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"You made a big mistake"

Updated: Jun 25

“Big Mistakes: Lost Deals and Lessons from Enterprise Selling”
"You made a BIG mistake. Big. Huge"

Last night, I was having a drink with a friend who runs transformation programs at a government department. The topic turned to salespeople (he politely tried to hide his contempt) and he told me a story: He’d reached out to a well-known tier 1 software vendor, wanting to transform a business process with data.


He didn’t hear back. Even after following up weeks later, nothing.


I’ll probably never hear the other side; whether they wrongly qualified him out as a NI/NA (No Influence / No Authority) or whether it was jotted down on a Post-it note and forgotten. Hanlon’s Razor (never attribute to malice what can be explained by incompetence) always deserves a hearing.


But it troubles me. We as vendors spend so much money and energy generating leads: BDRs, ads, outreach. And yet, when a client finally raises their hand, we don’t call them back?


I’ve seen many possible explanations for this close up. A client wants a price, but internally it triggers endless debate: different managers with big egos have different views on the “best approach.” Someone offshore needs to be consulted. Maybe a partner should be engaged? A meeting is booked, postponed, rebooked. Weeks pass.


The client is calling back, pleading: “Please, I just want a quote so we can get on with this.”

The rep is frozen with embarrassment, AVOIDING the client's calls...

Meanwhile, there are startups who’d raffle their organs just to get a meeting!


We spend so much energy strategising and forecasting. That’s fine, but let’s not forget the fundamentals:

  • Spend as much time as possible in front of customers

  • Listen more than you talk

  • Ask questions

  • Don’t be an asshole

  • Be easy to deal with

  • Follow up (and then follow up again) - even if it’s a no.

  • Provide value in every interaction - something real, not fluff.

  • Be honest about what you don’t know

  • Respect the customer’s time and process

  • Own the next step - always


What have I missed?


It’s not yet clear whether my friend will get to have his Pretty Woman moment - calling the vendor back to gleefully tell them that he has spent millions with a hungry startup.

But I hope I get to hear about it!


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