Questions to Ask a New Client
Questions to ask a new client, from the first call to the kickoff. The top 5 come first for when time is short: why now, what the work should achieve, the deadline, who decides and the budget. The rest cover the problem and goals, the people involved, money and time, how you will work together and how to close the meeting. Written for consultants, agencies and IT providers interviewing a business client for the first time, and for freelancers deciding which potential clients to say yes to. Under each question is a note on what a good answer sounds like, what a poor one warns you of, or what to ask next.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Top 5
What made you start looking for help now rather than six months ago?
Why ask it
The trigger explains the urgency and often the real brief. If a board deadline, a resignation or a failed launch sits behind the request, that is what the work will be judged against, whatever the written scope says.
What do you want this work to achieve, and how will you know it has?
Why ask it
Take the goal down in their words, then push for the measure and where it is reported: a sales figure, a support queue, an audit result. A client who cannot name one will judge the work on impression, and an impression is hard to deliver against.
When does this need to be done by, and what is driving that date?
Why ask it
Some dates are fixed from outside: a product launch, a regulatory filing, the end of a lease. Others came out of a planning spreadsheet and have room in them. Once you can tell the two apart, you know whether it is the scope or the schedule that has to bend when something slips.
Who has to say yes before work can start, and who can stop it later?
Why ask it
The person who approves the start and the person who can halt the work are not always the same, and the second tends to appear only once things are under way. Get names and roles, not a description of the process, and try to meet both.
What is the budget range, and where is it coming from?
Why ask it
Where the money comes from is as informative as the figure: an approved line item behaves differently from spending that still needs a business case. With a client who is shy of naming a number, sketch a small, a medium and a full version of the job and let them say which is closest.
Problem and goals
In your own words, what is the problem you want solved?
Why ask it
Worth asking even when there is a written brief, because the spoken version is seldom the same. Note the words they reach for, since those are the terms your proposal should use, and note what the document made a fuss about that never comes up.
What have you already tried, and what happened?
Why ask it
It stops you proposing the thing that failed here last year for reasons that still apply. Listen for whether the failure is put down to the approach or to a person, because the second kind of story may one day be told about you.
Have you worked with someone external on this before? How did it end?
Why ask it
The ending of the last arrangement is a fair preview of this one. Then ask what they would change on their own side next time. A client with an answer to that is a different prospect from one who lays every fault at the last agency's door.
Can you show me how this gets done today, and who touches it?
Why ask it
Ask to watch it on a real example if you can. People describe the official route from memory and then, at the keyboard, open the spreadsheet or the personal inbox that the official route depends on.
What about this costs you the most time in an ordinary week?
Why ask it
Small weekly irritations rarely make it into a brief. Fixing the login that fails every Monday or the report rebuilt by hand each Friday earns more goodwill than its size suggests, so list these separately from the main job.
Suppose you left this alone for another year. What would happen?
Why ask it
When the answer is that nothing much would change, the work is a nice-to-have and likely to be an early cut if money tightens. A named loss, such as a contract, a key member of staff or a renewal, is the thing to quote back in your proposal.
Which parts of the current setup do you like and want kept?
Why ask it
New suppliers tend to arrive with a broom. Find out what should survive it: a report layout the owner designed, a tool the team has only just learned, a contractor they are loyal to. Those are also the things you can build on without a fight.
How does the business make its money, and who are its best customers?
Why ask it
Knowing how the money comes in gives you the context for everything else they tell you, and a new client is usually glad to explain it. If the job on the table sits a long way from how they earn, expect it to lose arguments over time and attention.
Who do you count as your competitors, and what do they do well?
Why ask it
The names show who the client measures itself against, which is not always who its customers compare it with. What they admire in a rival is often the brief in disguise: a request for a new website can be a request to stop losing work to the firm down the road.
Where does this sit among everything else the business is trying to do this year?
Why ask it
You are asking for its rank, and you can say that openly. Work that sits third on someone's list gets slow replies and late feedback, which you can plan for if you hear it now.
When this is finished, what will exist that does not exist today?
Why ask it
Have them describe the thing itself: a signed-off design, a system the staff are logging into, a set of accounts filed. Two people on the client's side will sometimes describe different things, and this meeting is a far better place to find that out than the handover.
Is there an example of what you have in mind, yours or anyone else's, that you could show me?
Why ask it
Many people find it hard to describe what they want and easy to recognise it. Another company's website, a report from a different department or a product's packaging gives you both something to point at, and what they dislike about it is as useful as what they like.
