Do you *really* understand your prospect’s pain?


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For many of your potential prospects, most of the time, sticking with the status quo is usually the comfortable choice. It’s no wonder that so many complex sales cycles end up with the customer deciding to do nothing rather than embark on a potentially costly and risky change.

That’s why – in many complex sales environments – your biggest competitor is not another vendor, but the very real risk that your prospects will decide to “do nothing” and stick with what they’ve got.

There’s one overwhelming reason why these apparently promising sales opportunities came to nothing: the prospect’s current situation was simply not painful enough to force them into action.


It’s easy to be deceived by the prospect’s interest in your solution, and their willingness to invest their time (and consume yours) in learning more. If you’re to avoid being sucked into sales opportunities that are unlikely to ever result in a sale, you need to understand their hierarchy of pain:

  1. Something that is a minor irritation (or an issue that is vaguely interesting) can often trigger curiosity on the part of the prospect, and a desire to learn more.
  2. Something that is a significant problem (or an important issue) can often result in a serious and extensive evaluation of options.
  3. But only truly critical pain points (or truly strategic issues) are going to inevitably result in your prospect taking action.

That’s not to say that your prospects won’t sometimes buy in order to solve significant problems or to address important issues: it’s just that the more significant the pain, or the more strategic the issue, the more certain you can be that they will inevitably decide to do something, and to do it sooner rather than later.

That’s why understanding your prospect’s pain (and doing all you can to increase their sensation of pain) is such a critical element of a successful complex sales campaign.


But there are a number of potential problems: your prospect may be unwilling, particularly if they don’t know you or your organisation well, to initially acknowledge a critical pain. Or they may be unaware of the full implications and ramifications of a problem they are aware of. Or they may currently be completely oblivious to an issue that – if they were to become aware – they would feel forced to address.

True thought leadership marketing – materials and messages that genuinely introduce new concepts and ideas, and which cause your prospect to think differently – can help to set the scene. But once you’ve got them interested, there is no substitute for a thought leading sales conversation.

Thought leading sales conversations stimulate your prospect to take a fresh perspective, and allow you to uncover information that will prove essential to qualifying the prospect’s seriousness and shaping your sales strategy.


Let’s assume that your prospect acknowledges a problem (or an interest in an issue) that you know you can solve. Diving in straight in and pitching your solution is the worst possible thing you can do at this point – and yet it’s the most common sales behaviour, at least amongst less effective sales people.

Top sales performers know that this initial acknowledgement of a relevant problem or issue is a golden moment, not to be wasted. They know that this is their chance to really explore the prospect’s pain, and if possible progressively develop it from interesting > important > critical. And they know that if they cannot uncover or create critical pain, the chances that the prospect will act and their probability of winning are both dramatically reduced.

Here’s how top performers take advantage of this window of opportunity:

  • They ask how long the prospect has been aware of the issue, what they think caused it, what actions they have already taken to address it, and what the results (if any) have been
  • They explore the visible and invisible implications and consequences of the issue, sharing their experiences of other similar stakeholders and organisations, and introducing other relevant issues
  • They seek to understand the impact of the issue on their current contact, and what the implications are for their contact’s personal performance, that of their department and the organisation as a whole
  • They probe to find out who else is affected by the issue in the prospect’s organisation, what impact the problem is having on them, how aware they are of the issue, and how supportive they are of the need to invest in addressing it
  • They try and establish a connection between the issue, the organisation’s current strategic initiatives and priorities, and the CEO’s agenda
  • They work with the prospect to try and establish a business case that monetises the pain, highlights the cost of inaction and promotes the urgent need to take action
  • Throughout, they seek to understand what would happen if the prospect simply decided not to do anything, and if the answer is that the prospect could (and probably would) cope, they either seek to change the prospect’s perspective, or qualify the opportunity out


If they can’t engage in this sort of conversation with their current contact, there are two probable implications: either their current contact is an insufficiently powerful mobiliser to be able to drive action, or the pain isn’t significant enough to drive serious action.

But whatever the outcome of the conversation, the pursuit of the pain chain allows them to make more intelligent decisions about whether and how to pursue the opportunity.

What are your experiences? Do your salespeople always manage to get to the heart of the pain? And how many apparently promising opportunities might have been lost because the pain either never existed or wasn’t sufficiently developed to make action inevitable?

Republished with author's permission from original post.

Bob Apollo
Bob Apollo is the CEO of UK-based Inflexion-Point Strategy Partners, the B2B sales performance improvement specialists. Following a varied corporate career, Bob now works with a rapidly expanding client base of B2B-focused growth-phase technology companies, helping them to implement systematic sales processes that drive predictable revenue growth.


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