling & Dispatch Optimization
Q30 How do you currently schedule appointments?
Q31 Who manages scheduling?
Q32 Approximately how many field appointments per week?
Q33 Do you currently optimize routing to minimize travel time?
Q34 What would "optimized" look like to you?
Customer Intake & Pre-Qualification
Q35 How do new customers contact you or enter your pipeline?
Q36 What information do you collect upfront from new inquiries?
Q37 What percentage of your inquiries would you estimate are "straightforward" vs. "complex"?
Straightforward (clear solution, standard process)
/
Complex (extended discussion, custom solution)
Team Readiness & Hybrid Model
Q38 In our call, you expressed interest in a hybrid approach — AI handles routine admin work, your team handles complex decisions and customer relationships. Is that still the right vision?
Q39 What's your team's main concern about AI-assisted workflows?
Q40 How would your team prefer AI-assisted tools to work?

Return this whenever convenient. Your answers will help us identify the best quick win for your business and verify what we discussed on our call.