How to ask questions that convert cold prospects into clients

Converting cold prospects into clients can be the hardest part of the B2B sales cycle.

In contrast – NOT many people who are responsible for bringing in new business struggle with converting referrals into clients.

A brief word on referrals. (Bear with.)

Referrals are the hottest prospects you will ever have.

They’ve come pre-warmed by your network. And if you’re really lucky, those referrals are not just pre-warmed. They are provided boiling hot, ready to roll, having had you recommended, with your best services highlighted, prices explained and any objections already overcome. Yippee ! (More on referrals here).

So referrals are NOT who we are talking about here.

A cold prospect doesn’t know, like or trust you – yet.

Cold prospects are the hardest to convert. And we know exactly why.

Because they don’t know us (yet). And because they don’t know us, they can’t like us or trust us either, yet.

Not knowing, liking or trusting a potential supplier (yet) can lead to a whole raft of feelings on the part of your prospect which it’s important you are aware of.

The feelings a cold prospect can experience about you

  1. Downright suspicion. Are you who you even claim to be? Is your company a real one, with real employees, or does your glossy website cover up a much more fragile set-up that may disappear at a moment’s notice?
  2. Financial worries. If I use you, what are the possible risks? Am I paying the right amount or too much? Is your firm big enough to handle my project from start to finish?
  3. Concerns over personal fit. What are you like to work with? Will we understand each other? Will I enjoy working with you? Does your style of working fit with mine? Will I get to actually work with you (the grown-up doing the selling whom I am beginning to know and like) or will I be handed on down to an inexperienced junior account manager whose ‘phone keeps pinging in our briefing meetings?
  4. How good are you, really? Can I lean on you? Will you take the time to understand my business deeply? Can I rely on you not just to give me what I ask for but to go deeper and make suggestions. Will you push back if you think I’m asking for the wrong thing? Do you truly care about my business or do you just want my cash?

Feelings 1 and 2 – and the associated questions floating around the mind of your prospect – should get addressed through their own due diligence. They have to do their bit of research, check you out and you have to stack up.

Feeling #3 on personal fit is one which works both ways. Trying to be a good fit when you’re not typically leads (in the end) to an awkward relationship and an unprofitable client.

Feeling #4 is about trust. And this is where these questions come into their own.

Questions to build trust, and help convert cold prospects into clients

If you’re not a natural question-asker, then this approach might not come easily to you. But – like anything – you can get better with practice. So start by putting some of these questions to your current clients, and see how they respond. Then put them to referrals or warm prospects etc.

Being genuinely curious about other people’s businesses will make all the difference here. By the way – this works brilliantly as a strategy for client development as well, but that’s a different story. Which you can read all about here.

Asking questions helps to avoid ‘telling’ people about you – which automatically puts you into the position of someone who appears to be actively selling or trying to persuade somebody to think something. This is a feeling that nobody likes and can actively obstruct a new sales meeting.

Here we go…

Early stage questions which ignite serious discussion

  1. Tell me, why you have invited me in here to talk to you today?
  2. In an ideal world, what would you like to be thinking when you come out of our meeting?
  3. What approaches have you tried so far (to solve business problem X)?
  4. What has or hasn’t worked? Why do you think this is the case?
  5. Have you tackled this in-house before?
  6. How are you planning to measure your return on investment with this project?
  7. What other similar problems have you seen in other places you’ve worked/firms you’ve run?

Questions which build a more emotional connection

  1. What’s your relationship like with your best suppliers – how would you describe them?
  2. How close a relationship/how much communication do you like to have with your suppliers?
  3. What more do you feel a previous supplier/your incumbent could have done? (Be careful that you do not talk negatively about others. If anything, damn them with faint praise….). What do you think has prevented this happening?
  4. What do you think about splitting this work across more than one supplier? Do you think that might work well?
  5. What experiences have you had using consultants/service providers like us for work like this before?
  6. What would worry you most about potentially taking us on as a new supplier?

Questions which show your prospect you know your onions

  1. How does this work fit with your longer-term business plan? Are you happy to share that with us? (This could also be their product development plan / IT strategy / new business plan etc. as relevant to your area)
  2. If we were to put forward ideas around other parts of your plan, how do you feel about that?
  3. Have you ever tried approach B or C (explain and elaborate if they are interested, if they are mainly discussing approach A)?
  4. Which other parts of the business are also affected by the problems we’re discussing? Have you been able to involve or engage them in solving it? Would you like our help in engaging them?

These are just examples of the types of questions you can ask any prospect. Questions like these will generate a far more productive response than you will ever get by just explaining who you are and what services you offer.

But, please, remember..

You can’t just ask questions. You have to care about the answers.

It isn’t actually the asking of questions that helps convert prospects –  it is asking good questions, in the right way.

So, what is a good question? (And what is a really good one).

A good question is one that is open (i.e. not a yes or no answer), relevant and reaches around and about the problem your prospect has. It is asked by a person who cares. It is a question that is actively seeking answers and new insight. It is asked by a person who is genuinely interested in the response.

And the absolute best question is one that they haven’t thought of asking themselves yet.

When you ask one of these, a prospect’s head goes up and they look right at you and say. “Now, that is a REALLY GOOD QUESTION.”

That’s when you know your prospect is no longer cold, and could be a really good fit. Because you’ve already started adding value, simply by asking the right questions.

Need help with your sales and marketing?

You might now be thinking you could do with some help converting prospects, or even with drafting a marketing strategy to generate new prospects in the first place.

Or perhaps you’re already actively looking for a sales and marketing consultant in Hampshire and are wondering if I’m a good fit for you. Having a read of this, might help you answer that.


Leave a Reply

Your email address will not be published. Required fields are marked *

Am I the right person to help?


Call me on 07827 297569.

It’s the quickest way to find out whether I can help you. And whether I’m the right fit for you. If I am, the next step is a face-to-face meeting.

Get in touch