4 min read
Don’t be an Ahab
Everyone in sales has a white whale: a deal they chased with bitter, single-minded focus, to the detriment of the rest of their pipeline.
There’s a deal I didn’t close years ago, and it’s still painful to think or talk about. Truly, I start to get mild anxiety, and my body language closes up. So embarrassing. Everyone in sales has a white whale: a deal they chased with the bitter, maniacal, single-minded focus of Captain Ahab, to the detriment of the rest of their pipeline and responsibilities.
So how do you prevent it? No one wants to get this wrapped up in an unrealistic deal, so how can you tell a white whale from a viable opportunity? Unfortunately, there’s no silver bullet. But you can build checks into your process that signal whether to set sail on your quest or stay docked and wait for a better opportunity. Here are two easy tactics you can start using today.
Viability test #1: Test your champion in call one or two
Say you’re only talking to one person in a deal (this is called being single-threaded, and it deserves a whole post of its own). You ask to talk to someone else, bring in another department, or move forward on something like an NDA. If they say no, or something like “Let’s just keep this with me for now,” your chances of closing just dropped to 50/50 at best.
It doesn’t matter:
- How solid the use case is.
- Whether they’ve agreed on pricing.
- Whether you’ve sold into that company before.
Viability test #2: Ask why they wouldn’t buy
Ask your champion or buying committee one question:
Ask it like this
“Why wouldn’t you buy [your product]?”
This one is hard. You’re basically inviting them to think about doing the very thing you don’t want them to do, which feels counterintuitive. It also stings to hear about flaws in your product. But it’s an uncomfortable question for a reason: it’s illuminating. You need to know what you’re up against, whether that’s their internal processes, competitors, or a build-versus-buy project already underway. Every objection they raise becomes your sales roadmap.
Let the whale go
The hardest part of sales isn’t chasing deals. It’s knowing which ones to stop chasing. Every hour you spend on a white whale is an hour you’re not spending on a deal that could actually close. Test your champion early, ask the uncomfortable question, and believe the answers. A clean “no” in week two is a gift compared to a slow “maybe” in month six. Ahab never got his whale, but he could have had a pretty great voyage.
Not sure if you’re chasing a white whale?
Bring me the deal you can’t let go of. In a Deal Post-Mortem, I review the call recordings, emails, and CRM history for one deal and give you an honest read on whether it’s real, plus what to do next. Or book a 30-minute intro call and we’ll talk through your pipeline.
Written by Abigail Aragon