What would an early win look like, something visible in the first few weeks?
Why ask it
Pick something small enough to finish quickly and visible enough for your contact to show their own boss. Check who that audience is, since an early result nobody above them notices does little for the project's standing.
People
How did you hear about me, and what had you heard?
Why ask it
A referral arrives with expectations set by whoever recommended you, so find out what that person said and what you did for them. If the client found you through a search or an article, the page they read shows which of your services they think they are buying.
Have you hired a freelancer before, or have you mostly used agencies and staff?
Why ask it
A client used to employees may expect you at set hours and in every meeting, and one used to agencies may picture a team behind you. Explain early how a one-person business runs, including the days you are with other clients, and both surprises are avoided.
Once we are under way, how will decisions get made: by one person, or by a group?
Why ask it
A group usually needs more time and more rounds than a single owner, so allow for that in the price and the schedule. How the last comparable decision actually went is a better guide than how decisions are supposed to go.
Who on your side will I be working with day to day, and how much of their time do I have?
Why ask it
A named contact with two hours a week and no authority is a risk that seldom appears in a brief. Ask what else that person is responsible for over the same months, and which decisions they can make on their own.
Who else should I talk to before I write this up?
Why ask it
The names offered are people your contact trusts, and the ones left off can be as telling. Half an hour with whoever does the job every day often corrects the brief more than any document does.
Who will actually use what I deliver, and what do they need it to do?
Why ask it
Whoever signs the invoice may never open the thing you make. If the real audience is a sales team, a regulator or the client's own customers, try to get an hour with one of them before you design anything.
If this goes well, what changes for you personally?
Why ask it
It separates the organisation's goal from your contact's own. Someone whose promotion or credibility rests on this will behave very differently from someone carrying out a decision they did not make. It lands best one to one, not in front of their colleagues.
Who will have to change how they work because of this, and have they been told?
Why ask it
The people whose routine changes decide whether the finished work gets adopted or quietly ignored. If the news has not reached them, agree who breaks it and when, so that it is not you, by accident, in a first email.
Who will be unhappy if this succeeds?
Why ask it
Most projects take budget, attention or territory from someone. Asking outright brings the resistance into the open early, and a flat 'nobody' deserves a gentle second try, since few changes please everyone.
Which other suppliers or internal teams will I be working alongside?
Why ask it
Handovers get dropped where your work meets an accountant's, a web developer's or the existing IT provider's. Find out who has the final word at each join, and request an introduction before there is a problem to introduce you over.
When my part is finished, who keeps this going?
Why ask it
If the answer is a role nobody has been hired into yet, you are building something for a stranger to look after, so put handover notes and training in the scope. If the answer is you, this is the first stage of a longer arrangement and worth quoting as one.
Money and time
Are you talking to anyone else about this work, and what will the choice come down to?
Why ask it
Put lightly, as a planning question, this tends to be answered plainly. Pay most attention to what will decide it: a choice made on price is a different sale from one made on trust or on who can start soonest.
If you had to rank speed, cost and quality for this job, what order would you put them in?
Why ask it
Everyone wants all three, so make them choose. A client who puts speed first will usually forgive rough edges, and one who puts cost first needs warning before every extra hour.
If time or money runs short, what is the one thing that still has to be delivered?
Why ask it
It forces a ranking while nobody is under pressure. Write the answer down as they say it and put it in the proposal, so that it is already agreed on the day something has to be cut.
When will you or your team be hard to reach in the coming months?
Why ask it
Holidays, a trade show, the busiest weeks of their year, a planned leave. Put those dates in the schedule now, with a named stand-in for approvals, so that a quiet fortnight is not mistaken for a stalled project.
Would you rather have one fixed price, pay for the hours worked, or a monthly retainer?
Why ask it
The preference often shows what worries them. Fixed-price buyers tend to fear an open-ended bill, hourly buyers fear paying for padding, and retainer buyers want to know you will pick up. Price in whichever risk you are being asked to carry.
Is this a one-off job, or do you expect to need this kind of work regularly?
Why ask it
A single project and a client who may come back every month call for different plans in a freelancer's calendar. Be wary of cutting the price on the promise of more to come: quote the job in front of you, and let repeat work earn its own terms when it arrives.
What paperwork has to be in place before I can start: a contract, a purchase order, supplier forms?
Why ask it
Large organisations can take longer to set up a supplier than to agree the work. Find out who runs that process and start it the same day, and if they want their own contract terms, read them before you promise a start date.
Who will own the finished work, and may I show it in my portfolio?
