The question bank
The 117 questions we ask before building operations software
These come from documenting a real operation, department by department — the leasing business behind our case study. They are what we work through before anything is scoped or priced. Steal them: run them on your own business even if you never call us. The uncomfortable ones are usually pointing at money.
Sales and enquiry
An enquiry arrives on a Tuesday morning. Walk me through the next four hours — who touches it, in what order, and where does it get written down?
How does an enquiry reach you at all — reference, website, someone's personal contact, an existing customer's colleague? Which of those closes best?
When someone calls asking about leasing, how do you find out whether they are even allowed to lease a car under their employer's policy?
How do you work out what car to suggest? Is it what they ask for, or is there a car you steer people towards, and why?
Are there cars you quietly avoid quoting? What made you learn that?
Who decides which product variant the customer gets offered? What question do you ask that tells you which one it should be?
What is your promise on how fast a quote goes out — and does that promise change if the vehicle is in another state?
Follow-up (if a promise exists): when the quote is going to be late, what happens? Who tells the customer, and how?
When you speak to someone at a company, how do you know whether they can actually authorise a lease or are just interested?
What information do you collect from the customer before anyone starts pricing, and how does it get to the person who prices it?
Follow-up (if there is a form): who fills it — you or the customer? What happens when it comes back half empty?
Has a deal ever gone a long way and then died because of something that should have been caught on day one? What was it?
Pricing and quotation
Someone has to turn a customer requirement into a number. Who is that person, and what do they open to do it — a spreadsheet, a template, something someone built?
Where does the vehicle price in that calculation come from, and how old is it by the time it is used?
Which numbers in a quote are fixed by policy, and which ones can a person change on their own judgement?
Follow-up: is there a floor — a margin, a rate, a residual — below which someone has to ask permission? Who grants it, and how is that permission recorded?
Who approves a quote before it goes to the customer, and what are they actually checking?
How many quotes does one customer typically end up with before something is signed? What happens to the old ones?
When a customer negotiates, what are the levers your team pulls to bring the number down? List them in the order you would use them.
How does the salesperson know which version of the quote is the final one?
Has a superseded quote ever been treated as the live one further down the process? What did that cost?
When the customer says yes, how is that yes captured? Verbally, on WhatsApp, on email, on paper?
Procurement and supplier
Who talks to the vehicle suppliers, and how many do they approach for one requirement?
What exactly do you ask a supplier for — a formal quotation document, or a price over the phone?
Follow-up (if suppliers sometimes give informal pricing): how does that verbal discount become something you can rely on later? Who writes it down, and where?
Discounts get quoted on different bases. How does your team make sure everyone is comparing the same number?
How do you confirm a vehicle actually exists and is available, versus the supplier saying it is available?
What is the gap between a vehicle being reserved for you and it physically leaving the supplier? Who tracks that, and how often do they chase?
Which details on a supplier's document have caused you problems when they were wrong — and who catches them now?
When the vehicle takes months to arrive, what happens if the supplier revises the price in the meantime? Who finds out, and what has to be redone?
Do you pay the supplier anything at the point of ordering? Who authorises it, and how does that person learn the amount?
Follow-up: how do you prove later that you paid it?
When a supplier is in a different state or tax jurisdiction, what changes about how you deal with them?
Who is the single person who would know today where every ordered vehicle currently is?
Registration and delivery
Walk me from the vehicle being paid for to the customer having keys. Every hand it passes through.
What documents must be collected from the customer for registration, and at what point does someone discover one is missing?
Who physically deals with the registration authority — your staff, the supplier, an agent?
What part of registration depends on the customer being reachable at a specific moment? What happens when they are not?
Before a vehicle is handed over, who confirms it is the right vehicle in the right condition? What do they look at?
Is there any photographic record of a vehicle at handover? Who takes it and where does it live?
How does the delivery date that was promised to the customer get tracked against what actually happens?
Are there customers with extra paperwork at delivery? What triggers that, and who knows it applies?
Contracts and documentation
How many different agreement templates exist, and what decides which one a deal gets?
Who fills them in, and what do they copy the details from?
Follow-up: if the same customer detail appears in three documents, is it typed three times?
What has to physically exist on paper — stamps, signatures, originals — and who is responsible for having it ready before it is needed?
When a customer's legal team wants changes, who handles that conversation, and how long does it typically add?
Where are executed agreements kept? If I asked for one from two years ago, how long would it take?
Are there fields in your agreements that different templates fill in differently — dates, payment terms, account details? How would you know?
