Our Thinking
Posted: 16 April 2025

How To Run Your First Meeting With A Prospect

There is no one right way of running a first meeting with a prospect. However, there are several principles I’ve found that make these meetings more effective and help you build greater momentum with a prospect.


The goal of your first meeting with a prospect

As counterintuitive as it sounds, the goal of your first meeting is not to sell your solution.

At any point in a sales cycle, it’s important to understand what the prospect needs to believe to move to the next stage in their buying cycle.

In the first meeting, what they probably need to believe is that you may be able to solve a problem that is high priority for them, and that you seem a credible person and company to talk further with about solving this problem.

So your goal in this first meeting is simply to do three things well:

  • Understand what their high-priority problem is (and whether your solution is a good fit)
  • Show enough of your product so they believe you may be able to solve this problem
  • Get them booked in for the next meeting

We’ll come back to each of these as we go through the meeting phases.


How to prepare for your first meeting

Most meetings fail because of a lack of preparation so don’t be tempted to skip these steps.

Research the person / people

You’re looking to understand more about what role the attendees might play in the sales cycle so check:

  • Their LinkedIn / Social Media Profile
  • Job title and how long they’ve been at the company
  • Do you have any connections in common?

See my blog on understanding Stakeholders

Prepare your discovery questions

You’ll want to document your discovery and refer to your notes live during the meeting, so:

  • Create a new discovery doc beforehand
  • Write out your discovery questions

See my blog on Discovery for example questions.

Send an agenda email the day before

You’ll want to make the best use of your and their time, so this will:

  • Remind them about the meeting ( reducing no-shows)
  • Set an upfront meeting “contract” (see below and at the end of this blog for an example agenda email)


How to structure your first meeting for maximum impact

To give you the best chance of achieving these goals, it’s important to think about how you organise your meetings. The following structure breaks the first meeting into different phases to make sure you have enough time allocated to complete each of your goals:

Structure your first meeting for maximum impact

Phase 1 – Intros, rapport building and agenda

Once you’ve done the initial intros, it’s important that you set the agenda for the meeting to let your prospect know what to expect, and also set yourself up with permission to ask them some questions. You can say something along the lines of:

‘We’ve got 30 minutes today, and my goal is to make this meeting as useful as possible for you. As I mentioned in my email, I thought our rough agenda could be as follows:

  • First I’d like to start by understanding a little bit more about your current situation and get an idea of what you’re looking for
  • Then I can show you what we do and answer any questions you have
  • And then if we feel like there may be something of interest here, we can talk about potential next steps.

Does that work for you? Is there anything else you’d like to cover?’

Just a reminder, it’s much easier to set this agenda if you’ve sent your agenda email the day before as outlined above.

Phase 2 – Discovery – Current Situation + Negative Impact

Here you’re going to understand where they’re at today and, ideally, any negative impact of the current situation. It’s not always possible to understand negative impact in the first meeting, so start with asking questions about where they are today and what they’re trying to achieve.

The absolute golden rule with this stage is to NOT talk about your solution. You’re doing discovery at this point, you’re listening, being curious, really trying to understand where they’re at and where they’re trying to get to. You’re NOT selling.

It’s very easy, particularly if you hear about a problem you know you can solve, to go into solution mode. RESIST the temptation to do this (make a note of the problem you heard as you’ll get to show the solution in the demo phase of the meeting).

For a more detailed dive into Discovery, along with a list of sample questions you can use in this phase, see my recent post Why Poor Discovery Is Killing Your Deals (And How To Fix It)

You can see in the figure above that at the end of this phase, you’re also going to Playback and Recap what you’ve heard. Here, you want to try and summarise what you’ve heard into the key pain points you’ve understood. This is really important for three reasons:

  • It allows you to start building a structured framework of the problem your prospect wants to solve, which is as important for your prospect as it is for you
  • It shows your prospect you really were listening, and allows you to check that you properly understood what they’ve said
  • It sets you up to do a personalised demo / presentation highlighting the solution to those specific pain points (rather than a BORING generic demo which will have little impact on them)

To bring this discovery phase to an end and do the recap, you can say something like:

‘If I could play back to you what I’ve heard, it sounds like your key priorities are to find a solution to <Key problem 1>, <Key problem 2> and also <Key problem 3>. Have I got that right, did I miss anything important?’

