The 3-Step Sequence of Killer Questions

I was at a sports bar with Tom D., one of our city’s best commercial bankers. We were commiserating about never having enough time to really prepare for a sales call—or any management meeting.
But we shared the belief that the best thing that can happen in a meeting was for the prospect or CEO to shout, “That’s a great question!” A great question leads them to the solution, so they feel like a hero.
There’s a Napkin Somewhere
That naturally took us to: “Wouldn’t it be great if we could click a button and get three great questions to take into any meeting?” We started to sketch a single-screen tool to make our dream come true. That sketch led to The Index of Management Terms & Practices, now a free resource for managers and salespeople.
A Pattern Emerges
The Index worked! Years go by and then a pattern emerges: there was a certain sequence of questions that could take 15 minutes out of a meeting and a meeting out of the sales cycle:
- A question to elicit a story
- A question to explore the issue
- A question to lead to action
Generic Version (Boring)
- Story: When did you experience X?
- Exploration: What was the root cause of X?
- Action: What should we do about X?
There are two better examples below, but first let me elaborate on the three question types:
Story: If nothing else, asking for a story helps you shut up and listen. Their story will provide data, let you know how they feel about the issue, and how they think about it. If you’re talking to a group and get several stories, you get more information and also see if they think about the issue differently.
Exploration: If nothing else, an exploratory question keeps you from leaping to a conclusion. It’s natural for salespeople to want to a) look like a hero and b) get a sale, but you’ve got to keep your ego out of it. Hearing how people think about causes, assumptions, and perspectives will teach you more about their thinking and priorities, it’ll teach you how to speak in their terms.
Action: A sale—a relationship, really—begins with a low risk trial, so a question like, “What would be a small win or some first few steps?” I cringe thinking about my younger self lugging my laptop to a meeting, droning on about myself for 50 minutes, then never getting asked back. I mean, couldn’t they tell how amazing I was?
Crafting three questions takes research, good writing skills, and creativity. While even the generic questions (above) will make a big improvement, here are some sample question sets to spark your thinking:
Sales questions (example for a seller of safety equipment)
- Story: When did a piece of safety equipment let you down?
- Exploration: Was this a problem of training, equipment, or both?
- Action: What’s the biggest barrier to getting your folks to change?
Best practice question (example: improving customer service)
- Story: What was the best customer service experience you ever had?
- Exploration: What do we know about our competitors’ customer service?
- Action: What combination of staffing, training, and tech would get us 5 stars?
How to Try It: ¼-Page Meeting Planner
For goodness’s sake, don’t go into a sales meeting with a brochure or even a thick pad of paper.
After rapport-building pleasantries, say, “Thanks for your time. I’ve got three questions I’d like to ask: is that OK?” Then take out your ¼-Page Meeting Planner—which will get their curiosity—and dive in.
Here’s where to get the free Planner. (It’s “1/4 page” because you can fold it up and stick it in pocket, purse, or small notebook.) People love hearing you say, “I was thinking of you… and I have these questions.”
Resources for Extra Credit
Each term in The Index includes a “3 Good Questions” section; the Index’s 4-level outline lets you quickly zero in on the issues
I’ve seen users holding their smartphone under the table, scrolling frantically through The Index to understand what everyone’s talking about and find a killer question.
See the How to Use video.
“The Mom Test,” by Rob Fitzpatrick, drives home that you have to ask the Hard to Ask Questions after making a list of what you Need to Know.
No one likes hearing what they don’t want to hear, but good salespeople and managers know not to push a sale or project until they’re certain it will provide a lot of value.
They also know it’s important to bail out when things aren’t adding up. Your career goes backwards when you successfully pitch an idea that doesn’t really work.
It’s Not a Trick: It’s Servant Selling
The point of asking great questions isn’t to manipulate anyone. It’s to get at the truth of the matter, to learn if it’s important, and to determine if what you’re pitching will make a noticeable difference.
It’s great to have the reputation for asking the questions that always make the difference.