What Don't You Know About Your Deals?

If you are a West Wing fan, you may be familiar with a great line from the show:

Toby: "Mr. Vice President, what do you know that I don't?"

Hoynes: "Toby, the total tonnage of what I know that you don't could stun a team of oxen in its tracks."

This is exactly how I feel in too many deal reviews. Sellers tell me everything they know - the last conversation, the people they're talking to, the next steps - but what really matters is the total tonnage of what we don't know.

It is crucial to ask probing questions to understand where the gaps are and how we can fill them. These questions map to the MEDDPICC framework I discussed previously. Note that each of these questions is very specific:

Question 1: "How has the Champion demonstrated they are really a Champion?"

Weak answer: "The Champion is very responsive to all of our messages."

The problem: This doesn't demonstrate they're a champion, just that they're reactive. Are they advocating for our solution internally? Have they given us access to power? Have they shared political insights about how decisions get made?

Responsiveness is nice, but it's not championship.

Question 2: "Have we confirmed who the Economic Buyer is?"

Weak answer: "The EB will be the VP Marketing."

The problem: This sounds like an assumption. Have we been told by reliable sources that this individual can sign off on our deal?

Have we heard of other cases where they've bought a similar product and this individual made the commitment? Or are we just guessing based on the org chart?

Question 3: "Have we had direct feedback from the EB that this project is of consequence to them?"

Weak answer: "The Champion says this project is really important to the finance team."

The problem: Does the CFO know we exist? How high up their priority list is this project? Third-hand assurances from a Champion are not the same as hearing commitment directly from the person who controls the budget. We need to get in front of the Economic Buyer.

Question 4: "What have they agreed the Decision Criteria are?"

Weak answer: "We have to meet the technical requirements, satisfy their security team and have good financials."

The problem: That's true for any purchase by any company anywhere. What are those specific technical requirements? Why are they the technical requirements? Do they make it more likely they will select us? What is their understanding of the commercials today? What ROI are they expecting? Generic criteria tell us nothing about whether we're positioned to win.

Question 5: "Have we agreed a timeline with the Champion when they want to go live? Who else needs to agree?"

Weak answer: "They would like to be live ASAP."

The problem: What does that mean? Who suffers if it takes longer? What will cause them to commit to a date and move towards it? "ASAP" is not a timeline - it's a polite way of saying "we haven't thought about this seriously yet." Without a real date and consequences for missing it, there's no urgency.

Question 6: "Do we know exactly what steps are necessary from here to contract signature?"

Weak answer: "Once the POC is successful we get the contract signed."

The problem: What does it take to make the POC successful? Has the EB confirmed that they will move ahead following a successful POC? How many other people have to give us the thumbs up - IT, security, finance, legal, procurement? What is the contracting process? One successful demo doesn't magically turn into a signature.

We avoid asking these harder questions because it's uncomfortable to expose what we don't know. Knowing things feels good. It feels like progress. We can report activity, meetings, enthusiasm. 

The best sales teams I work with have inverted this instinct. In their pipeline reviews, they don't celebrate what they know - they ruthlessly hunt for what they don't know. They ask the uncomfortable questions early, when there's still time to fill the gaps or qualify out.

Start your next deal review with this question: "What's the tonnage of what we don't know?" Then work systematically to reduce it

I’d love to hear your thoughts. Comment here or reply.