

When I teach powerful questions, there is a moment I have learned to expect. The "draft your own" is where people get stuck. In the pair/trio practice, it is pretty normal to skip that part of the exercise. Almost every time, someone asks me: "So what is your favorite question to ask, Diane?"
I totally get it. Drafting a truly open question, in real-time, in the middle of a conversation, is genuinely hard. I find the process of drafting causes many to give up and go back to their original way of doing things, which usually involved just telling the person what to do. So to counter this, I hand out a starter list in my workshops, because borrowing a question helps the hurdle feel less high. But, I always say the same thing when I hand over this list:
Once you have the feel of it, your own will be better than any list.
Because a question is not powerful because it came from some list. It is powerful because of what it does to the other person's thinking. Let me show you what I mean.
Many of you are preparing for year-end evaluations. So let's imagine the below conversation. How many problems can you find in the manager's questions?
Manager: "So, overall, are you happy with how this year went?"
Team member: "Yeah, mostly."
Manager: "Why did this deal not come through?"
Team member: "The client had some budgeting issues..."
Manager: "Don't you think you should have flagged that earlier? I mean, what I always did in your position was raise it in the weekly pipeline calls, because otherwise how could the rest of us help you push the client.. does that make sense?"
Team member: "err... I guess so..." (or silently nods)
The first question is closed. It invites a yes or no, and so of course, it got one. The adjustment is minor: "How would you rate this year on a scale of 1 to 10? And what drives that rating?" Same intent, but now there is something real to talk about.
The second question leads with "why," and "why" can cause a person to feel they are on trial. The person prepares a defense instead of a thought. Try instead:
"What is your view on what happened with this deal?"
It's now open, inviting their reflection. The third question has two problems in one breath. The answer the manager wants is already inside it, which makes it advice wearing a question mark. And then it keeps explaining itself, which tells the other person the manager is more interested in being right than in their reply. Try instead: "If another deal gets into this situation, what would you want to see happen to influence the outcome?"
But my favorite question in this conversation was never asked, and no list could have written it in advance. The team member said: "The client had some budgeting issues..." And the manager drove right past it.
"You said budgeting issues. Say more about that."
Eight words. It opens their thinking exactly where their thinking already was. And it does a second job in a subtle way: your team member hears their own words come out of your mouth. It shows you were listening to them. This is where trust builds.
Year-end conversations are coming and they are not exactly the best place to try a new skill for the first time. So practice now, in the everyday conversations you can keep experimenting in each time.
In your next 1on1, try out a question like this one: "What are you most proud of in the last quarter?" It cannot be answered with a yes or a no, and it starts the conversation somewhere worth being.
Then, don't stress about more "powerful questions". Instead, listen for the sentence to build on. The best question is usually hiding in the last thing they said.
If this has sparked some curiosity, I would love to continue the conversation at diane@ptminsights.com. I am also happy to share a list of powerful questions with anyone who requests one. Just let me know where and when you want to use it!