Design Leadership

Leading with Powerful Questions

Julie Stanescu
Founder, RETHINK

Illustration by Ivan Haidutski

While sometimes it is easier to provide answers, consider what becomes possible if we shift focus to being curious and asking questions that expand our understanding.

Being able to ask powerful questions, especially in uncertain times is a key skill as a leader in order to drive influence and get alignment. Being more intentional about how we frame our questions helps us elevate our listening skills and lead to better outcomes.

The asking questions approach forces your conversations to become less about your thoughts, your input, and the answer you think will work.

You start listening—really listening—to the other person.

What makes a question “powerful?”

- Provokes thinking deeply

- Empowers the person responding to choose the direction they want to take

- Sparks creative ideas and explores what is possible

- Goes below the surface and helps us understand what is important


Tactics for Developing Asking Skills

There is one simple principle I've learned over the years about asking powerful questions: have a clear understanding of what is the purpose of your question.  

For example: A team member needs to make a tough decision and they need to look at it from multiple angles. What type of questions would you ask to get to the desired outcome in your conversation?  

Challenge

PURPOSE: Do you want to challenge them, pointing out inconsistencies? Are you asking the person to reach higher, offering a new perspective?

QUESTION: "What was the motive behind... ? Have you considered ... ?"

Discovery

PURPOSE: Do you want to find out more since you don't have the answers yet?

QUESTION: "What are your struggles with making a decision here?"

Guiding

Do you want to help them see what you can see?

"Have you noticed that.....?"

Leading

PURPOSE: Do you want to guide the discussion towards the desired outcome?

QUESTION: "Tell me about the problems you have with your team."

"How will you make that decision here?"

"What other decision strategies could you use?"


Open

PURPOSE: Do you want to elicit a reaction, idea or explanation?

QUESTION: "Tell me more about what factors will make the most difference for you when making a decision?"

Closed

PURPOSE: Do you want a short yes/ no answer

QUESTION: "Did you make a decision about ... ?"


Curious to hear other perspectives here. What tips have worked for you to ask powerful questions?

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Illustration by Ivan Haidutski

While sometimes it is easier to provide answers, consider what becomes possible if we shift focus to being curious and asking questions that expand our understanding.

Being able to ask powerful questions, especially in uncertain times is a key skill as a leader in order to drive influence and get alignment. Being more intentional about how we frame our questions helps us elevate our listening skills and lead to better outcomes.

The asking questions approach forces your conversations to become less about your thoughts, your input, and the answer you think will work.

You start listening—really listening—to the other person.

What makes a question “powerful?”

- Provokes thinking deeply

- Empowers the person responding to choose the direction they want to take

- Sparks creative ideas and explores what is possible

- Goes below the surface and helps us understand what is important


Tactics for Developing Asking Skills

There is one simple principle I've learned over the years about asking powerful questions: have a clear understanding of what is the purpose of your question.  

For example: A team member needs to make a tough decision and they need to look at it from multiple angles. What type of questions would you ask to get to the desired outcome in your conversation?  

Challenge

PURPOSE: Do you want to challenge them, pointing out inconsistencies? Are you asking the person to reach higher, offering a new perspective?

QUESTION: "What was the motive behind... ? Have you considered ... ?"

Discovery

PURPOSE: Do you want to find out more since you don't have the answers yet?

QUESTION: "What are your struggles with making a decision here?"

Guiding

Do you want to help them see what you can see?

"Have you noticed that.....?"

Leading

PURPOSE: Do you want to guide the discussion towards the desired outcome?

QUESTION: "Tell me about the problems you have with your team."

"How will you make that decision here?"

"What other decision strategies could you use?"


Open

PURPOSE: Do you want to elicit a reaction, idea or explanation?

QUESTION: "Tell me more about what factors will make the most difference for you when making a decision?"

Closed

PURPOSE: Do you want a short yes/ no answer

QUESTION: "Did you make a decision about ... ?"


Curious to hear other perspectives here. What tips have worked for you to ask powerful questions?

GRATITUDE

People who support Leadership Circle

Deepest thanks to the following people who graciously offered feedback
and support while beta testing Leadership Circle.

Leslie Yang

Director, Product Design
OpenTable

Jeff Smith

Senior Design Manager
Coinbase

Julie Zhuo

Co-Founder
Sundial

Aniruddha Kadam

Product Design Manager
LinkedIn

Jen Kozenski-Devins

Head of Google
Accessibility UX

Jian Wei

Design Manager
‍Zendesk

Courtney Kaplan

Leadership Coach

Cammy Lin

Product Design Manager
Everlaw

Sun Dai

Senior Product Designer
Facebook

Liana Dumitru

Design Manager
Plaid

Mike Dick

Co-Founder
Gather