Questions to Ask a Client on First Meeting
For consultants, freelancers, agencies and advisers working out what questions to ask in a first business meeting with a new or prospective client. The 55 questions run in the order the hour usually goes: opening the meeting, their business, the problem and what set off the search, what success would look like, the decision and the money, then fit and next steps. Take a dozen into the room, not the whole list.
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The questions
Each question, and why to ask it
Opening
Before we start, what would make this a good use of your hour?
Why ask it
Their answer is the agenda, and it catches a mismatch while there is still an hour to fix it: they may have come expecting a pitch when you came to listen. Write it down and check it against your notes five minutes before the end.
Who is joining us today, and what does each of you look after?
Why ask it
Titles on an invitation rarely tell you who owns the problem and who was sent to observe. Hearing each person describe their own part also shows you who talks first and who waits to be asked.
How did you find me, and what made you think I might be the right fit?
Why ask it
A referral from someone they trust starts you in a different place from a search result or a shortlist of five. Their reason for thinking you fit is the expectation you are walking into, so hear it before you describe yourself.
How much do you already know about what I do?
Why ask it
Without asking, you either recite your own website to people who have read it or skip an introduction that someone at the table needed. Fill the gap they name in two minutes and hand the conversation back, since the meeting is about their business.
What is your own role in this, and how did it end up with you?
Why ask it
The person who lives with the problem and the person handed the task of finding a supplier want different things from you. The second often has to make a case upward, and that changes what you send afterwards.
How long do we have, and does anyone need to leave early?
Why ask it
An hour in the diary is often forty minutes in practice. Knowing that the senior person leaves at half past tells you to put the decision and budget questions in the first half, not the last ten minutes.
Do you mind if I take notes, and is anything we cover today confidential?
Why ask it
Asking permission is a small courtesy that also signals you intend to use their exact words. If something is sensitive, such as a planned restructure, you want to be told before it goes into a written summary that gets forwarded. Recording a call is a separate request: the rules on consent differ by country and state, so ask everyone on it first.
Their business
How would you describe what the business does to someone who has never heard of it?
Why ask it
You will have read the website, and the spoken answer is rarely the same as the website. The parts they stress and the parts they skip tell you what they are proud of and what they would sooner not lead with.
Who are your best customers, and what do they come to you for?
Why ask it
Almost any work you do for a client reaches these customers eventually, so learn who they are in the first meeting. Listen for whether best means largest, most profitable or simply easiest to deal with.
How has the past year gone compared with what you expected?
Why ask it
Left this open, they choose between the good news and the bad, and the choice is telling. A firm growing faster than it can cope with buys differently from one that is cutting costs, even when the two briefs read the same.
What is the business trying to get done over the next twelve months?
Why ask it
Work that connects to a stated company priority keeps its time and money when things get busy. If what they want from you links to nothing on that list, expect it to be the first thing postponed.
How is the team set up, and where does your part sit in it?
Why ask it
A quick sketch of who reports to whom saves you from guessing later. Draw it as they talk and check it with them, because it becomes your map of whose agreement the work will need.
What is changing in your market that you are having to respond to?
Why ask it
New rules, a competitor's launch or a shift in what customers ask for often sits behind a request that sounds purely internal. You also hear whether they see themselves as catching up or getting ahead.
What do you do better than the firms you compete with?
Why ask it
Whatever they name here is the thing your work must not damage. A hesitant answer is useful too, since it hints that the job may be bigger than the one you were invited to discuss.
The problem
What made you start looking for help with this now?
Why ask it
The need may be years old; the trigger is recent, and it tells you more. A board demand, a resignation, an audit finding and a failed vendor each imply a different budget, timeline and level of internal support for whoever comes next.
Walk me through how this works today, step by step.
Why ask it
A summary of a process tends to leave out the manual workaround somebody is quietly doing. Asking for the steps is how you find it, and the workaround is often sitting right next to the real problem.
When did this last cause a bad day, and what happened?
Why ask it
A recent, specific incident gives you names, dates and the order in which things went wrong. General descriptions of a problem are tidier than the event and leave out the detail you will need.
What is this costing you at the moment, in money, time or customers?
Why ask it
Plenty of clients have never worked it out, and doing rough sums together in the meeting is worth more than any figure you bring with you. The total also puts a sensible ceiling on what fixing it could be worth paying for.
What is your own theory about why this keeps happening?
Why ask it
They have lived with it far longer than you have, so their explanation is the best starting hypothesis on offer. Write it down as a theory to test, not a finding, and ask what evidence they have seen for it.
What have you already tried, and what stopped it?
Why ask it
Ask what stopped it, not what failed. An earlier attempt often ended with a change of sponsor, a budget freeze or a reorganization and not with a bad idea, and the same thing may well be waiting for you.
Which parts of the current setup work well and should be left alone?
Why ask it
Skip this and you may propose replacing something people like and rely on. It also lowers the temperature, because a meeting spent only on faults can leave a client feeling judged.
Who else is affected by this, and who has not been asked yet?
