#003: The Question Stack™


Hey, 👋 Scott from The Sales Mastermind here.

Today’s edition can be read in 3 minutes.


Asking great questions is an unrivalled sales skill.

Buyers will respect you more and It will differentiate you from other sellers.

Yet many sellers struggle with questioning because they don’t want to come across as sales-y or to cause offence.

To overcome this let’s go through The Question Stack™.

The Social Contract

Do you remember as a child a stranger asking you a question? Something innocuous like “How old are you?”

You tried hiding behind your parents' legs, they pulled away (traitors) and said “Come on, answer the question”.

You learned, when asked a question you answer it.

This was reinforced during school - “What is the answer?” and you answered.

The Question Stack™ takes advantage of this social contract.

3 Types of Yes

According to Chris Voss (former FBI hostage negotiator and author of Never Split the Difference) there are 3 types of Yes:

  1. The Confirmation Yes - Used by buyers to agree that the seller said something. It moves the conversation forward.
  2. The Counterfeit Yes - When a buyer really wants to say No, but says Yes as an escape route.
  3. The Commitment Yes - The only true yes.

Often sellers have happy ears. They hear a Commitment Yes when the buyer meant a Confirmation Yes or Counterfeit Yes

Closed Questions

Seller: “Does that make sense?” “Should we move forward?”

These are examples of closed questions. The only answers are “Yes” or “No”.

And they’re some of the worst questions you can ask. Yet sellers rely on them because they’re easy and buyers will not break the social contract.

When asking closed questions buyers will usually give a Confirmation or Counterfeit Yes. While sellers will hear a Commitment Yes.

Unless you are using the Question Stack™, avoid closed questions.

Open Questions

Seller: “What brought you to today’s conversation?” “What changed since we last spoke?”

These are examples of open questions. They’re impossible to answer with “Yes” or “No”.

Open questions are your friends as they allow the buyer to elaborate. They invite a conversation, not a sales monologue.

Whenever possible ask open questions.

Now the fun part… The Question Stack™

By combining closed and open questions they can become your superpower.

Do the easy bit first - ask a closed question.

The buyer will follow the social contract and say Yes.

Then immediately follow up with an open question and you’ll get the prospect talking, it’ll feel natural.

For example:

Seller: We just covered XXX, does that solve the pain we were just talking about?
Buyer: Yes.
Seller: Great, help me understand, where do you think that process would fit in your workflow?

Seller: We just covered XXX, is that what you were expecting?
Buyer: Yes.
Seller: Great, well now you’ve seen it, how well do you feel it solves the pain we were just discussing?

The key is to firstly ask a closed questions. Then immediately follow up with an open question to keep the buyer talking.


TLDR Wrap Up

  • Questions are one of your key skills as a seller
  • The Social Contract - When asked a question it’s impolite to not answer
  • 3 Types of "Yes" - Commitment, Confirmation, Counterfeit
  • Close questions are (mostly) bad
  • Open questions are much better
  • The Question Stack™ combines the two

And that’s a wrap….

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Until next time,
Scott Cowley

PS I help founders who sell, but aren't "sales"people. Whenever you're ready here are two ways I help:

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