Sales questions for founders: understand how your customer will decide

An enthusiastic conversation can feel like progress towards a sale. But enthusiasm does not tell you whether someone has the budget, authority or reason to buy.

I have taken a flight expecting to close a deal, only to learn that the finance director had pulled the budget. On another occasion, I received a purchase order from an IT department and discovered that the person who signed it did not have the authority to do so.

Experiences like those teach you to examine what you think you know.

It is tempting to conclude that the customer has been misleading. Sometimes circumstances change. Sometimes your contact does not understand the full process themselves. And sometimes you have accepted an encouraging answer without exploring it.

As a founder doing sales, your questions should help both of you understand whether there is a worthwhile reason to move forward and what that would involve.

Start with why the conversation is happening

Before explaining everything your product can do, understand what prompted the customer to speak with you.

Ask:

• What led you to look at this now?

• How are you handling it today?

• What is working well and what is difficult?

• What happens if you leave things as they are?

Listen for a specific situation rather than assuming the problem matches the one you expected.

Someone exploring possibilities for next year is in a different position from someone who needs to replace a failing service this month. Both conversations may be useful, but they require different expectations.

If the customer sees little reason to change, more product information may not move the discussion forward.

Understand what a useful result would look like

Ask what the customer wants to achieve and how they would judge whether a purchase had been worthwhile.

For example:

“If this worked well, what would be different for you and your team?”

Follow up on broad answers. If they want to save time, which work takes too long? Who does it? What would they use the time for instead?

If they want to reduce costs, explore which costs and how they would assess the saving.

You are looking for enough detail to understand whether you can help. Avoid exaggerating the problem or encouraging the customer to agree with benefits they have not identified themselves.

Their priorities should shape the conversation.

Ask how the buying decision works

Your contact may be a potential user, an enthusiastic supporter or the person responsible for the purchase. Find out rather than assuming.

Useful questions include:

• How would a purchase like this normally be agreed?

• Who else would need to be involved?

• What would each person need to understand?

• Are there any reviews or approvals we should allow for?

• How did you make a similar decision last time?

Ask in a way that helps your contact explain the process without feeling that you are questioning their importance.

They may be able to introduce you to other people involved. Where that would help, discuss it openly and agree how to proceed.

A strong relationship with one person is valuable. You still need to understand how the organisation will decide.

Discuss budget without making assumptions

Budget can mean several things. Money may already be allocated, it may need approval or the customer may still be working out whether the problem warrants spending.

Ask where they are in that process.

You might say:

“Have you set aside a budget for this, or would you need to build a case for it?”

Then explore any conditions. Is the spending dependent on another project, a funding decision or a particular result?

Be clear about your own pricing early enough to discover whether there is a realistic fit. Avoid spending weeks developing a proposal around expectations neither of you has discussed.

If the budget is too low, consider whether a smaller scope would still deliver a useful outcome. Do not promise the same work for less without understanding what that means for your business.

Explore what could prevent a purchase

Ask about the obstacles while there is time to address them.

What might make the customer hesitate? What has caused a similar initiative to stall before? What would make their team prefer to stay with the current approach?

The concern may involve implementation, time, trust or the effort of changing how people work.

A useful question is:

“Even if you felt this was the right solution, what could stop it going ahead?”

Treat the answer as information to understand. You may be able to address the concern, adjust the proposal or recognise that the timing is wrong.

Not every obstacle can be resolved by a better pitch.

Understand the alternatives they are considering

Ask what else the customer is evaluating, including doing the work internally or making no change.

Explore what matters in the comparison.

Price may be one factor, but so might familiarity, support, reliability or the work required to get started.

This helps you explain the relevant differences in your offering. It also gives you a chance to recognise when another approach may suit them better.

Avoid criticising a competitor based on assumptions. Keep the discussion grounded in what the customer needs and what you can demonstrate.

Listen to the answer before choosing the next question

A prepared set of questions can help you remember important areas. It can also become a distraction if you are concentrating on what to ask next.

Follow the answer you receive.

If someone mentions a concern you had not considered, explore it. If they use a phrase that could mean several things, ask them to explain.

Summarise important points and invite correction:

“My understanding is that your team wants to proceed, but the budget still needs approval. Is that right?”

That gives you a more reliable basis for planning than leaving with an optimistic interpretation.

For more on this, read how to listen as a founder before responding.

Agree a useful next step

Before ending the conversation, discuss what should happen next.

That might be involving another decision-maker, reviewing a proposal or clarifying a requirement. Sometimes the sensible outcome is to pause.

Make clear who will do what and when. Check that the next step serves a purpose for the customer as well as for you.

“Send me some information” leaves plenty open. Ask what information would help and what they want to assess from it.

If there is no clear reason to continue, acknowledge that. A courteous decision to stop can save time for both sides.

Practise without turning the conversation into a script

Working through sales conversations with a colleague can help you notice unclear questions and assumptions.

Choose a situation you regularly encounter. Identify what you need to understand, then practise asking about it in your own words.

Use open questions where you want to explore. Use direct questions where a specific fact needs confirming.

Afterwards, compare what the other person said with what you understood. Did you fill in any gaps? Did you miss a concern because you were preparing your response? Did a question point towards the answer you wanted?

The purpose is to become more attentive and comfortable, so you can respond naturally in the real conversation.

Use what you learn to make better choices

Record the facts, the uncertainties and the agreed actions while the conversation is fresh.

Keep those distinctions visible when reviewing an opportunity. A possible budget is different from an approved one. A preferred supplier is different from a signed agreement.

Over time, review why customers proceed, delay or decline. Those patterns can help you improve your targeting, offer and expectations.

If sales conversations leave you second-guessing yourself, avoiding difficult questions or holding on to unlikely opportunities, it may help to explore what is happening for you too.

If you would value space to work through those patterns and your approach to founder-led sales, explore working with me through founder coaching and mentoring.

Cheers,

Duncan