Why ask it
The person missing from the discovery meeting is frequently the one who blocks adoption later. Get their name now and ask to speak with them before you write anything.
Has anything already been decided, such as a tool, a supplier or an approach?
Why ask it
A platform bought last quarter or a method the director favors is a fixed point, whether or not it appears in the brief. Finding it after you have recommended the alternative spends credibility you did not need to spend.
What happens if you do nothing for another six months?
Why ask it
Sometimes the honest answer is not much, and it is better to know that before you write a proposal. Consequences with dates attached are what separate an interesting conversation from a project.
Success
What does done look like, concretely enough that we could both check it?
Why ask it
Push until you get something observable: a number, a report that gets produced, a process that runs without a particular person. Clients who cannot answer will end up judging the work on feeling.
If only one thing could go right, which would you choose?
Why ask it
Long wish lists hide the single result the client would trade the rest for. Once you know it, you can plan the work so that item is delivered first and protected when time runs short.
Is there a number you hope this moves, and where does it stand today?
Why ask it
Without today's figure, nobody can show afterwards that anything changed. If they do not measure it yet, setting up that measurement may turn out to be the first piece of work.
What would you need to see in the first month to feel good about this?
Why ask it
Whatever they name is your first milestone, and meeting it buys goodwill for the harder middle stretch. If the pace they expect is one you cannot keep, this is the moment you can still say so.
What result would leave you wishing you had never started?
Why ask it
Failure is often easier to picture than success, so this answer can be the more precise of the two. Listen for a risk the brief left out, such as staff leaving, customers noticing a disruption or a system going down in a busy week.
Who has done this well in your view, and what did you like about it?
Why ask it
The example they admire may be one you would never have guessed, or one a firm your size cannot copy. Hearing it in the first meeting is cheaper than hearing it in a review of your first draft.
What worries you most about getting this done?
Why ask it
The worry is frequently about their own side: a team with no spare capacity, or a system nobody wants to touch. Write what they name into the plan, which does more for them than being told it will be fine.
What would you consider outside the scope of this?
Why ask it
Getting the exclusions said out loud in the first meeting saves the argument in month three. Silence here usually means they assume rather more is included than you do.
Who else needs this to go well, and what will they want to be able to report?
Why ask it
Beside the practical result there is often a political one, and it is rarely written in the brief. A sponsor who has to stand in front of a board in the autumn needs something to show by then, whatever date the project plan ends on.
Who will own this once I am gone?
Why ask it
A named internal owner is the difference between work that lasts and work that quietly reverts once you leave. If nobody can be named, put handover and training in the price instead of hoping.
Decision and money
How does a decision like this get made here, and who is involved?
Why ask it
You want the sequence and the names: who recommends, who signs and who can say no. If nobody in the room can describe it, treat every start date you are given as provisional.
Is there someone who will want to meet me before a decision is made?
Why ask it
Arranging that meeting now is easier than learning about it after your proposal has stalled. Offer to keep it to a short call, and ask what that person tends to worry about.
What budget has been set aside for this, and who set it?
Why ask it
Who set it is more informative than the number. A figure invented in the meeting behaves very differently from an approved line in a plan, and only one of them survives a slow quarter.
How do you usually pay for work like this: a fixed price, by the day or monthly?
Why ask it
Some finance teams can only approve one of these, and a proposal priced the wrong way comes back whatever the total. Payment terms and tax treatment differ by country and by company, so ask how it works there before you quote.
What is the deadline, and what is driving it?
Why ask it
Dates with nothing behind them move. Dates tied to an audit, a contract expiry, a season or a launch do not, and those are the only ones worth building a schedule around.
Are you speaking to anyone else about this, and what will the choice turn on?
Why ask it
Asked without sounding wounded, this usually gets a straight answer. The second half matters more: price, speed, sector experience and who they simply got on with each call for a different proposal.
What would a proposal need to contain for it to be approved?
Why ask it
Approvers often want things the person in front of you would never think to mention, such as references, a named team or a break clause. Collecting that list now is far cheaper than writing a second draft.
Does this need to go through procurement or legal, and how long does that normally take?
Why ask it
Supplier forms, insurance certificates and contract review can add weeks between a yes and a start date. The rules vary a great deal from one organization to the next, so ask for the actual steps and who runs each one.
If the answer were yes, how soon could work actually begin?
Why ask it
Their calendar is a check on the urgency they described. A client who needs it by spring but cannot free anyone until after year end has just told you the real schedule.
Fit and next steps
Have you hired someone for work like this before, and what would you want done differently?
Why ask it
The complaints are a list of their working preferences, given without your having to ask for one: slow replies, jargon, or being sold a senior team and handed a junior one. If this is their first time buying this kind of help, plan to explain more of how the process runs.
Who would I be working with day to day, and how much of their week is free for this?
Why ask it
Work like this can stall at the client's desk as easily as at yours. If the named contact already has a full job, agree in this meeting what happens when you are waiting on them.
How do you want to be updated, how often, and who else should see it?
Why ask it
The distribution list matters as much as the cadence, since it tells you who is watching without being in the room. Agree the format now and you avoid a monthly argument later.
