“If you think as a leader you can and should have all the answers, then you’re both wrong and significantly constraining the capacity of the organization to be creative.”
—IDEO CEO Tim Brown

In our most recent Creative Confidence Podcast chat, IDEO U Dean Suzanne Gibbs Howard sat down with IDEO CEO Tim Brown for a conversation on Tim’s evolving thoughts on creative leadership and his focus on asking better questions.

Listen on Apple Podcasts or Spotify

As Tim Brown says, old school models of leadership are not enough anymore. Top-down mandates and telling people what to do doesn’t lead to the creativity and innovation that allows modern companies to make an impact. Instead, leadership is about generating, embracing, and executing bold ideas—“even when the path is not clear.” And that all starts with asking questions.

Why Asking Better Questions Is Essential to Creative Leadership

“If you think as a leader you can and should have all the answers, then you’re both wrong and significantly constraining the capacity of the organization to be creative,” Tim says. Even worse, if you’re waiting for teams to come to you for answers and decisions, you’re leading them down a path that’s neither productive nor creative enough. Instead, it’s your job to ask the right questions, to help teams frame the challenge they’re designing for, and make sure they’re considering the end user and their needs. “Not only does it stop you from assuming you have to have the answer, it leaves the space for the individual or team you’re working with to express their own creativity and their own innovation,” he says.

You can also use questions to encourage your teams to take a step back and look at the bigger picture. “The thing that teams are often the least good at is knowing how ambitious to be, or even knowing where to look,” Tim says. “And what you do have as a leader is perspective. So if you’re thoughtful and can offer the right kinds of questions, then you can help teams look in the right place, and offer them the right perspective. And that’s a very powerful form of leadership.”

“The best leaders are not coming up with answers, they are coming up with great questions.”
Tim Brown

How to Get Better at Asking Questions That Spark Innovation

For Tim, there’s nothing less stimulating than trying to brainstorm alone with a blank sheet of paper. If you want to know how to get better at asking questions, it begins with staying curious, engaging in conversations, stepping into new contexts, and learning from the world around you. 

He often reflects by asking himself: What are the implications of what I’m seeing and what I’m learning? The more you dig in, the more nuanced and powerful your questions become. “The deeper you go, the less obvious question you get to, the more likely the idea that ultimately results is going to be more creative,” he says.  “One of the things we’re trying to do when we design is reveal needs that should be met. They’re never obvious. To dig down far enough to understand people and their interactions, you have to keep asking why.”

When leading with questions, especially in team settings, your prompts should follow what Tim calls the Goldilocks Principle. They need to strike the right balance: open enough to allow for unexpected, creative exploration, yet focused enough to feel tangible and actionable. If a question is too abstract, it may leave the team directionless. Too narrow, and it might yield incremental results instead of bold ideas.

Great questions should center on who you want to serve and the impact you want to make, without hinting at a specific solution. The goal is to create space for your team to surprise you with insights you wouldn’t have arrived at on your own.

Interested in more brainstorming exercises? Check out our Brainstorming Resources page.

Practical Tips for Getting Better at Asking Questions as a Leader

1. State the Question First

If you’re presenting to a leadership team or key stakeholders, put the question you’re trying to answer at the beginning of any sort of presentation. “Leaders spend so much time processing enormous amounts of information, if you don’t let them know within the first minute what the question is that you’re trying to solve for, and that you want their input on, you’ve already lost them.”

2. Use Questions to Shift Mindsets

A critical skill in leading with questions is knowing how to help others think differently. Tim shares a lesson from design school: students would display their work for critique, often guided by questions like “How did you think about this?” or “How did you arrive at this solution?” These kinds of questions don’t challenge authority; they shift perspective and promote curiosity.

In a team setting, asking the right kind of question can be more effective than offering direct feedback. If a solution feels too narrow, ask if the team considered another user group. If it feels too large, ask them to reframe the challenge on a smaller scale. This is where the mindset of leadership meets the art of inquiry, framing questions to unlock growth, rather than constraining it.

“There’s a very close relationship between asking questions and curiosity. They’re two sides of the same coin.”
Tim Brown

According to Tim, one of the most important things to remember is that the last thing people want to hear is that you don’t like their idea, or that you think you have a better one. “Many of the colleagues who I respect most and love working with are really good at asking me questions that get me to think differently, in a way that’s not combative, nor do they bow to a sense of hierarchy. These are peer-level, intellectually stimulating, insightful questions.”

Ready to lead with questions, not just answers? Join IDEO CEO Tim Brown in Leading for Creativity and learn how to empower your team through curiosity, not control.

Good Reads That Help You Get Better at Asking Questions and Seeing Differently

A More Beautiful Question by Warren Berger

Powers of Ten by Charles & Ray Eames

The 4 Books Tim Can’t Put Down