Sales Questions To Run An Impressive First Meeting

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Simon Dethridge at BIG Consulting shared this helpful guide on how to prepare for that all important first meeting.

Why Customers Buy

It’s All About Them

You have secured the first meeting and you are excited to be able to connect with a prospect and pitch your product/service. Learn how to create buyer personas here

The first lesson is that your mindset should not be about you, but all about helping them to make a positive decision for themselves and their business.

Today, buyers are doing more for themselves and need salespeople less. All the information they require to self-assess their needs and consider potential solutions is available on the internet.

Salespeople are entering the buying process much later these days and no longer have “an information advantage” in terms of the product or service offering you represent.

So are salespeople about to become obsolete?

Not yet – but to be successful in modern selling they need to approach selling differently. The dialogue needs to change. Be sure to fine tune your dialogie to batch your ICP. Learn more about Developing an Ideal Customer Profile for your B2B customers here.


The Top Five Reasons Customers Buy Are

  1. The salesperson helped me to look at my situation with a new perspective and gave me ideas and insights I hadn’t considered before.
  2. The salesperson helped me to buy by working with me collaboratively through each stage of the decision-making process.
  3. They convinced me that their solution will deliver results
  4. They did more listening than telling
  5. They genuinely understood my needs

Price is often NOT the #1 reason they will buy

Note that price is seldom in the top 5 reasons why customers buy. You should avoid a conversation on price and use artful questions to shift the discussion to explore how they assess value.


“Price is what you pay, but value is what you get!”

Preparing For The First Meeting

  • Know who you are meeting with
  • Be clear on the purpose of the meeting
  • Set an agenda
  • Prepare your golden questions
  • Summarise and agree on next steps

Who are you Meeting with?

There is no such thing as a cold call – you should always go in warm.

Invest the time upfront to know who you will be meeting with and aim to achieve early connection.

  • How many people will be in the M1?
  • What are their names and roles?
  • Visit their LinkedIn page to learn about their career and find some items you have in common – people, industries, education, geographies. Use this to build early rapport.
  • What are their buying styles (hard to get if you have yet to meet them – you need an insider or a coach to help you!)
  • And then who will be representing your side? Just you or others? What role(s) will they play? Who will lead/follow/support?

What is the Purpose?

Be super clear on what success looks like from this initial meeting.

Are you opening up an opportunity or wanting to close it quickly?

Generally, a first meeting is designed to connect with the prospect and start the qualification process. You may need to earn the right to probe and pitch your solution first. Don’t be too quick – it’s about them – not you.

You may need to go SLOW at first, to go faster at the end!

Here are the typical Objectives of a first meeting

  • Create a connection with the decision-maker(s), to forge early rapport and create a foundation of trust
  • Learn – gather the information that supports, qualifies, clarifies the opportunity for both parties
  • Qualify – is this opportunity something that is worth pursuing to the next level? Is it on strategy? Can we deliver? Will it meet our benchmarks for return on effort/investment/resources?
  • Manoeuvre – ascertain the competitive landscape and who you are up against. Can you position yourself in a differentiated position to your rivals?
  • Earn trust – The first sale you need to make is YOU before you sell your company or your product/service. Make this your early focus to then earn the right to progress with a proposal or solution to help them to improve their context.

Set an Agenda

Offer to create the agenda in advance and invite the customer to contribute. Again – it is about what they want to achieve from the meeting – not just your need to fertilise a sale!

  • Keep the agenda points to just a handful.
  • Send it in advance if that helps to clarify intent for both sides.
  • Refer to it your opening comments at the meeting

Prepare your Golden Questions

Your initial questions are typically discovery and open in style to gather a width of information. You want the customer sharing their view of the current state before you have them imagine a better future.

You have 2 ears and 1 mouth – so dominate the listening!

First bank of questions help to understand the Current State

  • What is happening today that is giving you positive performance?
  • What is contributing to that performance (the drivers)?
  • How happy are you with those results?

Note this line of questioning is positive and designed to be a pleasurable exchange.

Then we switch to focus on their current pain which is designed to interrupt the status quo and provide a platform to suggest change!

  • What is NOT HAPPENING at present that is causing you concern?
  • What do you feel is influencing those sub optimal results?
  • Have you tried to affect the environment of late? How has that played out?
  • What is the impact on you and your business for the current situation?

Second bank of questions are to explore a Future State:

  • If you were successful in turning things around, what would that picture of success look like?
  • What do you think needs to happen in order to get there?
  • How well equipped are you to close the gap yourself?
  • Could you see merit in working with a specialist who can help you to get there sooner/reduce your risk/improve the outcomes?

Third bank of questions is to interrupt their view of the situation.

This is where you differentiate yourself from others looking to sell rather than educate the buyer.

  • Have you considered the changes that are happening in your space at present? (Embed those changes in your question)
  • When you think about X, Y or Z (refer to risks, insights, or opportunities), how do you plan to address these?
  • If you were to continue approaching (the situation) with your current settings,( i.e do nothing) what might that cost you or the business in terms of time/money/culture/market standing?

Summarise and agree on next steps

The final phase of your initial meeting is to feedback what you have uncovered, check the details, and then help them to recognise the implications and requirement to change.

You may be able to pitch a macro solution in the M1 but generally it will require you to go away and build the solution, with all the supporting pieces to present back in the M2 or second meeting.

  • Use summary and checking questions to confirm you have a clear picture of current and future state
  • Ask if there is anything you may have missed
  • Add a visual summary to the verbal summary to engage those who are visually dominant to “see” the situation as it has now been assessed – a sketch on a page/whiteboard/slide
  • Check on the feelings of the decision-makers as to the outcome of the initial conversation – connects with kinesthetic dominants
  • Then the key question is to convert their interest into action by testing the waters and their appetite to proceed to the next buying stage

“So from what we have discussed today, what would you like us to do next in order to help you make the best decision?”

  • Is that to go away and prepare a proposal?
  • Is it to consult with another stakeholder?
  • Is it to provide more information on capabilities or case studies?
  • Is it to wait? If so, find out what or who are we waiting for?
  • Aim to gain feedback on where you now stand as a result of the initial meeting and how much value you have created

Download Meeting 1 Template

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