Always ask this question

Sellers are often hesitant to ask tough questions, questions which will help them really understand the status of their deal. When challenged, the two main reasons they cite are:

1️⃣ "I can't ask that, it will be too intrusive" 

2️⃣ "They might tell me that they don't like the product."

To which I say:

1️⃣ "Yes you can. You must. But be polite." 

2️⃣ "For crying out loud that's the most important thing we need to hear!"

Here's how to overcome both objections at once. There's one question which should be asked again and again to multiple different people. It can feel intrusive but it will also reveal critical information.

"What are the steps to get from here to a live deployment?"

You can ask this in your very first discovery. Once you have confirmed that there is some value in your solution and the prospect has expressed interest, you say "It sounds like this would make some sense for you. What are the steps you need to take to go from here to make a decision?" And in nearly every case they won't give you much detail, so you follow up with further questions such as "who is it that has to approve the budget?"

The first time you meet the Economic Buyer, once you have established that they see real interest in your solution, you ask "could you help me understand how we get from this conversation to confirmation you wish to use the solution and then into production?" Again, what you will hear is unlikely to be complete and you can dig deeper.

Very often when I suggest this to AEs they will say "I know the answer to that…" Sometimes they have a very detailed and potentially accurate answer. Sometimes they have something much vaguer where there are many gaps to fill in. Either way, there are multiple reasons to keep asking nonetheless.

▶️ Things change. Especially in longer deals, budgets change, people change, processes change. Don't get caught out.

▶️ People know different things. Your Champion might be well connected and knowledgeable but the Economic Buyer will almost certainly know more.

▶️ People think more deeply when asked twice. Ask your Champion a question one week, then ask it again a week later phrased slightly differently. You'll get new details, deeper thinking, things they didn't consider the first time.

▶️ By telling you something, people become emotionally committed to it. If I tell you the next step is XYZ, I create an emotional commitment to make that happen. The more times I repeat that, the stronger the commitment becomes.

Yes, this question can feel intrusive. As do the follow-ups to clarify exactly who has to do what, or how that review happens, or when it's time to start that next conversation. But if we don't ask these questions we don't have visibility, we don't have control and deals will slip constantly.

A critical skill for great sellers is to ask difficult questions and sit quietly in slight discomfort while the prospect works out the answer.

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