Discovery questions to ask a service business before you set up its software

Short answer: good discovery questions follow the whole business, not one tool: how a customer finds them, calls, texts or books, how that becomes a quote, a scheduled job, an invoice and a payment, and what happens around it (marketing, reviews, the team, the admin that repeats every week). Ask about goals and pain first, then each step of the work, then the people, tools, data, reporting and budget. The 72 questions below are grouped in that order, with a 15-question version for a first call.

This list is for agencies, consultants, IT firms and bookkeepers who set up or replace the software that runs a small service business: HVAC, plumbing, electrical, cleaning, landscaping, and also agencies and consultants. Most of these businesses pay for five to ten separate apps, so the questions look at all of them, not only the customer list. You can use the list with any tool. Where it helps, we show how the answers turn into a setup on Alori.

How to use this list

Don't read the 72 questions out loud. Pick the groups that matter for this client, ask open questions, and let the owner talk. Your job is to hear three things:

• Pain: what costs them money, time or sleep today.
• Process: how work really moves, not how they think it should.
• Proof: numbers you can use later in your proposal and pricing.

Write answers down in the client's own words. Those words go straight into your proposal.

1. The business and its goals

Why it matters: the goal sets the scope. "Grow to five trucks" and "stop working nights" lead to different apps.

1. What do you sell, and which service makes you the most money?
2. How many people work here, in the office and in the field?
3. What does a normal week look like for you as the owner?
4. Where do you want the business to be in one year? In three?
5. If one thing changed by next month, what would make the biggest difference, and what have you already tried?

Listen for: "I do the paperwork at night" or "I can't grow because everything goes through me." That is the real buying reason.

2. How customers find you

Why it matters: a missed lead is a lost job. Capturing every lead is often the fastest win you can show.

1. Where do new customers come from: calls, website, Google, social media, referrals, ads, repeat customers?
2. Does your website bring work today? Who updates it, and how often?
3. How many leads do you get in a normal week? In your busy season?
4. Where do you write down a new lead today, and how fast does someone get back to it?
5. Do you know which source brings the best jobs?

Listen for: "The website is old and nobody touches it." A site the owner can change by asking is often part of the project.

3. Quoting and sales

Why it matters: slow quotes lose jobs, and quotes are where the money first shows up in the system.

1. Walk me through your last quote, from the first call to the answer.
2. Do you quote on site, by phone, or after a visit, and with what: template, spreadsheet, paper, software?
3. Do you have a price list or packages (for example good, better, best)?
4. How do you follow up on a quote that gets no answer?
5. How many quotes do you send in a month, and how many get a yes?

Listen for: "I mean to follow up but I forget." Automatic follow-ups pay for themselves quickly.

4. Scheduling and online booking

Why it matters: the schedule is the screen the office looks at all day. If it doesn't fit, nobody uses the app.

1. Who builds the schedule, and with what?
2. How do technicians or crews find out where they go each day?
3. What happens when a job runs late or an emergency comes in?
4. Do you book recurring work: maintenance visits, cleanings, seasonal tune-ups?
5. Can customers book online today? Which services could they book themselves, and which need a call first?
6. Do you send reminders before a visit, and do customers still forget?

Listen for: double bookings, "I text everyone the night before" or a whiteboard in the office. That is a scheduling pain.

5. Jobs in the field

Why it matters: what the crew records on site is what ends up on the invoice. Gaps here cost money.

1. What does a technician need to see before arriving at a job?
2. What do they record on site: notes, photos, parts, hours, a signature?
3. Do they use phones or tablets in the field? Is the signal reliable?
4. Do you use checklists for some jobs (inspections, installs, cleanings)?
5. How does the office know a job is done, and do you track equipment or service history at each address?

Listen for: "The tech writes it on paper and someone types it in." Double entry is the most common pain in the trades.

6. Invoicing and payments

Why it matters: this is where the owner feels cash flow. Late invoices and unpaid balances are easy to measure.

1. How long after a job does the invoice go out, and who creates it?
2. How do customers pay you today: card, check, transfer, cash?
3. How do you chase unpaid invoices, and how much is overdue right now?
4. Do you use accounting software, and who does your books?
5. Do you sell service plans or memberships that bill on a schedule?

Listen for: "Invoices go out on Friday, or whenever I get to it." A gap between job and invoice is money you can show them.

7. Phone, texts and after-hours answering

Why it matters: customers call and text first. Every unanswered call and every message on a personal cell is a lost job or lost history.

