The Leader’s Guide to Asking Better Questions to Break the Status Quo

Insights

May 23

Successful change doesn’t start with the answer. It starts with a better question.

At ChangeAccelerators, we believe that questioning is the most underrated power tool in a change leader’s kit. This belief was at the heart of our recent session at ACMP Change Chicago 2025: “Using the Art of Questioning to Disrupt Your Thinking and Break the Inertia of the Status Quo Once and For All.”

We didn’t lecture. We didn’t PowerPoint people to sleep.

We invited 200 change leaders into a mindset lab - a space to rediscover their childlike curiosity and reclaim the power of the question.

Why questions matter more than ever

Somewhere between age 5 and our first team meeting, most of us stopped asking. It is not because we become less curious, it is because we are conditioned to stop asking.

We are taught to be seen not heard. Then we are rewarded for not asking but memorizing, to pass standardized testing in school. Then, when we get hired for our first job, we are expected to have answers. And this continues as we get promoted. We learn to give advice and provide solutions. We get busy; we jump to getting it done with the what and how without taking the time to ask the why. We just become conditioned to NOT ask.

We also become risk averse, and we slip into our own status quo. We are prone to confirm and live our lives in the grooves of precedent - we don’t challenge it.

According to sociologist Amitai Etzioni: We tend to cling to stable knowledge rather than allowing transforming knowledge to challenge the basic assumptions of our systems. Once consensus has been reached, it is politically, economically, and psychology expensive for the decision makers to change these assumptions.

And so, the status quo lives on.

An article by an organization called Box of Crayons shares 3 Advice Monsters that get in the way of asking great questions:

1. The idea that “you have to have the answer” if you want to add value when the truth is, your advice is not nearly as good as you think it is.

2. The idea that “you have to save them” – you just want to help them; your advice comes from a good place and you should have their backs but there are times when it is ok for them to struggle a little, to work to figure it out, to stretch and grow.

3. The idea that “you have to maintain control” – with this one, you are adding value, you are saving them, and you are controlling the future; you're defining the terms, you are locking in how this ends; but at what cost to the culture? You risk creating less empowered, engaged, and autonomous employees

We all start out with the capacity to ask about things we don’t know. The ones who choose to keep asking get better at it.

For many, the biggest inhibitor is just not understanding how beneficial good questioning can be

The power of a good question

Answers don’t drive innovation better questions do.

In fact, questioning is one of the five essential skills of disruptive innovators (see The Innovator’s DNA) - a list that includes observing, networking, associating, and experimenting. And just like physical muscles, our questioning muscles atrophy if we don’t use them.

A good question doesn’t reinforce the status quo. It punctures it.

The good questions we seek are those that foster a mindset of curiosity and exploration.

These types of questions are effective at introducing a new way of thinking about something without exposing oneself, or others, to judgement.

These types of questions are free of opinion.

And these types of questions view answers merely as the steppingstones to better questions.

Think about that! These innovators don’t view the answers as the end – the ‘we have arrived’ point. They value answers only from the sense that they lead us to new and better questions!

This is why they believe Questions are the Answer (see the book by Hal Gregerson). Because behind every breakthrough is a better question.

During the workshop, we explored questions that led to game-changing innovations:

“Why can’t photography be made easier?” led to Kodak’s early rise.
“How might we use this weak adhesive?” led to Post-it Notes.
“Why not rent out air mattresses to conference attendees to help cover our rent?” led to Airbnb.

The most catalytic questions challenge assumptions, open minds, and invite new perspectives. They don’t just solve problems - they reveal better ones to solve.

We introduced participants to QuestionStorming, a rapid-fire technique that shifts focus from ideas to inquiry. Think of it as brainstorming's more disruptive cousin.

Here’s how it works:

Identify a belief, behavior, or process that no longer serves you.
Set a timer or a goal to generate a certain number of questions.
Generate as many questions as possible—no answers allowed.
Look at your questions then: Reframe. Refine. Sort. Prioritize.
Act based on your most catalytic questions.

Do multiple rounds. Mix up the teams. Invite others who have no stake in the problem for a fresh perspective. Aim for 50 questions!

This method works for strategic planning, stakeholder engagement, team alignment—or even rethinking how your kid does homework

The ‘Ask This, Not That’ question shift

We also explored subtle but powerful shifts in everyday conversations, such as:

Don’t ask “How was your day?” Ask “What was your favorite part of today?”
Don’t ask “When can you get this done?” Ask “How do we get this done?”
Don’t ask “Is there anything else?” Ask “What else?”
Don’t ask “What do you think?” Ask “What improvements do you suggest?”
Don’t ask “How did this happen?” Ask “How did you decide to take that course of action?”

The difference? Better answers. Deeper insights. Stronger connections.

10 habits of great questioners you can adopt today

You can adopt the 10 habits of great questioners. As you develop these habits, you will be demonstrating to others a new way of working. Your behavior can influence a culture change that, over time, fosters curiosity and exploration and a safe place to question fearlessly.

1. Turn off auto-pilot and observe what is going on around you; question it. We spend too much time just going through the motions and missing the wonder that surrounds us.

2. Ask a question in every meeting; read the agenda and prepare questions in advance.

3. Keep a question log - and keep it with you; write down questions as they come to you; reflect on them; how can you ask it in a better way?

4. Start conversations with asking vs telling; we all have a lot to say but I think we have even more to learn; this sets the tone for the interaction.

5. Practice with family - ask richer questions; let them know you are building this muscle.

6. Be excited about what you don’t know you don’t know; be humble; challenge your long-held assumptions.

7. Reflect on past mistakes; what questions could have helped?

8. Engage in active listening; listen to understand other perspectives not to wait for your turn to talk.

9. Seek out contradictory information; spend time reading other points of view; instead of insisting on your point of view, ask how they came to that different conclusion.

10. Surround yourself with diverse thinkers to help challenge each other’s assumptions.