Who is the last person to read an agreement before it goes to the customer, and what are they checking for?
What happens to the paperwork after signature — who collects it, who files it, who needs a copy?
Finance and funding
Where does the money to buy vehicles come from, and does the process differ by funder?
Follow-up: how many different funder processes does your team have to remember, and where is each one written down?
What has to be assembled and sent for a funder to release money? Who assembles it?
Between what the funder pays and what the vehicle costs, someone covers the difference. Who calculates that figure, and who checks it?
What is the document or list that tells finance exactly what to pay and to whom? Who prepares it, who verifies it?
Follow-up: how does a late change — an extra discount, a price revision — reach that list before payment goes out?
How do you verify a supplier's bank details before paying them?
Once a vehicle is on the road, what triggers the first invoice — and how does the invoicing person learn the trigger has happened?
Where do customer payments land, and does that vary by contract? Who would know which account applies to which customer?
Insurance and claims
Who arranges insurance on a new vehicle, and at what point in the process?
Whose name goes on the policy, and what decides that?
Who checks the policy against the actual vehicle and the actual contract before it is accepted?
When a vehicle is damaged, who does the customer call first? What happens in the next hour?
Who follows a claim to completion, and how do they remember to?
Renewals — how does anyone know a policy is about to expire?
Has a claim ever been complicated by something on the policy not matching reality? What was it?
Fleet in service and aftersales
Once a vehicle is with a customer, what are the things your team is still responsible for?
How does a customer raise a problem, and who receives it? Is that the same person every time?
How do you know a vehicle's servicing is being done, and who chases it?
How is actual usage — distance covered — tracked against what the contract assumed? Who checks, and how often?
Follow-up: what happens when a vehicle is clearly going to breach the contracted usage? At what point does someone tell the customer?
What statutory or periodic obligations attach to each vehicle, and where is the list of what falls due when?
When a contract is approaching its end, who starts that conversation and how far in advance?
A vehicle comes back at the end of a term — who inspects it, who photographs the condition, and who decides what the customer is charged?
Follow-up: how is that charge negotiated, and who has authority to waive it?
Collections
When a customer does not pay, how long before someone notices?
Who notices — a person checking, or a customer complaining about something else?
What is the sequence of chasing, and who does each stage?
At what point does it escalate, and to whom?
Where is the record of what was said to a customer about an overdue amount?
How does the person chasing payment know whether the customer has a genuine dispute versus is simply late?
What is the oldest unpaid amount on your books, and could you tell me that without asking anyone?
Management, data and IT
What report do you personally look at to know how the business is doing, and who prepares it?
Follow-up: how long does preparing it take, and how much of that is copying from one place to another?
When two people give you different numbers for the same thing, how do you decide which is right?
If someone asked you today how many vehicles you have on lease, how long would it take to answer with confidence?
Which single spreadsheet, if it were lost tomorrow, would hurt the most?
Who has access to it, and is there a copy anywhere else?
Where does the same information get typed in more than once across the business?
Which step in your whole process most often stalls, and what is it waiting for?
If one specific person did not come to work for a month, what would stop?
What do you currently not know that you wish you knew?
The project itself
What they already run
What software is your business using right now — accounts, banking, tracking, anything — and who inside the company actually opens each one?
Which of those does the new system have to talk to, and which could be replaced entirely?
Follow-up: for the ones it must talk to — what would need to pass between them, in which direction, and how often?
Is there anything you're required to file or report to an outside body — and does that come out of one of these systems today?
What history comes across
What data would you want inside the new system on day one, and how far back does it go?
Where does that data physically live — one spreadsheet, twenty, a system someone built, paper files?
Follow-up: if I opened that spreadsheet right now, would every row be filled in the same way, or has each person entered things their own way over the years?
Who uses it
How many people would log in — and for each team, are they at a desk, on a phone, or out on site?
Who needs to see everything, and who should only see their own work?
Is there anyone who has to use this who doesn't currently use software for their job at all?
History with software
Have you bought or built software for this before? What happened to it?
Follow-up: if it stopped being used, what was the actual reason — it was wrong, it was slow, one person left, people just went back to Excel?
What's the one thing a new system could do that would make your team choose it over what they do today?
The bad day
Describe your busiest, worst day of the month or the year. What breaks first?
When an audit or an outside check happens, what does someone have to go and assemble by hand?
Who decides
Who signs off on something like this, and what do they need to see before they will?
What else is competing for the same budget this year?
If this goes ahead, who inside your company owns it — who do my team speak to every week?
What would make you consider this project a failure twelve months from now?
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