OOOOOOO 👻
AHHHHHHH 👺
Grab your costumes for this one — it’s officially spooky season.
To celebrate all you sales ghouls out there, we’re running a Halloween Special Newsletter.
Today, we’re reviewing the scariest deal killers that haunt your quota from prospecting to close — and how to keep them from killing your deals:
- The Problem That Disappears Beneath the Lake
- The Deal with No Power to Protect You from Monsters
- The Never-Ending Pit of Vendor-Review Despair
Let’s get spooky.
1.) The Problem That Disappears Below the Surface of the Lake
Is there anything scarier than going through a month-long evaluation… and then getting ghosted?
Deals usually go six feet under because you only uncover surface-level pains instead of connecting to the 6–7 figure nightmares that keep execs awake at night.
Keep your deal alive by using a Discovery Tree to dig beneath the surface and uncover executive-level problems.
Here’s what that sounds like — using background checks as an example:
1. Uncover Situations with “Why’d You Take the Call?”
"My guess is you don’t take calls with everyone who reaches out. What prompted you to take this one today?"
(Let’s say they give you something fuzzy like “our background-check process isn’t scalable.”)
2. Uncover Operational Problems with Multiple-Choice Questions
“Usually when teams run into background-check nightmares, it’s one of three things: 1) The process is slower than a zombie chase scene, 2) Compliance skeletons keep popping out of the closet, and 3) The candidate experience is a total horror show. Which one’s haunting you the most?”
(They mention hiring remote workers where every state has different rules.)
3. Uncover Executive Problems with “Magic Moment” Questions
“My guess is you didn’t just wake up one morning and realize your process was cursed. When did you first sense something was off? Did a background check go wrong? Did a compliance ghoul jump out of nowhere? Or are you just trying to keep those horrors from resurfacing again?”
Nine times out of ten, they’ll tell a scary story about a noncompliant background check that caused a legal nightmare.
That’s your executive-level problem — and the thing that keeps your deal from ending up in the graveyard.
2.) The Deal with No Power to Protect You From Monsters
Here’s the terrifying truth about selling without power:
You can have the perfect champion — swearing this problem is their personal nightmare.
But if power doesn’t share the fear, your deal’s getting eaten alive by monsters.
In this economy, single-threaded deals don’t close… they vanish into the fog.
And once they’re gone, they don’t come back from the dead.
Instead of just selling to champions, try these three tricks to summon power and protect your deal from an early death:
1. Map a Path to Your Deal in Advance
Before your discovery call, map your path to the deal. For example: I need to win over Jack-o-Lantern the Champion, then The Big Bad Wolf Executive Buyer, then Frankenstein the Procurement Goon.
2. Establish Next–Next Steps
Don’t spook your prospect by suddenly summoning every exec into the deal. Use Next–Next Steps to guide them through the process and set expectations for when power should appear.
“Next, we’ll do a deeper dive on how the analytics dashboards can save you 3 candies per trick-or-treater. If that goes well, we’ll probably want to loop in Mike, your CFO, to quantify the economic impact of a 20% sugar deficiency. Does that sound right?”
Now you’re leading them through the process as the expert and increasing your chances of power actually joining a future call.
3. Get Your Leadership Involved
Bring your own execs and SMEs into the process early. Power attracts power — when your leaders show up, theirs usually do too. For example, if an executive gets brought into a demo, bring your leadership as well.
3.) The Never-Ending Pit of Vendor Review Despair
Think you’ve survived the negotiation?
Here comes the big bad IT wolf — ready to eat your deal alive one security question at a time.
And behind him lurks the even bigger, badder Legal wolf, starving to redline your deal to death.
Even after you’ve “won” the deal, vendor review can drag on for weeks — until your deal dies because you missed the go-live date you promised your buyer.
Instead, protect your deal from the graveyard with these three plays:
1. Build a Mutual Action Plan Early
Work backward with your buyer to when they need to be live, then map every milestone from there. When vendor review delays pop up, your buyer can pressure their internal teams, not you, to keep things moving.
2. Run Reviews in Parallel
Don’t run legal, security, and procurement reviews one after the other — run them at the same time. That eliminates spooky five-week review processes and shrinks them into one or two.
3. Set a Redline Deadline
Agree upfront on exact dates for when legal sends edits, when you’ll respond, and when you’ll review together. Here’s how it sounds:
“We’re targeting end of November to get this signed. That gives us about three weeks. Our team’s fast on redlines — when could your team get us the first cut?”
Remember: The hardest part of legal review is getting them to prioritize it in the queue at all.
The scares don’t end here…
There are 2 more deal killing ghouls in our YouTube Halloween special 👻
(PS: It’d mean the world if you subscribed and hit the bell to support the channel, folks)
