Why Your "Sure Thing" Deals Slip

Hello Predictable Revenue community,

Book update: I had to go back to square one with the audiobook editor, they didn’t do a great job so I decided to start over. I’ll hopefully have them to share later this month.

Pre-order benefits: For anyone that pre-orders the book, I have a monthly zoom call where we work on revenue problems plus you get access to the Investor list I shared a few weeks back. I have something interesting coming next week or two and you’ll get that too once it’s live…

You can order the book here. Email me your receipt and I'll add you to the event/share the sheet.

Ok, now onto the newsletter.

The deals you're most excited about? They're often the ones that crash and burn.

I learned this the hard way with a $600,000 Olympic security contract. I had the PO, had verbal approval from four different organizations, had 76 generators sitting in a yard ready to deploy. Then got the call: "Sorry, we're not going to do it."

That one still stings. But it taught me something important about enterprise deals: they're unpredictable as hell, and the stuff that kills them is usually hiding in plain sight.

The Vancouver Olympics were coming up, and there was real concern about security after the London tube bombing and 9/11. They wanted to test all the security systems ahead of time, but couldn't get 220-volt power to the remote locations in time. So I organized 76 generators from across Canada to provide temporary power for a two-week testing period. We had everything lined up, contracts signed, generators sitting in the yard ready to deploy.

Then they called and said they'd run out of time to do the testing properly. They were just going to wing it during the actual Olympics. Six hundred thousand dollars, gone. My boss gave me a 2% consolation prize from the $60k consulting fee we negotiated for our trouble. I was livid. But that deal taught me more about enterprise sales than any course ever could.

Why Big Deals Really Stall

Been thinking about this after a client call this week. Their pipeline is looking strong—multiple six-figure deals moving forward, champions engaged, verbal commitments. But I've seen this movie before.

Big deals typically stall because you missed something. It could be a holiday with a key buying influence, a requirement that's really a deal killer, or an influencer with a competing project. When all you're focused on is giving your demo, you're not spending enough time asking the real questions that will de-risk the deal and find the things that will stall or kill it.

Most sales reps fall into the demo trap. They get excited when a prospect says "show me what you've got" and rush straight into product mode. But what they should be doing is digging deeper. Who else needs to see this? What happened to the last vendor you evaluated? What would make this project not happen? What other priorities are competing for budget this quarter?

The stuff that kills deals is rarely about your product. It's about timing, politics, budget cycles, and personalities. Your champion gets promoted and their replacement has different priorities. The CFO decides to freeze all new spending. A key stakeholder goes on sabbatical right when you need their approval. Someone in procurement has a relationship with your competitor.

Every unknown in your deal is basically 100% risk. The more unknowns you have, the more likely you are to get that "sorry, we're not moving forward" email. This is why I've become obsessed with what my friend Megan Wilson (one of the best enterprise closers I know) calls "de-risking deals." Every piece of information you gather, every process step you understand, every stakeholder you identify removes a bit of that risk.

The problem is most of us treat sales like we're fortune tellers. We look at a deal and make up a probability based on gut feel. "This one feels like 80%." But what if there's a technical requirement you don't know about? What if your champion doesn't actually control the budget? What if they're planning a hiring freeze next quarter? Your 80% might actually be 20%.

Even deals with verbal commitments can disappear overnight. I've seen it happen more times than I can count. Your champion gets fired. Budget priorities change. A competitor comes in with a relationship you didn't know about. The company gets acquired and all purchasing decisions get frozen. Wild stuff happens in enterprise sales, and the bigger the deal, the more opportunities there are for things to go wrong.

Two Things That Actually Help

Ask About Their Timeline (But Do It Right)

On your second or third call, ask: "When do you ideally want to have something like this in place?" Not "when do you want to buy?" Just when they want the problem solved. This question is magic because it gets them thinking about their own process—what approvals they need, when budget cycles hit, if anyone's going on vacation.

You'll learn more from this one question than from three discovery calls. They'll start thinking out loud about all the steps that need to happen. "Well, we'd need to get it through security review first, and Jennifer handles that but she's going on maternity leave in October. And then legal would need to look at it, which usually takes about six weeks. Oh, and we can't implement anything new in Q4 because of the product launch."

Suddenly you understand their real timeline and all the potential roadblocks. You're not selling to them anymore—you're helping them solve a logistics puzzle. This one question reveals the decision-making process, the stakeholders involved, the budget cycle, and potential timing conflicts. It's the difference between hoping for the best and actually understanding what needs to happen.

But here's the key: you have to actually listen to what they tell you. When they mention that Jennifer handles security review, ask about Jennifer. When do you need to get this to her? What does she typically look for? Has she killed deals before? When they mention the Q4 implementation freeze, dig into that. Why the freeze? Who decided that? Are there any exceptions?

Use a Mutual Action Plan

Sounds fancy, but it's just a shared project plan before they're a customer. Once you know their timeline, work backwards. When do we need to finish the trial? When does this need to go through legal? When do we need budget approval? Who needs to sign off at each step?

Put it in a simple spreadsheet with owners and dates. Include things like "Security review completed by Jennifer" and "Legal approval received" and "Budget confirmed with finance team." Share it after they're engaged (never on the first call—that's weird).

The beauty is you're not pushing them to buy. You're helping them figure out their own process. You become their sherpa, not their vendor. And when things start to slip, you can point to the plan and say, "Hey, we agreed Jennifer needed to finish the security review by the 15th. Should we push everything back a week, or is there another way to handle this?"

I got this idea from Tom Williams at Clari Align when I had him on my podcast. He's the head of their sales collaboration platform and has been thinking about this stuff for years. He even shared a template, which I'll dig up and send to anyone who replies to this email asking for it. The whole concept is about lowering risk through collaboration—not just with your champion, but with everyone involved in the buying process.

The mutual action plan works because it forces everyone to be honest about what actually needs to happen. No more vague "we'll probably sign next quarter" conversations. Instead, you have specific milestones with specific owners and specific dates. When someone says they can get budget approval "soon," you can look at the plan together and say, "Okay, if we want to go live by January 15th, we need budget approval by December 1st. Does that work with your finance team's schedule?"

Tom's approach goes beyond just timeline planning though. He maps the stages to the buyer's journey instead of your sales process. What do they need to educate themselves about? How do they validate vendors? What jobs do they need to get done internally? Then you build the plan around helping them accomplish those things, not just hitting your sales milestones.

Reply with the word MAP and I’ll share Tom’s template.

Your Next Move

Pick one thing to try this week. Ask that timeline question on your next call and really listen to what they tell you about their process. Sketch out a simple action plan for your best deal—just a list of the steps that need to happen and when. Start tracking where your champions go when they change jobs.

The deals you're most excited about will probably crash and burn. The ones that sneak up on you become your biggest wins. My client's biggest deal this quarter came from a guy they thought had gone dark months ago. He just re-engaged out of nowhere because his priorities changed and suddenly the problem became urgent.

Focus on the process, not counting the money. Every deal teaches you something about how these things really work. Even the ones that blow up in your face… Especially those ones.

Hit reply if you've got a deal that went sideways in a weird way. I love hearing these stories. 

Collin 

PS - reply back with MAP if you want the mutual action plan template from Tom Williams - I'll dig it up and send it over.