Here let me read it to you. Best to listen straight off Spotify though, the browser version is buggy.

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“I think they really liked it”

Losing a big sale hurts. All those countless hours you put in. Epic documents created. The late nights refining the pitch. The cab chat on the way back to your office after the presentation, where you all analyse each client eyebrow tilt and chin stroke for signs of favour. “I think they really liked it.”

No they didn’t and you lost.

It’s remarkable how many businesses don’t want to know why. For so many reasons. Shame. Disorganisation. Personal agendas. Everyone involved internally has a crack at the forensic work. All based on random reckonings.

You’ve heard it all before. Competitors undercut us. It wasn’t apples for apples. Someone else had the inside running.

Price is the number one excuse people use. Guess what? Buyer research reveals price isn’t even in the Top 10. We’ll come back to the research shortly.

The secret of good sales

Cian McLoughlin has made it his mission to find the real story behind every lost sale. I met him through the blog, he was a very early reader. Weirdly, given he is a non-drinker, the story that made him get in touch was Ten Tips For Business Drinking. Disclosure before you read further, we are seed investors in his new software platform.

He’s one of the best people I’ve met in the sales industry, in that he does not feel in any way like a sales guy. He’s a really good listener and knows a bunch of wise, useful stuff. Stuff he doesn’t say until he’s finished listening. So the sales process becomes more like an interesting chat about things you both have in common.

He did not ask us to invest. We offered. As did all the other seed investors.

And right there is the secret of good sales: be helpful and trustworthy all the time, not just when you want something. Then people come to you.

A career suicide mission

The story of how Cian got into Win/Loss Analysis is instructive. A backpacking trip from his native Ireland led him to a life in Australia, working as an enterprise software sales rep for one of the biggest global players. Big ticket deals, tens of millions. When they lost a sale, he used to wonder why.

He asked his boss, “May I go and ask that client why they didn’t choose us?”

Good idea, young Cian. When you write it down like this, it seems a really obvious thing to do.

I’ve written before of author and advertising legend Bryce Courtenay, who got to the very top of his industry by asking the client why after every pitch they lost. How can we improve, he would ask. Courtenay would almost always win that client next time they pitched.

Not so much at Giant Global Software Corp.

“No,” said Cian’s boss. “That’s not what we do here.”

After a few more frustrating losses, Cian went rogue. An undercover, against-orders trip to the client find out what was behind their choice to go elsewhere. It was both educational, and ominous for Cian’s career.

The client had liked most of the sales team, and felt that they’d put a good case. But also singled out a very senior exec on Cian’s side whose involvement had killed the whole deal.

It put Cian in quite the bind. Imagine going back to the office, confessing to disobeying direct orders, then dropping that report. So rather than commit career suicide, he left to set up Trinity Perspectives, a Win/Loss evaluation consultancy.

The real story why you won and lost

Businesses that had lost big deals would send Cian and his team to talk to the client and find out why that client bought from someone else.

Many of the reasons are variations on that classic school exam trap: didn’t answer the question. The client asked something specific. You, however, had a head full of things you really wanted to say, so you said those instead. About your product, mainly.

That was not what they were asking, so you did not win.

Cian recently collated ten years of feedback from buyer clients on why they chose suppliers, or didn’t chose others. It’s fascinating.

Here’s the Top 9 reasons why you did and didn’t win the sale. (For context, these are B2B sales for mostly tech, telco and professional services companies, with deal values north of $100k, so usually multiple customer interactions in the sales cycle.)

Why you lost:

• Focused too much on your solution, not enough on their problem
• Generic marketing content/RFP
• Seen as: too risky, too cheap, too niche
• Seen as unprofessional or unethical
• No internal coach & poor C-Suite engagement
• Not seen as industry leader
• Failed to create any emotional connection
• Weak or no win themes
• Poor use of resources

Why you won:

• Went beyond marketing, to thought leadership
• Added value at each step of the buying process
• Strong win themes
• Constantly validated assumptions
• Focused on your customers customer
• Answered the ‘so what’ question
• Managed risk and cultural fit
• Strong peer feedback vs references
• Seen as easy to do business with

You could write a book on each of those points but I’ll just leave them there for you to ponder. Follow Cian’s socials if you want more detail.

Price is not the factor salespeople think

The most interesting reason? Price. Because it doesn’t appear on either list as a deciding factor, in terms of clients wanting a cheaper deal like salespeople assume.

In fact it only appears in the opposite context: the price was too cheap, so the client assumed there was something wrong with it.

Most sales people go into the deal without spending enough time, thought or research on their client. So they come across as generic sales reps, one of half a dozen options to fill out the RFT cattle call.

Then they blame the CFO and marketing for setting the price too high.

That old excuse about someone else having the inside running? They did. The excuse implies unfairness, as if the client was the winner’s uncle or they belonged to the same golf club, but it’s not that.

It was because they did all the groundwork you didn’t do. By the time the pitch came around, the client already had a clear preference for a supplier who clearly understood them and their business.

Your worst nightmares become reality

Sometimes Cian’s process picks up feedback that would make any of us break out in a cold sweat.

The most nightmarish? The bid that was submitted as a PDF document with all the team’s comments and edits still visible 💀.

Comments including “We just made this case study up.” 💀💀

Then the response, “That’s ok, just put it in anyway.” 💀💀💀

Straight to the Fuck-Up Hall of Fame.

Part of managing this analysis is not using it as a threat hanging over sales reps’ heads, but rather a source of feedback to help them win more deals. Nobody was punished over the PDF incident, but it was quietly added to the checklist for future pitches.

Why we invested in it

Cian recently launched a digital version of his win/loss analysis process, working with his technical partner Sam Jenkins, a New Zealand ex-soccer pro and Olympian who has reviewed a few game tapes in his time.

It gets feedback from customers about everything they liked, and didn’t like, along the buying journey. Then uses AI to create feedback and guides for sales teams on how to improve next time.

So far so good, it’s already been picked up by a lot of corporates looking to learn the real story from their customers. In a big win last week, Salesforce in Australia will add it to their App Exchange so salespeople can trigger a review straight out of their CRM.

I’ll keep you posted on how it goes but it seems to make sense. When you think about how much businesses spend on SEO to bring in leads. Then hand them to sales reps with a 10% win rate. It feels like there’s time, effort and money to be saved.

As a business owner, I want to know all the news, but particularly the bad stuff. If you stick your fingers in your ears, there will be tears at some point.

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