How do successful sales people diagnose the symptoms of customer pain?

Blog written by ESP Director James Egersdorff.

Technology sales expert Greg White outlines a winning strategy on how to take your customers along an effective buying journey.

As part of an exercise at a recent workshop, Greg and I were tasked with exploring “The impact of failing to reveal customer pain and gain consensus and commitment along the buyer’s journey”.

Greg shaped the following strategy and delivered a fantastic whiteboard presentation that was voted by industry peers as the best of the session.


A salesperson from a cloud technology business receives an inbound lead from a prospect who has an IT challenge he needs to address. The prospect is familiar with this cloud technology and thinks the solution can solve their problem.

The salesperson goes along to meet the prospect, outlines the solution and after a short meeting where the prospect shows keen interest, quickly moves the conversation on to discuss pricing. The sales person leaves the meeting having mentally spent the commission. This deal feels in the bag.

However, over the following weeks procurement is engaged and a competitor is suddenly in the mix, the price comes under pressure and the customer requirements seem to be a moving target. The discount rises and the solution fit doesn’t feel as strong as it originally was, and ultimately the competitor walks away with the deal.

What Happened?

The prospect, while acting in good faith, was neither the economic buyer, nor were they sufficiently senior to own and steer the deal to conclusion. As the prospect articulated the seller’s value proposition internally the value to the business was soon understood, but it merely triggered thinking at senior levels regarding how the underlying business challenge (in this case an element of GDPR compliance) could be solved – hence the scope creep. Procurement introduced a competitor to help drive a better deal, but the competitor engaged at a more senior level and was able to move the goal posts by bringing additional factors where they could play to their advantage. They had senior sponsorship and the buyer felt more confident that the competitor’s offer would benefit the business.

Greg’s strategy:

1) Get High.

The original lead comes from an individual who has a functionally relevant role; it could be a technical analyst, a team leader, a mid tier manager etc, but they either have no budget of their own, or a relatively small budget. They are really only interested in trying to solve the problem they’ve been tasked with. They don’t have ownership or maybe even visibility of the primary business issue. The risks here are that selling too low in an organisation means smaller deals, the seller being perceived as being of little or no strategic importance, and increased likelihood of the deal being de-prioritised or trumped by a stronger competitor.

Frame questions to uncover the business driver that has lead to the inquiry. Every solution ultimately must have impact on a measurable that is important at C level, typically, in a quoted company, this boils down to share price impact. But there are contributing strategic measurables owned by senior management that we should map to the relevant stakeholders. So for example, the VP of Sales and Marketing will be focused on initiatives that drive revenue and customer satisfaction; the CFO will have many metrics that drive the bottom line including costs, asset management etc. This will lead us to the correct pain that we need to reveal to them and sell against.

2) Don’t show up and throw up.

Rather than reveal the solution at the first opportunity we should identify both the business drivers/objectives, and the stakeholders and metrics important to them. Revealing the solution too early runs the risk that we get level-locked with an individual who cannot buy our optimal solution forcing us into a tactical sale of lesser value because he doesn’t feel empowered to raise our solution to higher levels in the organisation.

Remember, that as soon as the customer believes they understand what the solution is, your opportunity for discovery will be reduced, and when procurement are engaged they sometimes shut that dialogue down altogether. So we have to focus on selling business outcomes not product – especially in the early stages. The indication of of positive business outcomes can help our initial sponsor raise our proposition higher in the organisation. By contrast details of the technical aspects of our solution soon become of little interests to higher levels of management. Show the prospect how to avoid a fine equivalent to 4% of Global revenue (a GDPR penalty) and the higher tiers will take interest. Show them how to secure a firewall or process a data access request and you will get level-locked with the technical tier.

3) Research. 

So many sales people go into the sales call knowing little about the Company or Individual they are meeting. A 2016 CSO Insights study found that 20% of sales organisations cited a poor approach from sales personnel to follow sales processes resulted in barriers to success with customers. As a result, the poorly prepared salesperson focuses on selling their product blind – they have no idea whether it fits or how it fits. There are plenty of information sources. Google, LinkedIn, services like FirstRain, D&B etc. For US companies there are key documents like the annual 10K, or for European companies there is the prospectus and annual report. These sources will help to map the organisation and identify the drivers above. The higher quality news services like WSJ and FT provide a wealth of third party view information as well as regulator and competitor actions that threaten the prospects business. Successful sales people must go armed knowing these…don’t talk about how pretty the atrium is when you are in the lift on the way up to their office for that first meeting, talk about the insight you have discovered about their market position or initiatives. Get into a business driver conversation from the first moment. 

4) Don’t play alone.

To reduce the risk of getting level-locked and to demonstrate credibility, particularly in a high value opportunity, the sales person should map stakeholders against the resources at his disposal. This may mean for example leveraging an Exec sponsor from his own C-Level to map against theirs. This may mean mapping Head of Legal to Head of Legal, Compliance Officer to Compliance Officer, CISO to CISO or CFO to CFO for example, as well as the obvious technical to technical. The skill to orchestrate these high level resources is a true indicator of a great sales person. This will keep the dialogue on a business footing, and build credibility.

About Greg

Greg is a technology sales professional with 35 years experience. Currently Director of Enterprise Security and GRC for ServiceNow EMEA, Greg has previously held pivotal sales leadership roles with the likes of Symantec, ForgeRock and NetIQ.

About James

James is an experienced IT Sales recruiter, who has worked at Enterprise Sales Personnel Ltd for the last ten years, having progressed through the business to Director Level.

He specialises in recruiting Scotland-based IT consultants, sales and pre-sales professionals.

If you would like to speak to James about expanding your IT sales team or if you are looking for your next IT sales career move in Scotland, please call 0161 446 4160 or email