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Mastering the sales conversation

Knowing what to ask on an initial call with a prospect can seem hard. May people will avoid this and try send someone off to a questionnaire, but the impact of having a 20min phone call and asking the right questions could likely be the advantage you are looking for to help land better, more profitable clients. 


Imagine someone is requesting a logo design.

There are 2 ends of the spectrum where someone might have pre-qualified themselves as a good fit (either by referral or consuming my content). They might ask something like “I’m interested in getting a brand created, what’s the process and next steps?” - The other end of the spectrum is someone who might just say “How much for a logo?”. In both instances, what questions I ask are pretty much the same things, but what I’m watching and looking out for in the conversation is very different.

The pre-qualified person, I’m trying to just make sure they stick with me and still on the same page at the end. With the non-qualified person, I’m very much pushing them away and looking out for a point where it clicks for them, where they really get what I can do for them.


So, onto the questions.

Part A:

The first thing I will do is say something like "before we get started, let's get a bit of a picture of where you are at." As you can tell, these questions are just about them.

  • What is your business and what do you do?
  • Who is your market? What sort of people buy from you?
  • How long has the business been established?
  • In general, how is the business tracking? (growing, slowing, steady?)

I’ll then explain that there is a lot more digging we’d need to do, some of which might be challenging but that is a part of the discovery process for when the project goes ahead. This helps to position myself as an expert who will think strategically. It might weed out some of those people who are not a good fit. These questions also give me an idea of what type of prospect I am talking to.


Part B:

These questions sound like you are pushing people away and technically you are - but the psychological impacts of the next line of questions show that you are confident, in control and willing to let a project go. This is attractive to people, no one wants to work with someone who is the opposite of those things (unsure and desperate). These questions will also get the client to rationalise themselves and they start to sell you to them for you. To me, these are almost “anti sales” questions. And they are (also, it’s important with these questions to dig deeper, you don’t want to settle on the first answer).

  • Why do you want a logo? – What benefits will this bring?– Is that important? If so, why?– What’s motivated this?
  • What’s wrong with the current one? – What’s it not doing?– What makes you think this is holding you back?
  • Why are you doing this now? – Would it be better to wait a little while? – If it was urgent, should you have done this already? Is it too late? – What makes you think now is a good time?
  • What made you contact me to help? – Is this something you could do yourself? – Is this something that could be done by someone with less experience? – Would cheaper options suit you better?

If they explain to you why they need to do the job, why now is the right time, and why you are the right person to do the job, you don’t need to do anything else.


I know these questions SOUND scary but trust me, they are the real magic questions. People don’t ask them because they DO sound scary and it feels like you are risking the client saying “Oh you're right, we can wait another 6 months, goodbye” and then hang up. But this does not happen.

They have rung you up for a reason. They might not have even thought of what that is consciously, but they will find those answers when you ask them.

Psychologically, the real big win here is that you show you're more interested in the client's wellbeing than landing your next project. This will put you ahead of others.

Also, when they tell you their reasons why, they are actually taking the role of the salesperson in the conversation. They actually start selling themselves on you.

Be brave, try it out.

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