15 questions to design a system around your biggest challenge — understanding where AI can save you time, money and effort.
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Candidate Strategy
Question 01
Where does your best talent currently come from — and where does it dry up?
Referrals, LinkedIn searches, job boards, your own database? Which channels are working and which have gone quiet?
Candidate Strategy
Question 02
Describe your ideal candidate — the one you always need more of.
Seniority, background, current employer types, what makes them hard to find.
Candidate Strategy
Question 03
How do you currently approach a candidate you have never spoken to before?
Walk through the actual process — where you find them, what you send, what gets a response.
Candidate Strategy
Question 04
What is your honest conversion rate from first contact to a meaningful conversation?
Roughly — how many cold outreach messages do you send to get one genuine conversation?
Relationship Management
Question 05
How do you currently stay in touch with candidates who are not ready to move yet?
The best people are rarely urgently looking. How do you maintain warmth over 6 to 12 months?
Relationship Management
Question 06
What signals usually mean a senior candidate is about to become open to a move?
We will build automated monitoring around these triggers. Select all that apply.
Database and Tools
Question 07
How healthy is your existing candidate database — and how is it currently used?
Size, how recently updated, what system it lives in, and how often you go back to it.
Database and Tools
Question 08
What CRM or ATS does your business currently use — and what are its biggest limitations?
Be honest about what is broken or being ignored.
Content and Brand
Question 09
What does your business's LinkedIn presence look like today?
At exec level, brand matters. Candidates need to believe in who they are talking to.
Content and Brand
Question 10
What content would genuinely attract senior your sector candidates?
What would make a senior professional stop scrolling and think that firm gets it? Select all that apply.
Operations
Question 11
Walk me through what happens between finding a great candidate and them being successfully placed.
Where do things slow down or fall apart? Ghosting, timing, counteroffer, client fit?
Technology
Question 12
Which of these tools are you already using or open to?
Select all that apply. Claude Max replaces any need for a separate ChatGPT subscription.
Technology
Question 13
On a scale of 1 to 10, how comfortable are you with setting up and configuring technical tools?
1 = needs everything plug-and-play. 10 = happy in APIs and workflow builders independently.
5
Fully managedSelf-sufficient
Commercial
Question 14
What does commercial success look like in the next 6 months if this system works?
Numbers if you can — pipeline size, placements per month, revenue target, active clients.
Vision
Question 15
If you could describe your business in 3 years — having fully solved the candidate pipeline problem — what does the business look like?
Team size, market position, reputation, revenue. Be ambitious — this is the north star.
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