Once I send something over, how quickly does it get signed off here?
Why ask it
Ask about the last document that needed approval and how many people read it. A two-week review cycle is fine if you know about it, and ruinous if your timeline assumed two days.
If something goes wrong partway through, how do you want to be told?
Why ask it
Every project has a week where something slips. Clients differ sharply on whether they want a phone call within the hour or a line in Friday's report, and guessing wrong makes a small problem look like a concealed one.
What will I need access to before I can start, and who grants it?
Why ask it
Logins, building passes, data extracts and introductions all have an owner, and that owner is rarely in the first meeting. Collect the names now so week one is not spent waiting for a password.
Can I play back what I have heard, so you can correct what I got wrong?
Why ask it
Two minutes of summary near the end catches the misunderstanding that would otherwise surface in the proposal. Use their phrases, and watch which point they hurry to amend.
What have I not asked that I should have?
Why ask it
This is where the unmentioned constraint tends to come out: a pending acquisition, an office move, a colleague who will resist. Wait through the first "no, I think that covers it", because the real answer often comes a few seconds after.
Is there any reason this might not go ahead?
Why ask it
An uncomfortable closer that saves weeks of pursuit. Hiring freezes, an unfinished reorganization and an incumbent who is already favored tend to come out when the question is asked plainly.
What do you want to ask me before we finish?
Why ask it
Leave real time for this, not the last thirty seconds. Whether they ask about your other clients, your availability or your price shows what is still unsettled in their mind.
What should I send you after this, and who else will read it?
Why ask it
A one-page summary, a full proposal and a rough price range are three different jobs. Hearing that the finance director will see it tells you to write for someone who was not in the room.
Can we put the next conversation in the diary before we leave?
Why ask it
A date agreed in the room survives where a promise to be in touch does not. If they will not commit to one, you have learned how high this sits on their list.
Running a First Client Meeting
Practical guidance for the conversation itself
Choosing What to Ask
Take about a dozen into the room
An hour holds roughly a dozen questions asked properly, with follow-ups. Pick two from each group and mark the three you will not leave without: what set off the search, who decides, and what done looks like.
When it is a first business meeting and nobody is buying yet
An introduction to a possible partner, supplier or referrer is not a discovery session, and the budget questions would land badly. Stay in the opening and business groups, ask what they are trying to get done this year, and finish by agreeing whether there is a reason to talk again.
When they sent a brief beforehand
Skip whatever the document already answers, since asking it tells them you did not read it. Spend the meeting on what a written brief leaves out: why now, what was tried before, and who has not been consulted.
When more people turn up than you expected
Find out what each person looks after before you ask anything else, and put at least one question to everyone present. The quiet attendee is sometimes the one who will use what you deliver, or sign for it.
How to Run It
Say how the meeting will go in the first thirty seconds
Tell them you will ask questions for most of the time, that you will not present anything today, and when they will hear from you. Clients who expected a pitch relax, and you stop losing the first ten minutes to a mismatch.
Ask for the last time it happened, not the general case
"How do approvals usually work" gets you a policy. "Who signed off the last thing this size, and how long did it take" gets you the truth, including the step nobody documents.
Write down their words, not your paraphrase
The exact phrase a client uses for their problem should appear in your proposal. Reworded into your own vocabulary, it reads as though you were describing a different company.
Do not solve it in the room
The temptation to demonstrate value by proposing an approach in minute twenty is strong, and it usually ends the discovery. You will get a worse brief, and you will have given away the thinking for free.
Ask about money and decision rights out loud
Both feel rude and both are normal in a commercial conversation. Skipping them is a common reason a proposal sits unanswered, and a client with a real project to place will usually answer both without fuss.
What to Notice
- Whether they can name a budget owner. No name usually means the project is at the exploratory stage, whatever the urgency in the room suggests.
- Who the room looks at when you ask about money. In a group, the person everyone glances toward before answering tells you more than the titles on the invitation.
- Whether the deadline has a cause. Ask twice if the first answer is that leadership wants it soon.
- Whether they speak about their own team with respect. The way they describe the last provider and their own staff is a fair guide to how they will one day describe you.
- Whether two people describe the problem the same way. When the accounts differ, write down both: the gap between them is often the first piece of work.
- Whether they can say what happens if nothing is done. A long pause there suggests the meeting may not turn into a paid project, however friendly it was.
Common Pitfalls
Talking more than the client
If you did most of the talking in a discovery meeting, you ran a pitch. Look at your notes afterwards: a page of their words is a good sign, and a page of your own ideas is not.
Accepting the stated problem as the problem
Clients often arrive with a solution already framed as a need, such as wanting a new system when the issue is that two teams do not speak. Ask about the process before you accept the diagnosis.
Leaving without a next step and a date
Ending on a promise to send something over is how first meetings evaporate. Agree what you will send, when, and what they will do with it, before anybody stands up.
Naming a price before you have scoped
A price mentioned in the first meeting becomes the figure every later one is compared with, and before the scope is known it is likely to be wrong in one direction or the other. Give a range with the conditions attached, or nothing at all.