1. Who answers the phone, and what happens when nobody can, on a job or after hours?
2. Do calls and texts land on one shared business number, or on personal phones?
3. How do customers reach you besides the phone: email, website chat, Facebook, Instagram?
4. Do you send confirmations, "on my way" texts or follow-ups after a job?
5. What questions do customers ask again and again (prices, areas you serve, hours, "do you fix this brand")?
6. Would you be comfortable with an AI assistant that answers calls, texts and the website chat after hours, books simple jobs and passes the rest to you?

Listen for: "Calls go to voicemail when we're on a job" or "Customer texts go to my cell." Missed calls can be priced, and the owner knows the history leaves with the person.

8. Website, help content and marketing

Why it matters: the same business that loses calls often has an outdated site, no answers written down and a customer list it never emails. These are easy wins once everything lives in one app.

1. Is the answer to the questions from group 7 written anywhere: a FAQ, a help page, care instructions after a job?
2. Do you email or text your past customers: seasonal reminders, promotions, newsletters? With what tool?
3. How big is your list of past customers, and do you know who hasn't booked in a year?
4. Do you ask for Google reviews after a job? How, and who remembers to do it?
5. How do you answer reviews today, good and bad?
6. Who handles marketing: you, someone on the team, an outside agency? What do you pay for it?

Listen for: "We should email our old customers before the fall rush, but we never do." A seasonal campaign to an existing list is one of the cheapest jobs to win.

9. Team, roles and HR basics

Why it matters: roles decide who sees what, and the people who use the app every day decide whether it sticks.

1. Who does what: owner, office manager, dispatcher, technicians, sales?
2. Who should see prices, costs and margins? Who shouldn't?
3. How do employees track hours, ask for time off and get scheduled around it?
4. Where do you keep employee information: contact details, certifications, onboarding checklists?
5. How comfortable is the team with apps today, and who will resist a new tool?
6. Who will own the app on your side once it's live, and do you plan to hire this year?

Listen for: one office person who holds everything in their head. Win them over and the project works.

10. Repetitive admin and automations

Why it matters: the weekly admin nobody sees is where an app saves the most hours. Name each task and you can price the time saved.

1. Which tasks do you or the office repeat every week? Walk me through last Monday.
2. What do you copy from one tool to another: from texts to the schedule, from jobs to invoices, from forms to a spreadsheet?
3. What reminders do you send by hand: quote follow-ups, visit reminders, unpaid invoices, maintenance due?
4. What does the team need to know each morning, and how do they find out today?
5. What should happen on its own when a job is done, a quote is accepted or an invoice is late?
6. Do you already use automation tools like Zapier, Make or email rules? What breaks?

Listen for: "Every Friday I spend two hours sending reminders." Write the hours down. They go into your proposal.

11. Current tools and their costs

Why it matters: the tools you replace are your price anchor and your migration list.

1. List every app you pay for: customer list, field service, scheduling, booking, invoicing, phone, texting, email marketing, website, chat, forms, payroll or HR.
2. What does each one cost per month, and per user?
3. What do you like about each? What do you hate?
4. Which spreadsheets does the business run on?
5. When do your contracts renew?
6. Which tool would you never give up?

Listen for: "We pay per user and every new tech costs more." Fill in the pricing guide with these numbers.

12. Data and migration

Why it matters: data is the riskiest part of the project. Find out early what exists, where, and how clean it is.

1. Where does your customer list live, and roughly how many customers?
2. Can you export it, and from the other tools too? Who has the logins?
3. What history do you need to keep: past jobs, invoices, notes, photos, emails?
4. How clean is the data: duplicates, missing phone numbers, old addresses? What can we leave behind?
5. Is there a date when an old tool must be turned off, or a phone number that must move?

Listen for: "Only my ex-employee knows that system." Plan extra time. The data migration checklist walks through the full move.

13. Reporting, budget and decision

Why it matters: the owner pays for answers, and a great scope with no budget, no decision maker or no deadline doesn't close.

1. If you could see one screen each morning, what would be on it?
2. Do you know your close rate, average job value and unpaid total?
3. Who else needs to agree before you go ahead?
4. What budget did you have in mind for setup? For the monthly cost?
5. Is there a deadline: busy season, a new hire, a contract renewal?
6. What would make you say this project was worth it six months from now?

Listen for: a renewal date or a busy season coming. Timing is your strongest buying signal.

The 15 must-ask questions for a first call

Short on time? Copy this list into your call notes. It covers the whole business in about 30 minutes.