Why ask it
Ownership and usage rights depend on the contract and on the law where each of you is based, so settle it in writing and ask how it works there if you are unsure. The portfolio half matters to a freelancer more than it sounds, since past work is how the next client finds you.
How do invoices get paid here: who approves them, and on what terms?
Why ask it
Payment terms and habits differ from one company and one country to the next, so find out theirs before you assume your own apply. Learning that invoices need a reference number or go out in one monthly run spares you a late first payment and an awkward chase.
Are you comfortable paying part of the fee before I start?
Why ask it
A deposit is how many one-person businesses cover the risk of starting, and the reaction to the request tells you something before any money moves. Customs differ by trade and country, so say what you normally ask for and find out what they normally pay.
When something new comes up mid-project, how would you like to handle the cost and the time?
Why ask it
Extra requests are close to a certainty, so settle the routine while there is nothing to argue about. Some clients want a short written quote for each addition and others prefer a block of spare hours, and both beat a surprise on the final invoice.
How many rounds of changes do you picture before this is signed off?
Why ask it
'One or two' usually comes from someone who has bought this kind of work before. 'Until it is right' describes an open-ended job, so put a number in the quote and a price on each round beyond it.
Working together
What do you expect from me, and what will you be doing yourselves?
Why ask it
Plenty of projects stall on the client's side of the line: the content that never arrives, the interviews nobody books. Naming their tasks in the first conversation makes it much easier to bring one up later when it is late.
How involved do you want to be: every decision, or only the big ones?
Why ask it
Hands-on clients feel ignored by a supplier who goes quiet for a fortnight, and hands-off clients feel pestered by daily questions. Get a recent example of each kind of decision, since many people overestimate how much time they will have.
How do you prefer to be kept up to date, and how often?
Why ask it
Settle the channel along with the frequency, since a client who lives in email will not read updates posted in a shared tool. Agree who else is copied in as well, because that list is where office politics tends to show.
What are your working hours, and how quickly do you expect a reply from me?
Why ask it
Say your own hours aloud in the same breath. An expectation of same-evening replies is far easier to negotiate in the first week than after you have met it three times.
How do you like to give feedback: notes on the document, an email, a call?
Why ask it
Find out whether comments will come from one person or arrive separately from five. Asking for a single collected set of notes per round is a reasonable request on day one and a hard one to introduce in month three.
When I send something for sign-off, who looks at it, and how long does that usually take?
Why ask it
Review time is easy to underestimate, and in some organisations a legal or brand check adds weeks. Go by how long the last sign-off really took, not the official target, and build that into your dates.
Which systems, accounts or files will I need to get into, and who holds the admin rights today?
Why ask it
Waiting for logins is a common reason a start date slips. On IT and web work especially, check whether a former employee or the last supplier still holds the keys, and ask for an account of your own instead of a borrowed password.
What has to keep running, whatever else happens, while I do this work?
Why ask it
Payroll on the 25th, the till on a Saturday, the phone line customers ring: most businesses have something that cannot stop. Get the dates and hours as well as the names, and schedule anything risky well away from them.
What should I read or look at before I start?
Why ask it
Request the dull material as well as the polished: the price list, the staff handbook, last year's plan, the previous supplier's handover notes. Turning up to the kickoff already knowing their product names reassures a new client in a way a credentials slide does not.
What is confidential here, and how do you want me to handle your information?
Why ask it
Customer records, prices and staff details can carry legal duties that are different in each country and industry. Have the client tell you which rules bind them and who deals with that on their side. Raise the smaller matter too: whether they mind appearing on your client list.
Is there anything I should leave well alone: a system, a subject, a person?
Why ask it
It brings out the no-go areas, such as a system nobody is allowed to change or a team that should not be interviewed, before you walk into one. Clients seldom volunteer these, and you do not need the reason on day one, only the boundary.
If we hit a problem halfway through, how would you want me to raise it?
Why ask it
Some clients want a call the same day; others want it set out with options at the next meeting. Agree the route now, while nothing is wrong, and the awkward call will be shorter when it has to be made.
What is the best thing a supplier has ever done for you?
Why ask it
The cheerful twin of the question about how the last arrangement ended. People tend to remember small things: a call before bad news, an invoice that matched the quote, a handover someone could follow. Each is something you can start doing in the first week.
What would make you want to end this early?
Why ask it
An uncomfortable question, and worth the discomfort. Clients usually answer with particulars: missed check-ins, surprises on an invoice, being handed junior staff. Each marks a spot where you will need to be careful.