(It doesn’t have to be three, they may only have just one significant high-priority problem which can be enough to get a deal done)

Phase 3 – Do a tailored demo your solution as it relates to Discovery

This could be a demo on its own or a demo preceded with a couple of slides. The key here is to focus what you show on the key pain points you’ve uncovered during discovery.

Remember, your goal isn’t to show everything about your amazing product here. It’s to help your prospect believe that you solve a high-priority problem for them.

It’s quite possible you haven’t understood everything about their pains during the discovery phase. This is quite normal at this stage, you can get more into their problems in the second meeting (about which I’ll post next month). Here, you just need to show enough to get them interested in a deeper dive in that following meeting.

After you’ve done the recap above, you can move into the demo saying something like:

‘So, if we start with <Key problem 1>, let me show you how we’re addressing that in our solution today.’

And then do the same for <Key problem 2> and <Key problem 3>.

I know it’s not always easy to demo solutions to specific pain points, but this is what you’re aiming for. You may even decide for the key pains that you address that slides are easier to show rather than product.

However you do it, your goal is to NOT do a standard demo where you highlight the parts of your product which you think are great.

Your prospect couldn’t care less about how ‘great’ your product is, they care about solving their problems. So show them solutions to their problems, not a product tour.

The demo should be interactive, so ask questions to keep your prospect’s attention. Just avoid questions like ‘Do you have any questions?’ and ‘Does that make sense?’ as you’ll likely get ‘No’ and ‘Yes’ in response. If you can think of anything more speciifc, a good question to ask is:

‘How does that compare with how you / your team is doing X today?’

Whatever you do, don’t ask something like ‘If we could solve that problem for you, could you see this being something you’d buy?’ Too pushy. Too early. Too ugghhh!

Phase 4 – Map out and book next steps

Your absolute goal here is to book in the next meeting before you get off this call. See my post on How to Use BAMFAM To Avoid The Sales Valley of Death for more details on why this is so important and more strategies on how to get the next meeting booked in.

One of the keys to booking in the next step is to suggest it before your prospect does. If you leave it up to your prospect, they’re very likely to say something along the lines of ‘Let me think about it / take it back to the team, and I’ll get back to you.’ Which is the Sales Valley of Death, where you do not want to find yourself.

One way to make this suggestion is to say something along the lines of:

‘It sounds from what you’ve told me that it’d be worth exploring further how we might be able to help you. The next step we’d normally take at this point is to take a deeper dive into our solution – I can show more about our product and share some customer case studies with you. Would 2pm on Friday work for you to do that?’

The ‘next step we’d normally take at this point’ phrasing is very important here. You want to make this sound like a standard part of your process. It’s just the usual next step that everyone takes. This helps normalise booking in the next meeting and gives your prospect the confidence that you know what you’re doing.

It’s usually too early to start asking about their buying process in a first meeting with a prospect, but it can be a good idea to see if there’s someone else you’d like them to invite to the next meeting.

This is particularly true if you’re speaking to someone more junior, and you think it’s likely to be their boss, or their boss’s boss who’ll make the ultimate buying decision. If this is the case, once you’ve booked in the next meeting you can say something along the lines of:

‘I’ve often found it’s helpful to invite <Manager’s Role / Title> to these deep dive meetings – do you think that would be helpful for you?’

If they’re reluctant, don’t push too hard, your overall goal here is to get the person you’re speaking with to the next meeting. You’re going to do a lot more digging into the buying process in the second meeting, and that’s where you’ll really start to map out the key stakeholders in the buying chain you need to get in front of.

Of course, if you’ve discovered you’re clearly not a good fit for what they’re looking for, you should let them know that and perhaps direct them to other solutions that are better suited. No point wasting your or their time if that’s the case.

After the meeting you should send a short summary email of what you’ve discussed. This will help your prospect to remember you and will also help you set up the next meeting as well. I’ve put an example of this email at the end of this article as well.

Best of luck managing your first meetings with prospects!

Any questions, just DM me or email me at ben@crane.vc

Additional resources: Prospect Meeting email templates here.