FIRST CALL: 15 DISCOVERY QUESTIONS
Business: ____________   Date: ________   Contact: ____________

1.  What do you sell, and how many people work here?
2.  If one thing changed by next month, what would help most?
3.  Where do new customers come from?
4.  What happens when a call or text comes in and nobody can answer?
5.  Walk me through your last quote, from first call to answer.
6.  Who builds the schedule, and can customers book online?
7.  What does the crew record on site, and how does it reach the office?
8.  How long after a job does the invoice go out? How much is overdue?
9.  Do you email past customers or ask for reviews?
10. Which admin tasks do you repeat every week?
11. Which apps and spreadsheets do you pay for or rely on? Cost per month?
12. Where does your customer list live, and can you export it?
13. What one screen would you want to see every morning?
14. Who else decides, and is there a deadline?
15. What would make this worth it six months from now?

How to run the discovery session

Who should be in the room

• The owner. They decide and they pay.
• The office manager or dispatcher. They know how work really moves and answer most calls.
• One field lead or senior technician. They tell you what will work on a phone in a basement.
• The bookkeeper, for 15 minutes. Only if invoicing, payroll or accounting is in scope.

Keep it to four people. More than that and the meeting becomes a debate.

A 60 to 90 minute agenda

Tip: ask them to open their real tools during the call. A screen share of their current schedule or their phone's text inbox tells you more than ten answers.

Record the call if they agree, so you can focus on listening.

How to turn answers into a scope

After the call, sort every pain into one of three buckets: must have at launch, next month, and later. Then map each must-have to a module or an automation.

Keep the first release small: the three biggest pains, working well, in front of the people who use them every day. Write the rest into a roadmap. The software implementation plan turns this scope into a week-by-week rollout, and the proposal and SOW templates turn it into a document the owner can sign.

Red flags: when it is not a fit

Discovery is also where you walk away. Watch for these:

• No owner in the room, ever. If the decision maker won't give you an hour, they won't give you a decision.
• "We just need a cheaper Jobber." If price is the only pain, you will compete on price forever.
• Nobody will own the app. Without a champion on their side, the team goes back to paper in a month.
• They want every feature at launch. A 40-item must-have list means they haven't decided what matters.
• The data can't be reached. No export, no login, and no one who knows the old system.
• Requirements you can't meet. Strict compliance rules (for example health data), deep integrations with a tool that has no access, or a feature your platform doesn't have yet. Say so early.
• No budget and no deadline. Interest without timing is a newsletter subscriber, not a client.

One red flag is a conversation. Three is a polite no.

Doing this on Alori

On Alori, discovery and building can happen in the same week. Alori is one app that runs the whole service business, so most answers on this list map to something you can turn on rather than another tool to connect. You can describe the client's business in plain English right after the call and show a working app built on that client's real services at the next meeting: customers and deals, quotes, booking, schedule, jobs, invoices, employees, calls, texts, email, campaigns, the website, website chat and a help center. The bot answers customers and runs the automations from group 10. Changes are made by asking in chat, so a "next month" item is often a short request rather than a new project.

With agency mode, you build the app in a separate client account, copy a version you made for a similar client as a starting point, invite the owner when it's ready, and earn a markup on what the client pays Alori. The partner program explains how it works, and the playbook hub has the other guides for selling and delivering.

FAQ

How many discovery questions should I ask on a first call? About 15. Cover the money path from first contact to payment, how calls and messages are answered, the weekly admin, the tools they use and the decision. Save the detailed groups for the full discovery session.

Should discovery be free? A first call of 30 minutes usually is. A full 60 to 90 minute session with a written scope can be paid, or credited against the setup fee if they go ahead.

What is the difference between discovery questions and requirements gathering? Discovery finds the pain and decides if there is a project. Requirements gathering comes after, and details what each screen, message and automation must do. The same questions feed both, at different depths.

Why ask about the website, marketing and HR when the client asked about scheduling? Because they usually pay for a separate tool for each, and the same data (customers, jobs, staff) is typed into all of them. Asking about the whole business shows the full cost of their current stack, which is what makes replacing it worth it.

Who should I talk to if the owner is too busy? Start with the office manager to map the process, but get the owner for goals, budget and the final decision. Without the owner, don't send a proposal.

Can I use these questions for clients outside the trades? Yes. For agencies and consultants, read "job" as project and "technician" as team member. The path from first contact to payment is the same.