Closing
What is your biggest worry about this?
Why ask it
Wait for the second answer, because the first is usually the polite one. Fear of the bill growing, of losing control of their own project or of being let down again each calls for a different promise from you, so reply to the one you actually heard.
At the end of this, what would make you recommend me to someone else?
Why ask it
It finds out what they value in a supplier without sounding like a survey, and the reply is seldom about the deliverable alone. Keep it, because it is also what to return to when the work is finished and you would like a referral or a testimonial.
What were you expecting me to ask that I have not?
Why ask it
Late in the meeting this often turns up something that changes the plan, usually a constraint the client assumed you already knew. Give it a real pause before you fill the silence.
What would you like to ask me?
Why ask it
Leave real time for it and not the last minute of the hour. The questions a new client asks show what they are unsure of, and a client with none has either decided already or not yet pictured working with you.
What is the next step on your side, and when should I check in?
Why ask it
Settle who sends what and by which day before anyone stands up. Naming the date on which you will ring also turns the follow-up into an appointment, so neither of you has to chase.
Scoping a first client conversation
Practical guidance for the conversation itself
Running the call
If you only get five, ask the first five
The Top 5 group is the short version of the whole page: why now, what the work should achieve, the deadline, who decides and the budget. With those answered you can write a sensible proposal. With any one missing you are guessing at it.
Spread the rest over the first few conversations
The Problem and goals group and the People group belong to the first call. Money and time comes before you quote. Working together is for the kickoff, once the client has said yes, and the Closing questions end every meeting. No client should have to sit through all of them in one interview.
Spend the first call listening, not pitching
A new client is mostly working out whether you understood the problem. Hold back the description of your approach until you can tie it to something they said, even if that means a second conversation.
Ask about the trigger before the requirements
The written brief is a summary of a decision already made. Understanding what prompted it often shows a different, more useful problem underneath, and clients rarely object to being asked.
Get the money conversation done early
The budget range and where it comes from are fair things to raise in the first call, and doing so can save both sides weeks. If the client is reluctant to name a figure, ask which scale of solution they have in mind instead.
Screen potential freelance clients before you quote
Working alone, you have nobody to absorb a late payment or a job that doubles in size, so the first call is your interview of the client as much as theirs of you. Find out whether they have hired a freelancer before, then put the Money and time questions about a deposit, rounds of changes, who owns the finished work and whether more work is likely. A client who is put out by any of them has given you an answer too.
Write the scope back to them in their words
Send a short summary using their phrasing for the goal, the deadline and what finished means. Being corrected on that note is a one-line email, and far better than finding the misunderstanding in the first draft.
Adapt the wording to your trade
The list is written to fit any service. An IT provider will spend longest on access, admin rights, what has to keep running and who looks after the systems today, a designer on examples and feedback, a bookkeeper on records, dates and who approves payments. Where the work is ongoing, say account or retainer in place of project. If your client is one person you coach or advise, keep the questions on goals, working style and the close, and leave the procurement ones out.
What to listen out for
Signals worth slowing down for
- Everything wrong is attributed to the previous supplier, with no account of their own role.
- The person you are speaking to cannot name who approves the budget.
- The deadline has no reason behind it, or the reason changes when you ask twice.
- Success is described only in adjectives, with no measure and no artefact.
- You are asked to start before terms are agreed, because the timeline is tight.
- Nobody on their side has time allocated to the project.
Signals that the work is likely to go well
- They can describe what happens to the output after you leave.
- They name the internal resistance without being pushed.
- They have a specific number they are trying to move.
- They ask you what you will need from them.
Common mistakes
Answering the brief as written
A brief often describes the solution the client has already imagined. Delivering exactly that, when the underlying problem was something else, is how competent work still ends up disappointing.
Avoiding the awkward questions to keep the mood good
Budget, approvals and what would make them end the arrangement all feel risky to raise in a first call. Each one is an awkward minute now, or a much harder conversation once the work has begun.
Leaving the client's obligations vague
Data access, interviews, reviews and sign-off all sit on their side. Write them down with owners and dates. Otherwise a delay that starts there is likely to be remembered as yours.
Treating enthusiasm as commitment
A warm first call with someone who cannot authorise spend often goes nowhere. Find out who else needs to be in the next conversation, and ask that they join it.
Reading the list aloud
A new client should come away feeling listened to, not processed. Choose the questions whose answers you do not already have, and when an answer is going somewhere useful, stay with it and drop the next three on your list.