I spent twelve months on a deal that was never going to close. Sixteen meetings. At least twenty hours of prep. This is what I learned.
The short version
A deal that looks like a gift can be a trap. Inheriting a warm opportunity is no substitute for qualifying it properly. When you want a deal to be real, you find reasons to keep going — instead of reasons to stop.
Use this tomorrow
Ask early: "When can we get time with the decision maker?" If the answer is vague or keeps moving, that is your answer.
Ask: "Who else needs to be involved before this moves forward?" Don't accept the first answer — push gently to surface hidden stakeholders and blockers.
I inherited this opportunity from a colleague who left the team. On paper it looked like a gift. The prospect had already seen the product. They understood the value. It was supposedly just a matter of paperwork and timing. A done deal waiting to be done.
I should have been suspicious of it perhaps being too good to be true.
Here's what I told myself for twelve months: I have a champion, or at least I thought I did. They want to buy. I just need to keep pushing and deliver on anything they ask for.
Here's what was actually true: I was so focused on closing — on the commission, on the number, on making the inherited deal count — that I stopped qualifying it properly. This deal would reach my quota and hit presidents club.
I didn't ask the hard questions early. I ignored the red flags. No clear access to the real decision maker. Vague alignment between what we offered and what they actually needed.
My manager was in the room for half those meetings and neither of us called it. We both wanted to believe.
That's the trap. When you want a deal to be real, you find reasons to keep going instead of reasons to stop.
In a recent training I came across a phrase that I haven't been able to stop thinking about: qualify to disqualify.
The idea is simple but uncomfortable. In the early stages of a sales cycle, your job isn't only to build momentum — it's to also find reasons not to continue. Be ruthless about fit. If access to decision makers isn't there, flag it. If the value alignment story doesn't land naturally, question it. If the prospect's timeline keeps moving, ask why.
The goal of early qualification is to eliminate wishful thinking from your pipeline. Because a pipeline full of hope isn't a pipeline — it's the reason for missing quota.
If I had that year back, here's what I'd do differently from day one. Ask the disqualifying questions first — not to be difficult, but to protect everyone's time.
Ask it early and ask it directly. Frame it as standard process — because it is. If the answer is vague, deflected, or indefinitely postponed, that's your answer. No access to the decision maker is not a hurdle to manage later. It's a reason to pause now.
Don't accept the first answer. A useful way to probe: "In my experience, even when the CFO has signed off the budget, there's often still an informal blessing needed from the CEO or another senior stakeholder. Is that the case here?" Push gently, but push.
Build a realistic pipeline, not a comfortable one. There's a difference between an opportunity and a wish. Be honest about which one you're looking at.
One exception worth naming: if you're early in your career or just starting at a new company, it can make sense to let a few more conversations run longer than they should — you're learning the product, the objections, the customer. That's a fair trade. But don't let it become a habit.
Twelve months. Sixteen meetings. Dozens of hours.
The deal taught me more than most of the ones I closed that year. But I'd rather have learned this lesson cheaper.
Qualify to disqualify. Put the hard questions at the beginning, not the end.
What's a deal you held onto for too long? I'd genuinely like to hear — hit reply and tell me.