Build a Learning Culture with Powerful Questions


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“Your most unhappy customers are your greatest source of learning.” — Bill Gates

If you want better answers, ask better questions.

If you want to create a culture of learning and improvement, then focus on learning and improvement.

Ask questions that reveal insight and what’s right, rather than focus on what’s wrong or laying blame.

In the book, Anticipate: The Art of Leading by Looking Ahead, Rob-Jan de Jong shares how you can build a culture of learning through the art of asking powerful questions.

Leading Through Questioning

Some leaders do a great job of building a learning culture.  They ask questions that move the ball forward.

Via Anticipate: The Art of Leading by Looking Ahead:

“One of the leaders I used to work with applied a leadership style best described as leading by questioning: He has built up a repertoire of powerful questions for various occasions.”

What Options Do You See Now?

One way to build a learning culture is to ask people to reflect on their mistakes, and ask them what options they see now, that they didn’t see before.

Via Anticipate: The Art of Leading by Looking Ahead:

“He puts two powerful questions on the table: 1) What have you learned from what happened? and 2) What options do you see now that you didn’t see before?  This way he aims to build a learning culture and to encourage entrepreneurship, which he considers vital for his organization.”

Mindfully Learn from Mistakes

Don’t punish people for mistakes.  Reward them for learning.

Via Anticipate: The Art of Leading by Looking Ahead:

“He’s well known for never penalizing anyone for making a mistake; in fact, you might even get rewarded if the failure involved entrepreneurial risks.  But he does expect people to reflect and learn, and to be able to demonstrate increased insight.  It really ticks him off when someone doesn’t mindfully learn from a mistake.”

What Surprised You?

Some leaders use a technique called Conversation Surprise to build a learning culture.

They ask new hires what surprised them, so that they can gain new insight and improve their culture and processes.

Via Anticipate: The Art of Leading by Looking Ahead:

“The conversation focuses on only one question: ‘What has surprised you since you started working with us?

Knowing that most people adapt to company culture rather quickly, Carrefour wisely exploits the fact that in their first few weeks, newcomers still dare to challenge the assumptions older employees live by, so they are, in that short time frame, a great source of ideas for improvement.”

If You Were the CEO for a Day, What Would You Do?

Some leaders interview frontline staff to get a fresh perspective, to stay connected to where the action is, and to build empathy, while building and reinforcing a learning culture.

Via Anticipate: The Art of Leading by Looking Ahead:

“At Hertz, the largest publicly traded rental-car operator in the United States, the main senior leadership team does formal ‘skip level’ reviews at least twice a quarter.  They interview frontline staff members, without their managers or HR present, using only a handful of powerful questions, such as, ‘If you were the CEO for a day, what would you do?’ and ‘If you had a magic wand, how would you change Hertz?’  

This institutionalized process of inquiry ensures that the executives at Hertz do not alienate themselves from reality, and allows them to initiate–and possibly sponsor–high-impact changes.”

Appreciative Inquiry

Rather than focus on dysfunction which can lead to paralysis, frustration, and negativism, Appreciate Inquiry focuses on what’s going right, and how to do more of it.

Via Anticipate: The Art of Leading by Looking Ahead:

“Appreciative Inquiry (AI) is instead concerned with what is going very well.  Based on research revealing that a focus on strengths and positive attributes motivates people to understand and value the best features of their culture, AI encourages improvement by creating a very clear understanding of what works well and focusing energy on those things people seem to do effortlessly.”

Develop a Set of Appreciative Inquiry Questions

As a leader, if you use Appreciative Inquiry, it may help you better inspire and engage everyone.

Via Anticipate: The Art of Leading by Looking Ahead:

“Developing a set of appreciative inquiry questions could alter your leadership behavior in a  very favorable way.  By appreciating and acknowledging other’s strengths, by focusing on the positive, you can better inspire and engage them. “

What Was the Best Thing That Happened Today?

How was your day?  O.K.?   Well, what was your favorite part?   Now that’s an entirely new question that reveals new insight, and can lead to some great follow-up conversation.

Via Anticipate: The Art of Leading by Looking Ahead:

“And, by the way, this applies equally well to your non-business role as a partner or parent.  Try it tonight.  Rather than asking your loved one how their day was, or how they are doing, ask this appreciative inquiry question: ‘What was the very best thing that happened to you today?’ Pay attention to the conversation that unfolds and explore it and how it differs from the usual one.”

What Has Become Clear Since We Last Met?

Emerson liked to ask what changed since we last met.  It’s a simple question, but cuts right to the chase and can reveal some surprising insight.

Via Anticipate: The Art of Leading by Looking Ahead:

“Philosopher Ralph Waldo Emerson was known to greet friends and visitors with the question: ‘What has become clear to you since we last met?’  It might be a bit intimidating while you’re hanging  up your coat, but it’s a great question that sparks interest and curiosity straight away.”

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  1. First of all, love your book, the 3 outcomes a week per day by itself was a gamechanger.

    Great bits if information, I personally liked the Hertz example a lot, certainly something I would do if I was a Sr. Manager. Also feedback analysis, which is an old Peter Drucker recommendation works wonders, I
    have 2 labels in my email: positive & negative and review them about each quarter..

    What I think companies miss out is to implement internal self and group learning within the company.
    It’s crazy how much companies spend on MBA’s but don’t even provide book recommendations and thinking about it, just the extra commute time is time where someone could go into a room and read.

    Take 150 people office,
    take 3-5 disciplines: communication, marketing, process management etc..

    people have different styles so they should be able to pick discipline and learning material (book, online course, workshop etc)

    to group people together maybe just offer 2-3 disciplines per semester with 2-3 methodologies to pick.

    • Thank you.

      I’m a fan of post-mortems. One of the teams I was on had an intense focus on experimenting and learning.

      We created some space after our big projects to step back and figure out what worked, what didn’t work, and what we could do better.

      Sure there was some noise in the beginning, but over time, we got better, and the little improvement patterns paid off.


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