A business owner told me recently that his discovery calls always go well and almost never convert. I asked what he asks on them. He listed four questions, all of which were versions of what are you looking for.
That is the whole problem in one sentence. What are you looking for gets you a description of a solution the buyer has already imagined, usually wrong, and it tells you nothing about whether they will ever buy anything at all.
The mistake that ruins most discovery calls
The common failure is talking about your service in the first ten minutes. It feels helpful and it feels like momentum. It costs you the call.
Once you have described what you do, every subsequent answer the buyer gives is shaped around what they now think you sell. You stop hearing their actual situation and start hearing a version of it edited for your benefit. You also lose the chance to position the work against their problem, because you positioned it against nothing.
Hold your service description until you can say it in their language. That usually takes twenty minutes of questions. Resist the urge to fill silence with your own credentials.
The second failure is taking every stated problem at face value. A buyer who says we need better marketing has not diagnosed anything. They have named a department. Your job on the call is to find what actually happens in the business that made them pick up the phone.
Questions about the trigger
The most useful thing you can learn early is why this is a topic now rather than a year ago.
Ask directly. What happened that made this something you are looking at this month. Then wait. Owners often need a few seconds, because nobody has asked them and the answer is not pre-packaged.
What comes back is usually specific and useful. We lost a large account. A competitor turned up in a pitch we thought was ours. Our best salesperson left. We hired two people and the phone did not get busier. Each of these tells you what the real project is, and none of them would have surfaced from what are you looking for.
A buyer with no trigger is browsing, which is a question of who you are actually trying to reach rather than a question about this call. That is not a criticism, and browsers sometimes become buyers later. But a call with no trigger should not become a proposal this week, and knowing that saves you three hours of writing.
Questions about the cost of doing nothing
This is the highest-value question on the call and most sellers never ask it.
What happens if you leave this as it is for another year. Said plainly, without a threatening tone, as a genuine question.
The answer sorts your pipeline better than any scoring model. If the buyer says we carry on, it is annoying, we manage, then you have a nice-to-have and the deal will lose to something urgent in month three. If the answer involves a number, a named lost customer, or a person who will quit, you have a live deal.
Follow it with a quantifying question where it fits naturally. Roughly what does one of those lost jobs cost you. Do not press if they resist, and do not treat the number as precise. What matters is whether a number exists in their head at all, because a buyer who has already done that arithmetic has already half-decided.
This question also does something useful for the buyer. Many owners have never sat down and worked out what a stalled problem costs them per quarter. Asking makes the cost visible, which is more persuasive than anything you could assert.
Questions about who decides
You need the approval path and you need it without sounding like you are checking their rank.
The blunt version, who is the decision maker, invites a defensive answer and often gets a false one, because the person on the call would like it to be them. Ask about process instead.
Try: when you have bought something similar before, how did that usually get approved. Or: apart from you, who else will want a say in this. Or, at the end of a good call: if you and I agreed this made sense, what would the next few steps look like on your side.
These get you the real structure. You learn that the owner signs anything under twenty thousand, that the operations manager has an effective veto, that the last vendor decision took two months because it went to a board meeting. All of that changes how you write the proposal and when you follow up.
At a 10 to 50 person company there is often one decision maker and two influencers, and the influencers are the risk. The operations lead who was not on your call and dislikes new software will kill the project quietly. Ask who else touches this, then ask whether it is worth including them next time.
Questions about what they have already tried
What have you tried so far, and what happened. This is the question that saves you from a dead deal you cannot see.
If they have used two agencies in three years and both ended badly, you are walking into a room full of scar tissue. That is workable, but only if you know. You will need to address it directly, which is impossible if you never asked.
Listen for what they blame. A buyer who says the last agency did not understand our industry is telling you what your proposal has to prove. A buyer who says nothing was ever measured is telling you to lead with reporting. A buyer who blames themselves, we never gave it enough time, is telling you they may do the same again unless the engagement has early checkpoints.
Ask also what they liked. A previous vendor who was good at something gives you a standard to match, and you would rather hear it now than in month two.
Questions about money, without being awkward
Do not ask what is your budget on a first call at a small company. Most owners genuinely do not have one yet, and the question makes them feel they are being sized up.
Give a range instead and watch the reaction. Work like this usually runs between X and Y depending on scope. Does that sound like the right neighbourhood.
You will get one of three responses. A yes, which means proceed. A visible flinch, which means either scope down or stop. Or a question about what makes it X versus Y, which is the best answer available, because they are now thinking about scope rather than whether to spend.
Saying a number out loud early costs you some calls and saves you a great deal of time. That trade is worth taking when you are an owner doing your own selling.
How to end the call
The last two minutes matter more than the middle twenty.
Summarise what you heard, in their words, and check it. So the situation is that enquiries come in reasonably steadily, nobody owns following up, and you reckon you are losing three or four a month. Have I got that right. Corrections here are gold, and agreement gives you your proposal opening.
Then say plainly whether you think you can help. If the answer is no, say so on the call. It costs nothing, it earns more referrals than any marketing, and it saves you both a fortnight.
If yes, propose one specific next step with a date attached. Not I will send something over. A document by Thursday and a 20 minute call on Monday to go through it. Book the Monday call while you are still on the phone, because a scheduled call converts at a different rate than a promised email.
Write it down straight after
Ten minutes after the call, write the trigger, the cost of inaction, the approval path, and the exact phrases they used. Put it in the CRM rather than a notebook, because the notebook version is invisible to everyone else and gone in a month.
This is the material your proposal is built from and the reason your follow-up sounds like it came from a person who was listening. It is also the difference between a pipeline you can forecast and a list of names. If getting the team to do this consistently is the hard part, that is a CRM adoption problem rather than a sales skill problem.
The takeaway
Ask why now, ask what happens if nothing changes, ask how decisions like this get approved, and ask what they have already tried. Hold your service description until you can put it in their words.
Then end by saying what you heard, saying honestly whether you can help, and booking a dated next step before you hang up. A good discovery call should leave you knowing whether to write a proposal at all, which is the only outcome that saves you real time.